1-Hydroxycyclohexanecarbonitrile

Base Information

• Chemical Name: 1-Hydroxycyclohexanecarbonitrile
• CAS No.: 931-97-5
• Molecular Formula: C7H11 N O
• Molecular Weight: 125.17
• European Community (EC) Number: 213-246-0
• NSC Number: 52190,14493
• UN Number: 2811
• UNII: ON43942N5P
• DSSTox Substance ID: DTXSID2024878
• Nikkaji Number: J48.538A
• Wikidata: Q27285744
• ChEMBL ID: CHEMBL1569015
• Mol file: 931-97-5.mol

Synonyms:1-Hydroxycyclohexanecarbonitrile;931-97-5;Cyclohexanone cyanohydrin;1-Hydroxy-1-cyclohexanecarbonitrile;1-hydroxycyclohexane-1-carbonitrile;1-Cyano-1-hydroxycyclohexane;Cyclohexanone, cyanohydrin;Cyclohexanecarbonitrile, 1-hydroxy-;1-Hydroxy-cyclohexanecarbonitrile;NSC 14493;NSC 52190;CCRIS 4608;1-Hydroxycycloheptanecarbonitrile;EINECS 213-246-0;BRN 1634973;UNII-ON43942N5P;AI3-37039;DTXSID2024878;ON43942N5P;NSC-14493;NSC-52190;4-10-00-00021 (Beilstein Handbook Reference);Cyclohexanoncyanhydrin;cyclohexanone cyanhydrin;SCHEMBL18010;1-Hydroxy-1-cyanocyclohexane;DTXCID304878;Cyclohexanone cyanohydrin, 98%;CHEMBL1569015;Cyclohexanecarbonitrile,1-hydroxy-;NSC14493;NSC52190;1-oxidanylcyclohexane-1-carbonitrile;Tox21_200377;1-hydroxy-cyclohexane-1-carbonitrile;MFCD00003818;AKOS009157962;LS-1952;SB84201;NCGC00091113-01;NCGC00091113-02;NCGC00257931-01;AC-18710;CAS-931-97-5;CS-0312430;FT-0633129;F53384;A844473;Q27285744

Chemical Property of 1-Hydroxycyclohexanecarbonitrile

Chemical Property:

• Appearance/Colour: Colourless solid. Typical sharp nitrile odor
• Vapor Pressure: 0.0113mmHg at 25°C
• Melting Point: 32-35ºC
• Refractive Index: 1.4693
• Boiling Point: 232.1 °C at 760 mmHg
• PKA: 11.45±0.20(Predicted)
• Flash Point: 112.1 °C
• PSA: 44.02000
• Density: 1.06 g/cm³
• LogP: 1.20518
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 125.084063974
• Heavy Atom Count: 9
• Complexity: 138
• Transport DOT Label: Poison

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cyclohexanone cyanohydrin 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 28
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(CC1)(C#N)O
• Uses: Cyclohexanone cyanohydrin was employed as substrate during high-throughput screening assay for hydroxynitrile lyase activity. It was used in preparation of 1-aminomethyl cyclohexanol via catalytic hydrogenation reaction.

Technology Process of 1-Hydroxycyclohexanecarbonitrile

There total 22 articles about 1-Hydroxycyclohexanecarbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 1-hydroxy-1-cyclohexanecarbonitrile (931-97-5)

Guidance literature:

With Hevea brasiliensis (S)-hydroxynitrile lyase; pH=4.5; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.tetlet.2012.02.025

Reference yield: 95.0%

potassium cyanide + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1-hydroxy-1-cyclohexanecarbonitrile (931-97-5)

Guidance literature:

With carbon dioxide; In ethanol; at 20 ℃; for 18h; under 760.051 Torr; Sealed tube;

DOI:10.1002/chem.202003623

Reference yield: 94.0%

trimethylsilyl cyanide (7677-24-9) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1-hydroxy-1-cyclohexanecarbonitrile (931-97-5) + 1-trimethylsilanyloxycyclohexanecarbonitrile (24731-36-0)

Guidance literature:

With trimethylsilyl bis(trifluoromethanesulfonyl)imide; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1080/00397919608003546

upstream raw materials:

1,4-dioxane

hydrogen cyanide

cyclohexanone

ethanol

Downstream raw materials:

1-tetrahydropyran-2-yloxy-cyclohexanecarbonitrile

1-hydroxy-cyclohexanecarboxylic acid

1-cyano-1-(cyclohexylamino)cyclohexane

1-(1-Cyanohexyl)-2-phenylhydrazine

Refernces

• 1、 Aman, Hasil,Chiu, Wei-Hua,Chuang, Gary Jing,Liu, Pin-Heng. "Radical-mediated aerobic oxidation of substituted styrenes and stilbenes". . p. 20103 - 20106. Retrieved 2021/12/02.
• 2、 -. "SPIRO-OXAZOLONES". Page/Page column 75. . Retrieved 2015/09/28.