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2-Amino-6-chlorobenzoic acid

Product Name2-Amino-6-chlorobenzoic acid
CAS2148-56-3
MFC7H6ClNO2
MW171.58
EINECS218-416-8
MOL File2148-56-3.mol

Chemical Properties

Melting point	158-160 °C (lit.)
Boiling point	250°C (rough estimate)
Density	1.3246 (rough estimate)
refractive index	1.5560 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
form	Crystalline Powder
pka	0.97±0.10(Predicted)
color	Light yellow to beige
Water Solubility	Very soluble in water. Soluble in methanol.
BRN	2804041
Major Application	peptide synthesis
InChI	InChI=1S/C7H6ClNO2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,9H2,(H,10,11)
InChIKey	SZCPTRGBOVXVCA-UHFFFAOYSA-N
SMILES	C(O)(=O)C1=C(Cl)C=CC=C1N
CAS DataBase Reference	2148-56-3(CAS DataBase Reference)
NIST Chemistry Reference	2-Amino-6-chlorobenzoic acid(2148-56-3)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36-37/39
WGK Germany	3
Hazard Note	Irritant
HS Code	29224999
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
2-Amino-6-chlorobenzoic acid	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2-Amino-6-chlorobenzoic acid is used as intermediate for medicine.

Application

The tricyclohexyltin 2-amino-6-chlorobenzoate was synthesized by the reaction of the tricyclohexyltin hydroxide with the 2-amino-6-chlorobenzoic acid.

Preparation

A, in the reaction vessel being provided with agitator, thermometer, reflux condenser, Dropping funnel, add cerium chloride 0.16mol, 4-hydroxy 3-methoxybenzene ethanol solution 0.19mol, Klorvess Liquid 400-500ml, control mixing speed and exist 160-190rpm, rising solution temperature, to 60-65°C, is slowly added to 2-chloro-6-nitrobenzoyl acid solution 0.13mol, sulfurous acid Hydrogen potassium solution 200ml, raises mixing speed to 260-310rpm, back flow reaction 5-7h；
B, reduction solution temperature, to 15-19°C, separate out solid, filter, and add diammonium hydrogen citrate solution 150-in filtrate 180ml, concentrating under reduced pressure, separate out solid, filter, dehydrant is dehydrated, brine, and pyridine solution washs, ethyl acetate solution Middle recrystallization, obtains crystal 2-amino-6-chlorobenzoic acid (C7H6ClNO2).

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

6575-11-7

2148-56-3

In a 250 mL round-bottomed flask, 5 g (32.77 mmol, 1.0 eq.) of 2-amino-6-chlorobenzonitrile was dissolved in 50 mL of a 30% aqueous potassium hydroxide (KOH) solution, followed by the addition of 3 mL of hydrogen peroxide (H2O2). The mixture was reacted under reflux conditions overnight. Upon completion of the reaction, the reaction mixture was washed sequentially with ether and dichloromethane each, followed by acidification. The acidified mixture was extracted with dichloromethane and ethyl acetate, and after separating the organic layer, the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give 5.31 g (30.95 mmol, 94% yield) of 2-amino-6-chlorobenzoic acid as an orange solid.

References

[1] Patent: KR2017/74380, 2017, A. Location in patent: Paragraph 0175-0178
[2] Patent: US2018/105527, 2018, A1. Location in patent: Paragraph 0439-0441

2-Amino-6-chlorobenzoic acid

Chemical Properties

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MSDS

Usage And Synthesis

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