Methyl 3-AMino-5-broMo-2-Methylbenzoate Chemical Properties

Melting point:

52 °C

Boiling point:

336.0±37.0 °C(Predicted)

Density 

1.506

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

2.23±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C9H10BrNO2/c1-5-7(9(12)13-2)3-6(10)4-8(5)11/h3-4H,11H2,1-2H3

InChIKey

NMLOSXSDLWFBKT-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC(Br)=CC(N)=C1C

CAS DataBase Reference

1000342-11-9

Safety Information

RIDADR 

UN2811

HS Code 

2922.49.3700

Methyl 3-AMino-5-broMo-2-Methylbenzoate Usage And Synthesis

Uses

Methyl 3-amino-5-bromo-2-methylbenzoate is used as an intermediate in organic synthesis and is widely used in the manufacture of pharmaceuticals (e.g., anticancer drugs, antimicrobials and pesticides) and dye products.

Synthesis

General procedure for the synthesis of methyl 2-methyl-3-amino-5-bromobenzoate from methyl 5-bromo-2-methyl-3-nitrobenzoate: methyl 5-bromo-2-methyl-3-nitrobenzoate (17 g, 62 mmol) was dissolved in a mixed solvent of ethanol (150 ml) and water (75 ml), followed by addition of ammonium chloride (17 g, 318 mmol) and iron powder ( 27.8 g, 498 mmol). The reaction mixture was stirred at 90°C for 1 hour. After completion of the reaction, the reaction mixture was filtered while hot and the filtrate was concentrated under vacuum, saturated aqueous sodium bicarbonate solution was added and extracted with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate and subsequently concentrated in vacuum to give 15 g of methyl 2-methyl-3-amino-5-bromobenzoate in 99% yield.

References

[1] Patent: WO2012/118812, 2012, A2. Location in patent: Page/Page column 312
[2] Patent: WO2012/142513, 2012, A1. Location in patent: Page/Page column 268
[3] Patent: US2014/107122, 2014, A1. Location in patent: Paragraph 0161; 0162
[4] Patent: CN105037360, 2016, B. Location in patent: Paragraph 0205; 0206; 0207
[5] Patent: WO2015/104677, 2015, A1. Location in patent: Page/Page column 69

Methyl 3-AMino-5-broMo-2-Methylbenzoate(1000342-11-9)Related Product Information

• Ethyl 4-bromobenzoate
• 4-Bromobenzoic acid
• Methyl 3-(bromomethyl)benzoate
• Tosyl chloride