Skip to Content
Merck
All Photos(2)

Documents

658235

Sigma-Aldrich

Lithium dimethylaminoborohydride solution

1 M in THF

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C2H9BLiN
CAS Number:
53042-33-4
Molecular Weight:
64.85
MDL number:
MFCD07784404
UNSPSC Code:
12352000
PubChem Substance ID:
24884338
NACRES:
NA.22

reaction suitability

reagent type: reductant

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

Related Categories

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.

Signal Word

Danger

Hazard Statements

H225,H302,H319,H335,H351

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

Borane tetrahydrofuran complex solution 1.0 M in THF

Sigma-Aldrich

176192

Borane tetrahydrofuran complex solution

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)
Saikia, P.P.
Synlett, 995-995 (2007)
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
Pasumansky, L. et al
Aldrichimica Acta, 38, 61-61 (2005)
View All Related Papers

Articles

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.

Related Content

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service