1327238-72-1

Basic information

• Product Name: 2,7-bis[(4-N,N-dimethylamino)phenylethynyl]pyrene
• CAS NO: 1327238-72-1
• Molecular Weight: 488.632
• Mol File: 1327238-72-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,7-bis[(4-N,N-dimethylamino)phenylethynyl]pyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-bis[(4-N,N-dimethylamino)phenylethynyl]pyrene(1327238-72-1)
• EPA Substance Registry System: 2,7-bis[(4-N,N-dimethylamino)phenylethynyl]pyrene(1327238-72-1)

Safety Data

• Hazardous Substances Data: 1327238-72-1(Hazardous Substances Data)

Upstream product

• 1379589-17-9 pyrene-2,7-bis(trifluoromethanesulfonate) 
• 17573-94-3 4-ethynyl-N,N-dimethylaniline 

Relevant articles and documents

Synthesis of 2-and 2,7-functionalized pyrene derivatives: An application of selective C-H borylation

An efficient synthetic route to 2-and 2,7-substituted pyrenes is described. The regiospecific direct C-H borylation of pyrene with an iridium-based catalyst, prepared in situ by the reaction of [{Ir(μ-OMe)cod}2] (cod=1,5-cyclooctadiene) with 4,4′-di-tert-butyl-2,2′-bipyridine, gives 2,7-bis(Bpin)pyrene (1) and 2-(Bpin)pyrene (2, pin=OCMe 2CMe2O). From 1, by simple derivatization strategies, we synthesized 2,7-bis(R)-pyrenes with R=BF3K (3), Br (4), OH (5), B(OH)2 (6), and OTf (7). Using these nominally nucleophilic and electrophilic derivatives as coupling partners in Suzuki-Miyaura, Sonogashira, and Buchwald-Hartwig cross-coupling reactions, we obtained 2,7-bis(R)-pyrenes with R=(4-CO2C8H17)C6H4 (8), Ph (9), Ca≡CPh (10), Ca≡C[{4-B(Mes)2}C 6H4] (11), Ca≡CTMS (12), Ca≡C[(4-NMe 2)C6H4] (14), Ca≡CH (15), N(Ph)[(4-OMe)C6H4] (16), and R=OTf, R′=Ca≡CTMS (13). Lithiation of 4, followed by reaction with CO2, yielded pyrene-2,7-dicarboxylic acid (17), whilst borylation of 2-tBu-pyrene gave 2-tBu-7-Bpin-pyrene (18) selectively. By similar routes (including Negishi cross-coupling reactions), monosubstituted 2-R-pyrenes with R=BF3K (19), Br (20), OH (21), B(OH)2 (22), [4-B(Mes)2]C 6H4 (23), B(Mes)2 (24), OTf (25), Ca≡CPh (26), Ca≡CTMS (27), (4-CO2Me)C6H4 (28), Ca≡CH (29), C3H6CO2Me (30), OC 3H6CO2Me (31), C3H 6CO2H (32), OC3H6CO2H (33), and O(CH2)12Br (34) were obtained from 2. These derivatives are of synthetic and photophysical interest because they contain donor, acceptor, and conjugated substituents. The crystal structures of compounds 4, 5, 7, 12, 18, 19, 21, 23, 26, and 28-31 have also been obtained from single-crystal X-ray diffraction data, revealing a diversity of packing modes, which are described in the Supporting Information. A detailed discussion of the structures of 1 and 2, their polymorphs, solvates, and co-crystals is reported separately. Copyright