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| | 2,6-Dichlorophenylacetic acid Basic information |
| | 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) | | pka | 3.80±0.10(Predicted) | | form | Solid | | 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) |
| | 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.] |
| | 2,6-Dichlorophenylacetic acid Preparation Products And Raw materials |
| Raw materials | 2,6-Dichlorobenzyl acetonitrile-->2,2,6,6-tetrachlorocyclohexan-1-one-->3,5-Dichloro-4-methylbenzoic acid-->2,4-DICHLORO-3-METHYLBENZOIC ACID-->Benzeneacetic acid, 2,6-dichloro-, ethyl ester-->2,6-Dichlorobenzyl chloride-->Diethyl malonate-->2,6-Dichloroaniline-->carbon monoxide-->2,6-Dichlorotoluene-->CARBON DIOXIDE | | Preparation Products | 2,6-DICHLOROPHENETHYLALCOHOL |
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