3,5-Dichlorobenzoic acid Chemical Properties

Melting point:

184-187 °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

pka

3.46±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

Water Solubility 

147.1mg/L(temperature not stated)

BRN 

2044776

InChI

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

InChIKey

CXKCZFDUOYMOOP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

51-36-5(CAS DataBase Reference)

NIST Chemistry Reference

3,5-Dichlorobenzoic acid(51-36-5)

EPA Substance Registry System

3,5-Dichlorobenzoic acid (51-36-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

DG7350000

HazardClass 

IRRITANT

HS Code 

29163990

Toxicity

mouse,LD50,intraperitoneal,237mg/kg (237mg/kg),BEHAVIORAL: REGIDITYBEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY),Journal of Medicinal Chemistry. Vol. 11, Pg. 1020, 1968.

MSDS

• Language:English Provider:3,5-Dichlorobenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,5-Dichlorobenzoic acid Usage And Synthesis

Chemical Properties

White to beige powder

Uses

3,5-Dichlorobenzoic acid is used in organic synthesis and pesticide and pharmaceutical intermediates. It can be used to synthesize 3,5-Dichloro-N-(4-hydroxyphenethyl)benzamide and (3,5-Dichlorophenyl)-(4-fluorophenyl)methanone.

Definition

ChEBI: 3,5-dichlorobenzoic acid is a chlorobenzoic acid that is benzoic acid in which the ring hydrogens at positions 3 and 5 are substituted by chloro groups. It has a role as a herbicide and a metabolite. It is a chlorobenzoic acid and a dichlorobenzene. It derives from a benzoic acid. It is a conjugate acid of a 3,5-dichlorobenzoate.

Preparation

Synthesis of 3,5-dichlorobenzoic acid: 200 parts of ethanol is slowly added to a solution, heated to 70°C, of the diazonium salt prepared as described in Example 1 from 412 parts of 3,5-dichloroanthranilic acid; elimination of nitrogen immediately takes place with evolution of heat. The mixture is stirred for another 15 minutes and 350 parts (92% of theory) of 3,5-dichlorobenzoic acid having a melting point of 176° to 178°C is isolated as described in Example 1.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 455, 1951 DOI: 10.1021/ja01145a145

Purification Methods

Crystallise the acid from EtOH and sublime it in a vacuum. [Beilstein 9 IV 1008.] 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.]

3,5-Dichlorobenzoic acid(51-36-5)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• 4-Nitrobenzoic acid
• Benzoic acid
• Estradiol benzoate
• 1,2-Dichloro-4-(chloromethyl)benzene
• 4-Aminobenzoic acid
• Citric acid
• Folic acid
• 4-Hydroxybenzoic acid
• Ascoric Acid
• 3,4-DICHLOROBENZOIC ACID
• ETHYL 3,5-DICHLORO-4-HYDROXYBENZOATE
• Tetrachlorophthalic anhydride
• Chlorthal
• Dacthal
• 3,5-Dichloro-4-hydroxybenzoic acid
• METHYL 3,5-DICHLORO-4-HYDROXYBENZOATE
• 2,3-DICHLOROBENZOIC ACID