71258-22-5

Basic information

• Product Name: BENZYL-2,3,4,5,6-D5 BROMIDE
• Synonyms: BENZYL-2,3,4,5,6-D5 BROMIDE;Benzyl-d5 BroMide
• CAS NO: 71258-22-5
• Molecular Formula: C₇H₇Br
• Molecular Weight: 176.07
• Product Categories: Intermediates, Isotope Labelled Compounds
• Mol File: 71258-22-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BENZYL-2,3,4,5,6-D5 BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL-2,3,4,5,6-D5 BROMIDE(71258-22-5)
• EPA Substance Registry System: BENZYL-2,3,4,5,6-D5 BROMIDE(71258-22-5)

Safety Data

• Hazardous Substances Data: 71258-22-5(Hazardous Substances Data)

Usage

Description

BENZYL-2,3,4,5,6-D5 BROMIDE is a deuterated organic compound characterized by the presence of five deuterium atoms (D5) at positions 2, 3, 4, 5, and 6 on the benzene ring. It is a derivative of benzyl bromide, where the hydrogen atoms are replaced by deuterium atoms, providing unique properties for specific applications in chemical synthesis and research.

Uses

Used in Organic Synthesis:
BENZYL-2,3,4,5,6-D5 BROMIDE is used as a protecting group agent for the synthesis of alcohols and carboxylic acids. The deuterated benzyl group serves as a temporary protective shield for these functional groups during chemical reactions, preventing unwanted side reactions and ensuring the desired product formation. The use of deuterium in this compound can provide valuable insights into reaction mechanisms and improve the understanding of isotope effects in organic chemistry.
Additionally, the deuterated benzyl group can be selectively removed under mild conditions, allowing for the controlled deprotection of the target molecule without affecting other functional groups present in the molecule. This selective deprotection is particularly useful in complex organic synthesis and the development of pharmaceutical compounds.

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 1076-43-3 benzene-d6 
• 50-00-0 formaldehyd 
• 1603-99-2 2,3,4,5,6-pentadeuteriotoluene 
• 68661-10-9 <2,3,4,5,6-D5>-benzyl alcohol 
• 1079-02-3 benzoic acid-2,3,4,5,6-d5 
• 4165-57-5 bromobenzene-d5 

Downstream Products

• 54335-88-5 2,3,4,5,6-pentadeuterio-benzyl 
• 17359-59-0 α,2,3,4,5,6-hexadeuteriotoluene 
• 923282-09-1 N,N-bis[2,3,4,5,6-2H₅]benzylamine 
• 1052101-91-3 C₁₃H₃⁽²⁾H₇F₃N 
• 1356471-20-9 benzyl-d5 trimethyl phosphonium bromide 
• 1512844-40-4 6-(p-tolylsulfanylmethyl)-benzene-1,2,3,4,5-d₅ 
• 1372784-13-8 (E)-methyl 3-{2-(p-tolylsulfinylmethyl)phenyl}acrylate 
• 1372784-14-9 3-[2-(toluene-4-sulfonylmethyl)phenyl]acrylic acid methyl ester 
• 52753-91-0 (E)-methyl 3-(2-formylphenyl)acrylate 
• 216572-78-0 3-(2-hydroxymethylphenyl)acrylic acid methyl ester 
• 1372783-78-2 6-(p-tolylthiomethyl)benzene-1,2,3,4,5-d₅ 

Relevant articles and documents

Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade

Bacteria of the Roseobacter clade are abundant marine bacteria and are important contributors to the global sulfur cycle. The volatiles produced by two of its members, Phaeobacter gallaeciensis and Oceanibulbus indolifex, were analyzed to investigate whether the released compounds are derived from sulfur metabolism, and which biosynthetic pathways are involved in their formation. Both bacteria emitted different sulfides and thioesters, including new natural compounds such as 5-methyl phenylethanethioate (16) and butyl methanesulfonate (21). The S-methyl alkanoates were identified by comparison with standards that were synthesized from the respective methyl alkanoates by a new method using an easily prepared aluminium/sulfur reagent. Phaeobacter gallaeciensis is also able to produce tropone (37) in large amounts. Its biosynthesis was investigated by various feeding experiments, showing that 37 is formed via a deviation of the phenylacetate catabolism. The unstable tropone hydrate 42 was identified as an intermediate of the tropone biosynthesis that was also released together with tropolone (38). The Royal Society of Chemistry 2010.

The remarkable electron impact mass spectrum of (2-benzyl-1,3-xylylene)-15- crown-4: Expulsion of triethylene glycol by double hydrogen transfer

During our investigations of the synthesis of magnesium-containing crown ethers, the mass spectral characterisation of a precursor, (2-benzyl-1,3- xylylene)-15-crown-4 (C21H26O4), leads to a surprising result: its electron

Mechanism of the reaction of methylene with benzene: A study of kinetic hydrogen isotope effects and theoretical calculations

The reaction mechanism of singlet and triplet methylene with benzene and related aromatic compounds was investigated by kinetic isotope effects (KIEs), solvent effects, and product studies. The results are further rationalized by a series of ab initio calculations at MP2/6-31G*//RHF/6-31G* and UMP2/6-31G*//UHF/6-31G* levels of theory. The proposed 1c intermediate for the triplet reaction was found by means of the calculations, whereas no singlet analog 1 could be found.