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79989

Sigma-Aldrich

Tetrabutylammonium cyanide

technical, ≥80%

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:
3598808
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

grade

technical

Quality Level

Assay

≥80%

form

crystals

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 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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Supplementary Hazards

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide
Holmes B, et al.
Tetrahedron, 61, 12339-12342 (2005)
Purnandhu Bose et al.
Chemistry, an Asian journal, 7(10), 2373-2380 (2012-07-26)
A new series of tris(2-aminoethyl)amine (tren)-based L-alanine amino acid backboned tripodal hexaamide receptors (L1-L5) with various attached moieties based on electron-withdrawing fluoro groups and lipophilicity have been synthesized and characterized. Detailed binding studies of L1-L5 with different anions, such as
Jacek Cieślak et al.
Current protocols in nucleic acid chemistry, Chapter 4, Unit4-Unit4 (2012-09-08)
The conversion of 3',5'-disilylated 2'-O-(methylthiomethyl)ribonucleosides to 2'-O-(phthalimidooxymethyl)ribonucleosides is achieved in yields of 66% to 94%. Desilylation and dephtalimidation of these ribonucleosides by treatment with NH(4)F in MeOH produce 2'-O-aminooxymethylated ribonucleosides, which are efficient in producing stable and yet reversible 2'-conjugates

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