Standard Article

Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction

  1. Tsutomu Katsuki1,
  2. Victor Martin2

Published Online: 15 APR 2004

DOI: 10.1002/0471264180.or048.01

Organic Reactions

Organic Reactions

How to Cite

Katsuki, T. and Martin, V. 2004. Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction. Organic Reactions. 48:1:1–299.

Author Information

  1. 1

    Faculty of Science, Department of Chemistry, Kyushu University, Japan

  2. 2

    Instituto Universitario de Bio-Organica, Universidad de la Laguna, Centro de Productos Naturales Organicos “Antonio Gonzalez,”, Tenerife, Spain

Publication History

  1. Published Online: 15 APR 2004

Chemistry Terms

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Abstract

In 1980, Sharpless and Katsuki discovered a system for the asymmetric epoxidation of primary allylic alcohols that utilizes Ti(OPr-i)4, a dialkyl tartrate as a chiral ligand, and tert-butyl hydroperoxide as the oxidant. Notably, this reaction exhibits high levels of enantioselectivity (usually > 90% ee). Like other metal-catalyzed epoxidations, this reaction also proceeds under mild conditions with good chemical yield and with high regio- and chemoselectivity. Various aspects of this reaction, including its mechanism, early synthetic applications, and further transformations of the epoxy alcohol product, have been reviewed. In this chapter, the full scope and limitations of this reaction, its synthetic applications, and typical experimental conditions are described.

Keywords:

  • epoxidation;
  • allylic alcohols;
  • Katsuki-sharpless reaction;
  • titanium tartrate;
  • mechanism;
  • reactivity;
  • stereoselectivity;
  • chemiselectivity;
  • regioselectivity;
  • product stability;
  • scope;
  • limitations;
  • asymmetric epoxidation. catalysts;
  • primary allylic alcohols;
  • secondary allylic alcohols;
  • asymmetric oxidation;
  • sulfides;
  • selenides;
  • amines;
  • epoxy alcohols;
  • transformations;
  • functional units;
  • Payne rearrangement;
  • ring opening;
  • kinetic resolution;
  • chiral substrates;
  • unfunctionalized olefins;
  • synthesis;
  • nonracemic epoxides;
  • experimental conditions;
  • 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:223.613
Molecular Formula:C10H6ClNO3
InChIKey:RHZBRCQIKQUQHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:CSASCUZDIRYDDE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:340.4883
Molecular Formula:C20H24O3Si
InChIKey:DPYJVPLZFFROJT-OALUTQOASA-N
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Compound Information
Molecular Weight:382.568
Molecular Formula:C23H30O3Si
InChIKey:RIWQDLYIJTYNQZ-FKBYEOEOSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:NYOQQRNIGAUVDR-SRQIZXRXSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:DCWMDKLXSJASHD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.2951
Molecular Formula:C10H23NO2
InChIKey:DPEPHYXTLUGMBM-ZJUUUORDSA-N
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Compound Information
Molecular Weight:282.139
Molecular Formula:C2F6O5S2
InChIKey:WJKHJLXJJJATHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3608
Molecular Formula:C13H28O
InChIKey:HKOLRKVMHVYNGG-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:BTSIZIIPFNVMHF-ARJAWSKDSA-N
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Compound Information
Molecular Weight:270.4507
Molecular Formula:C17H34O2
InChIKey:MFFOWBUXNIQYAH-KRWDZBQOSA-N
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Compound Information
Molecular Weight:237.2087
Molecular Formula:C11H11NO5
InChIKey:BPOPJHHLTDEVBN-XVKPBYJWSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:CMJCGBDPPLVSOH-WAYWQWQTSA-N
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Compound Information
Molecular Weight:175.2255
Molecular Formula:C8H17NO3
InChIKey:YJPNWKJJWDEYRP-BQBZGAKWSA-N
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Compound Information
Molecular Weight:237.2964
Molecular Formula:C16H15NO
InChIKey:LHFJYTISTQWBBQ-BWJIRVQHSA-N
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Compound Information
Molecular Weight:294.3429
Molecular Formula:C16H22O5
InChIKey:WXNBTUAWDDVQQC-GBJTYRQASA-N
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Compound Information
Molecular Weight:160.2108
Molecular Formula:C8H16O3
InChIKey:OIHIMGOSXYCYFS-PHDIDXHHSA-N
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Compound Information
Molecular Weight:286.3209
Molecular Formula:C14H22O6
InChIKey:XOAMZRPATLOQJY-FERCZAJWSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:MQIHFMKBICMPFT-YUMQZZPRSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:MRGITZIKRXYSEO-NTSWFWBYSA-N
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Compound Information
Molecular Weight:208.3398
Molecular Formula:C14H24O
InChIKey:GCZHSNAQBKAOKD-UELRPHRMSA-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:180.2005
Molecular Formula:C10H12O3
InChIKey:HHQOCVJWAKBBMR-ZJUUUORDSA-N
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Compound Information
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:FHBPYEQRIDZSBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:BMRWNKZVCUKKSR-BYPYZUCNSA-N
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Compound Information
Molecular Weight:138.23
Molecular Formula:C8H10S
InChIKey:VHILIAIEEYLJNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.3654
Molecular Formula:C10H22O3Si
InChIKey:GQXMFAIYVGQEJP-DTWKUNHWSA-N
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Compound Information
Molecular Weight:133.845
Molecular Formula:ILi
InChIKey:HSZCZNFXUDYRKD-UHFFFAOYSA-M
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Compound Information
Molecular Weight:216.0175
Molecular Formula:C4H9IO2
InChIKey:PEZCXJQLORQUBC-IUYQGCFVSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:PLZDBJRJRRIYJL-UHFFFAOYSA-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:102.103
Molecular Formula:C7H11Li
InChIKey:VNNJMEUFCDCYKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.114
Molecular Formula:I2Mg
InChIKey:BLQJIBCZHWBKSL-UHFFFAOYSA-L
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Compound Information
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:FEVALTJSQBFLEU-SNVBAGLBSA-N
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Compound Information
Molecular Weight:186.2912
Molecular Formula:C11H22O2
InChIKey:XTWFTQGRBSRDCS-QWRGUYRKSA-N
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:127.6
Molecular Formula:Te
InChIKey:VTLHPSMQDDEFRU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.087
Molecular Formula:CH3NaO3S
InChIKey:XWGJFPHUCFXLBL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:334.2363
Molecular Formula:C14H23IO
InChIKey:KQAISHDQSHFURF-DXIMFJFMSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:VQGLRWHETSUCPI-VHSXEESVSA-N
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Compound Information
Molecular Weight:261.3163
Molecular Formula:C15H19NO3
InChIKey:XJYBYSPDIFWWKY-ZLDLUXBVSA-N
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Compound Information
Molecular Weight:185.3592
Molecular Formula:C10H22OSi
InChIKey:BSEZMWVIHBZIOG-CMDGGOBGSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:ANKGQDQWYZFTDK-HYXAFXHYSA-N
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Compound Information
Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:AAFJXZWCNVJTMK-UNTFVMJOSA-N
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Compound Information
Molecular Weight:131.254
Molecular Formula:C2H3BrMg
InChIKey:XHHHAXOHMKAOSL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:PVALSANGMFRTQM-IUCAKERBSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:VHYFNPMBLIVWCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.1932
Molecular Formula:C8H14O6
InChIKey:YSAVZVORKRDODB-PHDIDXHHSA-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:424.448
Molecular Formula:C26H20N2O4
InChIKey:RSNKUQRYTWJCTB-MYDTUXCISA-N
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Compound Information
Molecular Weight:213.506
Molecular Formula:C10H10ClTi
InChIKey:QYXNZGBQFZOMOV-UHFFFAOYSA-M
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:BRYMKDNCWBMHIF-ARJAWSKDSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:SEDGGCMDYFKAQN-GBXIJSLDSA-N
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Compound Information
Molecular Weight:170.229
Molecular Formula:C8H10O2S
InChIKey:YYDNBUBMBZRNQQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.0843
Molecular Formula:O2Si
InChIKey:VYPSYNLAJGMNEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:324.3689
Molecular Formula:C17H24O6
InChIKey:CAXNOWXJBMSBBW-CAOSSQGBSA-N
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Compound Information
Molecular Weight:214.2582
Molecular Formula:C11H18O4
InChIKey:ZHTIMOYPBANZTQ-GXSJLCMTSA-N
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Compound Information
Molecular Weight:189.2951
Molecular Formula:C10H23NO2
InChIKey:QVBHPRUQLCOUJY-ZJUUUORDSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:CENIKOVZZYSSJM-SNAWJCMRSA-N
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Compound Information
Molecular Weight:324.435
Molecular Formula:C17H24O4S
InChIKey:DPTURXDQMJHFIW-IRXDYDNUSA-N
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Compound Information
Molecular Weight:230.0441
Molecular Formula:C5H11IO2
InChIKey:BSOKRJSHOYWINI-UHNVWZDZSA-N
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Compound Information
Molecular Weight:314.5356
Molecular Formula:C17H34O3Si
InChIKey:GJCUOSDUMWFQDQ-HZPDHXFCSA-N
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Compound Information
Molecular Weight:174.196
Molecular Formula:C2H6O5S2
InChIKey:IZDROVVXIHRYMH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2711
Molecular Formula:C15H14O
InChIKey:OGDCGPJYEBFECC-PTNGSMBKSA-N
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Compound Information
Molecular Weight:368.531
Molecular Formula:C20H32O4S
InChIKey:YWXOGAMCHSAQBV-PMACEKPBSA-N
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Compound Information
Molecular Weight:325.8198
Molecular Formula:CCs2O3
InChIKey:FJDQFPXHSGXQBY-UHFFFAOYSA-L
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:GLZPCOQZEFWAFX-JXMROGBWSA-N
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Compound Information
Molecular Weight:538.7901
Molecular Formula:C32H46O5Si
InChIKey:ZHDVORYRCXSAOU-ZWHQYRDASA-N
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Compound Information
Molecular Weight:76.141
Molecular Formula:CS2
InChIKey:QGJOPFRUJISHPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:614.7358
Molecular Formula:C44H30N4
InChIKey:YNHJECZULSZAQK-LWQDQPMZSA-N
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Compound Information
Molecular Weight:74.0785
Molecular Formula:C3H6O2
InChIKey:CTKINSOISVBQLD-VKHMYHEASA-N
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Compound Information
Molecular Weight:268.4778
Molecular Formula:C18H36O
InChIKey:NMNAESABLXLQEY-WUKNDPDISA-N
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Compound Information
Molecular Weight:284.4772
Molecular Formula:C18H36O2
InChIKey:YZFWQAZFXICNNE-QZTJIDSGSA-N
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Compound Information
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:IGDIEWAQBYLIGY-OOZYFLPDSA-N
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Compound Information
Molecular Weight:308.3695
Molecular Formula:C17H24O5
InChIKey:IGVWCBNYFPWAEA-PMPSAXMXSA-N
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Compound Information
Molecular Weight:75.016
Molecular Formula:C4H5LiO
InChIKey:XKFRCHVCZKFREY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:320.563
Molecular Formula:C15H32O3SSi
InChIKey:RUWKIKBBWUFSSS-QWHCGFSZSA-N
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Compound Information
Molecular Weight:30.026
Molecular Formula:CH2O
InChIKey:Not Available
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Compound Information
Molecular Weight:330.3579
Molecular Formula:C19H23O3P
InChIKey:HZLBKAKFUQAAHA-OTWHNJEPSA-N
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Compound Information
Molecular Weight:124.0755
Molecular Formula:C3H9O3P
InChIKey:Not Available
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Compound Information
Molecular Weight:141.928
Molecular Formula:C4H10BF3O
InChIKey:MZTVMRUDEFSYGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.647
Molecular Formula:C7H7ClO2S
InChIKey:YYROPELSRYBVMQ-UHFFFAOYSA-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:256.06
Molecular Formula:C11H17BO6
InChIKey:ZLCUACAHHUQLPA-RKDXNWHRSA-N
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Compound Information
Molecular Weight:234.2463
Molecular Formula:C10H18O6
InChIKey:Not Available
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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:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:31.9988
Molecular Formula:O2
InChIKey:MHAJPDPJQMAIIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:340.322
Molecular Formula:C16H36O4Ti
InChIKey:GRWPYGBKJYICOO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:IGRZECZSICIWJA-WDSKDSINSA-N
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Compound Information
Molecular Weight:214.2582
Molecular Formula:C11H18O4
InChIKey:FFIVBENSZANTHT-KOLCDFICSA-N
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Compound Information
Molecular Weight:440.6471
Molecular Formula:C26H36O4Si
InChIKey:SXVPRQPILYAMOY-OQUNMALSSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:JOODUMVMXMJPTD-WHFBIAKZSA-N
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Compound Information
Molecular Weight:278.3435
Molecular Formula:C16H22O4
InChIKey:ZYITVPRJLQKICB-OVPGCVMQSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:RQLYDIRJVONUSE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:360.401
Molecular Formula:C20H24O6
InChIKey:DCYKYFYDBJFJHO-KOWDEKHVSA-N
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Compound Information
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:ACZNIBVNGPLHAC-ONEGZZNKSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:YWTIDNZYLFTNQQ-SNVBAGLBSA-N
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Compound Information
Molecular Weight:22.964
Molecular Formula:H2LiN
InChIKey:AFRJJFRNGGLMDW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2004
Molecular Formula:C6H18N3OP
InChIKey:GNOIPBMMFNIUFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3501
Molecular Formula:C10H20O2Si
InChIKey:QOCHEGVXDQHFMS-UWVGGRQHSA-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:90.121
Molecular Formula:C4H10O2
InChIKey:CIHOLLKRGTVIJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:IAUCTWXOKNLSCI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:CDOSHBSSFJOMGT-SNVBAGLBSA-N
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Compound Information
Molecular Weight:158.72
Molecular Formula:F2Sn
InChIKey:NKCWZXPMTVCPSF-UHFFFAOYSA-L
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Compound Information
Molecular Weight:270.323
Molecular Formula:C17H18O3
InChIKey:OGNPKNLGALNBTL-WEVVVXLNSA-N
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Compound Information
Molecular Weight:642.9184
Molecular Formula:C42H54N6
InChIKey:FZFMLIXIPXHUHF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:UEQMKUTZHSNXJT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2055
Molecular Formula:CK2O3
InChIKey:BWHMMNNQKKPAPP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:188.694
Molecular Formula:C10H17ClO
InChIKey:BNXBPMUPFGVHRD-UWVGGRQHSA-N
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Compound Information
Molecular Weight:234.313
Molecular Formula:C10H18O4S
InChIKey:YGFAVAXIVBKZKQ-VHSXEESVSA-N
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Compound Information
Molecular Weight:73.1368
Molecular Formula:C4H11N
InChIKey:HPNMFZURTQLUMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.4191
Molecular Formula:C12H26O2Si
InChIKey:MXARXIIGGZUTLG-WOPDTQHZSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:XEVKRTIYWSUXHP-UHNVWZDZSA-N
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Compound Information
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:NBXDTVPBMCABGC-ACLDMZEESA-N
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Compound Information
Molecular Weight:42.094
Molecular Formula:CaH2
InChIKey:FAQLAUHZSGTTLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:JCAOQPBHDIRXPS-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:254.4513
Molecular Formula:C17H34O
InChIKey:HXMPDVFVKMCUHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:AHEQFVNIXIPVFB-NTSWFWBYSA-N
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Compound Information
Molecular Weight:175.2255
Molecular Formula:C8H17NO3
InChIKey:YFHNQMZYHJAVCQ-RNFRBKRXSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:RZRBXGPSHVAUQO-UWVGGRQHSA-N
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Compound Information
Molecular Weight:133.27
Molecular Formula:C2H5BrMg
InChIKey:TWTWFMUQSOFTRN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:FMBYRHUTUODDIU-ZETCQYMHSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:XXROGKLTLUQVRX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:335.461
Molecular Formula:C18H25NO3S
InChIKey:APMISARDTPPMKK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:328.3624
Molecular Formula:C18H20N2O4
InChIKey:BBYSAHVLSFBCMN-HZPDHXFCSA-N
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Compound Information
Molecular Weight:236.3068
Molecular Formula:C14H20O3
InChIKey:ZVASBUIIGZBTNB-XBFCOCLRSA-N
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Compound Information
Molecular Weight:302.3203
Molecular Formula:C14H22O7
InChIKey:QMYZHARYMHEUKZ-VVFUWANYSA-N
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Compound Information
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:SKBIQKQBLQHOSU-MDZDMXLPSA-N
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Compound Information
Molecular Weight:290.05
Molecular Formula:C12H28Sn
InChIKey:Not Available
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Compound Information
Molecular Weight:314.5356
Molecular Formula:C17H34O3Si
InChIKey:FFEAOROTWSOLCG-HZPDHXFCSA-N
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Compound Information
Molecular Weight:185.565
Molecular Formula:C7H4ClNO3
InChIKey:SKDHHIUENRGTHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.694
Molecular Formula:C10H17ClO
InChIKey:KXDWROOVWAKVCX-JARNTUPDSA-N
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Compound Information
Molecular Weight:190.2368
Molecular Formula:C9H18O4
InChIKey:CJKKQLDFHOEESH-YUMQZZPRSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:OMNANMRIETWFIM-VUQUXZKVSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:WMOVHXAZOJBABW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:288.3398
Molecular Formula:C20H16O2
InChIKey:DCYGAPKNVCQNOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:286.3224
Molecular Formula:C17H18O4
InChIKey:ZOFOYMOMMDTEGR-IRXDYDNUSA-N
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Compound Information
Molecular Weight:213.2735
Molecular Formula:C11H19NO3
InChIKey:GDGNFAYIQUUMAW-MWLCHTKSSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:QALDQGOOUKCKHN-DTWKUNHWSA-N
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Compound Information
Molecular Weight:254.184
Molecular Formula:C7H15ISi
InChIKey:FLDGWNPNLFEXIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:YQHLDYVWEZKEOX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WCASXYBKJHWFMY-NSCUHMNNSA-N
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Compound Information
Molecular Weight:314.3585
Molecular Formula:C19H23O2P
InChIKey:JWPCYMVTYHLQTL-NTEUORMPSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:ZKSUUAYICXTBLP-RYUDHWBXSA-N
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Compound Information
Molecular Weight:266.378
Molecular Formula:C10H18O4S2
InChIKey:JEWSOKJFFIJVSC-JGVFFNPUSA-N
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Compound Information
Molecular Weight:207.2689
Molecular Formula:C12H17NO2
InChIKey:ZQHXNROGKGKRAR-GFCCVEGCSA-N
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Compound Information
Molecular Weight:202.366
Molecular Formula:C10H22O2Si
InChIKey:VXUYJHAIRTUZGP-GUBZILKMSA-N
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Compound Information
Molecular Weight:120.557
Molecular Formula:C4H10AlCl
InChIKey:YNLAOSYQHBDIKW-UHFFFAOYSA-M
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:ZJRQJFZOFJOAMV-VIFPVBQESA-N
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Compound Information
Molecular Weight:280.1459
Molecular Formula:C10H17IO
InChIKey:AWAUZISYHREEIC-UWVGGRQHSA-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:254.3236
Molecular Formula:C17H18O2
InChIKey:FHPPXLILVYRVRK-IAGOWNOFSA-N
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:PDTOQFAZLRKIOK-RPHSKFLZSA-N
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:AUYRUAVCWOAHQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:ULFUGPDMXHHDDJ-VVXQKDJTSA-N
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Compound Information
Molecular Weight:190.45
Molecular Formula:CuI
InChIKey:LSXDOTMGLUJQCM-UHFFFAOYSA-M
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:GLZFKAYNZITDIA-BYPYZUCNSA-N
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Compound Information
Molecular Weight:238.3242
Molecular Formula:C17H18O
InChIKey:XRGVOYXCXOPABA-SAPNQHFASA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:QQHZNUPEBVRUFO-QWWZWVQMSA-N
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Compound Information
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:VFZLIXAOQTZVGW-QXMHVHEDSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:NIPDNHBQVFQMJA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:ZAMHMCZJTWKZHC-VWYCJHECSA-N
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Compound Information
Molecular Weight:264.338
Molecular Formula:C7H15F3O3SSi
InChIKey:WLLIXJBWWFGEHT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:149.89424
Molecular Formula:INa
InChIKey:FVAUCKIRQBBSSJ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:158.195
Molecular Formula:C8H14O3
InChIKey:BSUKAIZPTZNABM-BWZBUEFSSA-N
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Compound Information
Molecular Weight:226.2705
Molecular Formula:C15H14O2
InChIKey:ZEVYUFMALOLWIC-LSDHHAIUSA-N
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:CPEMSVQIDGEZCG-AATRIKPKSA-N
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Compound Information
Molecular Weight:65.409
Molecular Formula:Zn
InChIKey:HCHKCACWOHOZIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:392.3998
Molecular Formula:C20H24O8
InChIKey:RHGWQNPXQAWTBS-IOALQAGCSA-N
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Compound Information
Molecular Weight:126.926
Molecular Formula:C2Cl2O2
InChIKey:CTSLXHKWHWQRSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:KUQWZSZYIQGTHT-PHDIDXHHSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:XTHFKEDIFFGKHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.1932
Molecular Formula:C8H14O6
InChIKey:YSAVZVORKRDODB-WDSKDSINSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:PLZDBJRJRRIYJL-SNVBAGLBSA-N
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Compound Information
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:SKBIQKQBLQHOSU-KTKRTIGZSA-N
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Compound Information
Molecular Weight:186.2912
Molecular Formula:C11H22O2
InChIKey:XTWFTQGRBSRDCS-MNOVXSKESA-N
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Compound Information
Molecular Weight:234.2463
Molecular Formula:C10H18O6
InChIKey:XEBCWEDRGPSHQH-YUMQZZPRSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WCASXYBKJHWFMY-IHWYPQMZSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:QQHZNUPEBVRUFO-DMTCNVIQSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:CENIKOVZZYSSJM-PLNGDYQASA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:AHEQFVNIXIPVFB-WDSKDSINSA-N
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Compound Information
Molecular Weight:226.2705
Molecular Formula:C15H14O2
InChIKey:ZEVYUFMALOLWIC-CABCVRRESA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:CMJCGBDPPLVSOH-OMMCCPJFSA-N
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Compound Information
Molecular Weight:294.3429
Molecular Formula:C16H22O5
InChIKey:WXNBTUAWDDVQQC-APIJFGDWSA-N
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Compound Information
Molecular Weight:278.3435
Molecular Formula:C16H22O4
InChIKey:ZYITVPRJLQKICB-VOTDVEDPSA-N
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Compound Information
Molecular Weight:294.3429
Molecular Formula:C16H22O5
InChIKey:WXNBTUAWDDVQQC-YJNKXOJESA-N
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Compound Information
Molecular Weight:294.3429
Molecular Formula:C16H22O5
InChIKey:WXNBTUAWDDVQQC-KBXIAJHMSA-N
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Compound Information
Molecular Weight:314.3585
Molecular Formula:C19H23O2P
InChIKey:JWPCYMVTYHLQTL-JNMQVBFRSA-N
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Compound Information
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:VFZLIXAOQTZVGW-QYMJWVLRSA-N
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Compound Information
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:VFZLIXAOQTZVGW-VAWYXSNFSA-N
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Compound Information
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:VFZLIXAOQTZVGW-RUMSDORHSA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:UEQMKUTZHSNXJT-BDAKNGLRSA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:UEQMKUTZHSNXJT-IUCAKERBSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:CSASCUZDIRYDDE-SECBINFHSA-N
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Compound Information
Molecular Weight:335.461
Molecular Formula:C18H25NO3S
InChIKey:APMISARDTPPMKK-KRWDZBQOSA-N
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Compound Information
Molecular Weight:335.461
Molecular Formula:C18H25NO3S
InChIKey:APMISARDTPPMKK-QGZVFWFLSA-N
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Compound Information
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:FHBPYEQRIDZSBP-LBPRGKRZSA-N
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Compound Information
Molecular Weight:382.568
Molecular Formula:C23H30O3Si
InChIKey:RIWQDLYIJTYNQZ-FSSWDIPSSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:XEVKRTIYWSUXHP-WHFBIAKZSA-N
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Compound Information
Molecular Weight:261.3163
Molecular Formula:C15H19NO3
InChIKey:XJYBYSPDIFWWKY-MONRWBKMSA-N
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Compound Information
Molecular Weight:235.079
Molecular Formula:C8H19ClMgO2Si
InChIKey:CXIIDRCUVXGZBJ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:GDEAJQIWVBPHKB-UWVGGRQHSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:PLGQXTUULJHUAY-RYMQXAEESA-N
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Compound Information
Molecular Weight:386.4382
Molecular Formula:C22H26O6
InChIKey:IYGLNGNEXRUBCV-LJUYRKFLSA-N
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Compound Information
Molecular Weight:348.051
Molecular Formula:C15H10Cl4O
InChIKey:QBKJCYJNOLQDHY-YHYXMXQVSA-N
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Compound Information
Molecular Weight:340.4559
Molecular Formula:C22H28O3
InChIKey:TXZKGSVVWLPCNQ-AFOKVDMESA-N
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Compound Information
Molecular Weight:353.034
Molecular Formula:C20H42CuLi
InChIKey:FATVDZBYEFBBJO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.3868
Molecular Formula:C14H30O2
InChIKey:DKLRUJASAHUSCK-UONOGXRCSA-N
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Compound Information
Molecular Weight:334.4929
Molecular Formula:C21H34O3
InChIKey:ZGQAWLCSJFHXDF-QIOBGPQXSA-N
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Compound Information
Molecular Weight:194.184
Molecular Formula:C10H10O4
InChIKey:HQVUIBSUUABJDV-BDAKNGLRSA-N
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Compound Information
Molecular Weight:306.472
Molecular Formula:C17H26O3Si
InChIKey:KAROSNQUDVNUBY-RTKIROINSA-N
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Compound Information
Molecular Weight:300.4766
Molecular Formula:C18H36O3
InChIKey:OIIPAQHEUXKAON-FDPSAONLSA-N
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Compound Information
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:ICMWSAALRSINTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:QVJWRUISNQKFDB-VAWYXSNFSA-N
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Compound Information
Molecular Weight:378.3747
Molecular Formula:C22H18O6
InChIKey:WAYBDIURHCYITO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:59.1103
Molecular Formula:C3H9N
InChIKey:Not Available
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Compound Information
Molecular Weight:316.476
Molecular Formula:C18H36O4
InChIKey:JWEZDKPKIPBIGF-KZNAEPCWSA-N
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Compound Information
Molecular Weight:386.5259
Molecular Formula:C27H30O2
InChIKey:CAESJDMIMCDSQT-YWTICRPUSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:WAMJEZURWOAJOL-DRZSPHRISA-N
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Compound Information
Molecular Weight:20.00634
Molecular Formula:FH
InChIKey:KRHYYFGTRYWZRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:286.3209
Molecular Formula:C14H22O6
InChIKey:XOAMZRPATLOQJY-SDCVYYIZSA-N
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Compound Information
Molecular Weight:99.9943
Molecular Formula:CrO3
InChIKey:WGLPBDUCMAPZCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.4195
Molecular Formula:C17H30O
InChIKey:WLFCLYAUVYVJAP-FOCLMDBBSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:KSQBAPLQXNCSOC-QWRGUYRKSA-N
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Compound Information
Molecular Weight:262.2995
Molecular Formula:C12H22O6
InChIKey:USRKKSOXRCAYBX-HVFQMFNGSA-N
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Compound Information
Molecular Weight:388.477
Molecular Formula:C17H19F3O3SSi
InChIKey:AOMOJFWVOHXBTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3871
Molecular Formula:C17H26O2
InChIKey:QLPVREFGBCSPGC-IRXDYDNUSA-N
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Compound Information
Molecular Weight:274.3117
Molecular Formula:C16H18O4
InChIKey:WDLYKWVHMWCMCQ-HOTGVXAUSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:LFMFAKWCDVRYFC-IOJJLOCKSA-N
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Compound Information
Molecular Weight:147.1308
Molecular Formula:C8H5NO2
InChIKey:LURYMYITPCOQAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.894
Molecular Formula:BrNa
InChIKey:JHJLBTNAGRQEKS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:IYRZZSKRQNSOTP-ZKXNXJMVSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:ABZZOPIABWYXSN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.195
Molecular Formula:C8H14O3
InChIKey:OZYZQEWPEYGVRU-AVALRIAPSA-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:282.5044
Molecular Formula:C19H38O
InChIKey:HFOFYNMWYRXIBP-OALUTQOASA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:SJEFBCVKZKSDEH-MNOVXSKESA-N
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Compound Information
Molecular Weight:312.381
Molecular Formula:C15H20O5S
InChIKey:DMUNLDYFGILRRO-KGLIPLIRSA-N
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Compound Information
Molecular Weight:44.0095
Molecular Formula:CO2
InChIKey:Not Available
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Compound Information
Molecular Weight:291.4284
Molecular Formula:C18H29NO2
InChIKey:CXVLOLWKYUFGGM-NWYZTQOFSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:BEDUZGFZOBQCEB-RYUDHWBXSA-N
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Compound Information
Molecular Weight:150.722
Molecular Formula:C6H15ClSi
InChIKey:BCNZYOJHNLTNEZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:NHEHXQAETZMQIC-YIZRAAEISA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:YVCOJTATJWDGEU-IONNQARKSA-N
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Compound Information
Molecular Weight:208.726
Molecular Formula:C10H21ClO2
InChIKey:GJPBCRMQNITRTE-JTQLQIEISA-N
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Compound Information
Molecular Weight:236.947
Molecular Formula:C6H14Cl2O2Ti
InChIKey:LTEDQKPGOZDGRZ-UHFFFAOYSA-L
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