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358665

Sigma-Aldrich

Tetrabutylammonium cyanide

95%

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Synonym(s):
N,N,N-tributyl-1-butanaminium cyanide
Linear Formula:
(CH3CH2CH2CH2)4N(CN)
CAS Number:
10442-39-4
Molecular Weight:
268.48
Beilstein:
3598808
EC Number:
233-926-0
MDL number:
MFCD00043221
PubChem Substance ID:
24861981
NACRES:
NA.22

Quality Level

200

Assay

95%

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

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Application

Tetrabutylammonium cyanide (TBACN) can be used as a source of cyanide ion for colorimetric studies.
It can be employed as a reactant in the preparation of:
  • Tetrabutylammonium fluoride (TBAF), which can be used to remove silyl ether protecting groups.
  • Rhenium-based single-chain magnets, (DMF)4MReCl4(CN)2 (M = Mn, Fe, Co, Ni).
  • Phosphorescent blue light-emitting anionic iridium complexes.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H300 + H310 + H330 - H410

Hazard Classifications

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

Supplementary Hazards

EUH032

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis, characterization, and DFT/TD-DFT calculations of highly phosphorescent blue light-emitting anionic iridium complexes
Di Censo D, et al.
Inorganic Chemistry, 47(3), 980-989 (2008)
[ReCl4 (CN) 2] 2-: A High Magnetic Anisotropy Building Unit Giving Rise to the Single-Chain Magnets (DMF) 4MReCl4 (CN) 2 (M= Mn, Fe, Co, Ni)
Harris TD, et al.
Journal of the American Chemical Society, 132(11), 3980-3988 (2010)
Colorimetric detection of cyanide with a chromogenic oxazine
Tomasulo M and Raymo FM
Organic Letters, 7(21), 4633-4636 (2005)
Anhydrous tetrabutylammonium fluoride
Sun H and DiMagno SG
Journal of the American Chemical Society, 127(7), 2050-2051 (2005)
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
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