957470-88-1

Basic information

• Product Name: N,N-Diethyl-4'-methylbiphenyl-4-carboxamide
• Synonyms: N,N-Diethyl-4'-methylbiphenyl-4-carboxamide
• CAS NO: 957470-88-1
• Molecular Formula: C18H21NO
• Molecular Weight: 267
• Mol File: 957470-88-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 68-70℃
• Appearance: /
• CAS DataBase Reference: N,N-Diethyl-4'-methylbiphenyl-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Diethyl-4'-methylbiphenyl-4-carboxamide(957470-88-1)
• EPA Substance Registry System: N,N-Diethyl-4'-methylbiphenyl-4-carboxamide(957470-88-1)

Safety Data

• Hazardous Substances Data: 957470-88-1(Hazardous Substances Data)

Upstream product

• 106-38-7 para-bromotoluene 
• 7461-38-3 4-chloro-N,N-diethyl-benzamide 
• 90252-89-4 p-tolylzinc(II) chloride 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 10366-88-8 4-fluoro-N,N-diethyl-benzamide 
• 5892-99-9 4-bromo-N,N-diethylbenzamide 

Relevant articles and documents

Mono- and dinuclear pincer nickel catalyzed activation and transformation of C-Cl, C-N, and C-O bonds

Condensation of 2-NH2C6H4P(Et)Ph (2) with pyrrole-2-carboxaldehyde generated 2-(C4H4N-2′-CH - N)C6H4P(Et)Ph (3). Treatment of 3 with NaH and followed by (DME)NiX2 (X = Cl, Br) afforded mononuclear pincer nickel complexes [Ni{2-(C4H3N-2′-CH - N)C6H4P(Et)Ph}X] (4a, X = Cl; 4b, X = Br). Reaction of [2-NH2C6H4P(Ph)]2(CH2)n (5a, n = 3; 5b, n = 4) with pyrrole-2-carboxaldehyde or 5-tert-butyl-1H-pyrrole-2-carbaldehyde formed [2-(C4H4N-2′-CH - N)C6H4P(Ph)]2(CH2)n (6a, n = 3; 6b, n = 4) and [2-(5′-tBuC4H3N-2′-CH - N)C6H4P(Ph)]2(CH2)4 (6c). Respective treatment of 6a-c with NaH followed by (DME)NiX2 (X = Cl, Br) gave the dinuclear nickel complexes [Ni{2-(5′-RC4H2N-2′-CH - N)C6H4P(Ph)}X]2(CH2)n (7a, R = H, X = Cl, n = 3; 7b, R = H, X = Cl, n = 4; 7c, R = H, X = Br, n = 4; 7d, R = tBu, X = Cl, n = 4). Catalysis of the complexes for the activation and transformation of C-Cl, C-N, and C-O bonds was evaluated. Complex 7c exhibited excellent catalytic activity in the cross-coupling of aryl chlorides or aryltrimethylammonium iodides with arylzinc reagents as well as of aryl sulfamates with aryl Grignard reagents. The dinuclear nickel complexes 7b-d showed higher catalytic activity than the mononuclear complexes in each type of reaction.

Nickel-catalyzed cross-coupling of aryl fluorides and organozinc reagents

Ni(PCy3)2Cl2 was demonstrated to effectively catalyze cross-coupling of aryl fluorides and organozinc reagents. Both electron-poor and -rich aryl fluorides can react effectively with nucleophiles including aryl-, methyl-, and benzylzinc chlorides. A wide range of substituents and functional groups are tolerated. In the presence of a directing group, PhC(O), the reaction is selective for cleavage of the C-F bond ortho to the carbonyl substituent in a difluoroarene.

Amido pincer nickel catalyzed kumada cross-coupling of aryl, heteroaryl, and vinyl chlorides

Amido pincer nickel complexes {Ni(Cl)[2-P(Ph2)C 6H4NC(Ph)=NAr]} (Ar = 4-MeC6H4, 1; Ar = 4-ClC6H4, 2; Ar = 4-MeOC6H4, 3) were shown to efficiently catalyze the cross-coupling of activated, unactivated, and deactivated aryl chlorides, N-heteroaryl chlorides, 1,4-dichlorobenzene, and vinyl chlorides with aryl Grignard reagents. Georg Thieme Verlag Stuttgart, New York.