Mandelonitrile

Base Information

• Chemical Name: Mandelonitrile
• CAS No.: 532-28-5
• Deprecated CAS: 613-88-7
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.15
• Hs Code.: 2926 90 70
• European Community (EC) Number: 208-532-7
• NSC Number: 77668
• UN Number: 2810
• UNII: 584322E08A
• DSSTox Substance ID: DTXSID2025422
• Nikkaji Number: J6.985J
• Wikipedia: Mandelonitrile
• Wikidata: Q3844407
• Metabolomics Workbench ID: 123415
• ChEMBL ID: CHEMBL1393845
• Mol file: 532-28-5.mol

Synonyms:mandelonitrile;mandelonitrile, (+-)-isomer

Chemical Property of Mandelonitrile

Chemical Property:

• Appearance/Colour: yellow to brown liquid
• Vapor Pressure: 0.00156mmHg at 25°C
• Melting Point: -10 C
• Refractive Index: 1.5305 - 1.5335
• Boiling Point: 170 C (Decomposes)
• PKA: 10.50±0.20(Predicted)
• Flash Point: 97 ºC
• PSA: 44.02000
• Density: 1.117
• LogP: 1.24358
• Storage Temp.: Store below +30°C.
• Solubility.: alcohol: freely soluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 133.052763847
• Heavy Atom Count: 10
• Complexity: 141
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Mandelonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T:Toxic
• Statements: R23/24/25:
• Safety Statements: S24/25:; S45:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC=C(C=C1)C(C#N)O
• Uses: Mandelonitrile has been used to extract mandeloamide by the nitrilase variants.

Technology Process of Mandelonitrile

There total 71 articles about Mandelonitrile 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%

trimethylsilyl cyanide (7677-24-9) + benzaldehyde (100-52-7) → (RS)-mandelonitrile (532-28-5,613-88-7)

Guidance literature:

With Sc[(R)-BINOL]2Li; In toluene; at 20 ℃; for 2h;

DOI:10.1016/S0957-4166(01)00144-6

Reference yield: 98.0%

phenyl(trimethylsiloxy)acetonitrile (25438-37-3) → (RS)-mandelonitrile (532-28-5,613-88-7)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 2h;

DOI:10.1039/b900254e

Reference yield: 96.1%

benzaldehyde (100-52-7) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → (RS)-mandelonitrile (532-28-5,613-88-7)

Guidance literature:

In methanol; at 20 ℃; for 6h; Time;

upstream raw materials:

Benzil dicyanohydrin

ethanol

benzaldehyde

hydrogen cyanide

Downstream raw materials:

1-hydroxy-1,3-diphenylacetone

3,6-diphenyl-1,2,4,5-tetrazine

2-chloro-2-phenylacetonitrile

3,6-diphenylpyrazin-2(1H)-one

Refernces

• 1、 Yamagiwa, Noriyuki,Abiko, Yumi,Sugita, Mari,Tian, Jun,Matsunaga, Shigeki,Shibasaki, Masakatsu. "Catalytic asymmetric cyano-phosphorylation of aldehydes using a YLi3tris(binaphthoxide) complex (YLB)". . p. 566 - 573. Retrieved 2006.
• 2、 Rosenthaler. "-". . . Retrieved 1908.
• 3、 Li, Bo,Li, Yang,Qiu, Huayu,Xu, Jun,Yin, Shouchun,Zhang, Jinjin,Zhang, Pengfei,Zhang, Yueyue. "Constructing a triangular metallacycle with salen-Al and its application to a catalytic cyanosilylation reaction". supporting information. p. 10399 - 10402. Retrieved 2021/10/12.
• 4、 Sato, Eisuke,Fujii, Mayu,Tanaka, Hiroki,Mitsudo, Koichi,Kondo, Masaru,Takizawa, Shinobu,Sasai, Hiroaki,Washio, Takeshi,Ishikawa, Kazunori,Suga, Seiji. "Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis". supporting information. p. 16035 - 16044. Retrieved 2021/09/02.