908139-14-0

Basic information

• Product Name: 9-[4-(4-methylphenylamino)phenyl]-9H-carbazole
• Synonyms: 9-[4-(4-methylphenylamino)phenyl]-9H-carbazole
• CAS NO: 908139-14-0
• Molecular Weight: 348.447
• Mol File: 908139-14-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 9-[4-(4-methylphenylamino)phenyl]-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[4-(4-methylphenylamino)phenyl]-9H-carbazole(908139-14-0)
• EPA Substance Registry System: 9-[4-(4-methylphenylamino)phenyl]-9H-carbazole(908139-14-0)

Safety Data

• Hazardous Substances Data: 908139-14-0(Hazardous Substances Data)

Upstream product

• 17763-95-0 2,2'-bis-<<(trifluoromethyl)sulfonyl>oxy>biphenyl 
• 1806-29-7 2,2'-dihydroxybiphenyl 
• 19264-74-5 9-(4-methoxyphenyl)-9H-carbazole 
• 222620-05-5 N-(4-hydroxyphenyl)carbazole 
• 106-49-0 p-toluidine 
• 858516-23-1 4-bromo-N-(p-tolyl)aniline 
• 86-74-8 9H-carbazole 
• 57102-42-8 N-(4-bromophenyl)carbazole 

Relevant articles and documents

Palladium-catalyzed Selective Amination of Aryl(haloaryl)amines with 9H-Carbazole Derivatives

Palladium-catalyzed amination of aryl(haloaryl)amines with 9H-carbazole derivatives was investigated. In the amination of (4-bromophenyl)phenylamine with 9H-carbazole by the use of Pd2(dba)3/PtBu3/NaOtBu catalyst, the main product was desired 9-[4-(phenylamino)phenyl]-9H-carbazole in 60% yield with conversion of (4-bromophenyl)phenylamine >99%, and the concomitant formation of 9-[4-[phenyl[4-(phenylamino)phenyl]amino]phenyl]-9H-carbazole (15% yield), which is the consecutive by-product, was observed. When XPhos was used instead of PtBu3, the desired product was provided in 81% yield and the consecutive by-product was suppressed to 7.7%. The yield of the desired product reached 98% by the use of tBu-XPhos. Such excellent yields of the desired product were also obtained with other 2-di-tert-butyl- or 2-di(1-adamantyl)phosphino-1,1’-biaryls. Various 9-(arylamino)aryl-9H-carbazoles could be synthesized from aryl(haloaryl)amines and 9H-carbazole derivatives in high yields by the use of tBu-XPhos. The amination of 4-bromotoluene with a mixture of diphenylamine and 9H-carbazole gave only 9-o-tolyl-9H-carbazole with tBu-XPhos, while the use of PtBu3 or XPhos afforded the mixture of 9-o-tolyl-9H-carbazole and diphenyl(o-tolyl)amine, indicating that Pd2(dba)3/tBu-XPhos/NaOtBu catalyst high selectively favors 9H-carbazole over diphenylamine as an amination substrate. (Figure presented.).

METHOD FOR PRODUCING 9-(ARYLAMINO)ARYL-9H-CARBAZOLE

PROBLEM TO BE SOLVED: To efficiently produce 9-(arylamino)aryl-9H-carbazole. SOLUTION: A haloarylamine represented by formula (1) is reacted with a carbazole derivative in the presence of a palladium compound, a phosphine compound, and a metal alkoxide. (Each Ar is independently a phenylene group or the like, provided that the phenylene group or the like may be substituted with a C1-4 alkyl group or the like; each X is independently Cl, Br or I; p and q are each independently 1 or 2; each R1 is independently a C1-6 alkyl group, a phenyl group, a naphthyl group, a biphenylyl group or a pyridyl group; m is 1 or 2; n is 0 or 1; and m+n=2 is satisfied.) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Efficient synthesis of biscarbazoles by palladium-catalyzed twofold C-N coupling and C-H activation reactions

A new and efficient strategy for the synthesis of 3,9′- and 2,9′-biscarbazoles was developed. Our strategy relies on the cyclization of 1,1′-biphenyl-2,2′-diyl bis(trifluoromethanesulfonate) with 4- or 3-anisidine, transformation of the methoxy to a triflate group and subsequent oxidative Pd-catalyzed cyclization with various anilines. This journal is the Partner Organisations 2014.