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658243

Sigma-Aldrich

Lithium pyrrolidinoborohydride solution

1 M in THF

Synonym(s):

Lithium trihydro-1-pyrrolidinylborate

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About This Item

Empirical Formula (Hill Notation):
C4H11BLiN
CAS Number:
144188-76-1
Molecular Weight:
90.89
MDL number:
MFCD07784405
UNSPSC Code:
12352005
PubChem Substance ID:
24884339
NACRES:
NA.22

reaction suitability

reagent type: reductant

concentration

1 M in THF

refractive index

n20/D 1.425

density

0.890 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[Li+].[H][B-]([H])([H])N1CCCC1

InChI

1S/C4H11BN.Li/c5-6-3-1-2-4-6;/h1-4H2,5H3;/q-1;+1

InChI key

CUBZYJJJUFGOBJ-UHFFFAOYSA-N

Application

Lithium Aminoborohydride (LAB) Reagents

  • Reducing agent for reduction of carbonic and carboxylic acid derivatives
  • Reagent for reduction-amination reactions
Capable of reducing a variety of fuctional groups.[1][2][3][2]
LABs can transfer the amine moiety, as in the case of the reaction with halopyridines and primary alkyl methanesulfonates.[4][5]

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)

-17.0 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK1186
SHBH3415V
SHBG1936V
SHBD3545V
SHBC7085

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Saikia, P.P.
Synlett, 995-995 (2007)
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
Pasumansky, L. et al
Aldrichimica Acta, 38, 61-61 (2005)
Fisher, G. B. et al
The Journal of Organic Chemistry, 59, 6378-6378 (1994)
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

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.

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Singaram Group – Professor Product Portal

New asymmetric methodology meets the continuous demand for optically active compounds in various fields.

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