2-Amino-2-(3-chlorophenyl)acetonitrile

Base Information

• Chemical Name: 2-Amino-2-(3-chlorophenyl)acetonitrile
• CAS No.: 93554-79-1
• Molecular Formula: C8H7 Cl N2
• Molecular Weight: 166.61
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID20458706
• Nikkaji Number: J2.127.440B
• Mol file: 93554-79-1.mol

Synonyms:2-amino-2-(3-chlorophenyl)acetonitrile;93554-79-1;AMINO(3-CHLOROPHENYL)ACETONITRILE;Benzeneacetonitrile, alpha-amino-3-chloro-;SCHEMBL5740427;DTXSID20458706;MHUPYXJSGAMNFY-UHFFFAOYSA-N;AKOS000123142;AKOS016051329;Benzeneacetonitrile, -amino-3-chloro-;alpha-Amino-3-chlorobenzeneacetonitrile;alpha-(3-chlorophenyl)-aminoacetonitrile;EN300-57899;AB01007422-01

Chemical Property of 2-Amino-2-(3-chlorophenyl)acetonitrile

Chemical Property:

• PSA: 49.81000
• LogP: 2.56368
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 166.0297759
• Heavy Atom Count: 11
• Complexity: 172

Purity/Quality:

AMINO(3-CHLOROPHENYL)ACETONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)Cl)C(C#N)N

Technology Process of 2-Amino-2-(3-chlorophenyl)acetonitrile

There total 7 articles about 2-Amino-2-(3-chlorophenyl)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: 89.0%

2-(3-chlorophenyl)-2-hydroxyacetonitrile (97070-75-2,122047-10-3,137766-66-6,53313-92-1) → alpha-amino-(3-chlorophenyl)acetonitrile (93554-79-1)

Guidance literature:

With titanium(IV) isopropylate; ammonia; In methanol; at 40 ℃; for 18h;

DOI:10.1021/acs.orglett.9b03194

Reference yield: 81.0%

trimethylsilyl cyanide (7677-24-9) + m-Chlorobenzaldehyde (587-04-2) → alpha-amino-(3-chlorophenyl)acetonitrile (93554-79-1)

Guidance literature:

m-Chlorobenzaldehyde; With ammonia; In methanol; at 20 ℃; for 2h;

trimethylsilyl cyanide; In methanol; at 20 ℃; for 2h;

Reference yield: 81.0%

m-Chlorobenzaldehyde (587-04-2) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → alpha-amino-(3-chlorophenyl)acetonitrile (93554-79-1)

Guidance literature:

m-Chlorobenzaldehyde; With lithium hexamethyldisilazane; In tetrahydrofuran; at 25 ℃; for 4h;

2-hydroxy-2-methylpropanenitrile; In tetrahydrofuran; at 25 ℃; for 12h;

DOI:10.1081/SCC-200043270

upstream raw materials:

potassium cyanide

m-Chlorobenzaldehyde

2-hydroxy-2-methylpropanenitrile

ammonium hydroxide

Downstream raw materials:

D‐3‐chlorophenylglycine

L‐3‐chlorophenylglycine

2-(3-chlorophenyl)glycine

α-amino-(3-chlorophenyl)acetonitrile hydrochloride

Refernces

• 1、 Li, Qing-Hua,Li, Zhao-Feng,Tao, Jing,Li, Wan-Fang,Ren, Li-Qing,Li, Qian,Peng, Yun-Gui,Liu, Tang-Lin. "Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia". supporting information. p. 8429 - 8433. Retrieved 2019/10/14.
• 2、 Singh, Rahulkumar Rajmani,Pawar, Samir Kundlik,Huang, Min-Jie,Liu, Rai-Shung. "Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides to yield 1-amino-1H-indenes". supporting information. p. 11434 - 11437. Retrieved 2016/09/23.