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230170

Sigma-Aldrich

Tetrabutylammonium borohydride

98%

Synonym(s):

Tetra-n-butylammonium tetrahydridoborate

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(BH4)
CAS Number:
33725-74-5
Molecular Weight:
257.31
Beilstein:
4212332
EC Number:
251-658-2
MDL number:
MFCD00012035
UNSPSC Code:
12352107
PubChem Substance ID:
24853779
NACRES:
NA.22

Assay

98%

form

solid

reaction suitability

reagent type: reductant

mp

124-128 °C (lit.)

SMILES string

[BH4-].CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.BH4/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H4/q+1;-1

InChI key

GMBOFJFPOCGSOI-UHFFFAOYSA-N

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General description

Tetrabutylammonium borohydride is used for the reduction of carboxylic acids, aldehydes, and ketones.

Application

Selective reducing agent for β-ketoamides, β-ketoesters, and carbohydrate derivatives.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H261,H314

Hazard Classifications

Skin Corr. 1B - Water-react 2

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Tetrabutylammonium borohydride
Raber DJ and Guida WC
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Tetrahedron, 49, 11169-11169 (1993)
Chemistry Letters (Jpn), 1469-1469 (1992)
Matthew N McCarroll et al.
Nature communications, 10(1), 4078-4078 (2019-09-11)
Anesthetics are generally associated with sedation, but some anesthetics can also increase brain and motor activity-a phenomenon known as paradoxical excitation. Previous studies have identified GABAA receptors as the primary targets of most anesthetic drugs, but how these compounds produce
Abderrahman Atifi et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(53), 13076-13086 (2017-07-26)
The solvent environment around iron porphyrin complexes was examined using mixed molecular/RTIL (room temperature ionic liquid) solutions. The formation of nanodomains in these solutions provides different solvation environments for substrates that could have significant impact on their chemical reactivity. Iron
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