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

Physical properties

Crystals of 3,5-dichlorobenzoic acid were obtained from a water/ethanol mixture, mp186–187℃(lit. l85–187℃). Crystallization of 3,5-Dichlorobenzoic acid occurred in the monoclinic centrosymmetric space group P21/n (No. 14) with a = 3.7812(3), b = 13.996(2), and c = 14.514(2) Å, β = 95.183(8); and Z = 4. Chlorine substituents of four dimeric molecules of 3,5-Dichlorobenzoic acid formed square channels, ca. 3.54 Å on a side, which run parallel to the crystallographic a axis.

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.

Application

3,5-Dichlorobenzoic acid can be used as a pharmaceutical intermediate compound. Novel cyclopentquinoline and 3,5-dichlorobenzoic acid complexes possess antioxidant and neuroprotective effects, which can be used for the treatment of Alzheimer's disease. In addition, 3,5-Dichlorobenzoic acid has a stimulatory effect on skeletal muscle and can be used in the preparation of benzodiazepine derivatives for treating arrhythmias.

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
• Folic acid
• 4-Hydroxybenzoic acid
• Citric acid
• Ascoric Acid
• 3,4-DICHLOROBENZOIC ACID
• ETHYL 3,5-DICHLORO-4-HYDROXYBENZOATE
• Tetrachlorophthalic anhydride
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• METHYL 3,5-DICHLORO-4-HYDROXYBENZOATE
• 2,3-DICHLOROBENZOIC ACID