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111910

2-Chlorotoluene

Name: 2-Chlorotoluene
Brand: ALDRICH

99%

Synonym(s):

1-chloro-2-methylbenzene

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About This Item

Linear Formula:

CH₃C₆H₄Cl

CAS Number:

95-49-8

Molecular Weight:

126.58

NACRES:

NA.22

PubChem Substance ID:

24847049

eCl@ss:

39050205

UNSPSC Code:

12352100

EC Number:

202-424-3

MDL number:

MFCD00000562

Beilstein/REAXYS Number:

1904175

Assay:

99%

Form:

liquid

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Properties

vapor density

4.38 (vs air)

Quality Level

100

vapor pressure

10 mmHg ( 43 °C)

assay

99%

form

liquid

refractive index

n20/D 1.525 (lit.)

bp

157-159 °C (lit.)

mp

−36 °C (lit.)

solubility

H₂O: soluble

density

1.083 g/mL at 25 °C (lit.)

functional group

chloro

SMILES string

Cc1ccccc1Cl

InChI

1S/C7H7Cl/c1-6-4-2-3-5-7(6)8/h2-5H,1H3

InChI key

IBSQPLPBRSHTTG-UHFFFAOYSA-N

Description

General description

2-Chlorotoluene can be mineralized completely by Rhodococcus, strain OCT 10 DSM 45596(T). It is used in the preparation of 3-chloro-4-methylcatechol and 4-chloro-3-methylcatechol. The oxidation of 2-chlorotoluene is very well catalyzed by the enzymes: toluene dioxygenase of P. putida F1 and chlorobenzene dioxygenase from Burkholderia, strain PS12.

Application

2-Chlorotoluene can be used as a precursor to synthesize aryl coupling products via palladium-catalyzed Negishi cross-coupling. It can also be used in the Buchwald-Hartwig amination to synthesize arylamines.

pictograms

GHS02,GHS08,GHS07,GHS09

signalword

Warning

hcodes

H226,H332,H361d,H410

pcodes

P202 - P210 - P233 - P273 - P304 + P340 + P312 - P308 + P313

Hazard Classifications

Acute Tox. 4 Inhalation - Aquatic Acute 1 - Aquatic Chronic 2 - Flam. Liq. 3 - Repr. 2

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

109.4 °F - closed cup

flash_point_c

43 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品

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Metabolism of Chlorotoluenes by Burkholderia sp. Strain PS12 and Toluene Dioxygenase of Pseudomonas putida F1: Evidence for Monooxygenation by Toluene and Chlorobenzene Dioxygenases.

A Lehning et al.

Applied and environmental microbiology, 63(5), 1974-1979 (1997-05-01)

The degradation of toluene by Pseudomonas putida F1 and of chlorobenzenes by Burkholderia sp. strain PS12 is initiated by incorporation of dioxygen into the aromatic nucleus to form cis-dihydrodihydroxybenzenes. Toluene-grown cells of P. putida F1 and 3-chlorobenzoate-grown cells of Burkholderia

NIXANTPHOS: A Highly Active Ligand for Palladium Catalyzed Buchwald-Hartwig Amination of Unactivated Aryl Chlorides.

Mao J, et al.

Dalton Transactions, (26) (2018)

Flexible Steric Bulky Bis (Imino) acenaphthene (BIAN)-Supported N-Heterocyclic Carbene Palladium Precatalysts: Catalytic Application in Buchwald?Hartwig Amination in Air.

Lan X B, et al.

The Journal of Organic Chemistry, 82(6), 2914-2925 (2017)

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Global Trade Item Number

SKU	GTIN
111910-1KG	04061838344960
111910-100G	04061838699312
111910-4KG	04061838344977