Standard Article

Acetone Oxime

  1. Steven M. Weinreb,
  2. Kristina Borstnik

Published Online: 17 SEP 2007

DOI: 10.1002/047084289X.rn00765

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Weinreb, S. M. and Borstnik, K. 2007. Acetone Oxime. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. The Pennsylvania State University, University Park, PA, USA

Publication History

  1. Published Online: 17 SEP 2007

Chemistry Terms

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Abstract

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[127-06-0] C3H7NO (MW 73.09)

(a useful reagent for synthesis of isoxazoles and isoxazolidines; useful as an acetone equivalent for regiospecific C-alkylations)

Alternate Names:propan-2-one oxime, acetoxime.

Physical Data: mp 60–63 °C.

Solubility: soluble in most commonly used organic solvents.

Form Supplied in: white crystalline solid, widely available.

Preparative Method: most commonly synthesized by condensation of acetone with hydroxylamine hydrochloride.

Purification:1 solid can be recrystallized from petroleum ether, hexane, or can be sublimed.

Handling, Storage, and Precautions: sensitive to moisture; toxic by inhalation, in contact with skin, and if swallowed; may cause eye irritation.

Featured Compounds

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  1. 1 - 93
Compound Information
Molecular Weight:168.62
Molecular Formula:C9H9ClO
InChIKey:MFEILWXBDBCWKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.157
Molecular Formula:C6H11NO2
InChIKey:NCDNFHWIOCHUCL-UHFFFAOYSA-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:150.1745
Molecular Formula:C9H10O2
InChIKey:FQYUMYWMJTYZTK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:257.91
Molecular Formula:C5H9Cl4OP
InChIKey:VCEOWQZKUHULFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.248
Molecular Formula:C7H13NO3S
InChIKey:MUGRINGJVKYRLF-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:384.4257
Molecular Formula:C21H24N2O5
InChIKey:HYBXGOLOTGYCFR-IBGZPJMESA-N
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Compound Information
Molecular Weight:282.139
Molecular Formula:C2F6O5S2
InChIKey:WJKHJLXJJJATHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:22.98976928
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.9656
Molecular Formula:C2H5I
InChIKey:HVTICUPFWKNHNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.2111
Molecular Formula:C11H11NO
InChIKey:XFULVODBWSWOSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:235.97
Molecular Formula:C6H5BrSe
InChIKey:LCEFEIBEOBPPSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1124
Molecular Formula:C7H5FO
InChIKey:UOQXIWFBQSVDPP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:111.1418
Molecular Formula:C6H9NO
InChIKey:ZTDOHELHTVFODB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.2749
Molecular Formula:C6H15NOSi
InChIKey:JCLDHSJRFHTTHR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:PXAJQJMDEXJWFB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:64.055
Molecular Formula:C4H9Li
InChIKey:MZRVEZGGRBJDDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-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:275.113
Molecular Formula:C8H17Cl2N2O2P
InChIKey:MPZPJTUBYMCSAO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.3468
Molecular Formula:C15H22N2O3
InChIKey:BTVIHDWRYHCUSR-SDDRHHMPSA-N
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Compound Information
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:UMKGZMUPBGXRAO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:253.2958
Molecular Formula:C16H15NO2
InChIKey:JRQGXDVKAWWZRB-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:191.248
Molecular Formula:C7H13NO3S
InChIKey:RSESMDLDCOSXKT-LURJTMIESA-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:118.154
Molecular Formula:C4H6O2S
InChIKey:AFOSIXZFDONLBT-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:187.1931
Molecular Formula:C8H13NO4
InChIKey:FIMGZHKFJMGJES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.2683
Molecular Formula:C12H17NO3
InChIKey:BZEFIYJJIJBKMS-RAXLEYEMSA-N
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Compound Information
Molecular Weight:299.03
Molecular Formula:Cl5Sb
InChIKey:VMPVEPPRYRXYNP-UHFFFAOYSA-I
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Compound Information
Molecular Weight:454.4365
Molecular Formula:C28H24O2P2
InChIKey:IGVYKSIFKBGMFP-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:290.05
Molecular Formula:C12H28Sn
InChIKey:Not Available
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Compound Information
Molecular Weight:40.0639
Molecular Formula:C3H4
InChIKey:IYABWNGZIDDRAK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:OHLUUHNLEMFGTQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.2429
Molecular Formula:C11H15NO
InChIKey:XIEHRWVAKRNEOG-BENRWUELSA-N
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Compound Information
Molecular Weight:179.219
Molecular Formula:C9H13N3O
InChIKey:SVYOXGGTMYRMLN-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:37.833
Molecular Formula:BH4Na
InChIKey:YOQDYZUWIQVZSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.26
Molecular Formula:C13H19NOSe
InChIKey:FQFVMBGOUCNKEG-WCQYABFASA-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:58.6934
Molecular Formula:Ni
InChIKey:PXHVJJICTQNCMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:334.41
Molecular Formula:C16H14O4S2
InChIKey:MZRCSZMGBMHTJW-UHFFFAOYSA-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:100.1158
Molecular Formula:C5H8O2
InChIKey:JIGUQPWFLRLWPJ-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:407.504
Molecular Formula:C19H21NO5S2
InChIKey:WNKIKVQPEYSMBN-PKOBYXMFSA-N
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Compound Information
Molecular Weight:527.5303
Molecular Formula:C31H31NO3P2
InChIKey:BAUNYFIBYCOGIB-IGYGKHONSA-N
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Compound Information
Molecular Weight:102.1748
Molecular Formula:C6H14O
InChIKey:ZAFNJMIOTHYJRJ-UHFFFAOYSA-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:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1118
Molecular Formula:C7H4FN
InChIKey:GDHXJNRAJRCGMX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.219
Molecular Formula:C9H13N3O
InChIKey:XOHDHYYZLIUDBN-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:108.642
Molecular Formula:C3H9ClSi
InChIKey:IJOOHPMOJXWVHK-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:170.593
Molecular Formula:C8H7ClO2
InChIKey:Not Available
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Compound Information
Molecular Weight:269.2192
Molecular Formula:C13H10F3NO2
InChIKey:QGSKMWHHFBIKRS-GFCCVEGCSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:XTXRWKRVRITETP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:269.3367
Molecular Formula:C14H23NO4
InChIKey:NESNGXUQCAJWNN-GARJFASQSA-N
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Compound Information
Molecular Weight:200.2084
Molecular Formula:C13H9FO
InChIKey:DWFDQVMFSLLMPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:53.0626
Molecular Formula:C3H3N
InChIKey:NLHHRLWOUZZQLW-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:154.0964
Molecular Formula:C5H7NaO4
InChIKey:Not Available
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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:135.002
Molecular Formula:C4H7Br
InChIKey:AVMHMVJVHYGDOO-NSCUHMNNSA-N
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Compound Information
Molecular Weight:390.56
Molecular Formula:C3H6Cl6NSb
InChIKey:NMZBCXPKUJPSQP-UHFFFAOYSA-H
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Compound Information
Molecular Weight:155.2407
Molecular Formula:C8H17N3
InChIKey:LMDZBCPBFSXMTL-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:28.0101
Molecular Formula:CO
InChIKey:UGFAIRIUMAVXCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.202
Molecular Formula:C9H17O5P
InChIKey:HGUXWCBODIJKDZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1155.56
Molecular Formula:C72H60P4Pd
InChIKey:NFHFRUOZVGFOOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.3163
Molecular Formula:C15H19NO3
InChIKey:UKEQVZUQAYLCSG-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:126.583
Molecular Formula:C7H7Cl
InChIKey:KCXMKQUNVWSEMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.975
Molecular Formula:C3H5BrO
InChIKey:GKIPXFAANLTWBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:329.3472
Molecular Formula:C18H19NO5
InChIKey:CYYRLHUAMWRBHC-INIZCTEOSA-N
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Compound Information
Molecular Weight:141.1677
Molecular Formula:C7H11NO2
InChIKey:OVLPBLRLWIFGLB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2077
Molecular Formula:C8H12N4
InChIKey:OZAIFHULBGXAKX-VAWYXSNFSA-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:195.2167
Molecular Formula:C13H9NO
InChIKey:POCCWZYCZJRTQM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:98.078
Molecular Formula:H2O4S
InChIKey:QAOWNCQODCNURD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1353
Molecular Formula:C7H6N2O
InChIKey:NLMVYUBGWZWUGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:97.094
Molecular Formula:H3NO3S
InChIKey:IIACRCGMVDHOTQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.1305
Molecular Formula:C5H9NO2
InChIKey:GMZRHQOQCJMESC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:279.3067
Molecular Formula:C15H18FNO3
InChIKey:IRDDCOYQZAEWMD-UKTHLTGXSA-N
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Compound Information
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:DFLGWAFOSVGKKK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.559
Molecular Formula:C5H6ClNO3
InChIKey:PBTHMDPGQBXSLX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.1564
Molecular Formula:C6H11NO3
InChIKey:UEKRLIQRXMVTGC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.1407
Molecular Formula:C10H5F3O2
InChIKey:ABPAKMJTQTVEDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.926
Molecular Formula:C2Cl2O2
InChIKey:CTSLXHKWHWQRSH-UHFFFAOYSA-N
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