METHYL 2-AMINO-5-BROMOBENZOATE Chemical Properties

Melting point:

72-74 °C(lit.)

Boiling point:

286.3±20.0 °C(Predicted)

Density 

1.578±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO, Methanol

pka

1.76±0.10(Predicted)

form 

Solid

color 

White

Water Solubility 

Soluble in water.

BRN 

972720

InChI

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

InChIKey

QVNYNHCNNGKULA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

52727-57-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-37/38-36

Safety Statements 

26-36-37/39

WGK Germany 

3

HS Code 

29224999

MSDS

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

METHYL 2-AMINO-5-BROMOBENZOATE Usage And Synthesis

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.

Synthesis

1. Add carbon tetrachloride (100 mL) and methyl phthalate (149 mmol) to a 250 mL four-neck flask with stirring initiated. Bromine (156.45 mmol) was added slowly dropwise. After the dropwise addition, the reaction progress was monitored by HPLC. After completion of the reaction, the reaction solution was filtered and the resulting filter cake was washed with 200 mL of isopropyl ether and dried to give a yellow solid product. The purity of the product was 96.5% and the yield was 90%.

References

[1] Patent: CN108164469, 2018, A. Location in patent: Paragraph 0100; 0101
[2] Patent: CN107089919, 2017, A. Location in patent: Paragraph 0052; 0053; 0054; 0055
[3] Synthetic Communications, 2007, vol. 37, # 4, p. 581 - 585
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 21, p. 4644 - 4654

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