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79989

Tetrabutylammonium cyanide

≥80%, crystals, technical grade

Synonym(s):

N,N,N-tributyl-1-butanaminium cyanide

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(CN)
CAS Number:
10442-39-4
Molecular Weight:
268.48
NACRES:
NA.22
PubChem Substance ID:
329768102
UNSPSC Code:
12352116
EC Number:
233-926-0
MDL number:
MFCD00043221
Beilstein/REAXYS Number:
3598808
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Product Name

Tetrabutylammonium cyanide, technical, ≥80%

grade

technical

Quality Level

100

assay

≥80%

form

crystals

reaction suitability

core: ammonium

mp

89-92 °C (lit.)

SMILES string

[C-]#N.CCCC[N+](CCCC)(CCCC)CCCC

InChI

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

InChI key

KRRBFUJMQBDDPR-UHFFFAOYSA-N

Application

Tetrabutylammonium cyanide can be used as a catalyst:
  • For the deprotection of aliphatic thioacetate to synthesize free thiols in the presence of a protic solvent.
  • In the O-TMS cyanosilylation of carbonyl compounds to synthesize cyanohydrin trimethylsilyl ethers in the presence of trimethylsilyl cyanide (TMSCN).
  • For the ring expansion of β-lactams to synthesize γ-lactams through a bond cleavage of the β-lactam in the presence of acetonitrile.

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pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1

supp_hazards

EUH032

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC8121
BCBV9472
BCBQ1975V
BCBP5901V
BCBM0706V

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Tetrabutylammonium cyanide catalyzes the addition of TMSCN to aldehydes and ketones
Cordoba R, et al.
ARKIVOC (Gainesville, FL, United States), 4, 94-99 (2004)
Fabio Galeotti et al.
Journal of chromatography. A, 1284, 141-147 (2013-03-05)
In this study, by using tetrabutylammonium bisulfate as ion-pairing reagent, we were able to separate all the main heparin/heparan sulfate disaccharides generated by the action of heparinases along with the main Hep tetrasaccharide possessing a 3-O-sulfate group on the sulfoglucosamine
A J Chinchalikar et al.
The European physical journal. E, Soft matter, 35(7), 55-55 (2012-07-06)
Clouding is studied by small-angle neutron scattering (SANS) on a charged micellar system of sodium dodecyl sulphate (SDS) and tetrabutylammonium bromide (TBAB) with varying temperature and salt NaCl. We show that the clouding occurs as a result of increase in
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Global Trade Item Number

SKUGTIN
79989-100G04061833466827