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111910

Sigma-Aldrich

2-Chlorotoluene

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
Beilstein:
1904175
EC Number:
202-424-3
MDL number:
MFCD00000562
UNSPSC Code:
12352100
eCl@ss:
39050205
PubChem Substance ID:
24847049
NACRES:
NA.22

vapor density

4.38 (vs air)

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.)

SMILES string

Cc1ccccc1Cl

InChI

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

InChI key

IBSQPLPBRSHTTG-UHFFFAOYSA-N

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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.

Signal Word

Warning

Hazard Statements

H226,H332,H361d,H410

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

109.4 °F - closed cup

Flash Point(C)

43 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd (P (t-Bu) 3) 2 as a catalyst
Dai C, et al.
Journal of the American Chemical Society, 123(12), 2719-2724 (2001)
M Govindarajan et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 77(5), 1005-1013 (2010-09-28)
In this work, the vibrational spectral analysis was carried out using Raman and infrared spectroscopy in the range 100-4000 cm(-1) and 50-4000 cm(-1), respectively, for the title molecules. The molecular structure, fundamental vibrational frequencies and intensity of the vibrational bands
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