5275-42-3

Basic information

• Product Name: bromo(N,N-dimethylmethanamine)dihydridoboron
• CAS NO: 5275-42-3
• Molecular Formula: C₃H₁₁BBrN
• Molecular Weight: 151.8411
• Mol File: 5275-42-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: bromo(N,N-dimethylmethanamine)dihydridoboron(CAS DataBase Reference)
• NIST Chemistry Reference: bromo(N,N-dimethylmethanamine)dihydridoboron(5275-42-3)
• EPA Substance Registry System: bromo(N,N-dimethylmethanamine)dihydridoboron(5275-42-3)

Safety Data

• Hazardous Substances Data: 5275-42-3(Hazardous Substances Data)

Usage

General Description

Bromo(N,N-dimethylmethanamine)dihydridoboron, also known as Me2N-BH2Br, is an organoboron compound used in organic synthesis and as a reagent in the preparation of various organic compounds. It is a colorless, air-sensitive solid that is soluble in non-polar solvents such as diethyl ether and benzene. This chemical is primarily used as a source of the borohydride anion for reducing organic compounds. It is also known for its use in the hydroboration reaction, where the BH2 group is added to an unsaturated organic molecule in the presence of an alkene or alkyne. Bromo(N,N-dimethylmethanamine)dihydridoboron has applications in the pharmaceutical and agrochemical industries as a key intermediate in the synthesis of various compounds.

Upstream product

• 75-22-9 trimethylamine-borane 
• 10294-33-4 boron tribromide 
• 617-86-7 triethylsilane 
• 121-44-8 triethylamine 

Downstream Products

• 75-22-9 trimethylamine-borane 
• 1135446-19-3 [H₂B(ImMes)2]Br 

Relevant articles and documents

The kinetics and mechanism of trimethylamine-haloborane hydrolysis

The rates of solvolysis of trimethylamine-monohaloboranes in aqueous dioxane at 25° increase in the series (CH3)3NBH2Cl 3)3NBH2Br 3)3NBH2I. The diiodoborane adduct reacts more slowly than the monoiodo compound but faster than trimethylamine-borane. Only a very slight retardation in rate is observed on substitution of deuterium for hydrogen on boron in the diiodo derivative (kH/kD = 1.1); however, a noticeable solvent isotope effect (kH2O/kD2O = 1.8) is observed for hydrolysis of both the mono- and diiodoborane adducts in 67% aqueous dioxane at 25°. Rates increase with increasing water content of the aqueous dioxane solvent system. No significant effect on rate of acidity is seen for hydrogen ion concentrations as high as 0.3 M or hydroxide ion concentrations up to 0.1 M, nor is the rate appreciably affected by the addition of potassium chloride or potassium iodide up to 0.3 M. The results indicate a mechanism for hydrolysis of the halo compounds quite different from that postulated for amine-BH3 adducts. It is proposed that a rate-determining cleavage of a boron-halogen bond is followed by rapid collapse of an incipient boron(1+) ion. An analogy to nucleophilic substitution reactions in haloborane-amines leading to kinetically stable boronium ions is suggested.