ChemicalBook > CAS DataBase List > 2,6-Dichlorophenylacetic acid

2,6-Dichlorophenylacetic acid

Product Name
2,6-Dichlorophenylacetic acid
CAS No.
6575-24-2
Chemical Name
2,6-Dichlorophenylacetic acid
Synonyms
2-(2,6-DICHLOROPHENYL)ACETIC ACID;TIMTEC-BB SBB003503;RARECHEM AL BO 0115;2,6-Dichlorophenyla;Guanfacine Impurity;Guanfacine Impurity 1;2,6-Dichlorphenylessigsure;6-Dichlorophenylacetic acid;2,6-DICHLOROPHENYLACETIC ACID;2,6-DICHLORO BENZENEACETIC ACID
CBNumber
CB2481995
Molecular Formula
C8H6Cl2O2
Formula Weight
205.04
MOL File
6575-24-2.mol
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2,6-Dichlorophenylacetic acid Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
259241
Product name
2,6-Dichlorophenylacetic acid
Purity
97%
Packaging
25g
Price
$39.2
Updated
2023/06/20
Sigma-Aldrich
Product number
259241
Product name
2,6-Dichlorophenylacetic acid
Purity
97%
Packaging
100g
Price
$149
Updated
2023/06/20
TCI Chemical
Product number
D1897
Product name
2,6-Dichlorophenylacetic Acid
Purity
>96.0%(T)
Packaging
25g
Price
$133
Updated
2025/07/31
TRC
Product number
D436305
Product name
2,6-Dichlorophenylacetic acid
Packaging
25g
Price
$70
Updated
2021/12/16
AK Scientific
Product number
J93340
Product name
2,6-Dichlorophenylacetic acid
Packaging
5g
Price
$10
Updated
2021/12/16
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2,6-Dichlorophenylacetic acid Chemical Properties,Usage,Production

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

90793-64-9

6575-24-2

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

2,6-Dichlorophenylacetic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2,6-Dichlorophenylacetic acid manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd
Product
2,6-Dichlorophenylacetic acid 6575-24-2
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20 ton
Release date
2024-12-25
Hebei Chuanghai Biotechnology Co., Ltd
Product
2,6-Dichlorophenylacetic acid 6575-24-2
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-29
Hebei Chuanghai Biotechnology Co,.LTD
Product
2,6-Dichlorophenylacetic acid 6575-24-2
Price
US $9.00/KG
Min. Order
1KG
Purity
99.9
Supply Ability
1 ton
Release date
2024-08-15

6575-24-2, 2,6-Dichlorophenylacetic acidRelated Search:

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  • 2-(2,6-DICHLOROPHENYL)ACETIC ACID
  • 2,6-DICHLORO BENZENEACETIC ACID
  • 2,6-DICHLOROPHENYLACETIC ACID
  • RARECHEM AL BO 0115
  • TIMTEC-BB SBB003503
  • 2,6-Dichlorphenylessigsure
  • Guanfacine Impurity 1
  • Benzeneacetic acid, 2,6-dichloro-
  • 2,6-Dichlorophenyl acetic acid 98%
  • 2,6-Dichlorophenylacetic acid, 98+%
  • Acetic acid, (2,6-dichlorophenyl)-
  • 2,6-Dichlorophenylacetic acid,99%
  • 6-Dichlorophenylacetic acid
  • 2,6-two chlorophenyl acetic acid
  • 2,6-Dichlorophenyla
  • 2,6-DichlorophenylaceticAcid&gt
  • Guanfacine Carboxylic Acid Impurity
  • Guanfacine hydrochloride impurity B(2,6-Dichlorophenylacetic acid)
  • Guanfacine Hydrochloride Impurity 3
  • Guanfacine Impurity
  • 6575-24-2
  • C8H6Cl2O2
  • C8H6O2Cl2
  • Carboxylic Acids
  • Carbonyl Compounds
  • C8
  • Building Blocks
  • Organic Building Blocks
  • C8
  • Carbonyl Compounds
  • Carboxylic Acids
  • Aromatic Phenylacetic Acids and Derivatives
  • Phenylacetic acid
  • Acids and Derivatives