174913-47-4

Basic information

• Product Name: 1,3-dibromo-2-chloro-5-methoxybenzene
• Synonyms: 1,3-dibromo-2-chloro-5-methoxybenzene
• CAS NO: 174913-47-4
• Molecular Weight: 300.377
• Mol File: 174913-47-4.mol

Chemical Properties

• CAS DataBase Reference: 1,3-dibromo-2-chloro-5-methoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dibromo-2-chloro-5-methoxybenzene(174913-47-4)
• EPA Substance Registry System: 1,3-dibromo-2-chloro-5-methoxybenzene(174913-47-4)

Safety Data

• Hazardous Substances Data: 174913-47-4(Hazardous Substances Data)

Upstream product

• 860586-90-9 2,4-dibromo-3-chloro-6-methoxyaniline 
• 74137-36-3 3,5-dibromoanisole 
• 95970-05-1 2,6-dibromo-4-methoxyaniline 
• 95-03-4 5-chloro-2-methoxyaniline 
• 106-48-9 4-chloro-phenol 
• 20188-28-7 4-chloro-2,3,5,6-tetrabromophenol 
• 89-21-4 4-chloro-2-nitroanisole 
• 623-12-1 4-chloromethoxybenzene 
• 74104-19-1 2,6-dibromo-4-chlorophenol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1004322-71-7 2-chloro-5-methoxy-1,3-bis-trimethylsilanylbenzene 
• 872275-88-2 3,5-dibromo-4-chloro-2,6-dinitro-anisole 
• 74104-19-1 2,6-dibromo-4-chlorophenol 

Relevant articles and documents

Derivatives of m-Guaiacol, Their Preparation and Their Uses

The invention concerns derivatives of m-guaiacol, their preparation and their uses as biocides, in particular as antibacterials or disinfectants.

The β effect of silicon in phenyl cations

Irradiation of chloroanisoles, phenols, and N,N-dimethylanilines bearing a trimethylsilyl (TMS) group in the ortho position with respect to the chlorine atom caused photoheterolysis of the Ar-Cl bond and formation of the corresponding ortho-trimethylsilylphenyl cations in the triplet state. The β effect of silicon on these intermediates has been studied by comparing the resulting chemistry in alcoholic solvents with that of the silicon-free analogues and by computational analysis (at the UB3LYP/6-311+G(2d,p) level in MeOH). TMS groups little affect the photophysics and the photocleavage of the starting phenyl chlorides, while stabilizing the phenyl cations, both in the triplet (ca. 4 kcal/mol per group) and, dramatically, in the singlet state (9 kcal/mol). As a result, although triplet phenyl cations are the first formed species, intersystem crossing to the more stable singlets is favored with chloroanisoles and phenols. Indeed, with these compounds, solvent addition to give aryl ethers (from the singlet) competed efficiently with reduction or arylation (from the triplet). In the case of the silylated 4-chloro-N,N- dimethylaniline, the triplet cation remained in the ground state and trapping by π nucleophiles remained efficient, though slowed by the steric bulk of the TMS group. In alcohols, the silyl group was eliminated via a photoinduced protiodesilylation during the irradiation. Thus, the silyl group could be considered as a directing, photoremovable group that allowed shifting to the singlet phenyl cation chemistry and was smoothly eliminated in the same one-pot procedure.