95-72-7

Basic information

• Product Name: 2-Chloro-1,4-dimethylbenzene
• Synonyms: 1-CHLORO-2,5-DIMETHYLBENZENE;2-CHLORO-1,4-DIMETHYLBENZENE;2-CHLORO-4-METHYLTOLUENE;2-CHLORO-P-XYLENE;2,5-DIMETHYLCHLOROBENZENE;CHLORO-PARA-XYLENE;2-CHLORO-PARA-XYLENE;2-Chloro-1,4-dimethylbenzene, 2-Chloro-p-xylene
• CAS NO: 95-72-7
• Molecular Formula: C₈H₉Cl
• Molecular Weight: 140.61
• EINECS: 202-444-2
• Product Categories: Halogen toluene;Chlorine Compounds
• Mol File: 95-72-7.mol

Chemical Properties

• Melting Point: 2 °C(lit.)
• Boiling Point: 186 °C(lit.)
• Flash Point: 153 °F
• Appearance: Clear colourless to light yellow liquid
• Density: 1.049 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.524(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Ethyl Acetate
• BRN: 2040349
• CAS DataBase Reference: 2-Chloro-1,4-dimethylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-1,4-dimethylbenzene(95-72-7)
• EPA Substance Registry System: 2-Chloro-1,4-dimethylbenzene(95-72-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/38-36/37/38-20/21/22
• Safety Statements: 26-36
• RIDADR: 1993
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 95-72-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Studies:
2-Chloro-1,4-dimethylbenzene is utilized as a chemical intermediate in the synthesis of various organic compounds, dyes, and other chemicals. Its unique structure and properties make it a valuable component in the development of new chemical entities and processes.
Used in Solvent Applications:
As a solvent, 2-Chloro-1,4-dimethylbenzene is employed in various industrial processes due to its ability to dissolve a wide range of substances. Its solubility properties and low flash point contribute to its effectiveness as a solvent in different applications.
Used in Chemical Production:
2-Chloro-1,4-dimethylbenzene is used in the production of various chemicals, including dyes and other specialty chemicals. Its presence in these processes is essential for the synthesis of the desired end products.

Reactivity Profile

Simple aromatic halogenated organic compounds, such as 2-Chloro-1,4-dimethylbenzene, are very unreactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

InChI:InChI=1/C8H9Cl/c1-6-3-4-7(2)8(9)5-6/h3-5H,1-2H3

Upstream product

• 106-42-3 para-xylene 
• 95-78-3 2,5-Dimethylaniline 
• 609-54-1 2,5-dimethylbenzenesulfonic acid 
• 132907-18-7 3,6-dimethoxy-3,6-dimethylcyclohexa-1,4-diene 
• 124-63-0 methanesulfonyl chloride 
• 933-01-7 4-chloro-benzenesulfenyl chloride 
• 7553-56-2 iodine 
• 7782-50-5 chlorine 
• 75-52-5 nitromethane 
• 7446-70-0 aluminium trichloride 
• 7791-25-5 sulfuryl dichloride 
• 95-47-6 o-xylene 
• 1124-05-6 1,4-dichloro-2,5-dimethylbenzene 

Downstream Products

• 17961-81-8 Trimethyl-(2,5-dimethylphenyl)silane 
• 13152-96-0 (2,5-dimethylphenyl)(p-tolyl)methanone 
• 5162-82-3 3-chloro-4-methylbenzoic acid 
• 34633-69-7 1-chloro-2,5-dimethyl-4-nitrobenzene 
• 34840-79-4 2,3-dichloro-p-xylene 
• 1124-05-6 1,4-dichloro-2,5-dimethylbenzene 
• 7697-25-8 2-chloro-4-methylbenzoic acid 
• 16732-17-5 4-chloro-2,5-dimethyl-benzenesulfonic acid 
• 10388-10-0 2-chloro-1,4-bis-(trichloromethyl)-benzene 
• 10221-08-6 2-chloro-1,4-bis-chloromethyl-benzene 
• 1967-31-3 2-chloroterephthalic acid 
• 3411-03-8 3-Chlor-4-methyl-benzaldehyd 
• 89938-19-2 2-chloro-1,4-bis-iodomethyl-benzene 
• 88-49-3 4-chloro-2,5-dimethylbenzene-1-sulfonyl chloride 

Relevant articles and documents

Rate constant ratios in the consecutive chlorination of liquid-phase p-xylene with Cl2 and an iron(III) chloride catalyst

Given that p-xylene is an important chemical feedstock for many final products in the market from pesticides, pharmaceuticals, peroxides to dyes, its chlorinated derivatives are of interest in the chemical industry. In this paper, the rate constant ratios of the consecutive chlorination of p-xylene at 70°C in a gas–liquid semibatch reactor using molecular chlorine and iron(III) chloride as a catalyst was investigated up to the fourth successive reaction (tetrachloro-p-xylene production). The ratios were determined with both mathematical expressions and a graphical method proposed recently in the literature by use of the maxima of the successive products. The ratios found for monochloro-p-xylene (2-chloro-p-xylene), dichloro-p-xylene (the sum of 2,3-dichloro-p-xylene and 2,5-dichloro-p-xylene), trichloro-p-xylene (2,3,5-trichloro-p-xylene), and tetrachloro-p-xylene (2,3,5,6-tetrachloro-p-xylene) are k2/k1=?0.295, k3/k1=?0.0826, and k4/k1=?0.00383. The ratio of the dichlo-isomers produced was also determined as 2.12 in favor of 2,5-dichloro-p-xylene, which is reasonable since 2,3-dichloro-p-xylene is highly hindered by the adjacent groups on the aromatic nucleus. The existing knowledge found in the literature on the rate constant ratios of consecutive reactions was also extended in this paper with a new mathematical expression for the determination of the third stage product peak concentration. The standard uncertainties of the rate constant ratios, the standard deviation of the means, as well as the expanded uncertainties of the means, were calculated. Finally, the propagation of uncertainties for the trichloro-p-xylene was estimated using the partial derivatives of this product for each of the rate constants.

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides

A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.

Sulfur(VI) fluoride compounds and methods for the preparation thereof

This application describes a compound represented by Formula (I): (I) wherein: Y is a biologically active organic core group comprising one or more of an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which Z is covalently bonded; n is 1, 2, 3, 4 or 5; m is 1 or 2; Z is O, NR, or N; X1 is a covalent bond or —CH2CH2—, X2 is O or NR; and R comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group. Methods of preparing the compounds, methods of using the compounds, and pharmaceutical compositions comprising the compounds are described as well.

Photocatalytic activation of N-chloro compounds for the chlorination of arenes

Photoredox catalysis activates N-chloramines and N-chloro-succinimide (NCS) for the electrophilic chlorination of arenes. The photooxidation of the nitrogen atom to a radical cation induces a positive polarization on the chlorine atom, which results in a higher reactivity in electrophilic aromatic chlorination reactions.

Aromatic substitution in ball mills: Formation of aryl chlorides and bromides using potassium peroxomonosulfate and NaX

Aryl chlorides and bromides are formed from arenes in a ball mill using KHSO5 and NaX (X = Cl, Br) as oxidant and halogen source, respectively. Investigation of the reaction parameters identified operating frequency, milling time, and the number of milling balls as the main influencing variables, as these determine the amount of energy provided to the reaction system. Assessment of liquid-assisted grinding conditions revealed, that the addition of solvents has no advantageous effect in this special case. Preferably activated arenes are halogenated, whereby bromination afforded higher product yields than chlorination. Most often reactions are regio- and chemoselective, since p-substitution was preferred and concurring side-chain oxidation of alkylated arenes by KHSO5 was not observed. The Royal Society of Chemistry.

Photochemical dehalogenation mediated by macrocyclic nickel(II) complexes

A new photochemical dehalogenation system mediated by macrocyclic nickel(II) complexes was developed. Using this system, which consists of a macrocyclic nickel(II) complex catalyst, triethanolamine (TEOA) as a sacrificial reductant, and the ruthenium complex [Ru(bpy)3](ClO 4)2 as a photosensitizer, catalytic debromination of 1-bromo-4-t-butylbenzene in acetonitrile was effectively carried out. The catalytic capabilities of various macrocyclic nickel(II) complexes in debromination reactions were also elucidated.

Microwave assisted solid additive effects in simple dry chlorination reactions with n-chlorosuccinimide

Solid additives participate in the dry microwave assisted chlorination reaction of N-chlorosuccinimide with the xylenes affecting both yields and chemoselectivities. Total yields can be increased up to nine times for simple alkylaromatics and chemoselectivities can be altered according to the desired ring or α-side chlorination product by choosing the appropriate additive. We believe that in these reactions the solid additives play a very important role by increasing yields and affecting chemoselectivities, as well as behaving as microwave energy absorbers that consequently aid the transfer of heat to the active reagents.

Phosphonium nitrate ionic liquid catalysed electrophilic aromatic oxychlorination

Trioctylmethylphosphonium nitrate (P8,8,8,1NO3), an ionic liquid made via a green synthesis, catalyses electrophilic aromatic chlorination of arenes with HCl and air at 80 °C. The aromatic oxychlorination is truly catalytic in nitrate, proceeds without added solvents, and uses atmospheric oxygen as oxidant. The extent of chlorination can be controlled to yield selectively mono or dichlorinated products, and the ionic liquid catalyst can be recycled. Dependence of the chlorination rate on HCl and nitrate concentrations as well as on the rate of re-oxidation of the nitrogen intermediates by air, allowed us to propose a reaction mechanism.

Regiospecific chlorination of xylenes using K-10 montmorrillonite clay

Regiospecific chlorination of xylenes has been developed by employing NCS as a reagent and K-10 montmorrillonite clay as a solid support. Copyright Taylor & Francis Group, LLC.

Chlorination of aromatics with trichloroisocyanuric acid (TCICA) in bronsted-acidic imidazolium ionic liquid [BMIM(SO3H)][OTf]: An economical, green protocol for the synthesis of chloroarenes

A survey study on electrophilic chlorination of aromatics with trichloroisocyanuric acid (TCICA) in Bronsted-acidic imidazolium ionic liquid [BMIM(SO3H)][OTf] is reported. The reactions are performed under very mild conditions (at ～50°C) and give good to excellent yields, depending on the substrates. Chemoselectivity for mono- v. dichlorination can be tuned by changing the arene-to-TCICA ratio and the reaction time. The survey study and competitive experiments suggest that triprotonated/protosolvated TCICA is a selective/moderately reactive transfer-chlorination electrophile. Density functional theory was used as guide to obtain further insight into the nature of the chlorination electrophile and the transfer-chlorination step. CSIRO 2007.