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658235

Sigma-Aldrich

Lithium dimethylaminoborohydride solution

1 M in THF

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C2H9BLiN
CAS Number:
Molecular Weight:
64.85
MDL number:
UNSPSC Code:
12352000
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

reagent type: reductant

Quality Level

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

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


Certificates of Analysis (COA)

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Customers Also Viewed

Ab initio analysis of lithium dimethylaminoborohydride
Mogali S, et al.
The Journal of Organic Chemistry, 66(7), 2368-2373 (2001)
Lithium aminoborohydrides: powerful, selective, air-stable reducing agents
Pasumansky L, et al.
Organic Process Research & Development, 10(5), 959-970 (2006)
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
Fisher, G. B. et al
The Journal of Organic Chemistry, 59, 6378-6378 (1994)
Pasumansky, L. et al
Aldrichimica Acta, 38, 61-61 (2005)

Articles

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.

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