71079-03-3

Basic information

• Product Name: 2-AMINO-2-(4-BROMOPHENYL)ACETIC ACID
• Synonyms: AMINO(4-BROMOPHENYL)ACETIC ACID;2-AMINO-2-(4-BROMOPHENYL)ACETIC ACID;2-(4-Bromophenyl)glycine;α-Amino-4-bromobenzeneacetic acid;RS-4-Bromophenylglycine
• CAS NO: 71079-03-3
• Molecular Formula: C₈H₈BrNO₂
• Molecular Weight: 230.06
• Product Categories: pharmacetical
• Mol File: 71079-03-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 273-274°
• Boiling Point: 363.2 °C at 760 mmHg
• Flash Point: 173.5 °C
• Appearance: /
• Density: 1.673g/cm³
• Vapor Pressure: 6.51E-06mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.81±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-2-(4-BROMOPHENYL)ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-2-(4-BROMOPHENYL)ACETIC ACID(71079-03-3)
• EPA Substance Registry System: 2-AMINO-2-(4-BROMOPHENYL)ACETIC ACID(71079-03-3)

Safety Data

• Safety Statements: S22-24/25:
• HazardClass: IRRITANT
• Hazardous Substances Data: 71079-03-3(Hazardous Substances Data)

Usage

General Description

2-AMINO-2-(4-BROMOPHENYL)ACETIC ACID, also known as 4-Bromophenylglycine, is a chemical compound that belongs to the class of aromatic compounds known as phenylglycines. It is an amino acid derivative containing a 4-bromophenyl group that is attached to the C2 position of the glycine backbone. 2-AMINO-2-(4-BROMOPHENYL)ACETIC ACID is used in the synthesis of pharmaceuticals and organic compounds. It has potential activity as a herbicide and might also exhibit anticonvulsant properties. 2-AMINO-2-(4-BROMOPHENYL)ACETIC ACID can be found in a variety of natural sources, including foods and plants.

InChI:InChI=1/C8H8BrNO2/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7H,10H2,(H,11,12)/t7-/m1/s1

Upstream product

• 2835-06-5 phenylglycin 
• 60079-77-8 1-bromo-4-(1-bromo-1-methoxycarbonyl)toluene 
• 773837-37-9 sodium cyanide 
• 1122-91-4 4-bromo-benzaldehyde 
• 32549-34-1 1-(4-Bromophenyl)imidazolidine-2,4-dione 
• 7099-87-8 4-bromophenylglyoxylic acid 
• 6940-50-7 4-bromo-DL-mandelic acid 
• 67-66-3 chloroform 
• 2039-82-9 1-bromo-4-ethenyl-benzene 

Downstream Products

• 42718-15-0 methyl 2-amino-2-(4-bromophenyl)acetate 
• 917925-71-4 2-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)acetic acid 
• 42718-20-7 methyl 2-amino-2-(4-bromophenyl)acetate hydrochloride 
• 1312542-38-3 methyl 6-bromo-(1H)-isoindolin-1-one-3-carboxylate 
• 1452588-95-2 methyl 2-isocyano-2-(4-bromophenyl)acetate 
• 201403-02-3 (+/-)-2-amino-2-(4-bromophenyl)ethanol 
• 709665-73-6 methyl 2-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)acetate 

Relevant articles and documents

Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine

The transamination of α-keto acids with 2-phenylglycine is an effective methodology for directly synthesizing unprotected α-amino acids. However, the synthesis of 2-arylglycines by transamination is problematic because the corresponding products, 2-arylglycines, transaminate the starting arylglyoxylic acids. Herein, we demonstrate the use of commercially available l-2-(2-chlorophenyl)glycine as the nitrogen source in the transamination of arylglyoxylic acids, producing the corresponding 2-arylglycines without interference from the undesired self-transamination process.

Preparation method for D, L-phenylglycine and analogue thereof

The invention provides a preparation method for D, L-phenylglycine and an analogue thereof. According to the method, benzaldehyde, an analogue thereof and hydrocyanic acid are adopted as raw materials and subjected to cyanidation reaction, and then 2-hydroxy-benzyl cyanide or 2-hydroxy-benzyl cyanide analogue (cyanohydrin for short) is generated. Cyanohydrin reacts with carbon dioxide and the aqueous solution of ammonia, and then 5-phenyl-hydantoin and an analogue thereof (hydantoin for short) are generated. hydantoin is successively subjected to steam stripping, alkaline hydrolysis, steam stripping, decolorization, neutralization, crystallization, washing, centrifuging, drying and the like to obtain D, L-phenylglycine and the analogue thereof. Compared with the prior art, the preparation method for D, L-phenylglycine and the analogue thereof can significantly and effectively reduce the pollution, and fewer inorganic salt by-products are generated. Meanwhile, the prepared D, L-phenylglycine and the analogue thereof are high in product yield and high in purity. Counted in benzaldehyde and the analogue thereof, the yield of D, L-phenylglycine and the analogue thereof is larger than or equal to 96%, and the product purity is larger than or equal to 99%. Meanwhile, the process flow is simple and feasible, so that the method is worthy of market popularization and application.

Chemistry of unprotected amino acids in aqueous solution: Direct bromination of aromatic amino acids with bromoisocyanuric acid sodium salt under strong acidic condition

Brominations of unprotected aromatic amino acids such as phenylalanine, tyrosine, and glycine, with bromoisocyanuric acid mono sodium salt (BICA-Na) were conducted in 60% aq. H2SO4 at 0°C to give a mixture of mono-brominated products in good yield. Unexpectedly, meta-bromophenylglycine was obtained as main product accompanied by ortho- and para-substituted products, while phenylalanine gave only ortho- and para-substituted products. Bromination of 2-phenylethylamine or benzylamine showed a tendency similar to the corresponding amino acids.