Mandelonitrile benzoate

Base Information

• Chemical Name: Mandelonitrile benzoate
• CAS No.: 4242-46-0
• Molecular Formula: C15H11NO2
• Molecular Weight: 237.258
• NSC Number: 121785
• Nikkaji Number: J99.778A
• ChEMBL ID: CHEMBL1714899
• Mol file: 4242-46-0.mol

Synonyms:Mandelonitrile benzoate;4242-46-0;Mandelonitrile, benzoate (ester);.alpha.-Cyanobenzyl benzoate;Benzeneacetonitrile, .alpha.-(benzoyloxy)-;MLS002707138;2-(Benzoyloxy)-2-phenylacetonitrile;[cyano(phenyl)methyl] benzoate;Benzeneacetonitrile, alpha-(benzoyloxy)- (9CI);alpha-Cyanobenzyl benzoate;NSC 121785;(cyano-phenylmethyl) benzoate;[Cyano(phenyl)methyl]benzoate;Cyano(phenyl)methyl benzoate #;SCHEMBL2453510;CHEMBL1714899;AXAACNNFMJZAGJ-UHFFFAOYSA-N;Benzoesaure-[a-cyan-benzyl]-ester;NSC121785;Benzoic acid, alpha-cyanobenzyl ester;NSC-121785;Benzeneacetonitrile, alpha-(benzoyloxy)-;NCGC00246725-01;SMR001574533

Chemical Property of Mandelonitrile benzoate

Chemical Property:

• Vapor Pressure: 1.29E-06mmHg at 25°C
• Boiling Point: 400.2°C at 760 mmHg
• Flash Point: 195.2°C
• PSA: 50.09000
• Density: 1.194g/cm³
• LogP: 3.10828
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 237.078978594
• Heavy Atom Count: 18
• Complexity: 319

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C#N)OC(=O)C2=CC=CC=C2

Technology Process of Mandelonitrile benzoate

There total 41 articles about Mandelonitrile benzoate 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: 95.0%

benzoyl cyanide (613-90-1) + benzaldehyde (100-52-7) → 1-cyanobenzyl benzoate (4242-46-0)

Guidance literature:

With titanium(IV) isopropylate; triethylamine; (S)-3,3'-bis[(diethylamino)methyl]-2,2'-dihydroxy-1,1'-binaphthalene; In tetrahydrofuran; at 20 ℃; for 0.75h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.07.006

Reference yield: 94.0%

potassium cyanide (151-50-8) + benzaldehyde (100-52-7) + benzoyl chloride (98-88-4) → 1-cyanobenzyl benzoate (4242-46-0)

Guidance literature:

With 18-crown-6 ether; In dichloromethane; Ambient temperature;

Reference yield: 88.0%

potassium hexacyanoferrate(II) + benzoyl chloride (98-88-4) → 1-cyanobenzyl benzoate (4242-46-0)

Guidance literature:

potassium hexacyanoferrate(II); benzoyl chloride; at 160 ℃; for 3h;

With tributylphosphine; In tetrahydrofuran; for 1h; Temperature; Reagent/catalyst; Time; Reflux;

DOI:10.1007/s11164-013-1421-8

upstream raw materials:

benzoyl cyanide

(RS)-mandelonitrile

hydrogen cyanide

Benzil dicyanohydrin

Downstream raw materials:

benzoic acid ethyl ester

benzoic acid benzyl ester

1,2-diphenyl-2-oxoethyl benzoate

2-ethoxy-2-oxo-1-phenylethyl benzoate

Refernces

• 1、 Marvel et al.. "-". . p. 34. Retrieved 1949.
• 2、 Dai, Ling,Yu, Shuling,Lv, Ningning,Ye, Xuanzeng,Shao, Yinlin,Chen, Zhongyan,Chen, Jiuxi. "Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles". supporting information. p. 5664 - 5668. Retrieved 2021/08/01.
• 3、 Zhang, Di,Song, Hao,Cheng, Na,Liao, Wei-Wei. "Synthesis of 2,4,5-Trisubstituted Oxazoles via Pd-Catalyzed C-H Addition to Nitriles/Cyclization Sequences". supporting information. p. 2745 - 2749. Retrieved 2019/04/30.