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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:
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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

658235-25ML:4548173219646
658235-BULK:
658235-100ML:4548173314549
658235-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL0827
SHBG1715V
SHBC6509
22796DK
22405JE

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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
S Thomas et al.
Organic letters, 3(24), 3915-3918 (2001-11-27)
Lithium aminoborohydride (LAB) reagents initiate the amination or reduction of alkyl methanesulfonate esters, as dictated by reaction conditions. Alkyl methanesulfonate esters treated with unhindered LABs provide tertiary amines in excellent yield. Reduction to the corresponding alkane is achieved using a
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

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.

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.

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