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658308

Sigma-Aldrich

Lithium morpholinoborohydride solution

1 M in THF

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About This Item

Empirical Formula (Hill Notation):
C4H11BLiNO
CAS Number:
144240-18-6
Molecular Weight:
106.89
MDL number:
MFCD07784406
UNSPSC Code:
12352005
PubChem Substance ID:
24884341

reaction suitability

reagent type: reductant

concentration

1 M in THF

refractive index

n20/D 1.489

density

0.877 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[Li+].C[B-](C)(C)N1CCOCC1

InChI

1S/C4H11BNO.Li/c5-6-1-3-7-4-2-6;/h1-4H2,5H3;/q-1;+1

InChI key

FHKYRXRJDHFNMQ-UHFFFAOYSA-N

Application

Lithium Aminoborohydride (LAB) Reagents

  • Reagent for reduction-amination reactions
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 Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 2

target_organs

Respiratory system

supp_hazards

EUH014,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

flash_point_c

-17 °C

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Certificates of Analysis (COA)

Lot/Batch Number
09330KE
09123ED

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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)
Fisher, G. B. et al
The Journal of Organic Chemistry, 59, 6378-6378 (1994)
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
Saikia, P.P.
Synlett, 995-995 (2007)

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