Standard Article

Isopropylidenetriphenylphosphorane

  1. Thomas J. Fleck1,
  2. Carolyn L. Ladd2

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.ri084.pub2

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Fleck, T. J. and Ladd, C. L. 2013. Isopropylidenetriphenylphosphorane. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. 1

    The Upjohn Company, Kalamazoo, MI, USA

  2. 2

    Université de Montréal, Montréal, QC, Canada

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

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[16666-80-1] C21H21P (MW 304.39)

(highly reactive phosphorus ylide used in natural product alkene formation1-3 and gem-dimethylcyclopropane formation4)

Physical Data: red-colored ylide in solution.

Solubility: sol THF, DMSO, toluene, diethyl ether.

Drying: the precursor phosphonium salt should be vacuum dried before use to drive off any residual water.

Preparative Methods: prepared in situ from commercially available isopropyltriphenylphosphonium iodide or bromide and an appropriate base. An isopropyltriphenylphosphonium bromide–sodium amide ‘instant ylide’5 pre-mix is also available.

Handling, Storage, and Precautions: should be used immediately after formation. Most ylide solutions slowly decompose with time.

Featured Compounds

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  1. 1 - 97
Compound Information
Molecular Weight:304.3652
Molecular Formula:C21H21P
InChIKey:KNWIYLJZVYHGDV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:335.3
Molecular Formula:C14H23BrO2S
InChIKey:UGDYFHKYIMYXTL-QSLWVIQJSA-N
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Compound Information
Molecular Weight:301.262
Molecular Formula:C15H25BrO
InChIKey:NEJWBGSUEYGAGE-BTFPBAQTSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:ZYOKWTFVIWCSCJ-CABZTGNLSA-N
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Compound Information
Molecular Weight:432.2776
Molecular Formula:C21H22IP
InChIKey:HHBXWXJLQYJJBW-UHFFFAOYSA-M
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Compound Information
Molecular Weight:204.3511
Molecular Formula:C15H24
InChIKey:XUTBNOJXXIWRCB-WFASDCNBSA-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:78.133
Molecular Formula:C2H6OS
InChIKey:IAZDPXIOMUYVGZ-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:310.0464
Molecular Formula:C6F10O3
InChIKey:Not Available
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Compound Information
Molecular Weight:614.4116
Molecular Formula:C27H21F10O3P
InChIKey:UHJBUFSBYUEAJR-UHFFFAOYSA-M
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Compound Information
Molecular Weight:90.073
Molecular Formula:C4H3LiS
InChIKey:Not Available
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Compound Information
Molecular Weight:256.235
Molecular Formula:C10H9F5S
InChIKey:JXFWADFBMWDSQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.0314
Molecular Formula:C4F6O3
InChIKey:QAEDZJGFFMLHHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:514.3966
Molecular Formula:C25H21F6O3P
InChIKey:KHVZYZHZSKXPSJ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:206.228
Molecular Formula:C9H9F3S
InChIKey:QILTZQCHGQTRGE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.0993
Molecular Formula:C5H6O3
InChIKey:SYPLUFBJMSFMTN-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:182.2594
Molecular Formula:C11H18O2
InChIKey:ITNHSNMLIFFVQC-BDAKNGLRSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:KVAJOLKSQLKPHT-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:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:360.4871
Molecular Formula:C22H32O4
InChIKey:OGYMASQTERCZQQ-VLFIBQBSSA-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:99.1062
Molecular Formula:C5H6FN
InChIKey:Not Available
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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:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:376.2037
Molecular Formula:C10H12Cr2N2O7
InChIKey:LMYWWPCAXXPJFF-UHFFFAOYSA-P
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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:316.4345
Molecular Formula:C20H28O3
InChIKey:QPBAITGYXGUCGL-FKOZTGTQSA-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:142.218
Molecular Formula:C8H19Al
InChIKey:AZWXAPCAJCYGIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:NEFLTGMRGQSVHM-VHSXEESVSA-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:212.019
Molecular Formula:C7H5BF3KO
InChIKey:PEWVRVCGAOIWBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.099
Molecular Formula:C10H11BF3K
InChIKey:VWXCFKQVPQRAGH-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:86.1754
Molecular Formula:C6H14
InChIKey:VLKZOEOYAKHREP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.3535
Molecular Formula:C17H20N2O
InChIKey:HBSBTJBBPSOFGF-YTTRVJOFSA-N
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Compound Information
Molecular Weight:294.4338
Molecular Formula:C20H26N2
InChIKey:VTWSFNLQLFVLQV-KOQQBVACSA-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:268.4363
Molecular Formula:C20H28
InChIKey:MPJHIHRWZWHGCI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:JWUJQDFVADABEY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.1678
Molecular Formula:C7H12O4
InChIKey:MBZCXOZTJSRAOQ-HVYQYDHPSA-N
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Compound Information
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:MLUIQFVRBUSZRD-BDAKNGLRSA-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:138.2055
Molecular Formula:CK2O3
InChIKey:BWHMMNNQKKPAPP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:XEKOWRVHYACXOJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:424.4449
Molecular Formula:C20H28N2O8
InChIKey:LOXFXXGTOVWWQV-YKRRISCLSA-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:159.2261
Molecular Formula:C8H17NO2
InChIKey:AYXYPKUFHZROOJ-ZETCQYMHSA-N
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Compound Information
Molecular Weight:23.948
Molecular Formula:HLiO
InChIKey:WMFOQBRAJBCJND-UHFFFAOYSA-M
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Compound Information
Molecular Weight:140.43
Molecular Formula:H2O2Pd
InChIKey:NXJCBFBQEVOTOW-UHFFFAOYSA-L
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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: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:258.4017
Molecular Formula:C17H26N2
InChIKey:FYRRRTOAPSDPRH-LDADJPATSA-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:70.0898
Molecular Formula:C4H6O
InChIKey:VDOKWPVSGXHSNP-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:213.06
Molecular Formula:C10H6Cl2O
InChIKey:JQIUAKCMZXIOFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.06
Molecular Formula:C10H6Cl2O
InChIKey:OJXWQUDNDIYHMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1699
Molecular Formula:C10H8O
InChIKey:IVOQFIKQFGCRBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.277
Molecular Formula:AgZn
InChIKey:BSWGGJHLVUUXTL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.2046
Molecular Formula:C6H16N2
InChIKey:KWYHDKDOAIKMQN-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:170.2503
Molecular Formula:C13H14
InChIKey:WAWFNXPTYHQDNI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2503
Molecular Formula:C13H14
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:217.2206
Molecular Formula:C12H11NO3
InChIKey:DBCJWPPQXWNERC-VQHVLOKHSA-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:273.327
Molecular Formula:C16H19NO3
InChIKey:USPUMSYUYMHTFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:301.24
Molecular Formula:C16H14OSe
InChIKey:KZDFLJOKJUKILX-LXOGZNDWSA-N
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Compound Information
Molecular Weight:343.32
Molecular Formula:C19H20OSe
InChIKey:CEPRXUYTHIJXIQ-KUHUBIRLSA-N
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Compound Information
Molecular Weight:239.17
Molecular Formula:C11H12OSe
InChIKey:QMEAAFLEDXCKBF-JYOAFUTRSA-N
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Compound Information
Molecular Weight:281.25
Molecular Formula:C14H18OSe
InChIKey:ZSKKSSQTXXHCDR-YGRLFVJLSA-N
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Compound Information
Molecular Weight:301.24
Molecular Formula:C16H14OSe
InChIKey:BHKMLZJPTIQQSB-VBKFSLOCSA-N
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Compound Information
Molecular Weight:343.32
Molecular Formula:C19H20OSe
InChIKey:PFRVLTWTQGPREX-IEBWSBKVSA-N
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Compound Information
Molecular Weight:363.31
Molecular Formula:C21H16OSe
InChIKey:VXFSHDIVUKTRMX-SILNSSARSA-N
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Compound Information
Molecular Weight:405.39
Molecular Formula:C24H22OSe
InChIKey:DHWAGRAKULRLSZ-QPPBQGQZSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:RGACABDFLVLVCT-CMDGGOBGSA-N
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Compound Information
Molecular Weight:232.3181
Molecular Formula:C15H20O2
InChIKey:AQLXJTQYDLNJRA-OLZOCXBDSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:CAXIQKXPSQYDIR-CMDGGOBGSA-N
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Compound Information
Molecular Weight:216.3187
Molecular Formula:C15H20O
InChIKey:YYINYJXMFWIRAR-OLZOCXBDSA-N
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Compound Information
Molecular Weight:141.2108
Molecular Formula:C8H15NO
InChIKey:IYIAYDOBDLJVRC-AATRIKPKSA-N
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Compound Information
Molecular Weight:183.2905
Molecular Formula:C11H21NO
InChIKey:YOVWHEJLCBCQND-BDAKNGLRSA-N
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Compound Information
Molecular Weight:166.604
Molecular Formula:C9H7ClO
InChIKey:WOGITNXCNOTRLK-VOTSOKGWSA-N
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Compound Information
Molecular Weight:208.684
Molecular Formula:C12H13ClO
InChIKey:FEXVYFQXMAJBIL-ZJUUUORDSA-N
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Compound Information
Molecular Weight:244.2411
Molecular Formula:C11H16O6
InChIKey:IUMZIORBHMYPIM-ZETCQYMHSA-N
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Compound Information
Molecular Weight:286.3209
Molecular Formula:C14H22O6
InChIKey:PTDREFYBQAOTSA-RKDXNWHRSA-N
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