(R)-A-HYDROXY-1-CYCLOHEXENE-1-ACETONITRILE

Base Information

• Chemical Name: (R)-A-HYDROXY-1-CYCLOHEXENE-1-ACETONITRILE
• CAS No.: 148705-96-8
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.181
• Mol file: 148705-96-8.mol

Synonyms:(R)-A-HYDROXY-1-CYCLOHEXENE-1-ACETONITRILE;(R)-mhydroxy-1-cyclohexene-1-acetonitrile;(R)-α-hydroxy-1-cyclohexene-1-acetonitrile

Chemical Property of (R)-A-HYDROXY-1-CYCLOHEXENE-1-ACETONITRILE

Chemical Property:

• Boiling Point: 271.9±28.0 °C(Predicted)
• PKA: 11.65±0.20(Predicted)
• PSA: 44.02000
• Density: 1.104±0.06 g/cm3(Predicted)
• LogP: 1.37128

Purity/Quality:

99% ^*data from raw suppliers

(R)-ALPHA-HYDROXY-1-CYCLOHEXENE-1-ACETONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-A-HYDROXY-1-CYCLOHEXENE-1-ACETONITRILE

There total 4 articles about (R)-A-HYDROXY-1-CYCLOHEXENE-1-ACETONITRILE 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:

1-cyclohexene-1-carboxaldehyde (1192-88-7) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → (2S)-2-cyclohexenyl-2-hydroxyacetonitrile + (+)-(αR)-α-hydroxycyclohex-1-eneacetonitrile (148705-96-8)

Guidance literature:

With Prunus mume (R)-hydroxynitrile lyase; Na-citrate buffer; In di-isopropyl ether; at 25 ℃; for 21h; pH=4.0; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2006.02.003

Reference yield:

methyl cyclohex-1-ene-1-carboxylate (18448-47-0) → (+)-(αR)-α-hydroxycyclohex-1-eneacetonitrile (148705-96-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / DIBAL / diethyl ether / 1.) -70 deg C, 1 h, 2.) -70 -> -30 deg C, 1 h

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 1 h, 2.) CH₂Cl₂, -20 deg C, 2 h

3: 13.7 g / R-oxynitrilase (E_.C_. 4.1.2.10) / various solvent(s) / 20 h

With oxalyl dichloride; R-oxynitrilase (E_.C_. 4.1.2.10); diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In diethyl ether;

Reference yield:

1-cyclohexene-1-methanol (4845-04-9) → (+)-(αR)-α-hydroxycyclohex-1-eneacetonitrile (148705-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 1 h, 2.) CH₂Cl₂, -20 deg C, 2 h

2: 13.7 g / R-oxynitrilase (E_.C_. 4.1.2.10) / various solvent(s) / 20 h

With oxalyl dichloride; R-oxynitrilase (E_.C_. 4.1.2.10); dimethyl sulfoxide; triethylamine; In various solvent(s);

upstream raw materials:

hydrogen cyanide

1-cyclohexene-1-carboxaldehyde

2-hydroxy-2-methylpropanenitrile

methyl cyclohex-1-ene-1-carboxylate

Downstream raw materials:

methyl (-)-(αR)-α-hydroxycyclohex-1-eneacetate

methyl (+)-(αS)-α-hydroxycyclohex-1-eneacetate