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About This Item
Linear Formula:
(CH3CH2CH2CH2)4N(CN)
CAS Number:
Molecular Weight:
268.48
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352116
EC Number:
233-926-0
MDL number:
Beilstein/REAXYS Number:
3598808
Product Name
Tetrabutylammonium cyanide, technical, ≥80%
grade
technical
Quality Level
assay
≥80%
form
crystals
reaction suitability
core: ammonium
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
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.
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signalword
Danger
hcodes
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
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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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)

