4165-57-5

Basic information

• Product Name: BROMOBENZENE-D5
• Synonyms: BROMOBENZENE-D5;bromo(2H5)benzene;Bromobenzene-D5;BROMOBENZENE-D5, 99.5 ATOM % D;Bromobenzene-d5isotopic;Bromobenzene-d5,99%(Isotopic);Bromobenzene-d5, 99.5 atom% D, for NMR;Benzene-d5, bromo-
• CAS NO: 4165-57-5
• Molecular Formula: C₆H₅Br
• Molecular Weight: 162.04
• EINECS: 224-013-8
• Mol File: 4165-57-5.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 53 °C23 mm Hg(lit.)
• Flash Point: 124 °F
• Appearance: Clear colorless/Liquid
• Density: 1.539 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.12mmHg at 25°C
• Refractive Index: n20/D 1.5585(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Insoluble in water.
• BRN: 1866602
• CAS DataBase Reference: BROMOBENZENE-D5(CAS DataBase Reference)
• NIST Chemistry Reference: BROMOBENZENE-D5(4165-57-5)
• EPA Substance Registry System: BROMOBENZENE-D5(4165-57-5)

Safety Data

• Hazard Codes: Xi,N,F
• Statements: 10-38-51/53
• Safety Statements: 61
• RIDADR: UN 2514 3/PG 3
• WGK Germany: 3
• F: 8-10
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 4165-57-5(Hazardous Substances Data)

Usage

Description

BROMOBENZENE-D5, also known as deuterated bromobenzene, is a chemical compound that consists of a benzene ring with a bromine atom attached to it, where five hydrogen atoms are replaced by deuterium atoms. This deuterated form is commonly used in various chemical reactions and synthesis processes due to its unique properties.

Uses

Used in Chemical Synthesis:
BROMOBENZENE-D5 is used as a general reagent in palladium-catalyzed reactions for its ability to facilitate the formation of carbon-carbon bonds and other complex organic structures. The use of deuterium in this compound can provide valuable insights into reaction mechanisms and improve the understanding of the reaction pathways.
Used in Grignard Reagent Synthesis:
BROMOBENZENE-D5 is also used in the synthesis of Grignard reagents, which are important in organic chemistry for their ability to act as nucleophiles in various reactions. The deuterated version of bromobenzene can help in the preparation of Grignard reagents with enhanced stability and reactivity, making them suitable for a wide range of applications in organic synthesis.

InChI:InChI=1/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H/i1D,2D,3D,4D,5D

Upstream product

• 1076-43-3 benzene-d6 
• 108-86-1 bromobenzene 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 71-43-2 benzene 
• 7732-18-5 water 

Downstream Products

• 1486-01-7 biphenyl-d10 
• 855287-82-0 4,4'-dibromo-2,3,5,6-tetradeuterio-benzophenone 
• 60124-86-9 1-(1-d₅-phenylcyclohexyl)piperidine 
• 78486-57-4 1,2-di(phenyl-d5)benzene 
• 1079-02-3 benzoic acid-2,3,4,5,6-d5 
• 78486-58-5 1,3-di(phenyl-d5)benzene 
• 78486-59-6 1,4-di(phenyl-d5)benzene 
• 78486-61-0 3,3'-di(phenyl-d5)biphenyl 
• 78486-65-4 3,4'-di(phenyl-d5)biphenyl 
• 78486-62-1 4,4'-di(phenyl-d5)biphenyl 
• 78486-64-3 2,4'-di(phenyl-d5)biphenyl 
• 83160-30-9 N-ethyl-2-(pentadeuterioanilino)naphthalene 
• 78486-67-6 4,4''-di(phenyl-d5)-o-terphenyl 
• 78486-68-7 4,4'''-di(phenyl-d5)-o-quaterphenyl 

Relevant articles and documents

Entry to 1,2,3,4-Tetrasubstituted Arenes through Addressing the " Meta Constraint" in the Palladium/Norbornene Catalysis

Arenes with four different contiguous substituents, i.e. 1,2,3,4-tetrasubstituted arenes, are commonly found in bioactive compounds, but they are nontrivial to access via conventional methods. Through addressing the "meta constraint" in the palladium/norbornene (Pd/NBE) cooperative catalysis, which is the difficulty of tolerating a sizable meta substituent in aryl halide substrates, here a modular and regioselective approach is realized for preparing 1,2,3,4-tetrasubstituted arenes. One key is the use of a C2-amide-substituted NBE, and a combined experimental and computational study reveals its role in promoting the NBE insertion and the ortho C-H metalation steps. The scope is broad: A variety of electrophiles and nucleophiles could be introduced to the ortho and ipso positions, respectively, with 1,4-disubstituted aryl halides, leading to diverse unsymmetrical contiguous tetrasubstituted arenes. Application of this approach has been demonstrated in streamlined syntheses of several bioactive compounds.

Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions

Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.