108-41-8 Usage
Description
3-Chlorotoluene, a colorless liquid with a specific gravity of 1.072, is denser than water and has a flash point less than 141°F. Its vapors are irritating and narcotic in high concentrations. 3-Chlorotoluene is characterized by its aromatic odor and is insoluble in water but easily soluble in benzene, ethanol, ether, and chloroform. It serves as a versatile intermediate in the synthesis of various chemicals, dyes, and is also utilized as a solvent.
Uses
Used in Chemical Synthesis:
3-Chlorotoluene is used as a catalyst in the synthesis of glycidyl methacrylate grafted multi-walled carbon nanotubes/polypropylene nanocomposites. It plays a crucial role in the development of advanced materials with enhanced properties for various applications.
Used in Research:
3-Chlorotoluene is employed in the study of paramagnetic contributions from dioxygen to solute proton spin-lattice relaxation rate constants for a series of aromatic hydrocarbons and drug molecule fragments. This application aids in understanding the behavior of these compounds and their interactions with dioxygen, which can be valuable in the development of new drugs and materials.
Used in Pharmaceutical Industry:
3-Chlorotoluene is used as a reagent to synthesize 4-Arylchromene derivatives, which are compounds that induce apoptosis and act as anti-cancer agents. This application highlights the importance of 3-Chlorotoluene in the development of potential treatments for cancer.
Used in Cosmetics Industry:
3-Chlorotoluene is also used as an ingredient in deodorants. However, it is suspected to cause allergic contact dermatitis in humans, which is an important consideration for the cosmetics industry when formulating products to ensure safety and minimize adverse reactions.
Preparation
3-Chlorotoluene is obtained from m-toluidine by diazotization and substitution. Add m-toluidine to water, slowly add concentrated hydrochloric acid, and add sodium nitrite solution dropwise at 0-5°C. Then the diazo solution is added to the cuprous chloride for replacement reaction. The crude product generated is distilled to obtain the finished product. If the diazo salt is made into a zinc chloride complex salt of m-toluidine diazo salt, it is decomposed by reflux in ether, and the reactants are cooled, washed and dried. After recovering the ether, it is distilled at atmospheric pressure and m-chlorotoluene is obtained by collecting 160-162°C fraction. The advantage of this method is that the diazonium salt is not easy to hydrolyze and generate phenols.
Air & Water Reactions
Flammable. Slightly soluble in water.
Reactivity Profile
3-Chlorotoluene is generally unreactive. May be incompatible with strong oxidizing and reducing agents. May be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.
Hazard
Narcotic in high concentration. Avoid
inhalation.
Health Hazard
Inhalation causes upper respiratory irritation. Irritating to skin and eyes. May be absorbed through the skin. Prolonged exposure may result in systemic toxic effects. Harmful if swallowed.
Potential Exposure
o-Chlorotoluene is widely used as a solvent and intermediate in the synthesis of dyes, synthetic rubber; pharmaceuticals; and other organic chemicals. Used as an insecticide, bactericide.
Shipping
UN2238 Chlorotoluenes, Hazard Class: 3; Labels: 3-Flammable liquid.
Purification Methods
Purify it as for 2-chlorotoluene above. [Beilstein 5 IV 806.]
Incompatibilities
Incompatible with acids, alkalis, oxidizers, reducing materials; water
Waste Disposal
In accordance with 40CFR165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
Check Digit Verification of cas no
The CAS Registry Mumber 108-41-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 108-41:
(5*1)+(4*0)+(3*8)+(2*4)+(1*1)=38
38 % 10 = 8
So 108-41-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H7Cl/c1-6-3-2-4-7(8)5-6/h2-5H,1H3
108-41-8Relevant articles and documents
Evidence for Generation of the Unsaturated Sila-acetate Species Me(O-)Si=O by Dissociation of the Silanediolate Dianion m-ClC6H4CH2SiMe(O-)2
Chmielecka, Jadwiga,Chojnowski, Julian,Eaborn, Colin,Stancyzk, Wlodimierz A.
, p. 1337 - 1338 (1987)
Kinetic studies indicate that in the cleavage of m-ClC6H4CH2SiMe(OH)2 by NaOH in Me2SO-H2O there is a major contribution by unimolecular dissociation of the dianion m-ClC6H4CH2SiMe(O-)2 to give the acetate ion analogue Me(O-)Si=O.
Chemistry of superacids: 35. * NO2Cl-3MXN systems: Superelectrophilic aprotic nitrating agents for deactivated aromatics
Olah,Orlinkov,Ramaiah,Oxyzoglou,Prakash
, p. 924 - 927 (1998)
Superelectrophilic nitration of deactivated aromatics with NO2Cl-3MXn complexes in aprotic nonpolar solvents such as CH2Cl2 makes it possible to obtain the corresponding nitro derivatives in good to almost quantitative yields under mild conditions.
Deep compositional understanding of TBA: AlCl3 ionic liquid for its applications
Bhakthavatsalam, Vishnupriya,Chandra, Sudeshna,Choudhury, Rudra Prosad,Lande, Sharad V.,Pradhan, Jeevan,Sakhalkar, Mangesh
, (2020/07/31)
Chloroaluminate ionic liquids (ILs) have been immensely used as homogeneous catalyst in Friedel-Crafts reaction. We have recently synthesized chloroaluminate ILs by reacting aluminium chloride with a hydrophobic neutral ligand i.e. tributylamine (TBA:AlCl3). The current study elaborates on the investigations of the composition of the ionic liquids at various stages of their formation. The ionic liquids were synthesized using various mole ratios of tributyl amine and aluminium chloride in range of 1:1 to 1:2.3, in presence of an aromatic solvent in a one pot reaction. Various characterization techniques like Mass spectrometry, 27Al Nuclear Magnetic Resonance, 31P Nuclear Magnetic Resonance and Fourier Transform Infrared spectroscopy were used to elucidate the formation of various moieties of the TBA:AlCl3 Ionic Liquid. This study also elaborates on the investigations of the cationic and anionic moieties and their structure-property relationship for various applications. Various Friedel-Crafts reaction of industrial importance were performed using the ionic liquid having (Al2Cl7)?moiety to assess its performance and compared with conventional processes. The synthesized products were characterised by sophisticated analytical techniques like 1H NMR, 13C NMR, FTIR, GC–MS, GC-FID, to name a few. This class of ionic liquids also have importance in various electrochemical applications like aluminium deposition and aluminium batteries.
Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst
Ajda?i?, Vladimir,Nikoli?, Andrea,Simi?, Stefan,Manojlovi?, Dragan,Stojanovi?, Zoran,Nikodinovic-Runic, Jasmina,Opsenica, Igor M.
, p. 119 - 126 (2017/12/27)
A facile decarbonylation reaction of a variety of aromatic and heteroaromatic aldehydes using maghemite-supported palladium catalyst has been developed. The magnetic properties of catalyst facilitated an easy and efficient recovery of the catalyst from the reaction mixture using an external magnet. It was found that the catalyst could be reused up to four consecutive catalytic runs without a significant change in activity. In addition, the catalyst was also very effective in the dehalogenation of aryl halides. This is the first report on efficient utilization of directly immobilized Pd on maghemite in decarbonylation and dehalogenation reactions.
A process for preparing O-toluene
-
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.
