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658235

Sigma-Aldrich

Lithium dimethylaminoborohydride solution

1 M in THF

Sinónimos:

N-Methylmethanamine boron complex, Lithium (dimethylamino)trihydroborate, Lithium trihydro(N-methylmethanaminato)borate

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About This Item

Fórmula empírica (notación de Hill):
C2H9BLiN
Número de CAS:
53042-33-4
Peso molecular:
64.85
MDL number:
MFCD07784404
UNSPSC Code:
12352000
PubChem Substance ID:
24884338
NACRES:
NA.22

reaction suitability

reagent type: reductant

Quality Level

100

concentration

1 M in THF

refractive index

n20/D 1.423

density

0.882 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[Li+].[BH3-]N(C)C

InChI

1S/C2H9BN.Li/c1-4(2)3;/h1-3H3;/q-1;+1

InChI key

CEDUMRZWZLVFKS-UHFFFAOYSA-N

General description

Lithium dimethylaminoborohydride is a reagent exhibiting dual properties like a metal hydride and nitrogen nucleophile. It is generally considered as an alternative to lithium aluminum hydride (LAH) for the reduction of carbonyl compounds, amides, and lactams.

Application

Lithium Aminoborohydride (LAB) Reagents

Reactant for:
  • B-H oxidative addition reactions
  • Reduction and amination reactions
  • Reduction of N-alkyl lactams
  • Synthesis of tertiary amine-boranes
Capable of reducing a variety of fuctional groups.
LABs can transfer the amine moiety, as in the case of the reaction with halopyridines and primary alkyl methanesulfonates.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH019

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

Certificados de análisis (COA)

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Lithium aminoborohydrides: powerful, selective, air-stable reducing agents
Pasumansky L, et al.
Organic Process Research & Development, 10(5), 959-970 (2006)
Ab initio analysis of lithium dimethylaminoborohydride
Mogali S, et al.
The Journal of Organic Chemistry, 66(7), 2368-2373 (2001)
Shannon Thomas et al.
Organic letters, 5(21), 3867-3870 (2003-10-11)
[reaction: see text] Lithium aminoborohydride (LAB) reagents promote the amination of 2-fluoropyridine under mild reaction conditions, providing 2-(dialkylamino)pyridines in excellent yield and purity. Treatment of 2-fluoropyridine with 1.1 equiv of lithium aminoborohydride at room temperature affords complete conversion after 1
Saikia, P.P.
Synlett, 995-995 (2007)
Fisher, G. B. et al
The Journal of Organic Chemistry, 59, 6378-6378 (1994)
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Artículos

Lithium Aminoborohydride (LAB) Reagents

Lithium aminoborohydride (LAB) reagents are a new class of powerful and selective reagents developed in the laboratory of Professor Bakthan Singaram at the University of California, Santa Cruz.

Contenido relacionado

Singaram Group – Professor Product Portal

here are many optically active organic compounds of biological and medicinal significance. For example, statine analogs, antibiotics, anesthetics, heterocyclic compounds, unusual amino acids, and insect pheromones all contain stereogenic centers. There is, therefore, a continuous need for new asymmetric methodology.

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