19486-60-3

Basic information

• Product Name: 2-Isopropyl-1,1'-biphenyl
• Synonyms: 2-(1-Methylethyl)-1,1'-biphenyl;2-Isopropyl-1,1'-biphenyl;2-Isopropylbiphenyl
• CAS NO: 19486-60-3
• Molecular Formula: C₁₅H₁₆
• Molecular Weight: 196.2875
• Mol File: 19486-60-3.mol

Chemical Properties

• Melting Point: 24.5°C
• Boiling Point: 269.77°C
• Flash Point: 140.2°C
• Appearance: /
• Density: 0.9811 (estimate)
• Refractive Index: 1.5761 (estimate)
• CAS DataBase Reference: 2-Isopropyl-1,1'-biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isopropyl-1,1'-biphenyl(19486-60-3)
• EPA Substance Registry System: 2-Isopropyl-1,1'-biphenyl(19486-60-3)

Safety Data

• Hazardous Substances Data: 19486-60-3(Hazardous Substances Data)

Upstream product

• 98-82-8 Isopropylbenzene 
• 17333-73-2 phenylium 
• 75-26-3 isopropyl bromide 
• 92-52-4 biphenyl 
• 187737-37-7 propene 
• 66003-76-7 Diphenyliodonium triflate 
• 108-86-1 bromobenzene 
• 19099-54-8 2-isopropyliodobenzene 
• 108-24-7 acetic anhydride 
• 643-28-7 2-isopropylaniline 
• 2396-01-2 phenyl radical 

Downstream Products

• 50991-15-6 (+/-)-trans-2-Isopropyl-bicyclohexyl 
• 50991-15-6 (+/-)-cis-2-Isopropyl-bicyclohexyl 
• 7116-95-2 4-isopropylbiphenyl 

Relevant articles and documents

Palladium-catalyzed arylation of simple arenes with iodonium salts

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Isopropylation of biphenyl over ZSM-12 zeolites

ZSM-12 zeolites, ZSM-12L and ZSM-12S, with MTW topology were synthesized by using methyltriethylammonium bromide (MTEABr) and tetraethylammnoium bromide (TEABr) as structure directing agents (SDA), respectively, for the isopropylation of biphenyl (BP) usi

Shape-selective alkylation of biphenyl with propylene using zeolite and amorphous silica-alumina catalysts

The influence of zeolite structure for the alkylation of biphenyl with propylene was studied over various zeolites such as HY, HZSM-5, and dealuminated mordenite (DMOR), as well as amorphous SiO2/Al2O 3, in a stirred tank reactor. Biphenyl conversion was found to increase with reaction time for HZSM-5 and DMOR zeolites and reach a leveling off in 4 h, whereas for HY and amorphous SiO2/Al2O 3 a leveling off was reached within an hour. DMOR displayed the highest selectivity for 4,4′-diisopropylbiphenyl (4,4′-DIPB) even at temperatures as high as 300 °C, whereas for HY, HZSM-5 and amorphous SiO2/Al2O3 selectivities fell in the range of 10-35%; they were significantly lower than observed for DMOR. These differences in selectivity might be due to the structure and pore channels of the zeolites. DMOR was found to be an active catalyst, the selectivity for 4-isopropylbiphenyl (4-IPB) and (4,4′-DIPB) was high among isopropylbiphenyl (IPB) and diisopropylbiphenyl (DIPB) isomers, respectively, indicating DMOR possesses shape-selectivity. The selectivity of 4,4′-DIPB increased with time, while the corresponding selectivity of 4-IPB decreased for DMOR catalyst. Alkylation of biphenyl with propylene occurred with predominant formation of 4-IPB in the first step. 4-IPB is only a source in the second step of alkylation of biphenyl with propylene for the formation of 4,4′-DIPB, while 3-IPB does not participate in the formation of DIPB isomers.

Revealing a second transmetalation step in the Negishi coupling and its competition with reductive elimination: Improvement in the interpretation of the mechanism of biaryl syntheses

This paper presents an experimental and theoretical investigation of the Pd-catalyzed Negishi coupling reaction and reveals a novel second transmetalation reaction between an Ar1-Pd-Ar2 species and the organozinc reagent Ar2-ZnX. Understanding of this second step reveals how homocoupling and dehalogenation products are formed. Thus, the second transmetalation generates Ar2PdAr2 and Ar 1ZnCl, which upon reductive elimination and hydrolysis, respectively, give the homocoupling product Ar2-Ar2 and the dehalogenation product Ar1H. The ratio of the cross-coupling product Ar1-Ar2 and the homocoupling product Ar 2-Ar2 is determined by competition between the second transmetalation and reductive elimination steps. This mechanism is further supported by density functional theoretical calculations. Calculations on a series of reactions suggest a strategy in controlling the selectivity of cross-coupling and homocoupling pathways, which we have experimentally verified.

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