2,3-Dichlorobenzoic acid Chemical Properties

Melting point:

168-170 °C (lit.)

Boiling point:

273.68°C (rough estimate)

Density 

1.4410 (rough estimate)

refractive index 

1.4590 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

2.53±0.25(Predicted)

color 

White to Off-White

Water Solubility 

slightly soluble

BRN 

1946217

InChI

InChI=1S/C7H4Cl2O2/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3H,(H,10,11)

InChIKey

QAOJBHRZQQDFHA-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=CC(Cl)=C1Cl

CAS DataBase Reference

50-45-3(CAS DataBase Reference)

EPA Substance Registry System

2,3-Dichlorobenzoic acid (50-45-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36-24/25

WGK Germany 

2

RTECS 

DG6475000

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:2,3-Dichlorobenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,3-Dichlorobenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2,3-Dichlorobenzoic acid is the key intermediate for antiepileptic drug Lamotrigine (L173250) and other pharmaceuticals for the treatment of central nervous system (CNS) disorders and disease.

Definition

ChEBI: 2,3-dichlorobenzoic acid is a chlorobenzoic acid that is benzoic acid in which the ring hydrogens at positions 2 and 3 are substituted by chloro groups. It has a role as an impurity and a bacterial xenobiotic metabolite. It is a chlorobenzoic acid and a dichlorobenzene. It is functionally related to a benzoic acid. It is a conjugate acid of a 2,3-dichlorobenzoate.

General Description

2,3-Dichlorobenzoic acid is an intermediate metabolite of polychlorinated biphenyls (PCBs).

Synthesis

2,3-Dichlorobenzoic acid was prepared from 2,3-dichloroaniline by diazotization and Myerwine reaction to 2,3-dichlorobenzaldehyde, and then oxidized by potassium permanganate, with an overall yield of 45%.
Another synthesis of 2,3-dichlorobenzoic acid:
Step (a) A solution of 2,3-dichloroiodobenzene in sodium dried ether was added dropwise to magnesium turnings and a crystal of iodine with warming so as to form a Grignard reagent.
Step (b) The mixture of Step (a) was stirred and refluxed then cooled and transferred dropwise, under nitrogen, into a stirred mixture of sodium dried ether containing solid carbon dioxide.
Step (c) The mixture of Step (b) was stirred for 2 hours, left overnight to warm to room temperature, then treated with ice and aqueous hydrochloric acid, and the product extracted with ether. The combined ether extracts were washed with water then repeatedly extracted with an aqueous sodium hydroxide. These basic solutions were combined, stirred with activated charcoal for 10 minutes, filtered and the cooled filtrate was acidified with concentrated hydrochloric acid at lO.degree. C.
Step (d) The resultant solid was filtered off, washed with water (2.times.20 mis) and dried in vacuo. Yield 77.6%.

Purification Methods

Aromatic acid impurities (to <0.05%) can be removed via the (±)--methylbenzylamine salt as described for 2,4-dichlorobenzoic acid [Ley & Yates Organic Process Research & Development 12 120 2008.] Crystallise the acid from H2O, aqueous EtOH, or 30% aqueous AcOH and several times from *C6H6, then dry it in vacuo at 40o overnight. The methyl ester has m 35-39o . [Hope & Riley J Chem Soc 123 2478 1923, Lock Monatsh Chem 90 687 1959, Shorter & Mather J Chem Soc 4744 1961, Beilstein 9 II 228, 9 IV 998.]

2,3-Dichlorobenzoic acid(50-45-3)Related Product Information

• 3,5-DICHLOROBENZOIC ACID
• 2',4'-Dichloroacetophenone
• 1,3-Dichlorobenzene
• 1,2-Dichloroethane
• 4-Aminobenzoic acid
• Benzoic acid
• 4-Nitrobenzoic acid
• Citric acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 1,2-Dichloro-4-(chloromethyl)benzene
• Estradiol benzoate
• 2,4-Dichlorobenzoic acid
• Folic acid
• Lamotrigine Impurity 4
• 3-Dechloro-4-chloro Lamotrigine
• LaMotrigine Related CoMpound C
• (Z)-[cyano(2,3-dichlorophenyl)methylene]carbazamidine
• Lamotrigine Impurity 6