(R)-(+)-4-Methylmandelonitrile

Base Information

• Chemical Name: (R)-(+)-4-Methylmandelonitrile
• CAS No.: 10017-04-6
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 2926909090
• European Community (EC) Number: 623-367-4
• DSSTox Substance ID: DTXSID20429456
• Nikkaji Number: J74.260K
• Wikidata: Q76393908
• Mol file: 10017-04-6.mol

Synonyms:(R)-(+)-4-Methylmandelonitrile;10017-04-6;(2R)-2-HYDROXY-2-(4-METHYLPHENYL)ACETONITRILE;Benzeneacetonitrile, alpha-hydroxy-4-methyl-, (alphaR)-;(r)-4-methylmandelonitrile;(+)-p-Methyl-D-mandelonitrile;DTXSID20429456;(R)-2-hydroxy-2-p-tolylacetonitrile;AKOS024386624;(R)-(+)-4-Methylmandelonitrile, 97%;J-000060

Chemical Property of (R)-(+)-4-Methylmandelonitrile

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 52-58 °C(lit.)
• Refractive Index: 1.56
• Boiling Point: 300.029 °C at 760 mmHg
• Flash Point: 135.253 °C
• PSA: 44.02000
• Density: 1.13 g/cm³
• LogP: 1.55198
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-4-Methylmandelonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(C#N)O
• Isomeric SMILES: CC1=CC=C(C=C1)[C@H](C#N)O
• Uses: Useful intermediate in the preparation of optically active α-hydroxy carboxylic acids, α-hydroxy aldehydes, α-hydroxy ketones, and 2-amino alcohols.

Technology Process of (R)-(+)-4-Methylmandelonitrile

There total 36 articles about (R)-(+)-4-Methylmandelonitrile 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: 99.0%

4-methyl-benzaldehyde (104-87-0) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → (S)-2-hydroxy(4-methylphenyl)acetonitrile (4815-10-5,10017-04-6,58634-14-3,105452-15-1)

Guidance literature:

In di-isopropyl ether; at 5 ℃; for 99h; Sorghum bicolor shoots oxynitrilase, 0.1 M tartrate buffer, pH 5.4;

DOI:10.1016/0957-4166(96)00116-4

Reference yield: 94.0%

hydrogen cyanide (74-90-8) + 4-methyl-benzaldehyde (104-87-0) → 2-hydroxy-2-p-tolylacetonitrile (10017-04-6)

Guidance literature:

With hydroxynitrile lyase isozyme 5 from Prunus communis; In tert-butyl methyl ether; at 25 ℃; for 7h; pH=5; Enzymatic reaction;

DOI:10.1002/adsc.201601332

Reference yield: 90.0%

trimethylsilyl cyanide (7677-24-9) + 4-methyl-benzaldehyde (104-87-0) → (S)-2-hydroxy(4-methylphenyl)acetonitrile (4815-10-5,10017-04-6,58634-14-3,105452-15-1)

Guidance literature:

trimethylsilyl cyanide; 4-methyl-benzaldehyde; With cyanex-921; C₄₆H₅₄AlN₂O₂⁽¹⁺⁾*Cl^(1-); In dichloromethane; at 10 ℃; for 12h;

With hydrogenchloride; In water; at 20 ℃; for 4h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/ejoc.200701161

upstream raw materials:

hydrogen cyanide

4-methyl-benzaldehyde

trimethylsilyl cyanide

2-hydroxy-2-methylpropanenitrile

Downstream raw materials:

(R)-(-)-1-cyano-1-(4-methylphenyl)methyl acetate

C₁₈H₁₇NO₃

C₁₈H₁₇NO₃

(S)-2-acetyloxy-2-(4-methylphenyl)acetonitrile

Refernces

• 1、 Ma Moreno, Rosa,Rosol, Malgorzata,Moyano, Albert. "Salicylaldehyde Schiff bases derived from 2-ferrocenyl-2-amino alcohols. Part 1: New chiral ligands for the titanium-catalyzed enantioselective cyanation of aldehydes". . p. 1089 - 1103. Retrieved 2006.
• 2、 Hamashima, Yoshitaka,Sawada, Daisuke,Nogami, Hiroyuki,Kanai, Motomu,Shibasaki, Masakatsu. "Highly enantioselective cyanosilylation of aldehydes catalyzed by a Lewis acid-Lewis base bifunctional catalyst". . p. 805 - 814. Retrieved 2001.
• 3、 Zheng, Yu-Cong,Xu, Jian-He,Wang, Hui,Lin, Guo-Qiang,Hong, Ran,Yu, Hui-Lei. "Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications". . p. 1185 - 1193. Retrieved 2017.
• 4、 Solis, Aida,Luna, Hector,Perez, Herminia I.,Manjarrez, Norberto,Sanchez, Remedios,Gutierrez, Atilano. "(S)-naproxen as a derivatizing agent to determine enantiomeric excess of cyanohydrins by HPLC". . p. 8759 - 8762. Retrieved 1998.
• 5、 Wen, Ye Qian,Ren, Wei Min,Lu, Xiao Bing. "Highly active bifunctional salenTi(IV) catalysts for asymmetric cyanosilylation of aldehydes and TMSCN". . p. 1285 - 1288. Retrieved 2011.
• 6、 Kim, Sung Soo,Song, Dae Ho. "Asymmetric cyanohydrin synthesis catalyzed by Al(salen)/triphenylphosphane oxide". . p. 1777 - 1780. Retrieved 2005.
• 7、 Tan, Chunxia,Han, Xing,Li, Zijian,Liu, Yan,Cui, Yong. "Controlled Exchange of Achiral Linkers with Chiral Linkers in Zr-Based UiO-68 Metal-Organic Framework". supporting information. p. 16229 - 16236. Retrieved 2018/11/27.
• 8、 Thomas, Juliana Christina,Aggio, Bruno Bernardi,Marques de Oliveira, Alfredo Ricardo,Piovan, Leandro. "High-Throughput Preparation of Optically Active Cyanohydrins Mediated by Lipases". . p. 5964 - 5970. Retrieved 2016/12/26.