Standard Article

Enantioselective Reduction of Ketones

  1. Shinichi Itsuno

Published Online: 15 APR 2004

DOI: 10.1002/0471264180.or052.02

Organic Reactions

Organic Reactions

How to Cite

Itsuno, S. 2004. Enantioselective Reduction of Ketones. Organic Reactions. 52:2:395–576.

Author Information

  1. Toyohashi University of Technology:Toyohashi, Department of Materials Science, Japan

Publication History

  1. Published Online: 15 APR 2004

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Abstract

Enantioselective reduction of prochiral ketones is among the most important methods for preparing enantioenriched secondary alcohols, which are important starting materials for a number of enantiopure compounds, including natural products. Various methods for enantioselective reduction of ketones have been developed for producing enantioenriched alcohols. These methods involve the use of both stoichiometric reagents and catalytic reductions. Metal hydride reagents such as lithium aluminum hydride (LAH) and sodium borohydride (NaBH4) are easily modified by enantiopure compounds. For example, binaphthol-modified aluminum hydride reagent (BINAL-H) is a derivative of LAH in which the enantiopure diol 1,1′-bi-2-naphthol and one other alcohol replace three of the hydrogens. This reagent achieves high selectivity in many ketone reductions. The other impressive area of success is the use of enantiopure alkylboranes. The β hydride of enantiopure alkylboranes is delivered selectively, often exclusively, to one face of the carbonyl group of a ketone.

Despite remarkable success with stoichiometric reagents, their important drawback is that at least one equivalent of reagent is required for reduction of the ketone. Thus catalytic processes are desirable for enantioselective ketone reduction as well as for other asymmetric transformations. Hydrogenation and hydrosilylation of ketones are catalyzed by transition metal catalysts. Enantiopure ligand-transition metal complexes can be used as asymmetric catalysts for these reactions. Recent research makes it possible to achieve high enantioselectivity, not only for the reduction of functionalized ketones in which a transition metal can coordinate to an adjacent functional group, but also for simple ketones such as acetophenone. One of the most remarkable catalytic systems described in recent years is borane reduction in the presence of an oxazaborolidine, which contains adjacent donor (nitrogen) and acceptor (boron) sites. Many biologically active compounds have been synthesized by using oxazaborolidine-catalyzed borane reductions of ketones as the key step. Asymmetric reduction with enzymes is another important method. Some baker's yeast mediated ketone reductions have practical applicability.

This chapter addresses the enantioselective reduction of ketones by various methods including chirally modified hydride reductions, oxazaborolidine catalyzed reductions, Meerwein-Ponndorf-Verley (MPV) reductions, hydrogenations, hydrosilylations, and enzymatic reductions.

Keywords:

  • enantioselective reduction;
  • ketones;
  • chirally modified;
  • lithium aluminum hydride;
  • reagents;
  • scope;
  • limitations;
  • alcohols;
  • diols;
  • amino alcohols;
  • diamines;
  • chirally modified borohydride reagents;
  • quaternary ammonium salts;
  • carboxylic acids;
  • chiral compounds;
  • alkylborohydrides;
  • chiral host compounds;
  • boranes;
  • borohydride reductions;
  • diamine-metal hydride systems;
  • catalytic borane reductions;
  • catalyst;
  • Meerwein-Ponndorf-Verley reductions;
  • transition metal catalyzed reductions;
  • hydrogenation;
  • hydrosilylation;
  • enzymatic reductions;
  • baker's yeast;
  • dihydropyridine reagents;
  • experimental procedures;
  • tabular survey

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:KHIVAMOFBMZCLZ-YFKPBYRVSA-N
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Compound Information
Molecular Weight:319.248
Molecular Formula:C21H26BNO
InChIKey:FUVQOWKGWXFWHP-FQEVSTJZSA-N
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Compound Information
Molecular Weight:251.108
Molecular Formula:C13H8Cl2O
InChIKey:LLUPHTAYNHAVQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.3132
Molecular Formula:C13H22O
InChIKey:RIDGYKNISLSBIJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.1748
Molecular Formula:C6H14O
InChIKey:DFOXKPDFWGNLJU-YFKPBYRVSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:FWFSEYBSWVRWGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:XKGLSKVNOSHTAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:QRYJGVNQNLCGGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:85.941
Molecular Formula:C4H11BO
InChIKey:NPKJJCLQKCPGEZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:KQNPFQTWMSNSAP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:233.009
Molecular Formula:C14H27B2N
InChIKey:CKEJKOWOFPODPC-IQDIHOQSSA-N
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Compound Information
Molecular Weight:196.3291
Molecular Formula:C13H24O
InChIKey:IQOABZVBQBQUIS-CYBMUJFWSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:KWOLFJPFCHCOCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:KRIOVPPHQSLHCZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:421.4408
Molecular Formula:C21H29AlO7
InChIKey:WFGWESATXBXVRZ-MAKXIUBESA-N
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Compound Information
Molecular Weight:437.3971
Molecular Formula:C20H25AlO9
InChIKey:APRJFSLXRANRQT-UHFFFAOYSA-L
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Compound Information
Molecular Weight:219.2391
Molecular Formula:C11H15AlN2O
InChIKey:RTAPXCWHSAHBMI-IDMXKUIJSA-N
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Compound Information
Molecular Weight:234.197
Molecular Formula:C11H20AlLiO3
InChIKey:ZJJYJQJESPELGP-IATGMFGXSA-N
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Compound Information
Molecular Weight:110.1106
Molecular Formula:C6H6O2
InChIKey:IEMMBWWQXVXBEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2588
Molecular Formula:C11H17NO
InChIKey:FMCGSUUBYTWNDP-ONGXEEELSA-N
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Compound Information
Molecular Weight:366.3625
Molecular Formula:C18H22O8
InChIKey:FBCARUOUUSZNTG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:238.234
Molecular Formula:C13H20AlLiN2
InChIKey:FUWNSEYEXJMFOD-KCOFNFEMSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:PJGSXYOJTGTZAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.42
Molecular Formula:Pd
InChIKey:KDLHZDBZIXYQEI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1488
Molecular Formula:C5H12
InChIKey:OFBQJSOFQDEBGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:290.137
Molecular Formula:C17H14FeO
InChIKey:NOVVNDDNXWMHCU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.1846
Molecular Formula:C10H10O3
InChIKey:QKLCQKPAECHXCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.993
Molecular Formula:C17H20B2NO
InChIKey:YMDZZCFXTQPXFQ-INIZCTEOSA-N
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Compound Information
Molecular Weight:177.2429
Molecular Formula:C11H15NO
InChIKey:QMNXJNURJISYMS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:203.2402
Molecular Formula:C11H15AlN2
InChIKey:CFQPTXGMZCRTNV-XVSRHIFFSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.25
Molecular Formula:C18H31B
InChIKey:VCDGSBJCRYTLNU-CJGYBVCLSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:NTIZESTWPVYFNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.551
Molecular Formula:ClK
InChIKey:WCUXLLCKKVVCTQ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:315.122
Molecular Formula:C14H19BLiNO4S
InChIKey:SQHIYZHKLOVHSA-YBTMIULGSA-N
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Compound Information
Molecular Weight:446.5843
Molecular Formula:C27H36AlN3O
InChIKey:DVWQVFMINBWFNH-WZWODHENSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:DWPLEOPKBWNPQV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.679
Molecular Formula:C13H11ClO
InChIKey:DDCJHFYXAPQYLA-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:YIAPLDFPUUJILH-SECBINFHSA-N
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Compound Information
Molecular Weight:202.2954
Molecular Formula:C13H18N2
InChIKey:FHMOBTPNHZBTNZ-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:OVGORFFCBUIFIA-LLVKDONJSA-N
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Compound Information
Molecular Weight:216.663
Molecular Formula:C13H9ClO
InChIKey:CPLWKNRPZVNELG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.833
Molecular Formula:BH4Na
InChIKey:YOQDYZUWIQVZSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.3113
Molecular Formula:C13H20N2
InChIKey:UWCWUCKPEYNDNV-LBPRGKRZSA-N
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Compound Information
Molecular Weight:277.169
Molecular Formula:C18H20BNO
InChIKey:Not Available
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Compound Information
Molecular Weight:227.2568
Molecular Formula:C11H19AlO3
InChIKey:LNNILEMDBNUBCB-UIBZXLQUSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:ACIVJWAOSTYYEP-ZAZKALAHSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:TUAMRELNJMMDMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:131.1729
Molecular Formula:C6H13NO2
InChIKey:AGPKZVBTJJNPAG-AKGZTFGVSA-N
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Compound Information
Molecular Weight:170.2072
Molecular Formula:C12H10O
InChIKey:QQLIGMASAVJVON-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:HQZIAZCARGNEME-MRVPVSSYSA-N
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Compound Information
Molecular Weight:27.67
Molecular Formula:B2H6
InChIKey:NTJHUEGHVSASEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:339.238
Molecular Formula:C23H22BNO
InChIKey:GXAMQZFEKIDKAP-QFIPXVFZSA-N
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Compound Information
Molecular Weight:263.142
Molecular Formula:C17H18BNO
InChIKey:NSAZIMJIRLGSEG-INIZCTEOSA-N
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Compound Information
Molecular Weight:850.855
Molecular Formula:C52H48AlLiO9
InChIKey:QJSJMUVMZKLYKN-UHFFFAOYSA-L
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:DUTNTKTZIQAPGA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.94
Molecular Formula:C4H11BO2
InChIKey:QPKFVRWIISEVCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:NOOLISFMXDJSKH-KXUCPTDWSA-N
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Compound Information
Molecular Weight:455.494
Molecular Formula:C27H35AlLiNO3
InChIKey:HZHDMWSTBMNMJQ-BZDUAQFOSA-L
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Compound Information
Molecular Weight:180.2005
Molecular Formula:C10H12O3
InChIKey:SAXHIDRUJXPDOD-SECBINFHSA-N
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Compound Information
Molecular Weight:448.5538
Molecular Formula:C27H34AlNO3
InChIKey:JWCYQJLGPKIJBY-WZWODHENSA-L
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Compound Information
Molecular Weight:222.3266
Molecular Formula:C13H22N2O
InChIKey:YHUZDSAJGBBMCS-LBPRGKRZSA-N
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Compound Information
Molecular Weight:181.313
Molecular Formula:C6H5BrMg
InChIKey:ANRQGKOBLBYXFM-UHFFFAOYSA-M
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Compound Information
Molecular Weight:269.3813
Molecular Formula:C18H23NO
InChIKey:JUJJNFOJLOTLPM-JRZJBTRGSA-N
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Compound Information
Molecular Weight:227.3016
Molecular Formula:C15H17NO
InChIKey:FMBMNSFOFOAIMZ-LBPRGKRZSA-N
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Compound Information
Molecular Weight:37.954
Molecular Formula:AlH4Li
InChIKey:OCZDCIYGECBNKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.916
Molecular Formula:CCl2O
InChIKey:Not Available
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Compound Information
Molecular Weight:194.2734
Molecular Formula:C11H18N2O
InChIKey:AIBOXGBLHQZDGN-NSHDSACASA-N
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Compound Information
Molecular Weight:136.315
Molecular Formula:Cl2Zn
InChIKey:Not Available
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Compound Information
Molecular Weight:255.3547
Molecular Formula:C17H21NO
InChIKey:LNQVZZGGOZBOQS-INIZCTEOSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:KLQCAVMGXXCQHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:OGAAQVONYOTBGB-GFCCVEGCSA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.025
Molecular Formula:C6H18BN
InChIKey:ONRDAGWFOUZNLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:366.4532
Molecular Formula:C22H28AlNO2
InChIKey:VJILSRCQBBCKNO-GIKVJREKSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:DHHGVIOVURMJEA-SSDOTTSWSA-N
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Compound Information
Molecular Weight:292.153
Molecular Formula:C17H16FeO
InChIKey:FBUPGAQWVYCCBL-CURYUGHLSA-N
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Compound Information
Molecular Weight:161.3928
Molecular Formula:C6H19NSi2
InChIKey:FFUAGWLWBBFQJT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:379.407
Molecular Formula:C26H39BO
InChIKey:HUEIMRDBKQBEMV-WRGDXOCCSA-N
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Compound Information
Molecular Weight:350.4061
Molecular Formula:C19H26O6
InChIKey:CSVOEMJSHCCUHW-UYTYNIKBSA-N
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Compound Information
Molecular Weight:118.97
Molecular Formula:Cl2OS
InChIKey:FYSNRJHAOHDILO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.1748
Molecular Formula:C6H14O
InChIKey:WVYWICLMDOOCFB-LURJTMIESA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:COJJXYXOKBNPCL-VIFPVBQESA-N
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Compound Information
Molecular Weight:179.2588
Molecular Formula:C11H17NO
InChIKey:VELGOYBSKBKQFF-LLVKDONJSA-N
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Compound Information
Molecular Weight:428.49
Molecular Formula:C23H42BrNO
InChIKey:Not Available
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Compound Information
Molecular Weight:381.292
Molecular Formula:C20H33BO6
InChIKey:IAONNJKECNPSEC-NCXLMVEPSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:UABXUIWIFUZYQK-YFKPBYRVSA-N
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Compound Information
Molecular Weight:59.86
Molecular Formula:CH5BO2
InChIKey:Not Available
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Compound Information
Molecular Weight:539.6182
Molecular Formula:C33H33NO6
InChIKey:ODYGUJFUZIJKEO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:337.435
Molecular Formula:C20H19NO2S
InChIKey:KAOOZCLFNXOSQK-DEOSSOPVSA-N
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Compound Information
Molecular Weight:132.1592
Molecular Formula:C9H8O
InChIKey:QNXSIUBBGPHDDE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:233.009
Molecular Formula:C14H29B2N
InChIKey:RKNVCPYOGTUKLW-VHICAWHZSA-N
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Compound Information
Molecular Weight:121.93
Molecular Formula:C6H7BO2
InChIKey:HXITXNWTGFUOAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.663
Molecular Formula:C13H9ClO
InChIKey:VMHYWKBKHMYRNF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:303.3975
Molecular Formula:C21H21NO
InChIKey:KBXBDYRXZGBOIH-FQEVSTJZSA-N
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Compound Information
Molecular Weight:334.3
Molecular Formula:C16H28BKO4
InChIKey:MBHGTVDZEFYHOO-WYFSGWFLSA-N
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Compound Information
Molecular Weight:172.2231
Molecular Formula:C12H12O
InChIKey:CDRQOYRPWJULJN-SECBINFHSA-N
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Compound Information
Molecular Weight:176.2581
Molecular Formula:C11H16N2
InChIKey:MCHWKJRTMPIHRA-NSHDSACASA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:ZPVFWPFBNIEHGJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:89.0932
Molecular Formula:C3H7NO2
InChIKey:QNAYBMKLOCPYGJ-REOHCLBHSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:317.3795
Molecular Formula:C18H23NO4
InChIKey:VHSBBVZJABQOSG-INIZCTEOSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:CXGFWBPQQXZELI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:289.4125
Molecular Formula:C18H27NO2
InChIKey:XJPOVUGGVJWKQL-NYCLONFESA-N
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Compound Information
Molecular Weight:253.3389
Molecular Formula:C17H19NO
InChIKey:OGCGXUGBDJGFFY-INIZCTEOSA-N
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Compound Information
Molecular Weight:269.3813
Molecular Formula:C18H23NO
InChIKey:XECSMDWXBMBRDE-KRWDZBQOSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:JMSUNAQVHOHLMX-ZETCQYMHSA-N
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Compound Information
Molecular Weight:218.679
Molecular Formula:C13H11ClO
InChIKey:JGDRELLAZGINQM-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:207.355
Molecular Formula:C14H25N
InChIKey:DLYZMHLEVIPDRF-STQMWFEESA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:RYLFWQILVNWPEL-BBBLOLIVSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:ZNTAGWCDEVPITB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:231.2934
Molecular Formula:C13H19AlN2
InChIKey:ABBSLMPEMBNNAT-JNQXMBDASA-N
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Compound Information
Molecular Weight:117.1463
Molecular Formula:C5H11NO2
InChIKey:KZSNJWFQEVHDMF-BYPYZUCNSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:286.4516
Molecular Formula:C20H30O
InChIKey:IXLSHNRLPYQCKH-FFZBFBDNSA-N
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Compound Information
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:OJGMBLNIHDZDGS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.18
Molecular Formula:C11H16AlLiN2O
InChIKey:SQPKJGUTQLYVGD-XVSRHIFFSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:RIFKADJTWUGDOV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.642
Molecular Formula:C3H9ClSi
InChIKey:IJOOHPMOJXWVHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:UTIFIONYBLSHIL-LURJTMIESA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:PQANGXXSEABURG-LURJTMIESA-N
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Compound Information
Molecular Weight:373.394
Molecular Formula:C22H29AlLiNO2
InChIKey:HJESVCWTDLWAHF-PUTAQMJKSA-N
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Compound Information
Molecular Weight:39.0983
Molecular Formula:HK
InChIKey:NTTOTNSKUYCDAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:131.1729
Molecular Formula:C6H13NO2
InChIKey:ROHFNLRQFUQHCH-YFKPBYRVSA-N
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Compound Information
Molecular Weight:444.338
Molecular Formula:C20H26AlLiO9
InChIKey:PYSQDBXRMMBUIW-UHFFFAOYSA-L
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Compound Information
Molecular Weight:192.2112
Molecular Formula:C11H12O3
InChIKey:GKKZMYDNDDMXSE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:21.784
Molecular Formula:BH4Li
InChIKey:UUKMSDRCXNLYOO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:453.525
Molecular Formula:C27H37AlLiN3O
InChIKey:IKGQCNJKKCSQLN-BZDUAQFOSA-N
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Compound Information
Molecular Weight:247.2928
Molecular Formula:C13H19AlN2O
InChIKey:AUWWVDCLNGIDCW-LTCKWSDVSA-N
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Compound Information
Molecular Weight:136.862
Molecular Formula:C6H5ClMg
InChIKey:GQONLASZRVFGHI-UHFFFAOYSA-M
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Compound Information
Molecular Weight:455.501
Molecular Formula:C25H35AlLiN5O
InChIKey:YGKZBRGCFGKMLC-BZDUAQFOSA-N
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:GRWFGVWFFZKLTI-RKDXNWHRSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:210.181
Molecular Formula:C11H16AlLiN2
InChIKey:RBFDNDICEQOJMT-HZAYLZKLSA-N
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Compound Information
Molecular Weight:115.1305
Molecular Formula:C5H9NO2
InChIKey:ONIBWKKTOPOVIA-BYPYZUCNSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:DVIBDQWVFHDBOP-SNVBAGLBSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:DKGAVHZHDRPRBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:428.381
Molecular Formula:C21H30AlLiO7
InChIKey:QPNINDIWGMAEKK-XWIRJILASA-N
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Compound Information
Molecular Weight:286.324
Molecular Formula:C20H14O2
InChIKey:PPTXVXKCQZKFBN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.225
Molecular Formula:C19H34BLi
InChIKey:PAQJSLZAFWZCKQ-XDWOKLSGSA-N
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Compound Information
Molecular Weight:260.2836
Molecular Formula:C12H20O6
InChIKey:KEJGAYKWRDILTF-JDDHQFAOSA-N
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Compound Information
Molecular Weight:753.8334
Molecular Formula:C46H50CoN2O4
InChIKey:YWERUEBFDBRTJJ-WCLVFFLLSA-L
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Compound Information
Molecular Weight:171.2368
Molecular Formula:C9H17NO2
InChIKey:LPQZERIRKRYGGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:413.361
Molecular Formula:C30H28BN
InChIKey:HPUYEMHWJYQJKH-ZMBIFBSDSA-N
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Compound Information
Molecular Weight:357.3581
Molecular Formula:C22H17AlO3
InChIKey:DSVYNIJHXMWBSB-UHFFFAOYSA-L
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:COLNVLDHVKWLRT-QMMMGPOBSA-N
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Compound Information
Molecular Weight:253.124
Molecular Formula:C13H10Cl2O
InChIKey:DALLAISNTUBBNX-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:448.5604
Molecular Formula:C25H34AlN5O
InChIKey:FEPWGHBUXWJWNR-WZWODHENSA-N
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Compound Information
Molecular Weight:341.487
Molecular Formula:C22H31NO2
InChIKey:BCXARWAGLICOTL-FNAHDJPLSA-N
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Compound Information
Molecular Weight:386.347
Molecular Formula:C26H40BLiO
InChIKey:XJOCNAQVRHLSGK-VVNIIREUSA-N
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Compound Information
Molecular Weight:225.264
Molecular Formula:C10H11NO3S
InChIKey:LJWSDBHOEIBWJY-MRVPVSSYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:WAPNOHKVXSQRPX-SSDOTTSWSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:WAPNOHKVXSQRPX-ZETCQYMHSA-N
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Compound Information
Molecular Weight:130.2279
Molecular Formula:C8H18O
InChIKey:SJWFXCIHNDVPSH-QMMMGPOBSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:DYUQAZSOFZSPHD-VIFPVBQESA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:PQANGXXSEABURG-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:288.4675
Molecular Formula:C20H32O
InChIKey:YADVRLOQIWILGX-MIWLTHJTSA-N
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Compound Information
Molecular Weight:150.0868
Molecular Formula:C4H6O6
InChIKey:FEWJPZIEWOKRBE-JCYAYHJZSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:DYUQAZSOFZSPHD-SECBINFHSA-N
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Compound Information
Molecular Weight:122.016
Molecular Formula:C8H15B
InChIKey:FEJUGLKDZJDVFY-OCAPTIKFSA-N
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Compound Information
Molecular Weight:381.292
Molecular Formula:C20H33BO6
InChIKey:IAONNJKECNPSEC-NCXLMVEPSA-N
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Compound Information
Molecular Weight:256.3826
Molecular Formula:C18H24O
InChIKey:VZTCOMJNYWLOOB-IRXDYDNUSA-N
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Compound Information
Molecular Weight:102.1748
Molecular Formula:C6H14O
InChIKey:DFOXKPDFWGNLJU-RXMQYKEDSA-N
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Compound Information
Molecular Weight:164.158
Molecular Formula:C9H8O3
InChIKey:YLHXLHGIAMFFBU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:HQRWWHIETAKIMO-SNVBAGLBSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:BSMGLVDZZMBWQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:Not Available
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Compound Information
Molecular Weight:493.6407
Molecular Formula:C35H31N3
InChIKey:WUUIULKYRNYSHF-IKUWGASPSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:SYBYTAAJFKOIEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:693.21
Molecular Formula:C24H18Ar4O4P2Ru
InChIKey:URBCWHZHGXEXTP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:181.1885
Molecular Formula:C9H11NO3
InChIKey:PZMVOUYYNKPMSI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.3434
Molecular Formula:C16H20N2
InChIKey:BTHYVQUNQHWNLS-HZPDHXFCSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:XYIBRDXRRQCHLP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:PCYZZYAEGNVNMH-BYPYZUCNSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:LONAYYKXZPCZNH-ZETCQYMHSA-N
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Compound Information
Molecular Weight:156.609
Molecular Formula:C8H9ClO
InChIKey:DDUBOVLGCYUYFX-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:223.078
Molecular Formula:C14H14BNO
InChIKey:JBPPDQRJSBZUAD-UONOGXRCSA-N
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Compound Information
Molecular Weight:170.636
Molecular Formula:C9H11ClO
InChIKey:JZFUHAGLMZWKTF-SECBINFHSA-N
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Compound Information
Molecular Weight:419.366
Molecular Formula:C29H30BNO
InChIKey:NRHLEYDGMRUNLZ-NDEPHWFRSA-N
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Compound Information
Molecular Weight:505.6499
Molecular Formula:C33H35N3O2
InChIKey:OUFNIFKUDCHXIS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1699
Molecular Formula:C10H8O
InChIKey:UPEUQDJSUFHFQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.315
Molecular Formula:C7H14OS2
InChIKey:QZZQCERSJUGENM-LURJTMIESA-N
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Compound Information
Molecular Weight:671.702
Molecular Formula:C16H24Cl2Ir2
InChIKey:OPGJGIVNZIAVPD-UHFFFAOYSA-L
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Compound Information
Molecular Weight:194.3025
Molecular Formula:C10H14O2Si
InChIKey:ZWMGOOFTAPXXRN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:295.213
Molecular Formula:C12H23BrO3
InChIKey:GFFSKQYOJURSSC-LLVKDONJSA-N
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Compound Information
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:AQVDQMYAJRCDDR-ZETCQYMHSA-N
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Compound Information
Molecular Weight:871.936
Molecular Formula:C32H32Cl2Ir2
InChIKey:NGPRPYMSABFOBX-NEYRPJGASA-L
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Compound Information
Molecular Weight:168.62
Molecular Formula:C9H9ClO
InChIKey:KTJRGPZVSKWRTJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.3803
Molecular Formula:C15H26N2
InChIKey:SLRCCWJSBJZJBV-TUVASFSCSA-N
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Compound Information
Molecular Weight:115.1735
Molecular Formula:C6H13NO
InChIKey:DKUCGOKEZSOFOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:440.5302
Molecular Formula:C29H28O4
InChIKey:AKTULPLXKAOHKG-MUUNZHRXSA-N
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Compound Information
Molecular Weight:148.1586
Molecular Formula:C9H8O2
InChIKey:MSTDXOZUKAQDRL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.2915
Molecular Formula:C14H18O2
InChIKey:RYXHBYZYHRDWSN-GFCCVEGCSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:ZFJIOVJYDPJNHK-NSHDSACASA-N
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Compound Information
Molecular Weight:1150.24
Molecular Formula:C40H24Ar8P4Ru2
InChIKey:VVVIQIRGWMHVOV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:841.83
Molecular Formula:C48H38O4P2Ru
InChIKey:ZTYGAUKZDDXENY-UHFFFAOYSA-L
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Compound Information
Molecular Weight:258.291
Molecular Formula:C11H14O5S
InChIKey:BFRWVESIVGVDND-VIFPVBQESA-N
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Compound Information
Molecular Weight:182.2179
Molecular Formula:C13H10O
InChIKey:RWCCWEUUXYIKHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.762
Molecular Formula:C12H23ClO3
InChIKey:YWUCLFSFZIBCGK-LLVKDONJSA-N
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Compound Information
Molecular Weight:794.65
Molecular Formula:C44H32Cl2P2Ru
InChIKey:YSWFDCINVSIDPT-UHFFFAOYSA-L
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Compound Information
Molecular Weight:154.594
Molecular Formula:C8H7ClO
InChIKey:ZDOYHCIRUPHUHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.217
Molecular Formula:C10H14O2
InChIKey:DOMMDPHTJGBKEL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:ILPVOWZUBFRIAX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:293.197
Molecular Formula:C12H21BrO3
InChIKey:PVLXSQWDOVFOND-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:ROWKJAVDOGWPAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.129
Molecular Formula:C10H17AlCl2O
InChIKey:PUUCNDMGBCZLMI-NIRGHBCMSA-L
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Compound Information
Molecular Weight:224.2994
Molecular Formula:C12H20N2O2
InChIKey:ZSZOYMBXNYZPFL-NXEZZACHSA-N
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Compound Information
Molecular Weight:298.837
Molecular Formula:C14H19ClO3Si
InChIKey:XOBWJZCNSISOKC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:OIWBNCGEFFHTNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.334
Molecular Formula:C12H18O4S
InChIKey:LVWACITYGLNNDS-NSHDSACASA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:WJIFROMUSTWNOG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.345
Molecular Formula:C13H18O4S
InChIKey:XZMVAKKQJWUMIU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.25
Molecular Formula:C18H31B
InChIKey:VCDGSBJCRYTLNU-CJGYBVCLSA-N
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Compound Information
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:HEQOJEGTZCTHCF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.2331
Molecular Formula:C5H12O2Si
InChIKey:IKKLQUXMAOOELR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:FTGZMZBYOHMEPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:75.969
Molecular Formula:C2H9BS
InChIKey:Not Available
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Compound Information
Molecular Weight:118.1311
Molecular Formula:C5H10O3
InChIKey:Not Available
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Compound Information
Molecular Weight:304.706
Molecular Formula:C13H18ClO4P
InChIKey:KWAZQBAWJMJAPF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.914
Molecular Formula:C6H5BO2
InChIKey:CENMEJUYOOMFFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.647
Molecular Formula:C15H28BCl
InChIKey:RHXVDAZHBJUWAR-VOAKCMCISA-N
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Compound Information
Molecular Weight:636.891
Molecular Formula:C31H32ClO2P2Rh
InChIKey:JUNVKGPOLOXQGD-SEILFYAJSA-M
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Compound Information
Molecular Weight:210.228
Molecular Formula:C14H10O2
InChIKey:WURBFLDFSFBTLW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:522.6414
Molecular Formula:C31H44N2OP2
InChIKey:BREAVWOTKQHAAN-QCDSWUKFSA-N
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Compound Information
Molecular Weight:531.07
Molecular Formula:I3Sm
InChIKey:XQKBFQXWZCFNFF-UHFFFAOYSA-K
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:DBQLMDVZSFDTRL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:631.41
Molecular Formula:C22H44Br2P2Ru
InChIKey:VFVGLIVDYBYQRO-LHDDMMNKSA-L
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Compound Information
Molecular Weight:277.169
Molecular Formula:C18H20BNO
InChIKey:Not Available
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:WGQKYBSKWIADBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.275
Molecular Formula:C11H12O5S
InChIKey:KXVJMMKUBFYYDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.307
Molecular Formula:C11H16O4S
InChIKey:VJJAHHPPQFURCZ-JTQLQIEISA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:SERHXTVXHNVDKA-BYPYZUCNSA-N
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Compound Information
Molecular Weight:176.3
Molecular Formula:C7H12OS2
InChIKey:VMRQGIZTJXUKOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:390.5592
Molecular Formula:C30H30
InChIKey:FXZBQHAIFASFEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.217
Molecular Formula:C8H15NO3
InChIKey:SRLCEXBJBBTQIR-UHFFFAOYSA-O
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Compound Information
Molecular Weight:210.2744
Molecular Formula:C14H14N2
InChIKey:WFJMIULOCVZAIS-JASJWYONSA-N
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Compound Information
Molecular Weight:56.1056
Molecular Formula:HKO
InChIKey:KWYUFKZDYYNOTN-UHFFFAOYSA-M
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