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
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)
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
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.
N-Bromosuccinimide Price
- Product number
- 259241
- Product name
- 2,6-Dichlorophenylacetic acid
- Purity
- 97%
- Packaging
- 25g
- Price
- $39.2
- Updated
- 2023/06/20
- Product number
- 259241
- Product name
- 2,6-Dichlorophenylacetic acid
- Purity
- 97%
- Packaging
- 100g
- Price
- $149
- Updated
- 2023/06/20
- Product number
- D1897
- Product name
- 2,6-Dichlorophenylacetic Acid
- Purity
- >96.0%(T)
- Packaging
- 25g
- Price
- $133
- Updated
- 2025/07/31
- Product number
- D436305
- Product name
- 2,6-Dichlorophenylacetic acid
- Packaging
- 25g
- Price
- $70
- Updated
- 2021/12/16
- Product number
- J93340
- Product name
- 2,6-Dichlorophenylacetic acid
- Packaging
- 5g
- Price
- $10
- Updated
- 2021/12/16
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
- 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
- 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
- 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