2,6-Dichlorophenylacetic acid
- CAS NO.:6575-24-2
- Empirical Formula: C8H6Cl2O2
- Molecular Weight: 205.04
- MDL number: MFCD00004320
- EINECS: 229-504-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-29 18:21:28
What is 2,6-Dichlorophenylacetic acid?
Chemical properties
white crystalline powder
The Uses of 2,6-Dichlorophenylacetic acid
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.]
Properties of 2,6-Dichlorophenylacetic acid
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) |
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 for 2,6-Dichlorophenylacetic acid
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for 2,6-Dichlorophenylacetic acid
InChIKey | SFAILOOQFZNOAU-UHFFFAOYSA-N |
SMILES | C1(CC(O)=O)=C(Cl)C=CC=C1Cl |
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