(R)-2-Hydroxy-2-cyclohexylacetonitrile

Base Information

• Chemical Name: (R)-2-Hydroxy-2-cyclohexylacetonitrile
• CAS No.: 100007-62-3
• Molecular Formula: C₈H₁₃NO
• Molecular Weight: 139.197
• European Community (EC) Number: 631-194-0
• DSSTox Substance ID: DTXSID60447114
• Nikkaji Number: J274.189J
• Wikidata: Q76416134
• Mol file: 100007-62-3.mol

Synonyms:(R)-2-Hydroxy-2-cyclohexylacetonitrile;100007-62-3;(2R)-2-cyclohexyl-2-hydroxyacetonitrile;(R)-Cyclohexylhydroxyacetonitrile;DTXSID60447114;AKOS006307444

Chemical Property of (R)-2-Hydroxy-2-cyclohexylacetonitrile

Chemical Property:

• PSA: 44.02000
• LogP: 1.45118
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 139.099714038
• Heavy Atom Count: 10
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

(R)-2-HYDROXY-2-CYCLOHEXYLACETONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C(C#N)O
• Isomeric SMILES: C1CCC(CC1)[C@H](C#N)O

Technology Process of (R)-2-Hydroxy-2-cyclohexylacetonitrile

There total 50 articles about (R)-2-Hydroxy-2-cyclohexylacetonitrile 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%

benzoyl cyanide (613-90-1) + cyclohexanecarbaldehyde (2043-61-0) → 2-cyclohexyl-2-hydroxyacetonitrile (100007-62-3,107485-34-7,4354-47-6)

Guidance literature:

With water; In hexane; dimethyl sulfoxide; at 20 ℃; for 24h;

DOI:10.1021/ol0348295

Reference yield: 100.0%

2-hydroxy-2-methylpropanenitrile (75-86-5) + cyclohexanecarbaldehyde (2043-61-0) → 2-cyclohexyl-2-hydroxyacetonitrile (100007-62-3,107485-34-7,4354-47-6)

Guidance literature:

With titanium(IV) isopropylate; for 44h; Ambient temperature;

DOI:10.1246/cl.1990.1171

Reference yield: 99.0%

trimethylsilyl cyanide (7677-24-9) + cyclohexanecarbaldehyde (2043-61-0) → 2-cyclohexyl-2-hydroxyacetonitrile (100007-62-3,107485-34-7,4354-47-6)

Guidance literature:

With P(i-PrNCH₂CH₂)N; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/j.tetlet.2005.09.032

upstream raw materials:

hydrogen cyanide

cyclohexanecarbaldehyde

sodium cyanide

2-hydroxy-2-methylpropanenitrile

Downstream raw materials:

(R)-(-)-hexahydromandelic acid

(-)-2-cyclohexyl-2-hydroxyethylamine

(R)-2-cyclohexyl-2-hydroxyacetonitrile

(S)-2-cyclohexyl-2-hydroxyacetonitrile

Refernces

• 1、 Scharfbier, Jonas,Hazrati, Hamideh,Irran, Elisabeth,Oestreich, Martin. "Copper-Catalyzed Substitution of α-Triflyloxy Nitriles and Esters with Silicon Nucleophiles under Inversion of the Configuration". . p. 6562 - 6565. Retrieved 2017.
• 2、 Griengl, Herfried,Klempier, Norbert,Poechlauer, Peter,Schmidt, Michael,Shi, Nongyuan,Zabelinskaja-Mackova, Antonina A.. "Enzyme catalysed formation of (S)-cyanohydrins derived from aldehydes and ketones in a biphasic solvent system". . p. 14477 - 14486. Retrieved 1998.
• 3、 Fossey, John S.,Richards, Christopher J.. "Catalysis of aldehyde and imine silylcyanation by platinum and palladium NCN-pincer complexes". . p. 8773 - 8776. Retrieved 2003.
• 4、 Bolles, Amanda K.,Fujiwara, Rina,Briggs, Erran D.,Nomeir, Amin A.,Furge, Laura Lowe. "Mechanism-Based inactivation of human cytochrome p450 3A4 by two piperazine-Containing compounds". . p. 1471 - 1475. Retrieved 2014.
• 5、 Uang, Biing-Jiun,Fu, I-Pin,Hwang, Chyuan-Der,Chang, Chun-Wei,Yang, Chun-Tzu,Hwang, Der-Ren. "Development of β-hydroxyamide/titanium complexes for catalytic enantioselective silylcyanation of aldehydes". . p. 10479 - 10486. Retrieved 2004.
• 6、 Hernandez, Liliana,Luna, Hector,Solis, Aida,Vazquez, Alfredo. "Application of crude preparations of leaves from food plants for the formation of cyanohydrins with high enantiomeric excesses". . p. 2813 - 2816. Retrieved 2006.
• 7、 Wang, Zhigang,Fetterly, Brandon,Verkade, John G. "P(MeNMCH2CH2)3N: An effective catalyst for trimethylsilycyanation of aldehydes and ketones". . p. 161 - 166. Retrieved 2002.
• 8、 Steele, Rebecca M.,Monti, Chiara,Gennari, Cesare,Piarulli, Umberto,Andreoli, Federico,Vanthuyne, Nicolas,Roussel, Christian. "Enantioselective cyanosilylation of aldehydes catalysed by a diastereomeric mixture of atropisomeric thioureas". . p. 999 - 1006. Retrieved 2006.
• 9、 Abiko, Atsushi,Wang, Guo-Qiang. "BMPD, a novel C2-chiral 1,3-diketone ligand; synthesis and application to an asymmetric catalytic reaction". . p. 11405 - 11420. Retrieved 1998.
• 10、 Chang, Chun-Wei,Yang, Chun-Tzu,Hwang, Chyuan-Der,Uang, Biing-Jiun. "1,2-Diphenylethylenediamine linked chiral Ti(IV) complex - A new entry to the highly enantioselective silylcyanation of aliphatic and aromatic aldehydes". . p. 54 - 55. Retrieved 2002.