Standard Article

The Ramberg-Bäcklund Reaction

  1. Richard J. K. Taylor1,
  2. Guy Casy2

Published Online: 15 APR 2004

DOI: 10.1002/0471264180.or062.02

Organic Reactions

Organic Reactions

How to Cite

Taylor, R. J. K. and Casy, G. 2004. The Ramberg-Bäcklund Reaction. Organic Reactions. 62:2:359–475.

Author Information

  1. 1

    University of York, Department of Chemistry, Heslington, York, UK

  2. 2

    Chirotech Technology Ltd, Cambridge, UK

Publication History

  1. Published Online: 15 APR 2004

Chemistry Terms

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Abstract

The base-mediated conversion of alpha-halosulfones into region-defined alkenes was first described by Ludwig Ramberg and Birger Backlund. This transformation has proved to be of wide synthetic value and is known as the Ramberg-Backlund reaction (RBR). The facile nature of the RBR is surprising given the difficulties encountered when attempting to carry out nucleophilic substitution reactions on alpha-halosulfones. In contrast to halogens adjacent to carbonyls and related electron-withdrawing groups, polar, steric and field effects appear to combine leading to the marked deactivation of alpha-halosulfones. The stereochemical outcome of the reaction was also unexpected: a predominance of Z-alkenes is often observed with relatively weak bases, whereas stronger bases tend to favor E-alkenes. The mechanism of the RBR was therefore the subject of intense interest, particularly in the 1950s and 1960s.

From the synthetic viewpoint, the RBR is attractive for a number of reasons, for example, the accessibility of the precursor sulfide and sulfones; the conjunctive nature of the process; the unambiguous location of the resulting double bonds, among others. Organic sulfones are readily available, but the preparation of alpha-halosulfones can be problematic. In view of this, perhaps the most significant synthetic advance concerning RBR has been the development of Meyer's modification, which involves in-situ halogenation-RBR sequence and enables sulfones to be converted directly into alkenes. This chapter discusses the mechanism of RBR, its scope and limitations, applications of the reaction in natural product synthesis, and comparison of the RBR with related procedures. Representative experimental procedures are also given.

Keywords:

  • Ramberg-Backlund reaction (RBR);
  • stereoselectivity;
  • halosulfones;
  • chlorosulfides;
  • oxidation;
  • halogenation;
  • sulfones;
  • scope;
  • limitations;
  • Michael induced RBR;
  • non-halide leaving groups;
  • Meyer's variant;
  • acylic alkenes;
  • polyenes;
  • cyclic alkenes;
  • thiirane dioxides;
  • natural products;
  • bioactive target molecules;
  • isoprenoids;
  • insect pheromones;
  • steroids;
  • synthesis;
  • enediyne analogs;
  • unsaturated amino acids;
  • conduritols;
  • glycosides;
  • scope;
  • limitations;
  • other methods;
  • experimental procedures

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  1. 1 - 250
Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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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:56.0633
Molecular Formula:C3H4O
InChIKey:TVDSBUOJIPERQY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:376.064
Molecular Formula:C12H8Br2O2S
InChIKey:KSRJVHHNYDBYLF-TXEJJXNPSA-N
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Compound Information
Molecular Weight:269.156
Molecular Formula:C8H13BrO3S
InChIKey:VACIIHTUNGXUJQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.2268
Molecular Formula:C14H10O4
InChIKey:Not Available
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Compound Information
Molecular Weight:280.285
Molecular Formula:C7H11F3O4S2
InChIKey:RFSYYIUWZIWGNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.739
Molecular Formula:C2Cl6
InChIKey:VHHHONWQHHHLTI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:283.14
Molecular Formula:C8H11BrO4S
InChIKey:LXJVQQXBYWXADV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.2762
Molecular Formula:C14H16O
InChIKey:QTKLZDZLCADPSN-WDNDVIMCSA-N
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Compound Information
Molecular Weight:342.207
Molecular Formula:C10H16BrNO5S
InChIKey:RKZXCPNVPPMNDC-UUEFVBAFSA-N
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Compound Information
Molecular Weight:380.487
Molecular Formula:C14H27F3O4S2
InChIKey:FVUQYSKOOCOUHE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.827
Molecular Formula:C12H23ClO4S
InChIKey:JPHNLQZSBGCAAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.272
Molecular Formula:C12H10O2S
InChIKey:GRCAQMPUBVXMFJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.689
Molecular Formula:C8H11ClO3S
InChIKey:DLBWYOORQRKUSZ-KJFJCRTCSA-N
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Compound Information
Molecular Weight:404.156
Molecular Formula:C25H54ClN
InChIKey:XKBGEWXEAPTVCK-UHFFFAOYSA-M
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Compound Information
Molecular Weight:204.674
Molecular Formula:C8H9ClO2S
InChIKey:DQOOIGWCYGESQG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.473
Molecular Formula:C13H26O4S2
InChIKey:DRDWPKKMPDAAFU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:305.433
Molecular Formula:C14H27NO4S
InChIKey:VYVGNSBBEBPWKX-JTQLQIEISA-N
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Compound Information
Molecular Weight:406.559
Molecular Formula:C21H26O4S2
InChIKey:HUAUTZHLZNIDMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:456.616
Molecular Formula:C22H32O6S2
InChIKey:BGTCCMLZKDDDFO-AOHGFKCNSA-N
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Compound Information
Molecular Weight:308.02
Molecular Formula:C7H9BrCl2O2S
InChIKey:LKKMBADAJIYERW-USEPMLCBSA-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:122.1644
Molecular Formula:C8H10O
InChIKey:PIPHVRHNOZVJIH-OCAPTIKFSA-N
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Compound Information
Molecular Weight:267.183
Molecular Formula:C9H15BrO2S
InChIKey:PLSJTIKUSQUFML-HLTSFMKQSA-N
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Compound Information
Molecular Weight:17.0305
Molecular Formula:H3N
InChIKey:QGZKDVFQNNGYKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.816
Molecular Formula:CBr2F2
InChIKey:AZSZCFSOHXEJQE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:400.286
Molecular Formula:C13H22BrNO6S
InChIKey:TVQYVFSSKMCSAU-ZOCYIJKUSA-N
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Compound Information
Molecular Weight:198.239
Molecular Formula:C9H10O3S
InChIKey:HIMIWUFPDDVFQY-IUCAKERBSA-N
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Compound Information
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-VAWYXSNFSA-N
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Compound Information
Molecular Weight:156.631
Molecular Formula:C4H9ClO2S
InChIKey:PPLPUQSDHSUTOX-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:182.1302
Molecular Formula:C8H6O5
InChIKey:GLVYLTSKTCWWJR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:241.576
Molecular Formula:C7H10BrClS
InChIKey:WBLXLANFOOTYSL-WDSKDSINSA-N
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Compound Information
Molecular Weight:116.998
Molecular Formula:CH2Cl2S
InChIKey:SWYHWRRXAKMZLK-UHFFFAOYSA-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:297.168
Molecular Formula:C12H9BrO2S
InChIKey:AHBLGPKGDBXKMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
InChIKey:Not Available
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Compound Information
Molecular Weight:366.46
Molecular Formula:C13H25F3O4S2
InChIKey:RQHLQJACKABNNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.0453
Molecular Formula:C5H11I
InChIKey:BLXSFCHWMBESKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:QUXBXCLXGZYNFP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.3779
Molecular Formula:C11H22Si
InChIKey:MXBJYMQIMKJXKC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.123
Molecular Formula:C6H14LiN
InChIKey:ZCSHNCUQKCANBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:408.252
Molecular Formula:C14H17IO4S
InChIKey:DOLZAJFRFXREJS-STQMWFEESA-N
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Compound Information
Molecular Weight:134.97
Molecular Formula:Cl2O2S
InChIKey:YBBRCQOCSYXUOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:133.533
Molecular Formula:C4H4ClNO2
InChIKey:JRNVZBWKYDBUCA-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:108.1809
Molecular Formula:C8H12
InChIKey:DYEQHQNRKZJUCT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.996
Molecular Formula:CH2Cl2O2S
InChIKey:KQDDQXNVESLJNO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.823
Molecular Formula:CCl4
InChIKey:VZGDMQKNWNREIO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:347.644
Molecular Formula:C14H9Cl3O2S
InChIKey:CMQYUHJTVFZPHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:253.80894
Molecular Formula:I2
InChIKey:PNDPGZBMCMUPRI-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:269.199
Molecular Formula:C9H17BrO2S
InChIKey:UVUPHTMZSXDUSN-BQYQJAHWSA-N
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Compound Information
Molecular Weight:602.943
Molecular Formula:C31H42O4S3Si
InChIKey:MYDHCWNEMXVUNM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.271
Molecular Formula:C9H14O2S
InChIKey:NQJHVDQYUCJDFA-BDAKNGLRSA-N
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Compound Information
Molecular Weight:250.3764
Molecular Formula:C16H26O2
InChIKey:QACVHWAUNOKPFY-ATVPRXPUSA-N
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Compound Information
Molecular Weight:152.2367
Molecular Formula:C9H16N2
InChIKey:GQHTUMJGOHRCHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.4621
Molecular Formula:C16H36FN
InChIKey:FPGGTKZVZWFYPV-UHFFFAOYSA-M
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Compound Information
Molecular Weight:260.78
Molecular Formula:C12H17ClO2S
InChIKey:LEXJZMITORPMIH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.244
Molecular Formula:C8H12O3S
InChIKey:YADGUMVZVRLRQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.17
Molecular Formula:C4H8O2S
InChIKey:FAXAWLXXQOPCQN-ZXZARUISSA-N
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Compound Information
Molecular Weight:319.761
Molecular Formula:C12H14ClNO5S
InChIKey:FTFIBHSLKBBWOB-SMNKDYLDSA-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:182.2179
Molecular Formula:C13H10O
InChIKey:AFMVESZOYKHDBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:FJKHETFAHMBWCS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:ZPSOISAMGWYNQX-ONEGZZNKSA-N
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Compound Information
Molecular Weight:142.2386
Molecular Formula:C9H18O
InChIKey:XJHRZBIBSSVCEL-ONEGZZNKSA-N
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Compound Information
Molecular Weight:349.66
Molecular Formula:C14H11Cl3O2S
InChIKey:OLFNSMRIZMSPML-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.129
Molecular Formula:C7H11IO4S
InChIKey:IJPLSVJZGXOZCU-UHFFFAOYSA-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:114.166
Molecular Formula:C5H6OS
InChIKey:LJVFANGCLGJJFP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:ZCAXIDTXCHJYHT-UHFFFAOYSA-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:130.1864
Molecular Formula:C10H10
InChIKey:VYQSWAIOEVYAGK-UPHRSURJSA-N
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Compound Information
Molecular Weight:94.497
Molecular Formula:C2H3ClO2
InChIKey:Not Available
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Compound Information
Molecular Weight:316.156
Molecular Formula:C8H13IO3S
InChIKey:ZVYUJABINSEENO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:392.535
Molecular Formula:C10H13Br2ClO2S
InChIKey:BVFOZXRSLAOYNO-KHEBJJAPSA-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:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:68.074
Molecular Formula:C4H4O
InChIKey:YLQBMQCUIZJEEH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:YULMNMJFAZWLLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.197
Molecular Formula:C5H10O2S
InChIKey:BUGOPWGPQGYYGR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.0935
Molecular Formula:C3H9ISi
InChIKey:CSRZQMIRAZTJOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:MPQYLVUGJQUTPM-CMDGGOBGSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:HTEFASNITGSEJD-WBVMZDTFSA-N
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Compound Information
Molecular Weight:172.202
Molecular Formula:C7H8O3S
InChIKey:JOXIMZWYDAKGHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.368
Molecular Formula:C12H14O3S2
InChIKey:LIMYSVNAGHEPSK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.055
Molecular Formula:C4H9LiO
InChIKey:LZWQNOHZMQIFBX-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:330.375
Molecular Formula:C19H22O5
InChIKey:QDANUWUITADYED-ITJAQVFISA-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:112.2126
Molecular Formula:C8H16
InChIKey:KWKAKUADMBZCLK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:21.976
Molecular Formula:CH3Li
InChIKey:Not Available
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Compound Information
Molecular Weight:354.364
Molecular Formula:C10H17F3O6S2
InChIKey:DXPWXKKWHNCREE-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:350.111
Molecular Formula:C9H18Br2O2S
InChIKey:VGRDGLMKTMKVSZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.021
Molecular Formula:C7H9BrCl2S
InChIKey:VWXASORGWUPUSX-USEPMLCBSA-N
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Compound Information
Molecular Weight:152.599
Molecular Formula:C4H5ClO2S
InChIKey:XLJGOMXGCTZXDZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:371.877
Molecular Formula:C14H26ClNO6S
InChIKey:IMTDCRSSIKOFNF-RGURZIINSA-N
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Compound Information
Molecular Weight:56.077
Molecular Formula:CaO
InChIKey:ODINCKMPIJJUCX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.442
Molecular Formula:ClNaO
InChIKey:Not Available
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Compound Information
Molecular Weight:152.1919
Molecular Formula:C12H8
InChIKey:HXGDTGSAIMULJN-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:260.093
Molecular Formula:C5H9IO2S
InChIKey:LVZOPONVFXWBDM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:346.419
Molecular Formula:C14H18O6S2
InChIKey:RBXIXRKEOMVTLL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.194
Molecular Formula:C7H8O2S
InChIKey:FXJVNINSOKCNJP-UHFFFAOYSA-M
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Compound Information
Molecular Weight:196.695
Molecular Formula:C7H13ClO2S
InChIKey:JKLHQDFTZLNOTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.292
Molecular Formula:C11H14O3S
InChIKey:ARHZGRNPCKXFON-QWRGUYRKSA-N
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Compound Information
Molecular Weight:167.326
Molecular Formula:C6H18LiNSi2
InChIKey:YNESATAKKCNGOF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:340.415
Molecular Formula:C15H16O5S2
InChIKey:ALDNGTLZBAJNFU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:237.898
Molecular Formula:CH2Br2O2S
InChIKey:ZUQDPSRFJGYOPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.888
Molecular Formula:C3H6Br2
InChIKey:VEFLKXRACNJHOV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:983.1921
Molecular Formula:C63H66O10
InChIKey:YYNSDWPBZWHYGV-NZTPLXNPSA-N
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Compound Information
Molecular Weight:454.96
Molecular Formula:C12H7Br3O2S
InChIKey:HVSOPDPANQKLPI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.195
Molecular Formula:C3H5F3O4S2
InChIKey:YJEZMOWYAFJTBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:62.0678
Molecular Formula:C2H6O2
InChIKey:Not Available
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Compound Information
Molecular Weight:242.0548
Molecular Formula:C6H11IO2
InChIKey:RLZFVPPGVAHZPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:430.9
Molecular Formula:C19H23ClO7S
InChIKey:GWZGNONMZORWPA-DMOTWAINSA-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:264.34
Molecular Formula:C14H16O3S
InChIKey:KSSQJHINVXGMAZ-COVPZLACSA-N
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Compound Information
Molecular Weight:112.212
Molecular Formula:C4H9KO
InChIKey:LPNYRYFBWFDTMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.2469
Molecular Formula:C10H18O5
InChIKey:Not Available
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Compound Information
Molecular Weight:396.455
Molecular Formula:C19H24O7S
InChIKey:GFFCKOJTHIMCJG-CDEAQULNSA-N
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Compound Information
Molecular Weight:114.1648
Molecular Formula:C6H15Al
InChIKey:VOITXYVAKOUIBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2917
Molecular Formula:C7H15KO
InChIKey:LZDGSLFCXXQIQC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.252
Molecular Formula:C12H15LiO2S
InChIKey:BTQTVNGURNXUIX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:42.04
Molecular Formula:CH2N2
InChIKey:YXHKONLOYHBTNS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.3455
Molecular Formula:C13H26
InChIKey:NKLPGEJPQKIXSP-OUKQBFOZSA-N
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Compound Information
Molecular Weight:141.939
Molecular Formula:CH3I
InChIKey:INQOMBQAUSQDDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:388.617
Molecular Formula:C17H28O4S2Si
InChIKey:GTJCSGKSHIRJBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1836
Molecular Formula:C7H12N2
InChIKey:Not Available
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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:321.433
Molecular Formula:C14H27NO5S
InChIKey:JQJQKOWEJHCIKL-LPOBJOOYSA-N
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Compound Information
Molecular Weight:249.135
Molecular Formula:C14H10Cl2
InChIKey:GVLRAPLHURDGPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.243
Molecular Formula:C8H12O4S
InChIKey:XWEOEMGWCHSYSN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:288.833
Molecular Formula:C14H21ClO2S
InChIKey:PIMBMTRAAFMHOF-IUZLNWEFSA-N
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Compound Information
Molecular Weight:101.9613
Molecular Formula:Al2O3
InChIKey:TWNQGVIAIRXVLR-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:230.711
Molecular Formula:C10H11ClO2S
InChIKey:PNRAUUGFXZXSOA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:YAGNKYLIKNJGBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.77
Molecular Formula:C14H13ClO2S
InChIKey:SJMMZFZYGOFEGI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:RYHBNJHYFVUHQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.202
Molecular Formula:C7H8O2S
InChIKey:NVSONFIVLCXXDH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1049.272
Molecular Formula:C63H68O12S
InChIKey:NGFKIJDVWUQUAH-ZCZCELBRSA-N
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Compound Information
Molecular Weight:408.149
Molecular Formula:C14H16Br2O2S
InChIKey:CSYFNANEZMJFFX-KPWCQOOUSA-N
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Compound Information
Molecular Weight:196.4045
Molecular Formula:C12H24Si
InChIKey:DKBXKUMXJBOLOX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:271.3526
Molecular Formula:C14H25NO4
InChIKey:KBQGZWJDMSGALX-JTQLQIEISA-N
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Compound Information
Molecular Weight:222.389
Molecular Formula:C14H22S
InChIKey:GRVZLIXFVDBWAU-KGLIPLIRSA-N
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Compound Information
Molecular Weight:132.1987
Molecular Formula:C10H10
InChIKey:Not Available
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Compound Information
Molecular Weight:288.502
Molecular Formula:C12H20O2S2Si
InChIKey:LFEVPGXQODXCKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:BTAQCZNRMSONHM-UHFFFAOYSA-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:200.3193
Molecular Formula:C15H20
InChIKey:DSJNTPGTYINDMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.984
Molecular Formula:C4H4BrNO2
InChIKey:PCLIMKBDDGJMGD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.705
Molecular Formula:C8H13ClO3S
InChIKey:CQTMSCWBTBRYOK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.366
Molecular Formula:C12H22O3S
InChIKey:LBLMRADUGNMYJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:243.151
Molecular Formula:C8H12Cl2O2S
InChIKey:QJHHYCPPPHBQLQ-KVFPUHGPSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.339
Molecular Formula:C14H16O4S
InChIKey:UXNWJGOGRCBJMX-XQQFMLRXSA-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:315.215
Molecular Formula:C14H12Cl2O2S
InChIKey:NHUBBFMARHNTAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:159.808
Molecular Formula:Br2
InChIKey:GDTBXPJZTBHREO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.228
Molecular Formula:C8H10O3S
InChIKey:VUQUOGPMUUJORT-UHFFFAOYSA-N
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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:140.1797
Molecular Formula:C8H12O2
InChIKey:FJEGEQZRLGQSGP-UHFFFAOYSA-N
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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:239.213
Molecular Formula:C4H7F3O4S2
InChIKey:ROABNVMPEXKASY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:197.231
Molecular Formula:C10H15NO3
InChIKey:WRWWRZKGSMOPRP-ZETCQYMHSA-N
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Compound Information
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.747
Molecular Formula:C9H17ClO4S
InChIKey:CANYDPBLFNCHBZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.325
Molecular Formula:C14H14O2S
InChIKey:AWHNUHMUCGRKRA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.886
Molecular Formula:CCl4O2S
InChIKey:ZCPSWAFANXCCOT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:333.788
Molecular Formula:C13H16ClNO5S
InChIKey:QYFWFBCWBOELQG-QHIQZGGMSA-N
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Compound Information
Molecular Weight:146.164
Molecular Formula:C5H6O3S
InChIKey:HLFDOFKECCWFOF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:360.446
Molecular Formula:C15H20O6S2
InChIKey:CBGANFKDMITASI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:338.321
Molecular Formula:C9H13F3O6S2
InChIKey:KRTUWJPMKWVNTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:ORLJVINATUKLJQ-UHFFFAOYSA-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:983.1921
Molecular Formula:C63H66O10
InChIKey:YYNSDWPBZWHYGV-FEMIZGLISA-N
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Compound Information
Molecular Weight:267.183
Molecular Formula:C9H15BrO2S
InChIKey:PLSJTIKUSQUFML-VGMNWLOBSA-N
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
InChIKey:IAQRGUVFOMOMEM-ONEGZZNKSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:ZPSOISAMGWYNQX-ARJAWSKDSA-N
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Compound Information
Molecular Weight:288.833
Molecular Formula:C14H21ClO2S
InChIKey:RFORAPGFPZYQCW-KFTPUPIBSA-N
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Compound Information
Molecular Weight:269.199
Molecular Formula:C9H17BrO2S
InChIKey:UVUPHTMZSXDUSN-FPLPWBNLSA-N
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Compound Information
Molecular Weight:243.151
Molecular Formula:C8H12Cl2O2S
InChIKey:QJHHYCPPPHBQLQ-WZQOZDJLSA-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:376.064
Molecular Formula:C12H8Br2O2S
InChIKey:KSRJVHHNYDBYLF-RYUDHWBXSA-N
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Compound Information
Molecular Weight:271.3526
Molecular Formula:C14H25NO4
InChIKey:KBQGZWJDMSGALX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:20.0276
Molecular Formula:H2O
InChIKey:Not Available
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Compound Information
Molecular Weight:182.3455
Molecular Formula:C13H26
InChIKey:NKLPGEJPQKIXSP-SEYXRHQNSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:MPQYLVUGJQUTPM-HJWRWDBZSA-N
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Compound Information
Molecular Weight:450.5281
Molecular Formula:C36H18
InChIKey:CUIWZLHUNCCYBL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.281
Molecular Formula:C10H14O4S
InChIKey:BROOLENVBIPEFG-YIZRAAEISA-N
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Compound Information
Molecular Weight:197.2741
Molecular Formula:C11H19NO2
InChIKey:XUNAYZIHVQJKGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:289.21
Molecular Formula:C16H17Br
InChIKey:LXHISLGZQMNXJP-QVTHNMBSSA-N
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Compound Information
Molecular Weight:376.064
Molecular Formula:C12H8Br2O2S
InChIKey:KSRJVHHNYDBYLF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:408.7021
Molecular Formula:C30H48
InChIKey:NXJJBCPAGHGVJC-MAYJZIKRSA-N
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Compound Information
Molecular Weight:602.952
Molecular Formula:C40H58O2S
InChIKey:OSIGMVXDADMUGI-XBWCUBMNSA-N
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Compound Information
Molecular Weight:132.181
Molecular Formula:C5H8O2S
InChIKey:ABDQESHSEZGIGN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:536.8726
Molecular Formula:C40H56
InChIKey:OENHQHLEOONYIE-JLTXGRSLSA-N
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Compound Information
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:XQQUSVHISAVPIV-MUYAZXKQSA-N
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Compound Information
Molecular Weight:56.0666
Molecular Formula:C2H4N2
InChIKey:WLXALCKAKGDNAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.314
Molecular Formula:C10H18O2S
InChIKey:FVNOBOJNBYUMMH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:48.107
Molecular Formula:CH4S
InChIKey:LSDPWZHWYPCBBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:76.161
Molecular Formula:C3H8S
InChIKey:KJRCEJOSASVSRA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.309
Molecular Formula:C14H12O2S
InChIKey:ZXQADSQBNWPCCC-OKILXGFUSA-N
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Compound Information
Molecular Weight:315.215
Molecular Formula:C14H12Cl2O2S
InChIKey:MTTPKLOSMYAEAE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:231.14
Molecular Formula:C7H12Cl2O2S
InChIKey:AWPAMZIFUUFBEY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.282
Molecular Formula:C10H14O2S
InChIKey:RRUUFTRLQZJDPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.404
Molecular Formula:C9H20O2SSi
InChIKey:UMRMGKIAADNXNV-IUCAKERBSA-N
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Compound Information
Molecular Weight:298.399
Molecular Formula:C18H18O2S
InChIKey:QJWCAOAOTZODEO-PVRNWPCDSA-N
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Compound Information
Molecular Weight:644.891
Molecular Formula:C34H48O8SSi
InChIKey:UADMSVHQZNMVFA-WVRUKXMZSA-N
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Compound Information
Molecular Weight:284.8
Molecular Formula:C11H21ClO4S
InChIKey:XMPBZJAJKQUSBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.371
Molecular Formula:C14H20O4S
InChIKey:FIHFJHRKVMLTTA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:QCBJLUPNCWAGGU-VOTSOKGWSA-N
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Compound Information
Molecular Weight:206.068
Molecular Formula:C4H8Cl2O3S
InChIKey:DYDYMSCHKIEBBR-UHFFFAOYSA-M
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Compound Information
Molecular Weight:339.534
Molecular Formula:C16H37NO4S
InChIKey:SHFJWMWCIHQNCP-UHFFFAOYSA-M
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Compound Information
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:CVSIPMNQVKDOGV-PLNGDYQASA-N
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Compound Information
Molecular Weight:240.363
Molecular Formula:C16H16S
InChIKey:ZCWGQVMUFLRTTQ-KPKJPENVSA-N
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Compound Information
Molecular Weight:264.3184
Molecular Formula:C18H16O2
InChIKey:WIIFFAMHOBIVLI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.716
Molecular Formula:C8H18CuLi
InChIKey:UADBHFTWQBWLOF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.34
Molecular Formula:C11H20O2S
InChIKey:QQQCIMYTWWKLDS-HJWRWDBZSA-N
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Compound Information
Molecular Weight:520.68
Molecular Formula:C24H44N2O8S
InChIKey:ZKFQTTWKFXRVQX-WNRNVDISSA-N
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Compound Information
Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:LRUBQXAKGXQBHA-KVTDHHQDSA-N
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Compound Information
Molecular Weight:234.743
Molecular Formula:C10H15ClO2S
InChIKey:HRVFVLXCWCDNQX-VQHVLOKHSA-N
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Compound Information
Molecular Weight:253.3804
Molecular Formula:C15H27NO2
InChIKey:NZTXICIUAZQWDK-SNAWJCMRSA-N
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Compound Information
Molecular Weight:232.3196
Molecular Formula:C18H16
InChIKey:BOBLSBAZCVBABY-FJJINHQHSA-N
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Compound Information
Molecular Weight:416.573
Molecular Formula:C24H32O4S
InChIKey:PRDWAVCNIRRUNX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:396.501
Molecular Formula:C26H20O2S
InChIKey:LPXMIHHGJRUKDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:678.833
Molecular Formula:C41H42O7S
InChIKey:RVWRBAMWLVDHHG-WWGFXPMHSA-N
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Compound Information
Molecular Weight:239.3538
Molecular Formula:C14H25NO2
InChIKey:JIMGKWHFSZAXRL-SNAWJCMRSA-N
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Compound Information
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-QXMHVHEDSA-N
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Compound Information
Molecular Weight:244.759
Molecular Formula:C16H17Cl
InChIKey:SSDAAWNAOMYFNL-QVTHNMBSSA-N
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Compound Information
Molecular Weight:240.3832
Molecular Formula:C18H24
InChIKey:MYAQCFUVBVNRBR-HWAYABPNSA-N
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Compound Information
Molecular Weight:255.967
Molecular Formula:C8H9BrCl2
InChIKey:SEZIXMOPJSDHOU-CNYLLVADSA-N
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Compound Information
Molecular Weight:334.069
Molecular Formula:C8H14Br2O2S
InChIKey:CCMMKCSWBBDPNF-HTQZYQBOSA-N
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Compound Information
Molecular Weight:512.442
Molecular Formula:C20H33IO5S
InChIKey:MRFBYFVLHWATRP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:336.2063
Molecular Formula:C10H14N2Na2O8
InChIKey:ZGTMUACCHSMWAC-UHFFFAOYSA-L
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Compound Information
Molecular Weight:198.368
Molecular Formula:C12H22S
InChIKey:WGENLDYYAASWFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:330.444
Molecular Formula:C18H22N2O2S
InChIKey:VIJAUEYXEYNXGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.215
Molecular Formula:C10H21Li
InChIKey:SHJXVDAAVHAKFB-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:396.501
Molecular Formula:C26H20O2S
InChIKey:KMRDMESTZKMOOZ-UHFFFAOYSA-N
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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:289.371
Molecular Formula:C11H15NO4S2
InChIKey:RQKWMEBDXWOOIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:YHHHHJCAVQSFMJ-FNORWQNLSA-N
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