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

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

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 
• 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 
• 307539-90-8 methyl 2-benzamido-5-bromobenzoate 
• 113117-62-7 5-bromo-2-(2-ethoxycarbonyl-acetylamino)-benzoic acid methyl ester 
• 29632-82-4 5-bromo-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one 
• 135484-71-8 N-(4-bromo-2-formylphenyl)benzenesulfonamide 
• 135484-68-3 N-(4-Bromo-2-hydroxymethyl-phenyl)-benzenesulfonamide 
• 135484-88-7 1-Benzenesulfonyl-5-bromo-2-methylsulfanyl-1H-indole 
• 159847-81-1 methyl 2-AMINO-5-CYANOBENZOATE 

Relevant articles and documents

A Practical Procedure for Regioselective Bromination of Anilines

A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.

METHOD FOR PRODUCING AROMATIC HALOGEN DERIVATIVE

PROBLEM TO BE SOLVED: To provide a highly efficient and economically advantageous method for producing a halogen compound. SOLUTION: The method produces a halogen compound represented by formula (2) (X is a halogen atom, and b is an integer of 1-5) by reacting an aniline derivative represented by formula (1) (R1 is an ester group, a carbonyl group, a nitrile group, a nitro group, an optionally substituted alkyl group or an optionally substituted aralkyl group, and a is an integer of 0-4) with a halogenating agent in the presence of a copper catalyst and a persulfate. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

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