95-49-8 Usage
Description
2-Chlorotoluene is a colorless liquid with an aromatic odor, denser than water, and poorly soluble in water. It can be mineralized completely by Rhodococcus, strain OCT 10 DSM 45596(T). It is a flammable chemical compound.
Uses
Used in Chemical Synthesis:
2-Chlorotoluene is 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.
Used in Organic Chemicals and Dyes:
2-Chlorotoluene is used as a solvent and intermediate for organic chemicals and dyes. It is used for permanganate oxidation to give o-chlorobenzoic acid and in the preparation of 3-chloro-4-methylcatechol and 4-chloro-3-methylcatechol.
Used in Pharmaceutical and Synthetic Rubber Industries:
2-Chlorotoluene is used as a solvent and in the synthesis of dyes, pharmaceuticals, and synthetic rubber compounds.
Preparation
The solution of cuprous chloride is cooled in an ice bath 0-5° C temperature. In this cold solution, the 2-methylbenzenediazonium is poured with constant shaking and allowing the mixture to come to room temperature. After about 10 minutes, the mixture gradually warmed with a good shaking.As the temperature rises the brown addition product begins to decompose with the evolution of nitrogen and with the formation of an oily layer of 2-chlorotoluene. When the decomposition reaction is at an end, the mixture is steam distilled, continuing the process only as long as oily droplets are present in the distillate, for the product is not appreciably soluble in water. The layer of 2-chlorotoluene is carefully separated and washed twice with an equal volume of concentrated sulfuric acid, which removes both the 2-cresol and the azo compound. Then 2-chlorotoluene is washed with water in order to remove the inorganic acid. Finally, 2-chlorotoluene is dried over calcium chloride, distilled, using an air condenser and collecting the product boiling at 153-158° C. Pure 2-chlorotoluene boils at 157° C. The yield is 25-30 g.Experiments in Organic Chemistry, L. F. Fieser, 216, 1941Highly Selective Oxidative Monochlorination To Synthesize Organic Intermediates: 2-Chlorotoluene, 2-Chloroaniline, 2-Chlorophenol, and 2-Chloro-4-methylphenol
Synthesis Reference(s)
Journal of the American Chemical Society, 101, p. 768, 1979 DOI: 10.1021/ja00497a063Organic Syntheses, Coll. Vol. 1, p. 170, 1941
Reactivity Profile
2-Chlorotoluene may be incompatible with strong oxidizing and reducing agents. Also may be incompatible with amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. Reacts violently with dimethyl sulfoxide .
Hazard
Toxic by inhalation. Eye, skin, and upper
respiratory tract irritant.
Health Hazard
Inhalation of vapor may cause respiratory irrtation. Prolonged and repeated vapor exposures may produce systemic toxic effects.
Flammability and Explosibility
Flammable
Safety Profile
Moderately toxic by
unspecified routes. Flammable when
exposed to heat or flame. When heated to
decomposition it emits toxic fumes of Cl-.
See also TOLE CHLORIDE and
CHLORINATED HYDROCARBONS,
AROMATIC.
Purification Methods
Dry 2-chlorotoluene for several days with CaCl2, then distil it from Na using a glass helices-packed column. [Beilstein 5 IV 805.]
Check Digit Verification of cas no
The CAS Registry Mumber 95-49-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 5 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 95-49:
(4*9)+(3*5)+(2*4)+(1*9)=68
68 % 10 = 8
So 95-49-8 is a valid CAS Registry Number.
95-49-8Relevant articles and documents
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McMaster,Carol
, p. 218 (1931)
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Rate enhancements due to ultrasound in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic compounds in presence of KHSO4/KCl
Rajanna,Rao, A. Sambashiva,Chakravarthi,Reddy, K. Rajendar
, p. 167 - 170 (2017/12/26)
Chlorination of aromatic compounds underwent magnificent rate accelerations in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic hydrocarbons in the presence of KCl and KHSO4. Reaction times reduced highly significantly from 4-5 h in conventional protocol to 30-40 min under sonication, followed by high yields of monochloro derivatives as products with high regioselectivity.
A process for preparing O-toluene
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Paragraph 0015-0018, (2018/10/11)
The present invention provides a process for preparing dichloro toluene, relates to the field of preparation of organic intermediates. The invention relates to 2, 3 - dichloro toluene, 2, 4 - dichloro toluene and 2, 5 - dichloro toluene in more than one type of raw materials, supported palladium as the catalyst, a fixed bed continuous reaction preparation of O-toluene. This invention uses the industrial by-product 2, 3 - dichloro toluene, 2, 4 - dichloro toluene and 2, 5 - dichloro toluene as the raw materials, supported palladium catalyst good selectivity, long-time use, O-chlorotoluene high yield.