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2-Amino-5-chlorobenzoic acid

Product Name2-Amino-5-chlorobenzoic acid
CAS635-21-2
MFC7H6ClNO2
MW171.58
EINECS211-230-8
MOL File635-21-2.mol

Chemical Properties

Melting point	204-206 °C (dec.) (lit.)
Boiling point	250°C (rough estimate)
Density	1.3246 (rough estimate)
refractive index	1.5560 (estimate)
storage temp.	Sealed in dry,Room Temperature
solubility	DMSO (Slightly), Methanol (Slightly)
form	Solid
pka	4.57±0.10(Predicted)
color	White to Pale Grey
Water Solubility	Soluble in water.
BRN	639027
Major Application	peptide synthesis
InChI	1S/C7H6ClNO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H,10,11)
InChIKey	IFXKXCLVKQVVDI-UHFFFAOYSA-N
SMILES	Nc1ccc(Cl)cc1C(O)=O
CAS DataBase Reference	635-21-2(CAS DataBase Reference)
NIST Chemistry Reference	Benzoic acid, 2-amino-5-chloro-(635-21-2)
EPA Substance Registry System	Benzoic acid, 2-amino-5-chloro- (635-21-2)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38-37/38-36
Safety Statements	26-36-37/39
WGK Germany	3
Hazard Note	Irritant
TSCA	TSCA listed
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

2-Amino-5-chlorobenzoic acid is used in the preparation of disease-modifying antirheumatic drugs (DMARDs). Also used to produce 6-chloro-3H-quinazolin-4-one at temperature of 180°C.

Uses

2-Amino-5-chlorobenzoic acid is a chlorinated derivative of antharilic acid,it is a metabolite of the pesticide Chlordimeform and it is used in the preparation of disease-modifying antirheumatic drugs (DMARDs).

Uses

5-Chloroanthranilic Acid is a chlorinated derivative of anthranilic acid. 5-Chloroanthranilic Acid is a metabolite of the pesticide Chlordimeform. 5-Chloroanthranilic Acid is used in the preparation o f disease-modifying antirheumatic drugs (DMARDs).

Definition

ChEBI: 2-amino-5-chlorobenzoic acid is a member of the class of chlorobenzoic acids that is benzoic acid in which the ring hydrogens at positions 2 and 5 are replaced by amino and chloro groups, respectively. It is an aminobenzoic acid, a member of monochlorobenzenes and a chlorobenzoic acid.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

2516-95-2

635-21-2

General procedure for the synthesis of 2-amino-5-chlorobenzoic acid from 5-chloro-2-nitrobenzoic acid: active Raney nickel (2 g) was added to the reaction flask, followed by the addition of an ethanol solution of 5-chloro-2-nitrobenzoic acid (20 g, 110 mmol). The reaction mixture was stirred at room temperature in a hydrogen atmosphere overnight. Upon completion of the reaction, the reaction solution was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to give 16 g of white solid product (96% yield). The product was characterized by 1H NMR (DMSO-d6): δ 6.77 (d, J = 8.9 Hz, 1H), 7.24 (dd, J = 2.9, 8.9 Hz, 1H), 7.62 (d, J = 2.9 Hz, 1H), 8.7 (br, 3H); EIMS: 170 (M-H).

References

[1] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 1, p. 86 - 109
[2] Patent: WO2004/74218, 2004, A2. Location in patent: Page 115-116
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 12, p. 2801 - 2809
[4] Chemical Biology and Drug Design, 2016, p. 710 - 723
[5] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1797,1801

2-Amino-5-chlorobenzoic acid

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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