ChemicalBook Product Catalog Chemical Reagents Organic reagents Esters Methyl ester compound METHYL 2-AMINO-5-BROMOBENZOATE

METHYL 2-AMINO-5-BROMOBENZOATE

Product NameMETHYL 2-AMINO-5-BROMOBENZOATE
CAS52727-57-8
MFC8H8BrNO2
MW230.06
EINECS610-890-8
MOL File52727-57-8.mol

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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

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

134-20-3

52727-57-8

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

METHYL 2-AMINO-5-BROMOBENZOATE

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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