19096-07-2

Basic information

• Product Name: 9-chloro-10-methylanthracene
• Synonyms: 9-Chloro-10-methylanthracene; anthracene, 9-chloro-10-methyl-
• CAS NO: 19096-07-2
• Molecular Formula: C₁₅H₁₁Cl
• Molecular Weight: 226.7008
• Mol File: 19096-07-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 385°C at 760 mmHg
• Flash Point: 184.4°C
• Density: 1.219g/cm³
• Vapor Pressure: 8.7E-06mmHg at 25°C
• Refractive Index: 1.697
• CAS DataBase Reference: 9-chloro-10-methylanthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 9-chloro-10-methylanthracene(19096-07-2)
• EPA Substance Registry System: 9-chloro-10-methylanthracene(19096-07-2)

Safety Data

• Hazardous Substances Data: 19096-07-2(Hazardous Substances Data)

Upstream product

• 779-02-2 9-methylanthracene 

Downstream Products

• 1308652-74-5 10-methyl-9-o-tolylanthracene 

Relevant articles and documents

Halogenations of Anthracenes and Dibenz[a,c]anthracene with N-Bromosuccinimide and N-Chlorosuccinimide

Halogenation of dibenz[a,c]anthracene (1) by NBS in CCl4 affords the products of 9- and 10-monobromination in the ratio of 9:1. The reaction is accelerated by iodine, and HBr effects rearrangement of 9-bromo product to the sterically less crowded 10-bromo isomer. The mechanism is proposed to involve reversible addition of Br2, followed by elimination of HBr. Reaction of NCS with 1 in CCl4 requires addition of HCl and affords exclusively 9-chlorination. The different reactivities of NBS and NCS are ascribed to the relative amounts of free halogen produced (due to differences in N-X bond strengths involving Br and Cl), and the different sizes of the halogens. Under similar conditions, NCS chlorinates 9-bromoanthracene (2a) to afford 9,10-dichloroanthracene and 9-bromo-10-chloroanthracene in the ratio of 65:35. This reaction ostensibly occurs by addition of Cl2 to 2a, followed by preferential loss of HBr rather than HCl. 9-Methylanthracene (3) affords exclusively 9-(bromomethyl)anthracene with NBS in the absence of iodine, but mainly (67%) 9-bromo-10-methylanthracene in the presence of iodine. Chlorination of 3 with NCS in the presence of HCl also affords mostly (65%) nuclear halogenation. Nuclear bromination of anthracene, 9-methylanthracene, and dibenz[a,c]anthracene by NBS in the absence of added HBr is accelerated by iodine. This effect is probably due to an increase in the amount of bromine produced from NBS in the presence of iodine.