869721-21-1

Basic information

• Product Name: 2-(bromomethyl)-4-chloro-1-methylbenzene
• Synonyms: 2-(bromomethyl)-4-chloro-1-methylbenzene;Benzene, 2-(bromomethyl)-4-chloro-1-methyl-
• CAS NO: 869721-21-1
• Molecular Formula: C₈H₈BrCl
• Molecular Weight: 219.50612
• EINECS: 604-604-1
• Mol File: 869721-21-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 251.7±25.0 °C(Predicted)
• Appearance: /
• Density: 1.491±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(bromomethyl)-4-chloro-1-methylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(bromomethyl)-4-chloro-1-methylbenzene(869721-21-1)
• EPA Substance Registry System: 2-(bromomethyl)-4-chloro-1-methylbenzene(869721-21-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 869721-21-1(Hazardous Substances Data)

Usage

General Description

2-(bromomethyl)-4-chloro-1-methylbenzene, also known as p-chloro-o-tolyl bromide, is a chemical compound with the molecular formula C8H8BrCl. It is a colorless to light yellow liquid at room temperature and is commonly used in organic synthesis as a building block for the production of pharmaceuticals, agrochemicals, and other fine chemicals. 2-(bromomethyl)-4-chloro-1-methylbenzene is also a versatile substrate for a variety of chemical reactions, including nucleophilic substitution and palladium-catalyzed cross-coupling reactions. Additionally, p-chloro-o-tolyl bromide is a key intermediate in the synthesis of many biologically active compounds, making it an important molecule in the field of medicinal chemistry.

Upstream product

• 615-60-1 4-chloro-1,2-dimethylbenzene 
• 58966-29-3 (5-chloro-2-methylphenyl)methanol 
• 95-64-7 4-amino-o-xylene 
• 58966-34-0 5-chloro-2-methylbenzaldehyde 
• 7499-06-1 5-chloro-2-methylbenzoic acid 

Downstream Products

• 58966-21-5 Ethyl-2-methyl-5-chlorbenzylsulfid 
• 58966-30-6 Ethyl-2-methyl-5-chlorbenzylsulfon 
• 1289647-90-0 C₂₃H₂₄ClN₃O₂ 

Relevant articles and documents

Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation

The enantioselective amination of C(sp3)-H bonds is a powerful synthetic transformation yet highly challenging to achieve in an intermolecular sense. We have developed a family of anionic variants of the best-in-class catalyst for Rh-catalyzed C-H amination, Rh2(esp)2, with which we have associated chiral cations derived from quaternized cinchona alkaloids. These ion-paired catalysts enable high levels of enantioselectivity to be achieved in the benzylic C-H amination of substrates bearing pendant hydroxyl groups. Additionally, the quinoline of the chiral cation appears to engage in axial ligation to the rhodium complex, providing improved yields of product versus Rh2(esp)2 and highlighting the dual role that the cation is playing. These results underline the potential of using chiral cations to control enantioselectivity in challenging transition-metal-catalyzed transformations.

SELECTIVITY AND MECHANISM IN THE SIDE-CHAIN HALOGENATION OF METHYLBENZENES PROMOTED PHOTOCHEMICALLY AND BY METAL COMPLEXES IN THE PRESENCE OF HALIDE IONS

The intramolecular selectivity in a variety of side-chain halogenations of alkyl-aromatics has been determined in AcOH by measuring the isomeric distribution in the reactions of 4-t-butyl- and 4-chloro-1,2-dimethylbenzene (1 and 2, respectively) with: Br2/hν, CAN/Br-, CAN=cerium(IV) ammonium nitrate, cobalt(III) acetate/Br-, S2O8=/Br-, N-bromosuccinimide (in CCl4), Cl2/hν, CAN/Cl-, cobalt(III) acetate/Cl-.In the bromination reactions selectivity is independent of the reaction conditions, thus suggesting that in all brominating systems Br. is the actual reacting species.Very surprisingly, with 1 as the substrate, Cl2/hν is a more selective system than Br2/hν.With 2 the two systems display similar selectivity.It has been suggested that in AcOH the transition state for photochlorination has an electron transfer character which increases as the substrate becomes more electron rich.The idea of a "variable" transition state for the photochlorination in AcOH is supported by data of relative reactivity of substituted toluenes indicating that the effect on the rate increases as the substituent becomes more electron donor.AcOH must have an essential role in this respect since in CCl4 situation returns to be "normal" with chlorination less selective than bromination.Selectivity of CAN/Cl- is very similar to that of Cl2/hν, whereas significant differences are observed with cobalt(III) acetate/Cl-.Probably Cl. and a cobalt(III) chloride complex are the reacting species in CAN/Cl- and cobalt(III) acetate/Cl-, respectively.