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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:
10442-39-4
Molecular Weight:
268.48
Beilstein:
3598808
EC Number:
233-926-0
MDL number:
MFCD00043221
UNSPSC Code:
12352116
PubChem Substance ID:
329768102
NACRES:
NA.22

grade

technical

Quality Level

100

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
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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Certificates of Analysis (COA)

Lot/Batch Number
BCCC8121
BCBV9472
BCBQ1975V
BCBP5901V
BCBM0706V

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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)
R Bryan Sears et al.
Journal of inorganic biochemistry, 121, 77-87 (2013-01-29)
The complex cis-[Ru(phpy)(phen)(CH3CN)2](+) (phpy=2-phenylpyridine, phen=1,10-phenanthroline) was investigated as a potential photodynamic therapy (PDT) agent. This complex presents desirable photochemical characteristics including a low energy absorption tail extending into the PDT window (600-850nm) and photoinduced exchange of the CH3CN ligands, generating
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
Oliver Bixner et al.
The Journal of chemical physics, 136(20), 204503-204503 (2012-06-07)
The interaction of exciton and charge transfer (CT) states plays a central role in photo-induced CT processes in chemistry, biology, and physics. In this work, we use a combination of two-dimensional electronic spectroscopy (2D-ES), pump-probe measurements, and quantum chemistry to
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