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

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

Downstream Products

• 42718-20-7 methyl 2-amino-2-(4-bromophenyl)acetate hydrochloride 
• 1312542-38-3 methyl 6-bromo-(1H)-isoindolin-1-one-3-carboxylate 
• 28115-12-0 N-(4-bromobenzylidene)-4-methoxyaniline 

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.

One-Pot Enantioselective Synthesis of d-Phenylglycines from Racemic Mandelic Acids, Styrenes, or Biobased l-Phenylalanine via Cascade Biocatalysis

Enantiopure d-phenylglycine and its derivatives are an important group of chiral amino acids with broad applications in thepharmaceutical industry. However, the existing synthetic methods for d-phenylglycine mainly rely on toxic cyanide chemistry and multistep processes. To provide green and safe alternatives, we envisaged cascade biocatalysis for the one-pot synthesis of d-phenylglycine from racemic mandelic acid, styrene, and biobased l-phenylalanine, respectively. Recombinant Escherichia coli (LZ110) was engineered to coexpress four enzymes to catalyze a 3-step reaction in one pot, transforming mandelic acid (210 mM) to give enantiopure d-phenylglycine in 29.5 g L?1 (195 mM) with 93% conversion. Using the same whole-cell catalyst, twelve other d-phenylglycine derivatives were also produced from the corresponding mandelic acid derivatives in high conversion (58–94%) and very high ee (93–99%). E. coli (LZ116) expressing seven enzymes was constructed for the transformation of styrene to enantiopure d-phenylglycine in 80% conversion via a one-pot 6-step cascade biotransformation. Twelve substituted d-phenylglycines were also produced from the corresponding styrene derivatives in high conversion (45–90%) and very high ee (92–99%) via the same cascade reactions. A nine-enzymeexpressing E. coli (LZ143) was engineered to transform biobased l-phenylalanine to enantiopure d-phenylglycine in 83% conversion via a one-pot 8-step transformation. Preparative biotransformations were also demonstrated. The high-yielding synthetic methods use cheap and green reagents (ammonia, glucose, and/or oxygen), and E. coli whole-cell catalysts, thus providing green and useful alternative methods for manufacturing d-phenylglycine. (Figure presented.).

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.