167024-66-0

Basic information

• Product Name: amino(4-bromophenyl)acetonitrile
• Synonyms: amino(4-bromophenyl)acetonitrile;BENZENEACETONITRILE, A-AMINO-4-BROMO-;OTAVA-BB 1125152
• CAS NO: 167024-66-0
• Molecular Formula: C₈H₇BrN₂
• Molecular Weight: 211.061
• Mol File: 167024-66-0.mol

Chemical Properties

• Boiling Point: 312.1 °C at 760 mmHg
• Flash Point: 142.6 °C
• Appearance: /
• Density: 1.549 g/cm³
• PKA: 4.83±0.10(Predicted)
• CAS DataBase Reference: amino(4-bromophenyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: amino(4-bromophenyl)acetonitrile(167024-66-0)
• EPA Substance Registry System: amino(4-bromophenyl)acetonitrile(167024-66-0)

Safety Data

• Hazardous Substances Data: 167024-66-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Amino(4-bromophenyl)acetonitrile is used as a building block in organic synthesis and pharmaceutical research. It is utilized in the production of various types of pharmaceuticals and other organic compounds due to its chemical reactivity and functional groups.
Used in Organic Synthesis:
Amino(4-bromophenyl)acetonitrile is used as a building block in organic synthesis, allowing for the creation of a wide range of organic compounds.
Safety Precautions:
Amino(4-bromophenyl)acetonitrile is handled with caution as it can be toxic and may pose health risks if not properly managed.

Upstream product

• 58289-69-3 2-(4-bromophenyl)-2-hydroxyacetonitrile 
• 773837-37-9 sodium cyanide 
• 1122-91-4 4-bromo-benzaldehyde 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Downstream Products

• 1132817-67-4 3-[4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,4-diazaspiro[4.4]non-3-en-2-one 
• 1132817-68-5 3-[4-(5-methyl-1H-imidazol-1-yl)phenyl]-1,4-diazaspiro[4.4]non-3-en-2-one 
• 1132817-32-3 2-{3-[4-(5-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,4-diazaspiro[4.4]non-3-en-1-yl}-N-[3-(trifluoromethyl)phenyl]acetamide 
• 1132817-33-4 2-{3-[4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,4-diazaspiro[4.4]non-3-en-1-yl}-N-[3-(trifluoromethyl)phenyl]acetamide 
• 950651-29-3 3-(4-bromophenyl)-1,4-diazaspiro[4.4]nonan-2-one 

Relevant articles and documents

Facile Access to 1,4-Disubstituted Pyrrolo[1,2- a ]pyrazines from α-Aminoacetonitriles

An efficient and practical synthetic protocol for the synthesis of 1,4-disubstituted pyrrolo[1,2- a ]pyrazine derivatives is described that originates from α-substituted pyrroloacetonitriles which, in turn, are readily available from aryl and alkyl aldehydes. The α-pyrroloacetonitriles were subjected to a Friedel-Crafts acylation with methyl chlorooxoacetate followed by reduction of the nitrile group under Pd-catalyzed hydrogenation conditions and finally aromatization with DDQ leading to the desired pyrrolo[1,2- a ]pyrazine derivatives. This method was generalized and successfully applied to various aryl, heteroaryl, and alkyl substrates. The developed protocol provides direct and convenient access to 1,4-disubstituted ring systems in moderate to good overall yields (51-68percent) without the need for purification of the intermediates. Further functionalization via the stepwise halogenation (bromination, iodination) and nitration was also demonstrated. In addition, the potential of the ester functionality for elaboration was demonstrated by manipulating into heterocyclic ring systems, exemplified by conversion into benzoxazole derivatives.

Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia

α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.

Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions

Gold-catalyzed oxidative couplings of two indoles and one α-cyano gold carbene to form bis(indolyl)methane derivatives are described. Two different indoles are compatible with these reactions to provide reasonable yields. A plausible mechanism is postulated to rationalize the experimental data including product distributions, D2O labeling, and the significant effects of gold catalysts and cyano groups.

Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides to yield 1-amino-1H-indenes

Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides yield 1-amino-1H-indenes in two distinct pathways; the success of these annulations relies on the high electrophilicity of α-cyano arylgold carbenes to activate an ionic pathway.

An efficient and scalable synthesis of the spirocyclic glycine transporter inhibitor GSK2137305

An efficient and scalable synthesis of a glycine transporter inhibitor is presented. The key steps in the synthetic sequence are the formation of a spirocyclic imidazolidinone from an -amino nitrile and a cyclic ketone and an arylation of 4-methyl imidazo

Development of a new α-aminonitrile synthesis

α-Aminonitriles are prepared upon reaction of aryl carboxaldehydes with LiHMDS and acetone cyanohydrin. This new method provides a general route to the synthesis of various substituted α-aminoarylacetonitriles in high yield and purity, and avoids the use of the highly toxic cyanide salts.