2-Amino-4-bromobenzoic acid Chemical Properties

Melting point:

230-234 °C

Boiling point:

352.4±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

4.71±0.10(Predicted)

color 

White to Orange to Green

Water Solubility 

Soluble in water (slightly).

InChI

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

InChIKey

BNNICQAVXPXQAH-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(Br)C=C1N

CAS DataBase Reference

20776-50-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36/37

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich

2-Amino-4-bromobenzoic acid Usage And Synthesis

Chemical Properties

slight yellow to white powder

Uses

2-Amino-4-bromobenzoic acid, , is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

2) Under stirring conditions, 4-bromo-2-nitrobenzoic acid (1.80 g, 7.83 mmol) was dissolved in 0.88 N aqueous sodium hydroxide (10 mL), followed by the sequential addition of ferric (III) chloride (133 mg) and isopropanol (0.7 mL). Hydrazine hydrate (1.1 mL) was slowly added dropwise to the above mixture and the reaction system was warmed up to 75 °C with continuous stirring for 2 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated to give the crude product. The crude product was washed with water to afford 4-bromo-2-aminobenzoic acid (1.73 g, 96% yield). The structure of the product was confirmed by 1H NMR (DMSO-d6): δ 6.62 (dd, J = 1.5, 8.5 Hz, 1H), 6.95 (d, J = 1.5 Hz, 1H), 7.56 (d, J = 8.5 Hz, 1H).

References

[1] Patent: US2004/116422, 2004, A1. Location in patent: Page/Page column 31
[2] Organic Letters, 2011, vol. 13, # 19, p. 5220 - 5223
[3] Journal of Organic Chemistry, 1997, vol. 62, # 5, p. 1240 - 1256
[4] Patent: WO2006/51290, 2006, A2. Location in patent: Page/Page column 111; 144
[5] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443

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