Standard Article

The Kulinkovich Cyclopropanation of Carboxylic Acid Derivatives

  1. Jin Kun Cha1,
  2. Oleg G. Kulinkovich2

Published Online: 13 JUL 2012

DOI: 10.1002/0471264180.or077.01

Organic Reactions

Organic Reactions

How to Cite

Cha, J. K. and Kulinkovich, O. G. 2012. The Kulinkovich Cyclopropanation of Carboxylic Acid Derivatives. Organic Reactions. 77:1:1–160.

Author Information

  1. 1

    Wayne State University, Department of Chemistry, Detroit, Michigan

  2. 2

    Belarusian State University, Department of Organic Chemistry, Minsk, Belarus

Publication History

  1. Published Online: 13 JUL 2012

Chemistry Terms

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Abstract

Cyclopropanes are characterized by high ring-strain energy and have been employed as useful building blocks in organic synthesis. The incorporation of a heteroatom donor substituent such as OH, OR, NR2, or SR on the ring imparts enhanced reactivity. Hydroxycyclopropanes (cyclopropanols) in particular have been thoroughly studied due to their facile ring cleavage. Among several known methods, a new method for preparation of cyclopropanols involves dialkoxytitanacyclopropane-mediated cyclopropanation (the Kulinkovich cyclopropanation) of esters with Grignard reagent in the presence of titanium isopropoxide. The striking feature of this method is the facile formation of a three-membered ring from a simple Grignard reagent which acts as a 1,2-dicarbanion equivalent through a pivotal dialkoxytitana-cycloproapne intermediate. These reactions benefit from the availability of inexpensive reagents, ease of operation, and high selectivity for cis-dialkylcyclopropanols. This cyclopropanation reaction has since been extended to other carboxylic derivatives to provide convenient access to several heteroatom-substituted cyclopropanes. The objective of this chapter is to provide an updated, comprehensive coverage of the literature on the Kulinkovich cyclopropanation reaction and related processes. Key mechanistic issues are summarized.

Keywords:

  • Kulinkovich cyclopropanation;
  • Carboxylic acid derivatives;
  • Grignard reagents;
  • Titanium alkoxides;
  • Cyclopropanol;
  • Carbonyl compounds;
  • Mechanisms;
  • Esters;
  • Aminocyclopropanes;
  • Imides;
  • Experimental procedures;
  • Comparison of methods

Featured Compounds

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  1. 1 - 250
Compound Information
Molecular Weight:1.00794
Molecular Formula:H
InChIKey:GPRLSGONYQIRFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:204.287
Molecular Formula:C9H16O3S
InChIKey:MVLZQCSHKSSOOR-OGSWXMBVSA-N
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Compound Information
Molecular Weight:299.75
Molecular Formula:C14H18ClNO4
InChIKey:KHQOTQZWBRBCEY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.3507
Molecular Formula:C10H20OSi
InChIKey:YMBCLMJHGZLWQO-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:376.3742
Molecular Formula:C18H24Cr2O2
InChIKey:RCYRVOPKUNTKGO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.3291
Molecular Formula:C13H24O
InChIKey:JVVRDTDXBGXUHD-WCQYABFASA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:OJEGXXJCQHBRDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.3031
Molecular Formula:C12H22
InChIKey:OHCCPFHZKRAKNR-ZHACJKMWSA-N
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Compound Information
Molecular Weight:184.113
Molecular Formula:Br2Mg
InChIKey:Not Available
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:588.086
Molecular Formula:C4H8Cl4Pt2
InChIKey:BKLJZEZJDPUGRS-UHFFFAOYSA-J
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Compound Information
Molecular Weight:137.2711
Molecular Formula:C8H18O
InChIKey:Not Available
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:HUVIPVAEVDLKMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.094
Molecular Formula:C8H18O2Ti
InChIKey:BEQZEFYOSPIBDP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.531
Molecular Formula:C4H10Zn
InChIKey:HQWPLXHWEZZGKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.4088
Molecular Formula:C14H22O2Si
InChIKey:VCIMVHXGXZOUFX-KBPBESRZSA-N
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Compound Information
Molecular Weight:78.133
Molecular Formula:C2H6OS
InChIKey:IAZDPXIOMUYVGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:PRBDXAKPEQFPRN-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:214.3061
Molecular Formula:C14H18N2
InChIKey:NANZRPOIAWSFHY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:300.38
Molecular Formula:C10H18Cl2Zr
InChIKey:NNXXSWLVKCQJIP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:252.3077
Molecular Formula:C17H16O2
InChIKey:YOLLTWVIOASMFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:FUDYLZSWQBNVOL-PWSUYJOCSA-N
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Compound Information
Molecular Weight:122.902
Molecular Formula:Cl2Cr
InChIKey:XBWRJSSJWDOUSJ-UHFFFAOYSA-L
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Compound Information
Molecular Weight:409.721
Molecular Formula:C24H47NO2Si
InChIKey:CTELQYHUNUIWJO-ZLNRFVROSA-N
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Compound Information
Molecular Weight:175.2701
Molecular Formula:C12H17N
InChIKey:KCILWLSZXAAOSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:332.5508
Molecular Formula:C17H36O4Si
InChIKey:XDLVSUYDBVKRIZ-DLBZAZTESA-N
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Compound Information
Molecular Weight:277.4033
Molecular Formula:C20H23N
InChIKey:BKAFMTVLBSOBOF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.2909
Molecular Formula:C14H17NO
InChIKey:RXIDWOGITHEWBC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.2322
Molecular Formula:C10H15NO
InChIKey:XODAXSHZSFXIST-UHFFFAOYSA-N
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Compound Information
Molecular Weight:275.111
Molecular Formula:C13H16BrLiO
InChIKey:XOWLUSRFJNNBNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.4197
Molecular Formula:C12H26OSi
InChIKey:YHPCDBASXAXMFB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:PDVWNHMJXREAJF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.2304
Molecular Formula:C10H16O6
InChIKey:AGZPNUZBDCYTBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.1937
Molecular Formula:C8H13NO3
InChIKey:GGJZFFVIARIPEX-POYBYMJQSA-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:154.2493
Molecular Formula:C10H18O
InChIKey:JAYDESAGFOCFBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:338.505
Molecular Formula:C19H30O3S
InChIKey:IYINWSIOEHTPHH-IEBWSBKVSA-N
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Compound Information
Molecular Weight:169.2209
Molecular Formula:C9H15NO2
InChIKey:YEBDZDMYLQHGGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:NNWOXVVHNGTGED-RNFRBKRXSA-N
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Compound Information
Molecular Weight:247.2897
Molecular Formula:C14H17NO3
InChIKey:VMEUNDGMWBOUKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:YHOKSPLERNNPEL-BURVXQHBSA-N
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Compound Information
Molecular Weight:209.366
Molecular Formula:C8H9BrMg
InChIKey:Not Available
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Compound Information
Molecular Weight:167.2911
Molecular Formula:C11H21N
InChIKey:WZZLDTPNGNRNOI-GHMZBOCLSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:JHVKFEXSRDRTMX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:161.323
Molecular Formula:C4H9BrMg
InChIKey:OKULOIZBIQQWSM-UHFFFAOYSA-M
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:DYEQHQNRKZJUCT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.615
Molecular Formula:C7H11ClO
InChIKey:BNNCBNKPJCBSRK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:HCAQKYMCZZDLGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:KXPWRCPEMHIZGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.215
Molecular Formula:C12H28O4Ti
InChIKey:VXUYXOFXAQZZMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:YQNUFNXWLWCHSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.1056
Molecular Formula:HKO
InChIKey:KWYUFKZDYYNOTN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:202.2954
Molecular Formula:C13H18N2
InChIKey:XOWCDVZSWMNBHV-OLZOCXBDSA-N
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Compound Information
Molecular Weight:258.3554
Molecular Formula:C17H22O2
InChIKey:FIYBUNLKMGCDKA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:PRCYIYOCMALJCX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.2013
Molecular Formula:C7H16O
InChIKey:Not Available
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Compound Information
Molecular Weight:420.85
Molecular Formula:C13H16HgO3
InChIKey:LPKJBJZEEIDSBP-UHFFFAOYSA-M
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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:112.1696
Molecular Formula:C7H12O
InChIKey:DWLNEMIXWHHTHQ-RNFRBKRXSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:UUIQMZJEGPQKFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.083
Molecular Formula:O2Pt
InChIKey:YKIOKAURTKXMSB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.316
Molecular Formula:C10H10Cl2Zr
InChIKey:QMBQEXOLIRBNPN-UHFFFAOYSA-L
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:GSCLMSFRWBPUSK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.4094
Molecular Formula:C14H22OSi
InChIKey:KVJGPJHZJBKXLH-KBPBESRZSA-N
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Compound Information
Molecular Weight:401.562
Molecular Formula:C23H31NO3S
InChIKey:BCTRVAQTACESKT-VJWVULDSSA-N
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Compound Information
Molecular Weight:232.3181
Molecular Formula:C15H20O2
InChIKey:QSDXMPIEARWWLD-GJZGRUSLSA-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:172.34
Molecular Formula:C9H20OSi
InChIKey:NXWCAMMJZLMBEH-IUCAKERBSA-N
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Compound Information
Molecular Weight:182.2594
Molecular Formula:C11H18O2
InChIKey:INLRKPMHRNQWQI-WDEREUQCSA-N
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Compound Information
Molecular Weight:411.3439
Molecular Formula:C19H19CrO7
InChIKey:UVHHEWQHTUFNRI-BERHYJCPSA-N
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Compound Information
Molecular Weight:118.1311
Molecular Formula:C5H10O3
InChIKey:JLEKJZUYWFJPMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.1592
Molecular Formula:C9H8O
InChIKey:KUIZKZHDMPERHR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:BAPJBEWLBFYGME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:508.462
Molecular Formula:C14H30Cl2OPtSi
InChIKey:XQMLQQFKRXZMLV-LOSFGHDGSA-L
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Compound Information
Molecular Weight:265.305
Molecular Formula:C14H19NO4
InChIKey:ZERGZCQVKPKSBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.1924
Molecular Formula:C13H8CrO6
InChIKey:DSQNYVFFLFPRJT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.4995
Molecular Formula:C15H32OSi
InChIKey:VLWMHHYDCQQLKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:LSUKQAJLVXCZOH-RNFRBKRXSA-N
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.195
Molecular Formula:C8H14O3
InChIKey:GUYSRRJLAXTUJS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.694
Molecular Formula:C10H17ClO
InChIKey:BGAYXHUDTCJDSZ-MYJAWHEDSA-N
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Compound Information
Molecular Weight:128.1308
Molecular Formula:C8H4N2
InChIKey:BHXFKXOIODIUJO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:490.676
Molecular Formula:C25H52BrNOSi
InChIKey:UXMPNDWIBJELNW-RPBOFIJWSA-N
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Compound Information
Molecular Weight:351.816
Molecular Formula:C16H30O4Zn
InChIKey:SFERHNQWAUBILW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.2386
Molecular Formula:C9H18O
InChIKey:GENAWPANTAGPNQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:FRVUBJIGRKFLNC-HTRCEHHLSA-N
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Compound Information
Molecular Weight:222.258
Molecular Formula:C4H9F3O3SSi
InChIKey:FTVLMFQEYACZNP-UHFFFAOYSA-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:41.0033
Molecular Formula:HNaO
InChIKey:Not Available
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Compound Information
Molecular Weight:26.0174
Molecular Formula:CHN
InChIKey:XFXPMWWXUTWYJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:34.0147
Molecular Formula:H2O2
InChIKey:MHAJPDPJQMAIIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:VJWAZNYFFGBQEN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:QYAWQNYOQLOYGV-SNPRPXQTSA-N
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Compound Information
Molecular Weight:387.494
Molecular Formula:C24H21NO2S
InChIKey:BLQMEESUEOOKGH-GWHMAVBBSA-N
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Compound Information
Molecular Weight:207.3119
Molecular Formula:C13H21NO
InChIKey:XLLXNGVIUHRVMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:65.0099
Molecular Formula:N3Na
InChIKey:PXIPVTKHYLBLMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:263.096
Molecular Formula:C10H22BNO6
InChIKey:LCFZZOGKVOTFPU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:MJFDVOWCBFYOOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:362.546
Molecular Formula:C23H38O3
InChIKey:RCEXEXFEOLFCND-ZOYANASSSA-N
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Compound Information
Molecular Weight:319.218
Molecular Formula:I2Zn
InChIKey:UAYWVJHJZHQCIE-UHFFFAOYSA-L
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Compound Information
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:PEIHJOOJFRSTMI-WPRPVWTQSA-N
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Compound Information
Molecular Weight:136.577
Molecular Formula:C5H9ClO2
InChIKey:ZCLGVXACCAZJOX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:378.5072
Molecular Formula:C24H30N2O2
InChIKey:XAJYRABZEDHMCO-ZBYYUNFXSA-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:225.3272
Molecular Formula:C13H23NO2
InChIKey:SRULFWVOVRBEOS-CBEDBXNCSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:NCOYFSPJKUQSEK-ZJUUUORDSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:YPADGQKGBPPEDU-SNAWJCMRSA-N
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Compound Information
Molecular Weight:167.205
Molecular Formula:C9H13NO2
InChIKey:QNIVFJNQCOPSJP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:402.959
Molecular Formula:C26H27ClN2
InChIKey:QQQWNUSYDKZRKX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:UAHWPYUMFXYFJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3178
Molecular Formula:C12H24O2
InChIKey:PSXNDMJWRZYVTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:HWUUJXHUDBJPRY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:BCKWPGYCZKJVLH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:22.98976928
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:161.189
Molecular Formula:C4H10F3NS
InChIKey:CSJLBAMHHLJAAS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.333
Molecular Formula:C5H9IMgO2
InChIKey:RCPJUYYGGSWSOG-UHFFFAOYSA-M
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Compound Information
Molecular Weight:216.322
Molecular Formula:C14H20N2
InChIKey:KYDBUXAAMRURTQ-KGLIPLIRSA-N
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Compound Information
Molecular Weight:318.5243
Molecular Formula:C16H34O4Si
InChIKey:WRTOOLWJPFJOQG-JKSUJKDBSA-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:181.028
Molecular Formula:C5H9BrO2
InChIKey:FQTIYMRSUOADDK-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:316.5084
Molecular Formula:C16H32O4Si
InChIKey:GPYMVVBQBHXBAD-ZIAGYGMSSA-N
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Compound Information
Molecular Weight:267.989
Molecular Formula:C8H12Br2
InChIKey:FSUUSJZVDVLHQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1843
Molecular Formula:C7H14O3
InChIKey:FYZFWKPOQGEMLL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:OQESGTHFMZQXMM-NXEZZACHSA-N
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Compound Information
Molecular Weight:147.297
Molecular Formula:C3H7BrMg
InChIKey:YQMARKZVVTYGOK-UHFFFAOYSA-M
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Compound Information
Molecular Weight:248.3175
Molecular Formula:C15H20O3
InChIKey:DPHICGSKFVHQEM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3178
Molecular Formula:C12H24O2
InChIKey:OOLJKHJQYTVCFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:UYOPRNGQFQWYER-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.3061
Molecular Formula:C14H18N2
InChIKey:DMKXNHCDVGMCTI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:342.253
Molecular Formula:C17H26O4Ti
InChIKey:NODAZBLCOMXLBN-YNTUAPIPSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:VTAKVKLCCICGLP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:64.055
Molecular Formula:C4H9Li
InChIKey:MZRVEZGGRBJDDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.242
Molecular Formula:C13H30O4Ti
InChIKey:YMHFRUKYSWCJAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.581
Molecular Formula:C9H21ClO3Ti
InChIKey:IFMWVBVPVXRZHE-UHFFFAOYSA-M
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Compound Information
Molecular Weight:214.4197
Molecular Formula:C12H26OSi
InChIKey:OKBYVPMZQWHMHZ-QWRGUYRKSA-N
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Compound Information
Molecular Weight:207.35
Molecular Formula:C8H7BrMg
InChIKey:Not Available
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Compound Information
Molecular Weight:324.085
Molecular Formula:C16H25BBrO
InChIKey:FCFYFANBUFBFMK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.211
Molecular Formula:Cl2Mg
InChIKey:TWRXJAOTZQYOKJ-UHFFFAOYSA-L
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:ZWGVKCZJCBBYSI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:149.2078
Molecular Formula:C10H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:159.307
Molecular Formula:C4H7BrMg
InChIKey:SMLLHQBZPPSOSR-UHFFFAOYSA-M
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Compound Information
Molecular Weight:178.3031
Molecular Formula:C10H14OSi
InChIKey:KJPBNYMAKNNPDA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:ASKDFGVMJZMYEM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.8918
Molecular Formula:INaO4
InChIKey:JQWHASGSAFIOCM-UHFFFAOYSA-M
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Compound Information
Molecular Weight:659.27
Molecular Formula:C21H30BrCl4OTiZr
InChIKey:ZXJZBXNYCASXNB-UHFFFAOYSA-I
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Compound Information
Molecular Weight:78.498
Molecular Formula:C2H3ClO
InChIKey:WETWJCDKMRHUPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:JPESGRFVIMPAIM-IUCAKERBSA-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:31.0571
Molecular Formula:CH5N
InChIKey:BAVYZALUXZFZLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3178
Molecular Formula:C12H24O2
InChIKey:ISAUKPDSJSJTQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:CZMVSHRYSKMUQD-HTQZYQBOSA-N
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Compound Information
Molecular Weight:515.406
Molecular Formula:C24H22INO2S
InChIKey:CWIJPNMQQLVTKT-DTSIOAQHSA-N
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Compound Information
Molecular Weight:202.2954
Molecular Formula:C13H18N2
InChIKey:SSBMXMNYZAOINF-STQMWFEESA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:PFDJPXDSJBDMCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.147
Molecular Formula:C10H22O2Ti
InChIKey:YKSNLEUPCHZJMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.457
Molecular Formula:C14H28OSi
InChIKey:YNMABEODPWYZBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:423.412
Molecular Formula:C23H37NO3Ti
InChIKey:QNUTVTMRZPZVJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.407
Molecular Formula:C16H29NO2
InChIKey:LWXKAVPXEDNHLL-VRUXTKGDSA-N
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Compound Information
Molecular Weight:261.3163
Molecular Formula:C15H19NO3
InChIKey:BIPBNJCVVILEIL-WFASDCNBSA-N
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Compound Information
Molecular Weight:322.0964
Molecular Formula:C10H11IO4
InChIKey:ZBIKORITPGTTGI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1411
Molecular Formula:C6H8N2
InChIKey:HKOOXMFOFWEVGF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:FTJATNSAFIFEDU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.4039
Molecular Formula:C12H24OSi
InChIKey:HFAWORYWEFOMEE-RYUDHWBXSA-N
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Compound Information
Molecular Weight:212.3285
Molecular Formula:C13H24O2
InChIKey:RJWSPFXWAYMEOT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.2542
Molecular Formula:C12H15N
InChIKey:GZSIZJWPWIDVTP-PWSUYJOCSA-N
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Compound Information
Molecular Weight:251.3645
Molecular Formula:C15H25NO2
InChIKey:TUPOUOWLSLFUPX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:293.4442
Molecular Formula:C18H31NO2
InChIKey:BGNPQNGJGYNJCE-CBZIJGRNSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:JKGMJZOZIJHPOH-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:112.557
Molecular Formula:C6H5Cl
InChIKey:MVPPADPHJFYWMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.4463
Molecular Formula:C13H28OSi
InChIKey:OOMQBNNFCKSNIM-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:355.6736
Molecular Formula:C21H45NOSi
InChIKey:XLUAHOXYVGMQRD-BGERDNNASA-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:113.1576
Molecular Formula:C6H11NO
InChIKey:GGYVTHJIUNGKFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.2795
Molecular Formula:C13H16N2
InChIKey:VISQPLPAQLRKCK-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:116.872
Molecular Formula:C4H9ClMg
InChIKey:UUNGXYVLXYGZKH-UHFFFAOYSA-M
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:AGMKVZDPATUSMS-AATRIKPKSA-N
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Compound Information
Molecular Weight:247.3327
Molecular Formula:C15H21NO2
InChIKey:NNRXGTXIPPJGEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.969
Molecular Formula:C3H4Cl2O
InChIKey:SUNMBRGCANLOEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:442.652
Molecular Formula:C24H42O5S
InChIKey:HJUKAHHTINXGLM-ICNQMIJOSA-N
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Compound Information
Molecular Weight:268.3966
Molecular Formula:C18H24N2
InChIKey:IOVRRYJPQLNCSB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:XEXCAMXTHVBPBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:JAGZUIGGHGTFHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:GBRNXUFZYPHLLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.2609
Molecular Formula:C6H14Si
InChIKey:HYWCXWRMUZYRPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.345
Molecular Formula:C19H18O2
InChIKey:WWZNHKNFIRONNI-FJHQEINZSA-N
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Compound Information
Molecular Weight:261.2732
Molecular Formula:C14H15NO4
InChIKey:PBCROUWGASHZRJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:RPRPDTXKGSIXMD-UHFFFAOYSA-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:185.2203
Molecular Formula:C9H15NO3
InChIKey:KGZRZIXNTTZVCN-IONNQARKSA-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:142.1956
Molecular Formula:C8H14O2
InChIKey:Not Available
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Compound Information
Molecular Weight:393.5234
Molecular Formula:C27H27N3
InChIKey:OPFXRNKNESEOCU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.2857
Molecular Formula:C15H15NO
InChIKey:OTHBCWKTCXJYAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.2209
Molecular Formula:C9H15NO2
InChIKey:OXLBIWPMLJGIRA-YUMQZZPRSA-N
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Compound Information
Molecular Weight:418.284
Molecular Formula:C19H19CrLiO7
InChIKey:FGSLKDXLIUFMFT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:NZSQYBUQMZYZPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.2795
Molecular Formula:C13H16N2
InChIKey:ZRWBTCRNRWMHOA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.467
Molecular Formula:ClH
InChIKey:Not Available
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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:207.43
Molecular Formula:Cl3Ru
InChIKey:RVSOQSOUWJXKOX-UHFFFAOYSA-K
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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:298.376
Molecular Formula:C10H18O6S2
InChIKey:BNJRUKAECMDDLR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.229
Molecular Formula:C12H24BrNO
InChIKey:OTALUMUICAGKKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2765
Molecular Formula:C11H20
InChIKey:AOURLWJJJBBGQZ-LLVKDONJSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:RUNPLARVCPUYBD-GQCTYLIASA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:WOBFRPMJRYQBFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:ODGMSFYULMJQFQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:330.535
Molecular Formula:C17H34O4Si
InChIKey:XYXOSASKDQEMER-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:IRUDFXLMSWSPBL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.0785
Molecular Formula:C3H6O2
InChIKey:KXKVLQRXCPHEJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:325.6046
Molecular Formula:C19H39NOSi
InChIKey:SJCPRLRLHDMJHI-MOPGFXCFSA-N
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Compound Information
Molecular Weight:210.137
Molecular Formula:C9H22O2Ti
InChIKey:JLCWABOZMHKGMK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:216.322
Molecular Formula:C14H20N2
InChIKey:SABZCHKLSWLFNX-MELADBBJSA-N
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Compound Information
Molecular Weight:146.615
Molecular Formula:C7H11ClO
InChIKey:IOWUZWABECHTIK-ZMONIFLSSA-N
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Compound Information
Molecular Weight:203.2802
Molecular Formula:C13H17NO
InChIKey:HNVAPAYWDOZRFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:274.3978
Molecular Formula:C18H26O2
InChIKey:LNFICUYHIFUBBV-RGBJRUIASA-N
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Compound Information
Molecular Weight:222.147
Molecular Formula:C10H22O2Ti
InChIKey:AHPJRHIRKMHPMJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.3746
Molecular Formula:C6H18NNaSi2
InChIKey:WRIKHQLVHPKCJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:249.4014
Molecular Formula:C14H22O2Si
InChIKey:JIAKIDQSDHQZKP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:193.082
Molecular Formula:C7H13BrO
InChIKey:UHWSSMXSTGKLNK-RNFRBKRXSA-N
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Compound Information
Molecular Weight:275.1999
Molecular Formula:C12H10N3O3P
InChIKey:SORGEQQSQGNZFI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3175
Molecular Formula:C15H20O3
InChIKey:PJARCWFWXRFLBZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:408.7653
Molecular Formula:C23H44O2Si2
InChIKey:VTVYVCBETJULLK-HCMJQZIKSA-N
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Compound Information
Molecular Weight:191.3125
Molecular Formula:C13H21N
InChIKey:ZMVGMWVMAINXFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:295.761
Molecular Formula:C15H18ClNO3
InChIKey:SVHNYVWNHSXRBQ-LBPRGKRZSA-N
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Compound Information
Molecular Weight:196.3291
Molecular Formula:C13H24O
InChIKey:FJQZOLZDUMHJBF-AVGNSLFASA-N
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Compound Information
Molecular Weight:239.108
Molecular Formula:C11H11BrO
InChIKey:DZKXRVKMDQHDNM-VOTSOKGWSA-N
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Compound Information
Molecular Weight:94.176
Molecular Formula:C3H10OS
InChIKey:VMIQGOWIVBBNEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:ZSPTYLOMNJNZNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:319.4815
Molecular Formula:C20H33NO2
InChIKey:LZFRDIJTURHHJC-YNIZLOQISA-N
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Compound Information
Molecular Weight:159.307
Molecular Formula:C4H7BrMg
InChIKey:XGPMCVZJKYCZED-UHFFFAOYSA-M
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:BHZQRZKURLIWHW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.2912
Molecular Formula:C11H22O2
InChIKey:YRHYCMZPEVDGFQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:YFHICDDUDORKJB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:AOLOKLDPBPVGSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.2643
Molecular Formula:C13H15NO
InChIKey:ZSZKITPILMVCKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:271.2665
Molecular Formula:C12H17NO6
InChIKey:MHRGLVWVNRVMMR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.8731
Molecular Formula:AgNO3
InChIKey:SQGYOTSLMSWVJD-UHFFFAOYSA-N
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