Standard Article

Acetone Cyclohexylimine

  1. Norbert De Kimpe

Published Online: 15 APR 2001

DOI: 10.1002/047084289X.ra015

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

De Kimpe, N. 2001. Acetone Cyclohexylimine. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. University of Gent, Belgium

Publication History

  1. Published Online: 15 APR 2001

Chemistry Terms

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Abstract

original image

[6407-36-9] C9H17N (MW 139.24)

(acetonyl equivalent via lithiation and reaction with electrophiles;1 mild directed aldol condensation;2 Pd-catalyzed α-arylation of ketones3)

Alternate Name:N-(2-propylidene)cyclohexylamine.

Physical Data: bp 180.6 °C,4 70–72 °C/16 mmHg,5 30 °C/1.8 mmHg;6 nD 20 1.4671.

Solubility: sol most organic solvents.

Form Supplied in: colorless liquid; not commercially available.

Analysis of Reagent Purity: GC; 1H NMR; IR (presence of ketone by hydrolysis).

Preparative Methods: condensation of Acetone with cyclohexylamine with or without various solvents (eq 1).4-7 The removal of water is performed afterwards with solid Sodium Hydroxide.4

original image(1)

Handling, Storage, and Precautions: very sensitive to hydrolysis; storage in closed vessels under inert atmosphere in the refrigerator. It is recommended to prepare the reagent freshly before each preparation. After some weeks of storage, purification by distillation is recommended. Use in a fume hood.

Featured Compounds

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  1. 1 - 113
Compound Information
Molecular Weight:179.2004
Molecular Formula:C6H18N3OP
InChIKey:GNOIPBMMFNIUFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2818
Molecular Formula:C16H14O
InChIKey:KCHQXPGUJBVNTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:328.331
Molecular Formula:C17H30BrN
InChIKey:PKRYPOVDFVGFPO-HTXNQAPBSA-N
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Compound Information
Molecular Weight:207.108
Molecular Formula:C8H15BrO
InChIKey:WGZAECCGCXUTDD-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:62.134
Molecular Formula:C2H6S
InChIKey:QMMFVYPAHWMCMS-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:178.315
Molecular Formula:C7H14OS2
InChIKey:GXFHOTQQXGFGQO-VOTSOKGWSA-N
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Compound Information
Molecular Weight:155.2374
Molecular Formula:C9H17NO
InChIKey:XKDFASKYYITIKW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.45
Molecular Formula:CuI
InChIKey:LSXDOTMGLUJQCM-UHFFFAOYSA-M
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Compound Information
Molecular Weight:79.07
Molecular Formula:C4H10LiN
InChIKey:AHNJTQYTRPXLLG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.3709
Molecular Formula:C14H27N
InChIKey:KHPMGJKNMKIMDO-SQFISAMPSA-N
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Compound Information
Molecular Weight:99.1741
Molecular Formula:C6H13N
InChIKey:UCJOAMOXKLJGST-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:VBCIOOKAKHGVMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:NAXZOZQQIIMORY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.631
Molecular Formula:C7H13ClO
InChIKey:ZWXFUUDOIJKOOD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.941
Molecular Formula:C5H10Br2
InChIKey:IBODDUNKEPPBKW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:ZPQAKYPOZRXKFA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:103.1213
Molecular Formula:C7H5N
InChIKey:JFDZBHWFFUWGJE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:ZHMCDZHVHDFSHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2173
Molecular Formula:C13H9N
InChIKey:DZBUGLKDJFMEHC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1998
Molecular Formula:C10H10N2
InChIKey:WJFCMLXARVNIJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:QCCDLTOVEPVEJK-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:193.082
Molecular Formula:C7H13BrO
InChIKey:OBHYAAHXAGULJT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.098
Molecular Formula:C7H15Br
InChIKey:LSXKDWGTSHCFPP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.008
Molecular Formula:C6H5Br
InChIKey:QARVLSVVCXYDNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.524
Molecular Formula:C3H5ClO
InChIKey:BULLHNJGPPOUOX-UHFFFAOYSA-N
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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:170.2918
Molecular Formula:C11H22O
InChIKey:KYWIYKKSMDLRDC-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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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:262.2855
Molecular Formula:C18H15P
InChIKey:RIOQSEWOXXDEQQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.3272
Molecular Formula:C13H23NO2
InChIKey:DRTQDGZZJMNBJM-KAMYIIQDSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:RTYRONIMTRDBLT-ONEGZZNKSA-N
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Compound Information
Molecular Weight:54.0904
Molecular Formula:C4H6
InChIKey:KAKZBPTYRLMSJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.914
Molecular Formula:C4H8Br2
InChIKey:ULTHEAFYOOPTTB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.061
Molecular Formula:C8H9Br
InChIKey:WMPPDTMATNBGJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.238
Molecular Formula:C9H17N
InChIKey:VMRJRAGKPXMWOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.2487
Molecular Formula:C10H17N
InChIKey:CQWOPAPYPLHGQM-KHPPLWFESA-N
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Compound Information
Molecular Weight:282.5044
Molecular Formula:C19H38O
InChIKey:YUPOCHDBBHTUBJ-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:283.3633
Molecular Formula:C15H25NO4
InChIKey:ZQEDTIUQYVQXCF-WJDWOHSUSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:FDPIMTJIUBPUKL-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:98.143
Molecular Formula:C6H10O
InChIKey:RNDVGJZUHCKENF-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:114.1424
Molecular Formula:C6H10O2
InChIKey:OJVAMHKKJGICOG-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:185.49
Molecular Formula:C5H10BrCl
InChIKey:PHHNNDKXQVKJEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.551
Molecular Formula:C4H7Cl
InChIKey:OHXAOPZTJOUYKM-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:58.6934
Molecular Formula:Ni
InChIKey:PXHVJJICTQNCMI-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:96.1271
Molecular Formula:C6H8O
InChIKey:ZSBWUNDRDHVNJL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:DPLGXGDPPMLJHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.0437
Molecular Formula:C3N2O3
InChIKey:YNKDRTCJDFVUTJ-UHFFFAOYSA-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:97.994
Molecular Formula:C6H15B
InChIKey:LALRXNPLTWZJIJ-UHFFFAOYSA-N
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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:321.4559
Molecular Formula:C22H27NO
InChIKey:KHQNCKWCVRHVII-PTGBLXJZSA-N
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Compound Information
Molecular Weight:304.64
Molecular Formula:C10H14O4Pd
InChIKey:JKDRQYIYVJVOPF-FDGPNNRMSA-L
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Compound Information
Molecular Weight:39.0983
Molecular Formula:K
InChIKey:NPYPAHLBTDXSSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.395
Molecular Formula:C10H20O2S2
InChIKey:IHSZSVCFXXYMNH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:39.0123
Molecular Formula:H2NNa
InChIKey:ODZPKZBBUMBTMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:KVKYWBUAOJTLOF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.657
Molecular Formula:C8H15ClO
InChIKey:CAYDCGNFWIEGCY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:367.552
Molecular Formula:C21H42N3P
InChIKey:JFOJQNLSYJAJBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.674
Molecular Formula:C8H17Cl
InChIKey:CNDHHGUSRIZDSL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.286
Molecular Formula:C12H19N
InChIKey:XARZFGTWMIEILW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
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:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-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:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-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:193.125
Molecular Formula:C8H17Br
InChIKey:Not Available
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Compound Information
Molecular Weight:120.976
Molecular Formula:C3H5Br
InChIKey:BHELZAPQIKSEDF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.3593
Molecular Formula:C16H22N2
InChIKey:GVTJGMBIVDNGCB-AXPVVUDUSA-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:211.3006
Molecular Formula:C12H21NO2
InChIKey:PFMZXZYYDKQAOO-KTKRTIGZSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:DGMYRPFYNFQCHM-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:151.045
Molecular Formula:C5H11Br
InChIKey:YXZFFTJAHVMMLF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:ZAJNGDIORYACQU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.099
Molecular Formula:C10H22BN
InChIKey:AIKLMEVZUSOEDK-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:86.0892
Molecular Formula:C4H6O2
InChIKey:BAPJBEWLBFYGME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.3874
Molecular Formula:C12H22O2Si
InChIKey:FUJDSRJVDPEVPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.3281
Molecular Formula:C12H22N4O3
InChIKey:IUCRRJKNOYHPOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.4513
Molecular Formula:C17H34O
InChIKey:WTJKUFMLQFLJOT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.2368
Molecular Formula:C9H17NO2
InChIKey:ZAVUHLXZFYNAMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2526
Molecular Formula:C9H18N2
InChIKey:HNEUCJXPPJPDCS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:YCIXWYOBMVNGTB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.975
Molecular Formula:C3H5BrO
InChIKey:VQFAIAKCILWQPZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.4448
Molecular Formula:C18H31NO
InChIKey:GOINHCSJFWIFTF-XDJHFCHBSA-N
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Compound Information
Molecular Weight:221.3816
Molecular Formula:C15H27N
InChIKey:HDELBDCKWIKVLL-OFALOCIGSA-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:240.297
Molecular Formula:C16H16O2
InChIKey:TWVOHPAOCXFGNY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.171
Molecular Formula:C9H16LiN
InChIKey:WYXLTYLPMDYGNX-VRTOBVRTSA-N
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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:108.524
Molecular Formula:C3H5ClO2
InChIKey:RIFGWPKJUGCATF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.463
Molecular Formula:C4H8BrCl
InChIKey:NIDSRGCVYOEDFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:FUSUHKVFWTUUBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.2221
Molecular Formula:C9H15N
InChIKey:NNGFTIABWNROGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.4552
Molecular Formula:C22H26N2
InChIKey:AVFJZRKRSCXUQZ-XQNSMLJCSA-N
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Compound Information
Molecular Weight:96.1034
Molecular Formula:C4H9NaO
InChIKey:MFRIHAYPQRLWNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:51.476
Molecular Formula:ClH2N
InChIKey:QDHHCQZDFGDHMP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.566
Molecular Formula:C7H5ClO3
InChIKey:NHQDETIJWKXCTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.2634
Molecular Formula:C10H19NO2
InChIKey:CWBUBKYPXOLPCF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1888
Molecular Formula:C6H14N2
InChIKey:XSBNZKOMEUOPFQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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