1667-04-5

Basic information

• Product Name: 2-CHLOROMESITYLENE
• Synonyms: 2,4,6-Trimethylchlorobenzene;2,4,6-Trimethylmonochlorobenzene;Benzene,2-chloro-1,3,5-trimethyl-;Mesitylene, 2-chloro-;Mesitylene,2-chloro-;1-CHLORO-2,4,6-TRIMETHYLBENZENE;2-CHLORO-1,3,5-TRIMETHYLBENZENE;2-CHLOROMESITYLENE
• CAS NO: 1667-04-5
• Molecular Formula: C₉H₁₁Cl
• Molecular Weight: 154.64
• Mol File: 1667-04-5.mol
• Article Data: 45

Chemical Properties

• Melting Point: -43.35°C (estimate)
• Boiling Point: 204-206°C
• Flash Point: 76.8 °C
• Appearance: /
• Density: 1.05
• Refractive Index: 1.5212
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-CHLOROMESITYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROMESITYLENE(1667-04-5)
• EPA Substance Registry System: 2-CHLOROMESITYLENE(1667-04-5)

Safety Data

• Hazardous Substances Data: 1667-04-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 116, p. 8414, 1994 DOI: 10.1021/ja00097a078

Upstream product

• 527-60-6 Mesitol 
• 3453-83-6 mesitylene sulfonic acid 
• 27876-29-5 acetic acid-(2,4,6,N-tetrachloro-anilide) 
• 64-19-7 acetic acid 
• 108-67-8 1,3,5-trimethyl-benzene 
• 88-05-1 2,4,6-trimethylaniline 
• 111149-52-1 4-methylchlorobenzene-2,6-dicarboxaldehyde 
• 102626-21-1 chloro-6-methylbenzene-2,4-dicarboxaldehyde 
• 102626-20-0 2-chlorobenzene-1,3,5-tricarboxaldehyde 
• 93201-55-9 2,4,6-trimethylphenyl fluoroformate 
• 5707-04-0 Phenylselenyl chloride 
• 938-18-1 mesitylene-2-carboxylic acid chloride 
• 7693-47-2 2,4,6-trimethylphenyl carbonochloridate 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 5324-68-5 1,3,5-trichloro-2,4,6-trimethylbenzene 
• 67396-77-4 2-chloro-1,3,5-trimethyl-4-nitrobenzene 
• 57386-83-1 1,3-dichloro-2,4,6-trimethylbenzene 
• 628302-82-9 2-chloro-1,3,5-tris-trichloromethyl-benzene 
• 56961-24-1 benzene-1,3,5-tricarboxylic acid chloride 
• 67396-86-5 2-Chloro-3,5-dimethylbenzylacetat 
• 67396-84-3 4-Chloro-3,5-dimethylbenzylacetat 
• 67396-85-4 1,5-Bisacetoxymethyl-2-chloro-3-methylbenzol 
• 26583-85-7 2-bromo-4-chloro-1,3,5-trimethylbenzene 
• 41571-69-1 2-Chlor-4,6-diiod-1,3,5-trimethylbenzol 
• 108244-61-7 1-chloro-2,4,6-trimethyl-3,5-dinitro-benzene 
• 67396-78-5 4-Chloro-1,3,5-trimethyl-4-nitrocyclohexa-2,5-dienylacetat 
• 4482-03-5 bimesityl 
• 42797-68-2 1-(2,4,6-trimethylphenyl)-2-propanone 

Relevant articles and documents

In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes

Efficient metal-free methods for the electrophilic chlorination of arenes using PIFA and simple chlorine sources are reported. The in situ formation of PhI(Cl)OCOCF3 from PIFA and KCl is proposed, which resulted in a chlorinating species for moderately activated arenes. Moreover, the in situ formation of PhICl2 from PIFA and TMSCl resulted in an excellent approach for the chlorination of a great variety of arenes (20 examples) in high yields, even when working on a multigram scale.

Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand

Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.

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.