2,6-Dichlorophenylacetic acid Chemical Properties

Melting point:

158-161 °C (lit.)

Boiling point:

294.45°C (rough estimate)

Density 

1.3806 (rough estimate)

refractive index 

1.5490 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.80±0.10(Predicted)

color 

White to Off-White

BRN 

1952744

InChI

InChI=1S/C8H6Cl2O2/c9-6-2-1-3-7(10)5(6)4-8(11)12/h1-3H,4H2,(H,11,12)

InChIKey

SFAILOOQFZNOAU-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

6575-24-2(CAS DataBase Reference)

NIST Chemistry Reference

2,6-Dichlorophenylacetic acid(6575-24-2)

EPA Substance Registry System

Benzeneacetic acid, 2,6-dichloro- (6575-24-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-26/37/39-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29163900

MSDS

• Language:English Provider:2,6-Dichlorophenylacetic acid
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,6-Dichlorophenylacetic acid Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

2,6-Dichlorophenylacetic acid is an inhibitor of isopenicillin N synthase (IPNS) and acyl-CoA: 6-APA acyltransferase. 2,6-Dichlorophenylacetic acid is also part of a group of phenylacetate derivatives that have cytostatic activity against tumour cells.

Preparation

The preparation of the 2, 6-dichlorophenylacetic acid:
the method comprises the following steps: 2, 6-dichlorotoluene is used as a raw material, and is catalyzed by a complex catalyst formed by transition metal and a ligand (wherein, a transition metal catalyst precursor is preferably palladium chloride, an oxidant is preferably TBP (tert-butyl peroxy ether), and a ligand is preferably Xantphos (4, 5-bis (diphenylphosphino) -9, 9-dimethyl xanthene)) in the presence of an alcohol and a catalyst and an oxidant to obtain 2, 6-dichlorophenylacetic acid, and the ethyl 2, 6-dichlorophenylacetate is prepared by hydrolysis and acidification, wherein the total yield is 68.4%. See patent document US2013303798, the reaction procedure is described as synthetic route 1.

In the above synthetic route 1, the preparation process of the intermediate ethyl 2, 6-dichlorophenylacetate requires the use of carbon monoxide for high-temperature and high-pressure reaction, and has poor operation safety, high equipment requirement, high cost, and is not favorable for cost reduction and green production of 2, 6-dichlorophenylacetic acid.

Purification Methods

Crystallise the acid from aqueous EtOH. [Beilstein 9 III 2272.]

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