2,6-Dichlorphenylessigsure

Bezeichnung:2,6-Dichlorphenylessigsure

CAS-Nr6575-24-2

Englisch Name:2,6-Dichlorophenylacetic acid

CBNumberCB2481995

SummenformelC8H6Cl2O2

Molgewicht205.04

MOL-Datei6575-24-2.mol

Synonyma

2,6-Dichlorphenylessigsure

2,6-Dichlorphenylessigsure physikalisch-chemischer Eigenschaften

Schmelzpunkt	158-161 °C (lit.)
Siedepunkt	294.45°C (rough estimate)
Dichte	1.3806 (rough estimate)
Brechungsindex	1.5490 (estimate)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
pka	3.80±0.10(Predicted)
Aggregatzustand	Solid
Farbe	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 Datenbank	6575-24-2(CAS DataBase Reference)
NIST chemische Informationen	2,6-Dichlorophenylacetic acid(6575-24-2)
EPA chemische Informationen	Benzeneacetic acid, 2,6-dichloro- (6575-24-2)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	37/39-26-26/37/39-36
WGK Germany	3
Hazard Note	Irritant
HS Code	29163900
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2

Gefahreninformationscode (GHS)

2,6-Dichlorophenylacetic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
white crystalline powder
Verwenden
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.
synthetische
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.
Synthese

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.
läuterung methode
Crystallise the acid from aqueous EtOH. [Beilstein 9 III 2272.]
Einzelnachweise
[1] Patent: US2013/303798, 2013, A1. Location in patent: Paragraph 0018; 0070; 0071

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