4-AMINO-3-BROMOBENZOIC ACID Chemical Properties

Melting point:

211-215 °C

Boiling point:

368.5±32.0 °C(Predicted)

Density 

1.793±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

4.47±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C7H6BrNO2/c8-5-3-4(7(10)11)1-2-6(5)9/h1-3H,9H2,(H,10,11)

InChIKey

BFIVZIVVJNFTIQ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

6311-37-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36-37/38-36/37/38-22

Safety Statements 

26-37/39-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29224999

4-AMINO-3-BROMOBENZOIC ACID Usage And Synthesis

Uses

4-Amino-3-bromobenzoic acid is a useful research chemical.

Chemical Properties

White to light yellow crystal powder

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of 3-bromo-4-aminobenzoic acid from 4-aminobenzoic acid: 4-aminobenzoic acid (100 mmol) was dissolved in N,N-dimethylformamide (DMF, 50 mL), followed by the addition of N-bromosuccinimide (NBS, 100 mmol). The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the mixture was poured into water (100 mL) and a solid was precipitated. The product was collected by filtration, washed with water and dried under vacuum to afford the target compound 4-amino-3-bromobenzoic acid in 70% yield. The structure of the product was confirmed by 1H NMR (D6-DMSO): δ 6.10 (s, 2H), 6.78 (d, 1H), 7.63 (dd, 1H), 7.89 (d, 1H), 12.39 (br s, 1H).

References

[1] Russian Journal of Applied Chemistry, 2009, vol. 82, # 9, p. 1570 - 1576
[2] Journal of the American Chemical Society, 2010, vol. 132, # 6, p. 1734 - 1735
[3] Tetrahedron Letters, 2009, vol. 50, # 9, p. 1007 - 1009
[4] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 3, p. 496 - 501
[5] Tetrahedron Letters, 2000, vol. 41, # 13, p. 2083 - 2085

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