13122-33-3

Basic information

• Product Name: Benzene-d, 4-bromo-
• Synonyms: Benzene-d,p-bromo- (7CI,8CI); 1-Bromo-4-deuteriobenzene; 4-Deuteriobromobenzene;Bromobenzene-4-d1; p-Bromobenzene-d
• CAS NO: 13122-33-3
• Molecular Formula: C6H4 Br D
• Molecular Weight: 158.002
• Mol File: 13122-33-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Benzene-d, 4-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene-d, 4-bromo-(13122-33-3)
• EPA Substance Registry System: Benzene-d, 4-bromo-(13122-33-3)

Safety Data

• Hazardous Substances Data: 13122-33-3(Hazardous Substances Data)

Upstream product

• 106-37-6 1.4-dibromobenzene 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 5467-74-3 4-Bromophenylboronic acid 
• 108-86-1 bromobenzene 
• 811-98-3 d⁽⁴⁾-methanol 
• 10448-07-4 2-bromobenzenediazonium tetrafluoroborate 
• 56075-37-7 1-(methylsulfonyl)-2-(4-bromophenyl)diazene 

Downstream Products

• 99532-28-2 3-(4-deuteriophenyl)-1-propane 
• 53907-53-2 2-(4-deuterio-phenyl)-ethanol 
• 113709-90-3 p-deuteriophenylacetylene 
• 19162-84-6 p-deuteriophenyllithium 
• 99234-94-3 4,4'-dideuterodiphenylamine 
• 99532-29-3 3-(4-deuteriophenyl)propene-3-d 

Relevant articles and documents

A Sustainable Heterogeneous Iron Catalyst Fe/SBA-15 towards Direct Arylation of Unactivated C(sp3)?H and C(sp2)?H Bonds with Arenes

Iron grafted over mesoporous silica (8 wt %Fe/SBA-15) is a sustainable, efficient heterogeneous iron catalyst for direct arylation of biphenyl methane C(sp3)?H and benzene C(sp2)?H bonds. The selective extraction deposition (SED) technique was adopted to graft iron easily over the mesoporous support SBA-15 by using LaFeO3 as an iron precursor. The synthesized catalyst has been characterized by EPR spectroscopy, diffuse reflectance UV/Vis spectroscopy, and temperature programmed reduction (TPR) analysis to understand the coordination environment and state of oxidic iron species grafted over the mesoporous SBA-15. TPR results confirm the presence of isolated, clustered, oligomeric oxidic iron species in the catalyst. The adopted SED technique is highly successful for grafting 8 wt % iron into the mesopores of SBA-15 without forming iron oxide particles. Unlike homogeneous iron, the 8 wt %Fe/SBA-15 catalyst does not need support from an electron-withdrawing group and additives to carry out arylation of benzene and could be successfully recycled five times.

Metal-Free sp2-C-H Borylation as a Common Reactivity Pattern of Frustrated 2-Aminophenylboranes

C-H borylation is a powerful and atom-efficient method for converting affordable and abundant chemicals into versatile organic reagents used in the production of fine chemicals and functional materials. Herein we report a facile C-H borylation of aromatic and olefinic C-H bonds with 2-aminophenylboranes. Computational and experimental studies reveal that the metal-free C-H insertion proceeds via a frustrated Lewis pair mechanism involving heterolytic splitting of the C-H bond by cooperative action of the amine and boryl groups. The adapted geometry of the reactive B and N centers results in an unprecedentently low kinetic barrier for both insertion into the sp2-C-H bond and intramolecular protonation of the sp2-C-B bond in 2-ammoniophenyl(aryl)- or -(alkenyl)borates. This common reactivity pattern serves as a platform for various catalytic reactions such as C-H borylation and hydrogenation of alkynes. In particular, we demonstrate that simple 2-aminopyridinium salts efficiently catalyze the C-H borylation of hetarenes with catecholborane. This reaction is presumably mediated by a borenium species isoelectronic to 2-aminophenylboranes.