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.

Synthesis

The general procedure for the synthesis of 2,6-dichlorophenylacetic acid from ethyl 2,6-dichlorophenylacetate was as follows: first, 2,6-dichlorotoluene (2.4 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 eq.), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol%) were added to a reactor and charged with carbon monoxide at 10 atmospheres. The reaction mixture was heated to 120°C and stirred continuously at this temperature for 16 hours. Upon completion of the reaction, carbon monoxide was released and purified by column chromatography to give 84 mg of ethyl 2,6-dichlorophenylacetate in 72% yield. The structure of the product was determined by 1HNMR (400 MHz, CDCl3) δ 1.25 (t, J=7.2 Hz, 3H), 4.01 (s, 2H), 4.17 (q, J=7.2 Hz, 2H), 7.14-7.18 (m, 1H), 7.31-7.33 (m, 2H); 13CNMR (100 MHz, CDCl3) δ 14.2,36.8,61.1,128.0,128.9,131.4,136.1,169.5; HRMS (ESI) calculated value of C10H10Cl2NaO2 [M+Na] was confirmed by analytical calculations of C10H10Cl2NaO2 [M+Na]: 254.9950 and measured value: 254.9949. Subsequently, the resulting ethyl 2,6-dichlorophenylacetate was dissolved in 1,4-dioxane, 6N sodium hydroxide solution was added and the reaction mixture was heated to 60°C. After 2 hours of reaction, the pH was adjusted with 2N hydrochloric acid to 1. After removal of the organic solvent under reduced pressure, the mixture was extracted with ethyl acetate to give 71 mg of 2,6-dichlorophenylacetic acid in 95% hydrolysis yield.

Purification Methods

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

References

[1] Patent: US2013/303798, 2013, A1. Location in patent: Paragraph 0018; 0070; 0071

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