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Merck

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

Product Name

Tetrabutylammonium cyanide, technical, ≥80%

InChI key

KRRBFUJMQBDDPR-UHFFFAOYSA-N

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

SMILES string

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

grade

technical

assay

≥80%

form

crystals

mp

89-92 °C (lit.)

Quality Level

100

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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.

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
BCCH7242
BCCC8121
BCBV9472
BCBQ1975V
BCBP5901V

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Benito Alcaide et al.
Organic letters, 7(18), 3981-3984 (2005-08-27)
Tetrabutylammonium cyanide (20 mol %) catalyzes ring expansion of 4-(arylimino)methylazetidin-2-ones 2 to 5-aryliminopyrrolidin-2-ones 3 through a novel N1-C4 bond cleavage of the beta-lactam nucleus. New, efficient one-pot protocols to enantiopure succinimide derivatives 3 and 4 from beta-lactam aldehydes 1 have
Tetrabutylammonium cyanide catalyzes the addition of TMSCN to aldehydes and ketones
Cordoba R, et al.
ARKIVOC (Gainesville, FL, United States), 4, 94-99 (2004)
Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide
Holmes B, et al.
Tetrahedron, 61, 12339-12342 (2005)
Matt Petrowsky et al.
The journal of physical chemistry. B, 116(33), 10098-10105 (2012-07-31)
Onsager's model of the dielectric constant is used to provide a molecular-level picture of how the dielectric constant affects mass and charge transport in organic liquids and organic liquid electrolytes. Specifically, the molecular and system parameters governing transport are the
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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