52727-57-8

Basic information

• Product Name: Benzoic acid,2-amino-5-bromo-, methyl ester
• Synonyms: Anthranilicacid, 5-bromo-, methyl ester (6CI);2-Amino-5-bromobenzoic acid methyl ester;5-Bromo-2-aminobenzoic acid methyl ester;5-Bromoanthranilic acid methyl ester;Methyl 5-bromo-2-aminobenzoate;Methyl5-bromoanthranilate
• CAS NO: 52727-57-8
• Molecular Formula: C₈H₈BrNO₂
• Molecular Weight: 230.0586
• EINECS: -0
• Product Categories: amine | carboxylic ester| alkyl bromide;Anilines, Amides & Amines;Bromine Compounds;C8 to C9;Carbonyl Compounds;Esters;Benzoic acid;Acids & Esters;Aromatic Esters
• Mol File: 52727-57-8.mol
• Article Data: 33

Chemical Properties

• Melting Point: 72-74℃
• Boiling Point: 286.3 °C at 760 mmHg
• Flash Point: 126.9 °C
• Appearance: White to light yellow crystal powder
• Density: 1.578 g/cm³
• Vapor Pressure: 0.00266mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: Room temperature.
• Solubility: DMSO, Methanol
• PKA: 1.76±0.10(Predicted)
• Water Solubility: Soluble in water.
• BRN: 972720
• CAS DataBase Reference: Benzoic acid,2-amino-5-bromo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid,2-amino-5-bromo-, methyl ester(52727-57-8)
• EPA Substance Registry System: Benzoic acid,2-amino-5-bromo-, methyl ester(52727-57-8)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot
• WGK Germany: 3
• Hazardous Substances Data: 52727-57-8(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow crystal powder

Uses

Methyl 2-amino-5-bromobenzoate acts as a potential PqsD inhibitor against pseudomonas aeruginosa infections. It is also used in the preparation of hepatitis C virus NS5b RNA polymerase inhibitors. It is involved in plant growth-regulator activity.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 7055, 1994 DOI: 10.1016/0040-4039(94)88224-X

General Description

Molecules of methyl 2-amino-5-bromobenzoate are linked by N-H...O bonds and consists of zigzag chains running along the b-axis direction. The nonlinear optical single crystal of M2A5B grown by Sankaranarayanan-Ramasamy (SR) Unidirectional growth method shows good optical transparency and mechanical stability.

InChI:InChI=1/C8H8BrNO2/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4H,10H2,1H3

Upstream product

• 75-87-6 chloral 
• 134-20-3 2-carbomethoxyaniline 
• 67-56-1 methanol 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 77-78-1 dimethyl sulfate 
• 544-92-3 copper(I) cyanide 
• 186581-53-3 diazomethane 
• 118-92-3 anthranilic acid 

Downstream Products

• 101080-26-6 2-amino-5-bromo-3-chloro-benzoic acid methyl ester 
• 606-00-8 2-amino-3,5-dibromo-benzoic acid methyl ester 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 120572-39-6 5-Bromo-2-(3-carboxy-propionylamino)-benzoic acid methyl ester 
• 96999-09-6 methyl N-(4-bromo-2-carbomethoxyphenyl)acetimidate 
• 135484-65-0 methyl 5-bromo-2-[(phenylsulfonyl)amino]benzoate 
• 96999-10-9 methyl N-(4-bromo-2-carbomethoxyphenyl)propionimidate 
• 49681-96-1 6-bromo-2,3-dihydro-2-thioxo-quinazolin-4(3H)-one 
• 112881-74-0 5-Bromo-2-((Z)-3-carboxy-acryloylamino)-benzoic acid methyl ester 
• 84646-91-3 Hydrazide of 2-amino-5-bromo-benzoic acid 
• 223526-84-9 methyl 5-bromo-2-{[(4-methylphenyl)sulfonyl]amino}benzoate 
• 307539-90-8 methyl 2-benzamido-5-bromobenzoate 
• 5344-90-1 2-Aminobenzyl alcohol 
• 20712-12-3 (2-amino-5-bromophenyl)methanol 

Relevant articles and documents

INHIBITORS OF ENCEPHALITIC ALPHAVIRUSES

Compounds of Formula I and Formula II: pharmaceutical compositions containing them, and use of the compounds as active ingredients to treat infection with alphavirus.

Imidazo[1,5-a]quinazoline-5(4H)-ketone derivative as well as preparation method and application thereof

The invention relates to an imidazo[1,5-a]quinazoline-5(4H)-ketone derivative as well as a preparation method and application thereof. The imidazo[1,5-a]quinazoline-5(4H)-ketone derivative disclosed by the invention can be used for preparing a BET protein

Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer

Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.