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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/REAXYS Number:
4212332
EC Number:
251-658-2
MDL number:
MFCD00012035
UNSPSC Code:
12352107
PubChem Substance ID:
24853779
NACRES:
NA.22

Quality Level

100

assay

98%

form

solid

reaction suitability

reagent type: reductant

mp

124-128 °C (lit.)

functional group

amine

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

signalword

Danger

hcodes

H261,H314

Hazard Classifications

Skin Corr. 1B - Water-react 2

Storage Class

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

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ4432
SHBP1985
SHBM1115
SHBK6795
SHBK6796

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Tetrabutylammonium borohydride
Raber DJ and Guida WC
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Chemistry Letters (Jpn), 1469-1469 (1992)
Tetrahedron, 49, 11169-11169 (1993)
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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