14941-51-6

Basic information

• Product Name: BENZENE-1,3-D2
• Synonyms: BENZENE-1,3-D2
• CAS NO: 14941-51-6
• Molecular Formula: C₆H₆
• Molecular Weight: 80.12
• Mol File: 14941-51-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 79.75 °C
• Appearance: /
• CAS DataBase Reference: BENZENE-1,3-D2(CAS DataBase Reference)
• NIST Chemistry Reference: BENZENE-1,3-D2(14941-51-6)
• EPA Substance Registry System: BENZENE-1,3-D2(14941-51-6)

Safety Data

• Hazardous Substances Data: 14941-51-6(Hazardous Substances Data)

Usage

Uses

Benzene-1,3-d2 (CAS# 14941-51-6) is a useful isotopically labeled research compound.

Upstream product

• 22069-96-1 bromobenzene-3-d₁ 
• 1684-46-4 1,4-dideuterobenzene 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 108-36-1 1,3-dibromobenzene 
• 1076-43-3 benzene-d6 

Relevant articles and documents

Thermal rearrangement, XXV: The automerization of benzene as a radical-initiated reaction

The thermal isomerization of [1,4-D2]-(3a) and [1,2-13C2]benzene (1a) has been studied in excess hydrogen at 750-850°C with contact time less than 1.2 s and very low partial pressure in a quartz flow system. In both cases, the main isomerization products are the corresponding meta isomers. The data suggest a radical intramolecular interchange of the benzene carbon atoms by 1,2-C shifts. The multistep reaction cascade is initiated by H addition to the benzene ring followed by transannular homoallyl rearrangements involving the intermediate formation of bicyclo[3.1.0]hexenyl and cyclopentadienylmethyl radicals. This pathway constitutes a side reaction competing with the direct stabilization of the cyclohexadienyl radicals formed preferentially at high temperature. VCH Verlagsgesellschaft mbH, 1996.

Isotope Effects in Arene C-H Bond Activation by

The isotope effects involved in the activation of arene C-H bonds by the intermediate have been investigated.The ratio kH/kD for coordination to a double bond in benzene (the rate-determining step of arene activation) is found to be 1.05(6), whereas kH/kD=1.4 for the second step in which the C-H bond of the coordinated arene undergoes oxidative addition.The isotope effect KH/D for the equilibrium between the more stable phenyl hydride complex (C5Me5)Rh(PMe3)(C6D5)H and the complex containing hydrogen in the ortho position of the phenyl ring (C5Me5)Rh(PMe3)(o-C6D4H)D shows a preference for hydrogen (vs. deuterium) on the metal of 2.7.The kinetic isotope effect for reductive elimination and dissociation of m-xylene from (C5Me5)Rh(PMe3)(3,5-C6H3Me2)H vs. (C5Me5)Rh(PMe3)(3,5-C6H3Me2)D is found to be inverse, with kH/kD=o.51.Analysis of the data for the deuterated benzene derivatives confirms that the kinetic isotope for the reductive elimination step is inverse.Attemps to prepare the complex (C5Me5)Rh(PMe3)(CH3)D by reduction of + with - resulted in the formation of both (C5Me5)Rh(PMe3)(CH3)D and (C5Me5)Rh(PMe3)(CH2D)H.