TRANS-2-CYANO-1-CYCLOHEXANOL

Base Information

• Chemical Name: TRANS-2-CYANO-1-CYCLOHEXANOL
• CAS No.: 125291-55-6
• Molecular Formula: C₇H₁₁NO
• Molecular Weight: 125.17
• Mol file: 125291-55-6.mol

Synonyms:

Chemical Property of TRANS-2-CYANO-1-CYCLOHEXANOL

Chemical Property:

• Melting Point: 46-49?°C
• Boiling Point: 87 °C

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

Useful:

Technology Process of TRANS-2-CYANO-1-CYCLOHEXANOL

There total 97 articles about TRANS-2-CYANO-1-CYCLOHEXANOL 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%

cyclohexane-1,2-epoxide (286-20-4) → trans-2-cyanocyclohexanol (63301-31-5,125291-55-6)

Guidance literature:

With sodium cyanide; zirconium tetrakis(dodecyl sulfate); In water; at 20 ℃; for 6h;

DOI:10.1002/hlca.200900239

Reference yield: 97.0%

sodium cyanide (773837-37-9) + cyclohexane-1,2-epoxide (286-20-4) → trans-2-cyanocyclohexanol (63301-31-5,125291-55-6)

Guidance literature:

With silica-bound 3-{2-[poly(ethylene glycol)]ethyl}-substituted 1-methyl-1H-imidazol-3-ium bromide; In water; at 90 ℃; for 0.75h; regioselective reaction;

DOI:10.1002/hlca.201200192

Reference yield: 96.0%

2-cyanocyclohexanone (4513-77-3) → cis-(1S,2S)-2-hydroxycyclohexane-1-carbonitrile (196801-10-2,125291-55-6)

Guidance literature:

With ketoreductase P₁-A₀₄; nicotinamide adenine dinucleotide phosphate; magnesium sulfate; isopropyl alcohol; In aq. phosphate buffer; at 30 ℃; for 24h; pH=7; stereoselective reaction; Enzymatic reaction;

DOI:10.1021/acs.orglett.6b01510

upstream raw materials:

2-cyanocyclohexanone

pimelonitrile

vinyl acetate

trans-2-cyanocyclohexanol

Downstream raw materials:

(1R,2S)-2-hydroxycyclohexane-1-carbonitrile

Butyric acid (1R,2S)-2-cyano-cyclohexyl ester

(1S,2R)-trans-2-hydroxycyclohexanecarbonitrile

trans-2-(trimethylsiloxy)-1-cyclohexanecarbonitrile

Refernces

• 1、 Clark,Ganem. "What about BOB? A synthetically useful protecting group". . p. 9523 - 9526. Retrieved 2000.
• 2、 Utczás, Margita,Székely, Edit,Forró, Enik,Szllsy, áron,Fül?p, Ferenc,Simándi, Béla. "Enzymatic resolution of trans-2-hydroxycyclohexanecarbonitrile in supercritical carbon dioxide". . p. 3916 - 3918. Retrieved 2011.
• 3、 Azizi, Najmedin,Qomi, Mahnaz,Saadat, Mostafa. "Greener and regioselective ring opening of epoxides with TMSCN using potassium salts of magnetic carbon nitride". . p. 1597 - 1602. Retrieved 2020/10/19.
• 4、 Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Rebolledo, Francisca. "Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles". supporting information. p. 3366 - 3369. Retrieved 2016/07/26.