Methyl 4-amino-3-bromobenzoate Chemical Properties

Melting point:

105-109 °C

Boiling point:

334.2±22.0 °C(Predicted)

Density 

1.6270 (rough estimate)

refractive index 

1.6120 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

0.41±0.10(Predicted)

form 

Crystalline Powder

color 

Brown

InChI

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

InChIKey

AIUWAOALZYWQBX-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

106896-49-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36-36/37/38

Safety Statements 

26-36/37-37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29163100

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Methyl 4-amino-3-bromobenzoate Usage And Synthesis

Uses

Methyl 4-amino-3-bromobenzoate is a carboxylic acid derivative and a commonly used pharmaceutical and chemical intermediate.

Chemical Properties

brown crystalline powder

Synthesis

General procedure for the preparation of methyl 4-amino-3-bromobenzoate: methyl 4-aminobenzoate (17 g, 0.1 mol) was dissolved in chloroform (250 mL). N-bromosuccinimide (20 g, 0.1 mol) was added slowly at 0 °C and the reaction mixture was stirred continuously for 3 h at this temperature. After completion of the reaction, the solvent was removed by distillation. Ethyl acetate (100 mL) was added to the residue for dissolution. Subsequently, the mixture was washed with aqueous sodium chloride to remove water-soluble impurities. The organic layer was separated and dried with anhydrous magnesium sulfate. After filtration, the product was purified by recrystallization from hexane to give the final methyl 4-amino-3-bromobenzoate (24.3 g, 93% yield). [1368] NMR data: 1H-NMR (CDCl3) δ 8.11 (1H, d), 7.79-7.77 (1H, m), 6.72 (1H, d), 4.51 (2H, br s), 3.85 (3H, s).

References

[1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10410 - 10416
[2] Patent: WO2010/93191, 2010, A2. Location in patent: Paragraph 1365-1368
[3] Organic Letters, 2015, vol. 17, # 12, p. 2886 - 2889
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2930 - 2936
[5] Synthesis (Germany), 2013, vol. 45, # 11, p. 1497 - 1504

Methyl 4-amino-3-bromobenzoate(106896-49-5)Related Product Information

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• 4-Aminobenzoic acid
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• METSULFURON METHYL
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