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358665

Sigma-Aldrich

Tetrabutylammonium cyanide

95%

Synonym(s):

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

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(CN)
CAS Number:
Molecular Weight:
268.48
Beilstein/REAXYS Number:
3598808
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

signalword

Danger

Hazard Classifications

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

supp_hazards

Storage Class

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

wgk_germany

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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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)
Colorimetric detection of cyanide with a chromogenic oxazine
Tomasulo M and Raymo FM
Organic Letters, 7(21), 4633-4636 (2005)
[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)
Anhydrous tetrabutylammonium fluoride
Sun H and DiMagno SG
Journal of the American Chemical Society, 127(7), 2050-2051 (2005)
Noelia Luque et al.
Journal of chromatography. A, 1248, 74-83 (2012-06-26)
The suitability of a mixed-mode sorbent made up of admicelles of sodium dodecyl sulphate (SDS) and tetrabutylammonium (TBA) to extract and preserve pesticides from river and underground water was assessed. Pesticides belonging to different structural groups (i.e. triazines, carbamates, phenylureas

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