Standard Article

Synthetic Applications of Phosphoryl-Stabilized Anions

  1. William S. Wadsworth Jr.*,*

Published Online: 15 JUL 2005

DOI: 10.1002/0471264180.or025.02

Organic Reactions

Organic Reactions

How to Cite

Wadsworth, W. S. 2005. Synthetic Applications of Phosphoryl-Stabilized Anions. Organic Reactions. 25:2:73–253.

Author Information

  1. South Dakota State University, Brookings, South Dakota

  1. *

    I wish to thank Ms. Carolyn Sidor of E. I. du Pont de Nemours and Company for much help with the literature search.

Publication History

  1. Published Online: 15 JUL 2005

Chemistry Terms

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Abstract

The successful synthesis of a wide variety of unsaturated compounds by treatment of phosphoranes with carbonyl compounds (the Wittig reaction) has stimulated the search for other synthetic methods that employ organophosphorus reagents. One of the most fruitful results has been the discovery that phosphoryl-stabilized carbanions have wide applicability in the preparation of unsaturated compounds and offer significant advantages over conventional procedures.

This review discusses the chemistry of carbanions stabilized by delocalization of their negative charge by means of a P(O) group. Carbanions obtained by treating phosphine oxides, phosphinates, and phosphonates, with a base have been explored in depth. In particular, the phosphonates have found great popularity because of their availability and ease of application. The use of Wittig-type reagents in synthesis has been reviewed and is not mentioned except by way of comparison.

Carbanions prepared from phosphinates have no known advantage over those prepared from phosphonates or phosphine oxides. Those carbanions obtained from phosphine oxides will be considered here only in the way of comparison.

Anions that have their negative charge located on an atom adjacent to a P(O) group gain stability owing to delocalization of the charge through the phosphoryl group. Although the exact nature of the delocalization is not well defined, the ability of phosphorus to become pentacovalent by use of its d orbitals is undoubtedly a contributing factor. It should be noted that the P(O) group is generally not so effective as the carbonyl group in stabilizing a negative charge. If other stabilizing groups are not present, formation of P(O)-stabilized carbanions generally requires more basic conditions than does the removal of a proton from a carbon atom alpha to a carbonyl group.

Horner and co-workers were the first to investigate the synthetic utility of P(O)-stabilized carbanions. The utility of phosphonate carbanions as synthetic intermediates was expanded by the discovery that, as olefin-forming reagents, phosphonates have certain advantages over both phosphoranes and phosphine oxides. As a result, the method has found favor because of the availability of reagents, ease of workup, and convenient reaction conditions. In particular, the reactivity of phosphonate carbanions has been taken advantage of in numerous ways. As indicated by a number of reviews, these carbanions have become one of the most frequently employed organophosphorus reagents.

The utility of phosphoryl-stabilized anions is apparent from the variety of materials that can be prepared by suitable structural modifications. Besides simple monoolefins and polyenes, a partial list would include allenes, unsaturated amides, aldehydes, esters, sulfides, sulfones, and nitrogen compounds such as imines, isocyanates, and ketenimines. In addition to their convenience for introducing unsaturation, these stabilized anions offer routes to cyclopropanes and heterocyclic systems. In this chapter, reactions that are of unusual interest are discussed separately; more routine reactions are included only in the tabular survey.

Olefin formation by means of phosphonate carbanions has been referred to as the Horner-Emmons or Wadsworth-Emmons modification of the Wittig reaction, whereas the use of phosphine oxide or phosphinate carbanions is generally referred to as the Horner modification. In order to prevent confusion and to avoid misdirecting credit, proper names are omitted and the synthesis of an olefin by phosphonate carbanions is termed phosphonate-olefin formation. Likewise, the term phosphine oxide-olefin formation is employed where appropriate.

Keywords:

  • phosphoryl-stabilized anions;
  • phosphoryl reagents;
  • substrates;
  • scope;
  • limitation;
  • carbonyl co-reactant;
  • sulfides;
  • sulfones;
  • ethers;
  • dienes;
  • alkynes;
  • olefin formation;
  • aldehydes;
  • ketones;
  • esters;
  • allenes;
  • imines;
  • bisphosphonates;
  • phosphoramidate anions;
  • double-bond migration;
  • Knoevenagel reaction;
  • experimental procedures;
  • phosphoryl-stabilized anions;
  • cyclopropanes;
  • aziridines

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:WTEVQBCEXWBHNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:341.3408
Molecular Formula:C19H20NO3P
InChIKey:RIEYPJZSSMFMLH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:364.3328
Molecular Formula:C17H21N2O5P
InChIKey:QSERTEBXUBWYIA-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:Not Available
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:RMCHQOWPUICMFO-YTXTXJHMSA-N
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Compound Information
Molecular Weight:138.1021
Molecular Formula:C4H11O3P
InChIKey:YHQMSHVVGOSZEW-UHFFFAOYSA-N
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Molecular Weight:Not Available
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Molecular Weight:Not Available
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:222.2185
Molecular Formula:C9H19O4P
InChIKey:OQIXRIAIMDDFBA-VQHVLOKHSA-N
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Compound Information
Molecular Weight:184.113
Molecular Formula:Br2Mg
InChIKey:Not Available
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Molecular Weight:Not Available
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Molecular Weight:Not Available
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Molecular Weight:Not Available
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Molecular Weight:142.114
Molecular Formula:C2H7O3PS
InChIKey:WWJJVKAEQGGYHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:371.185
Molecular Formula:C11H16BrO5PS
InChIKey:CIFWPPFDXPEZGN-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:303.087
Molecular Formula:C8H16BrO5P
InChIKey:JTMDGKZDQVZDKA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1553
Molecular Formula:C6H15O3P
InChIKey:BDZBKCUKTQZUTL-UHFFFAOYSA-N
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Molecular Weight:Not Available
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Compound Information
Molecular Weight:182.2179
Molecular Formula:C13H10O
InChIKey:RWCCWEUUXYIKHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:NASMNJMPHOXSQF-ONEGZZNKSA-N
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Compound Information
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:ZWKNLRXFUTWSOY-DAXSKMNVSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:Not Available
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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:250.2286
Molecular Formula:C10H19O5P
InChIKey:UBBRMCHLUWPZKH-VQHVLOKHSA-N
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Compound Information
Molecular Weight:134.604
Molecular Formula:C6H11ClO
InChIKey:YWGHUJQYGPDNKT-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:102.846
Molecular Formula:C3H7ClMg
InChIKey:Not Available
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Compound Information
Molecular Weight:210.1648
Molecular Formula:C7H15O5P
InChIKey:CTSAXXHOGZNKJR-UHFFFAOYSA-N
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Molecular Weight:Not Available
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Molecular Weight:Not Available
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Compound Information
Molecular Weight:192.123
Molecular Formula:C12H10LiP
InChIKey:WKUYEGHEUWHKIU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.299
Molecular Formula:C10H16S
InChIKey:ANPCVMFHOREQRH-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:174.1806
Molecular Formula:C7H15N2OP
InChIKey:GFLWZEAMSUWBAA-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:261.2976
Molecular Formula:C12H24NO3P
InChIKey:MSAXEVSZBONZIC-JLHYYAGUSA-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:180.1851
Molecular Formula:C6H17N2O2P
InChIKey:CYPHGERALDCUEM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.604
Molecular Formula:C9H6ClN
InChIKey:PPCNBCKABHGVMX-OWOJBTEDSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:107.123
Molecular Formula:C6H14LiN
InChIKey:ZCSHNCUQKCANBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.2454
Molecular Formula:C13H17O4P
InChIKey:DXTQIZGGRXEUCN-MDZDMXLPSA-N
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Compound Information
Molecular Weight:321.352
Molecular Formula:C16H19O3PS
InChIKey:WTJRBFUFKZUZFO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.137
Molecular Formula:C9H9BrS
InChIKey:PFNYEHYCFUOSQX-FARCUNLSSA-N
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Compound Information
Molecular Weight:252.2014
Molecular Formula:C9H17O6P
InChIKey:CIKPHTBQBJJKBV-FPLPWBNLSA-N
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Compound Information
Molecular Weight:224.258
Molecular Formula:C8H17O3PS
InChIKey:QMMZWLYLXHVKRN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.3853
Molecular Formula:C17H26O5
InChIKey:CNESDKRCGCWHEN-ZXQPSUMESA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:154.1015
Molecular Formula:C4H11O4P
InChIKey:UCQFCFPECQILOL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.2466
Molecular Formula:C13H12N2O2
InChIKey:SDXBSEVRKGMFKY-WQLSENKSSA-N
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Compound Information
Molecular Weight:332.477
Molecular Formula:C21H32O3
InChIKey:MOIQRAOBRXUWGN-VKEYXRQVSA-N
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Compound Information
Molecular Weight:320.32
Molecular Formula:C17H21O4P
InChIKey:SCFMQNLNZNELAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.2286
Molecular Formula:C10H19O5P
InChIKey:LXLODBXSCRTXFG-BQYQJAHWSA-N
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Compound Information
Molecular Weight:224.1913
Molecular Formula:C8H17O5P
InChIKey:Not Available
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Compound Information
Molecular Weight:176.1501
Molecular Formula:C7H13O3P
InChIKey:HSTDWLTWVXEIPZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:ZEQGQZDJDIKOEM-MJODGSQRSA-N
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Compound Information
Molecular Weight:176.1964
Molecular Formula:C7H17N2OP
InChIKey:TXFFVRGRSQZIBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:30.069
Molecular Formula:C2H6
InChIKey:OTMSDBZUPAUEDD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.2527
Molecular Formula:C13H18NO4P
InChIKey:HIESNIFYQQMODO-QWHCGFSZSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:AISZSTYLOVXFII-CMDGGOBGSA-N
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Compound Information
Molecular Weight:277.297
Molecular Formula:C12H24NO4P
InChIKey:QVFUPPTYEYKYAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.136
Molecular Formula:C9H9BrO2S
InChIKey:RMPNGDZBTAZMRN-FARCUNLSSA-N
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Compound Information
Molecular Weight:282.2527
Molecular Formula:C13H18NO4P
InChIKey:OJJKXDDXOZKJPT-QWHCGFSZSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:240.2369
Molecular Formula:C15H13OP
InChIKey:WKZPAHCFWJSILB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:ZMYIIHDQURVDRB-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:223.1822
Molecular Formula:C10H9NO5
InChIKey:MWPJNFPGFILHOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:235.2603
Molecular Formula:C10H22NO3P
InChIKey:BOAVGYXVWKIXDF-CSKARUKUSA-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:44.0526
Molecular Formula:C2H4O
InChIKey:IKHGUXGNUITLKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.284
Molecular Formula:C9H19O3PS
InChIKey:HVXIIDIWWLLFGS-VQHVLOKHSA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:FLSICIIYQVUVKU-VNPQWULESA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:QPPGEPODNBLBTG-UTLUCORTSA-N
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Compound Information
Molecular Weight:230.2212
Molecular Formula:C10H18NO3P
InChIKey:MIYSSLGDWDJZKS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:306.3349
Molecular Formula:C14H27O5P
InChIKey:JDRBGHOOWKDULL-OUKQBFOZSA-N
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Compound Information
Molecular Weight:178.658
Molecular Formula:C11H11Cl
InChIKey:HGHBKCXEZBAGBG-OZDSWYPASA-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:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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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:324.3502
Molecular Formula:C14H29O6P
InChIKey:YZEDLVRQLHUXIC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2491
Molecular Formula:C13H14O2
InChIKey:LCARQGAXDBMNCB-BNFZFUHLSA-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:22.98976928
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.584
Molecular Formula:C6H12ClO3P
InChIKey:MMODFFHHPZMITJ-GQCTYLIASA-N
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Compound Information
Molecular Weight:356.4984
Molecular Formula:C23H32O3
InChIKey:JVHLOLFSGIGPJC-VUDNZARFSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:158.0339
Molecular Formula:KMnO4
InChIKey:VZJVWSHVAAUDKD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:541.6344
Molecular Formula:C28H47O8P
InChIKey:AFJQOJRFBNBRHL-PYTURSCESA-N
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Compound Information
Molecular Weight:152.132
Molecular Formula:C4H13N2O2P
InChIKey:GWWWNAKRFFANNF-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:298.2934
Molecular Formula:C16H14N2O4
InChIKey:XNJIMFKNDKVEEO-PTNGSMBKSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.3487
Molecular Formula:C15H24O4
InChIKey:MBCXYYAZNQUCRV-CMDGGOBGSA-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:216.59
Molecular Formula:HgO
InChIKey:UKWHYYKOEPRTIC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:259.1544
Molecular Formula:C7H18O6P2
InChIKey:ITKPJSZKSAXTFC-UHFFFAOYSA-M
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Compound Information
Molecular Weight:205.2545
Molecular Formula:C15H11N
InChIKey:RDGWQFSLTSPRBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:99.1741
Molecular Formula:C6H13N
InChIKey:PAFZNILMFXTMIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:13.835
Molecular Formula:BH3
InChIKey:UORVGPXVDQYIDP-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:322.3343
Molecular Formula:C14H27O6P
InChIKey:WSYYAGFODVHLSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.1381
Molecular Formula:C6H12NO3P
InChIKey:KWMBADTWRIGGGG-UHFFFAOYSA-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:31.0571
Molecular Formula:CH5N
InChIKey:BAVYZALUXZFZLV-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:151.1195
Molecular Formula:C7H5NO3
InChIKey:BXRFQSNOROATLV-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:212.247
Molecular Formula:C7H17O3PS
InChIKey:JVORXUIQUWDQQF-UHFFFAOYSA-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:276.4137
Molecular Formula:C18H28O2
InChIKey:VVOCSRMUVJJEHU-XJKLVWMKSA-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:Not Available
Molecular Formula:Not Available
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:150.1592
Molecular Formula:C5H15N2OP
InChIKey:YRWJRJCUZYGLPN-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:275.3242
Molecular Formula:C13H26NO3P
InChIKey:RZUOQMFASFRSMP-QXMHVHEDSA-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:271.5
Molecular Formula:Cl2Hg
InChIKey:Not Available
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Compound Information
Molecular Weight:339.186
Molecular Formula:C11H16BrO3PS
InChIKey:BZRDPPZLHBSQPC-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:Not Available
Molecular Formula:Not Available
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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:AVPYQKSLYISFPO-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:JCOOCDUHQWDERL-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:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.3077
Molecular Formula:C13H23N2O2P
InChIKey:SMEFNRGANPHYKW-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:198.22
Molecular Formula:C6H15O3PS
InChIKey:RAABCCZMKIIGJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.4131
Molecular Formula:C18H28O3
InChIKey:COURCVNNWIAHFI-YXMSNVFVSA-N
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Compound Information
Molecular Weight:268.2454
Molecular Formula:C13H17O4P
InChIKey:NPSSMYNEXTYIJG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.2212
Molecular Formula:C10H18NO3P
InChIKey:MIYSSLGDWDJZKS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.201
Molecular Formula:C6H18N3P
InChIKey:XVDBWWRIXBMVJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:358.3487
Molecular Formula:C19H22NO4P
InChIKey:VROZCYIGVLUSJD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.1388
Molecular Formula:C6H13O4P
InChIKey:ZZWQVTBJLLXLPJ-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:Not Available
Molecular Formula:Not Available
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:234.2756
Molecular Formula:C10H23N2O2P
InChIKey:UOOUKGPQEWZBDC-VQHVLOKHSA-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:393.2678
Molecular Formula:C12H29O8P3
InChIKey:MUIPOEPBZJXSDW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.141
Molecular Formula:C3H9O2PS
InChIKey:BHFOAIMSKFAWOU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3606
Molecular Formula:C16H24O2
InChIKey:IQSWSJHDVVBQLC-DPOOUPBZSA-N
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Compound Information
Molecular Weight:234.2756
Molecular Formula:C10H23N2O2P
InChIKey:YKRHQZLYKJRPMV-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:252.3062
Molecular Formula:C14H20O4
InChIKey:ZFEQGEFQHOIZSN-KQQUZDAGSA-N
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Compound Information
Molecular Weight:88.0621
Molecular Formula:C3H4O3
InChIKey:Not Available
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:HPJQHAKEQZQQCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2491
Molecular Formula:C13H14O2
InChIKey:NLKBBWBCWHTRAJ-JMQWPVDRSA-N
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Compound Information
Molecular Weight:177.1381
Molecular Formula:C6H12NO3P
InChIKey:KWMBADTWRIGGGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.1015
Molecular Formula:C4H11O4P
InChIKey:UCQFCFPECQILOL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.2527
Molecular Formula:C13H18NO4P
InChIKey:HIESNIFYQQMODO-STQMWFEESA-N
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Compound Information
Molecular Weight:282.2527
Molecular Formula:C13H18NO4P
InChIKey:OJJKXDDXOZKJPT-STQMWFEESA-N
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Compound Information
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:ZWKNLRXFUTWSOY-QPJJXVBHSA-N
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Compound Information
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:QROGIFZRVHSFLM-QHHAFSJGSA-N
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Compound Information
Molecular Weight:282.2527
Molecular Formula:C13H18NO4P
InChIKey:HIESNIFYQQMODO-QWHCGFSZSA-N
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Compound Information
Molecular Weight:282.2527
Molecular Formula:C13H18NO4P
InChIKey:HIESNIFYQQMODO-STQMWFEESA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:283.2601
Molecular Formula:C13H18NO4P
InChIKey:KYVGDANLKKBKNI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:283.2601
Molecular Formula:C13H18NO4P
InChIKey:KYVGDANLKKBKNI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:ZWKNLRXFUTWSOY-QPJJXVBHSA-N
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Compound Information
Molecular Weight:268.3487
Molecular Formula:C15H24O4
InChIKey:MBCXYYAZNQUCRV-HJWRWDBZSA-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:Not Available
Molecular Formula:Not Available
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:222.2185
Molecular Formula:C9H19O4P
InChIKey:OQIXRIAIMDDFBA-VQHVLOKHSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:Not Available
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Compound Information
Molecular Weight:250.2286
Molecular Formula:C10H19O5P
InChIKey:UBBRMCHLUWPZKH-CLFYSBASSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:RMCHQOWPUICMFO-DEQVHDEQSA-N
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Compound Information
Molecular Weight:250.2286
Molecular Formula:C10H19O5P
InChIKey:UBBRMCHLUWPZKH-VQHVLOKHSA-N
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Compound Information
Molecular Weight:234.2756
Molecular Formula:C10H23N2O2P
InChIKey:UOOUKGPQEWZBDC-VQHVLOKHSA-N
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Compound Information
Molecular Weight:224.1913
Molecular Formula:C8H17O5P
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:184.2322
Molecular Formula:C10H16O3
InChIKey:UIYBXJLJRUINKX-BQYQJAHWSA-N
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Compound Information
Molecular Weight:260.2836
Molecular Formula:C12H20O6
InChIKey:WUBAIOHYHZYCDL-MDZDMXLPSA-N
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Compound Information
Molecular Weight:194.1654
Molecular Formula:C7H15O4P
InChIKey:Not Available
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Compound Information
Molecular Weight:123.1525
Molecular Formula:C7H9NO
InChIKey:NTBRBVDWJQGNBR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:352.118
Molecular Formula:C11H15BrNO5P
InChIKey:HQXDUCFRRPRPED-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:250.1871
Molecular Formula:C12H11O4P
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:370.3593
Molecular Formula:C18H18N4O5
InChIKey:OHDSOCIGUZLWGD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.117
Molecular Formula:C2H3NS
InChIKey:LGDSHSYDSCRFAB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:VUEGXHXUMOZKKN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.2348
Molecular Formula:C10H17F3O4
InChIKey:UUZCIVFUQIDWLG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:SGZHXNCMEIVLMG-JEGFTUTRSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:STNJBCKSHOAVAJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.1663
Molecular Formula:C8H11F3O3
InChIKey:RIZVJPDJHKBJHO-WAYWQWQTSA-N
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Compound Information
Molecular Weight:370.3771
Molecular Formula:C18H27O6P
InChIKey:LQFWDARGYJWNCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.132
Molecular Formula:C8H6O2
InChIKey:ZWLUXSQADUDCSB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.202
Molecular Formula:C9H17O5P
InChIKey:ISLZPJMIALHMEC-VOTSOKGWSA-N
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Compound Information
Molecular Weight:218.1883
Molecular Formula:C12H11O2P
InChIKey:BEQVQKJCLJBTKZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.2141
Molecular Formula:C7H15N3
InChIKey:FSAAFZOOYIDHJV-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:134.1736
Molecular Formula:C6H14O3
InChIKey:SBZXBUIDTXKZTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.2179
Molecular Formula:C9H19O5P
InChIKey:BVSRWCMAJISCTD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.3911
Molecular Formula:C16H28O4
InChIKey:POTGOKMCOWHUGZ-HNXSEKISSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:KRLWWWIBVSGXGK-GQCTYLIASA-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:228.2246
Molecular Formula:C11H17O3P
InChIKey:AIPRAPZUGUTQKX-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:526.4336
Molecular Formula:C21H27N4O10P
InChIKey:AKKRPBYGAQAEBZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2695
Molecular Formula:C12H18O3
InChIKey:DDISZVZJJKKIRH-ONNLMXTPSA-N
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Compound Information
Molecular Weight:370.4819
Molecular Formula:C23H30O4
InChIKey:MATMECYAPCZDQE-JLLUVORTSA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:323.2998
Molecular Formula:C13H25O7P
InChIKey:BBZXAYYNTWNLMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.2286
Molecular Formula:C10H19O5P
InChIKey:UBBRMCHLUWPZKH-VQHVLOKHSA-N
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Compound Information
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:CTOSODBTBIMMHC-VOTSOKGWSA-N
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Compound Information
Molecular Weight:207.2258
Molecular Formula:C11H13NO3
InChIKey:PECKJUIKFHWAGE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:TYDSIOSLHQWFOU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:332.437
Molecular Formula:C26H20
InChIKey:KJIBOKDTDPEIIZ-XPWSMXQVSA-N
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Compound Information
Molecular Weight:210.1648
Molecular Formula:C7H15O5P
InChIKey:CTSAXXHOGZNKJR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:301.3801
Molecular Formula:C18H23NO3
InChIKey:YGUHVQJOJOTUBW-FOWTUZBSSA-N
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Compound Information
Molecular Weight:378.3374
Molecular Formula:C16H28O6P2
InChIKey:Not Available
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Compound Information
Molecular Weight:195.1772
Molecular Formula:C6H17N2O3P
InChIKey:VRAYUFWTMOEDIT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.139
Molecular Formula:C14H10BrNO2
InChIKey:FELCASMKABNBRW-GXDHUFHOSA-N
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Compound Information
Molecular Weight:212.2854
Molecular Formula:C12H20O3
InChIKey:XJCIKCLDTSBESY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:42.0797
Molecular Formula:C3H6
InChIKey:QQONPFPTGQHPMA-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:196.2429
Molecular Formula:C11H16O3
InChIKey:HFCQVLXVTLKUKC-FPLPWBNLSA-N
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Compound Information
Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:HUUPVABNAQUEJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.1818
Molecular Formula:C8H16FO5P
InChIKey:FVPISMANESAJQZ-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:212.2854
Molecular Formula:C12H20O3
InChIKey:SUZRSVLRBYXDFA-CSKARUKUSA-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:508.4839
Molecular Formula:C31H26O3P2
InChIKey:NOUUDSDXCIQGKJ-UHFFFAOYSA-N
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