Basic information
- CAS
10442-39-4- Standard SMILES
CCCC[N+](CCCC)(CCCC)CCCC.[C-]#N- InChIKey
KRRBFUJMQBDDPR-UHFFFAOYSA-N- Molecular formula
- C17H36N2
- Average molar mass
- 268.5 g/mol
- Monoisotopic mass
- 268.28784915
Names & identifiers
- Preferred name
- Tetrabutylammonium Cyanide
- IUPAC
- tetrabutylazanium cyanide
- English name
- Tetrabutylammonium cyanide
- Molecular formula
- C17H36N2
- Molecular weight
- 268.48
Names & synonyms
Tetrabutylammonium cyanide10442-39-4DTXSID9065077RefChem:188408DTXCID9032878233-926-0tetrabutyl ammonium cyanidetetrabutylazanium;cyanide1-Butanaminium, N,N,N-tributyl-, cyanidetetra-n-butylammonium cyanideMFCD00043221EINECS 233-926-0
Show more names
Tetrabutylaminium·cyanidetrabutylammonium cyanidetetrabutylazanium:cyanideTetrabutylaMMoniuM cyanide 95%Tetrabutylammonium cyanide (7CI)n,n,n-tributyl-1-butanaminiucyanideN,N,N-Tributyl-1-butanaminium cyanide (1:1)Tetrabutylammonium cyanide technical, >=80%
n,n,n-tributylbutan-1-aminium cyanidetetrabutylammoniumcyanidetetrabutlyammonium cyanidetetrabutylammonium;cyanidetetra n-butylammonium cyanideSCHEMBL140587tetra-n-butyl ammonium cyanideCHEMBL1078151
Database identifiers
- CAS
10442-39-4- PubChem CID
- 165872
- DTXSID
DTXSID9065077- ChEMBL
CHEMBL1078151- EC Number
- 233-926-0
Properties
Computed structural properties
- Topological polar surface area
- 23.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 12
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 126
Experimental & physicochemical properties
Chemical ClassesToxic Gases & Vapors -> Cyanides
Physical DescriptionSlightly beige crystalline solid; Soluble in water; [MSDSonline]
Physicochemical properties
- Melting point
- 89 · 89-92 °C(lit.)
- storage temp.
- 2 · Storage temp. 2-8°C
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- color
- Pale Yellow to Pale Beige
- BRN
- 3598808 · 3598808
- Stability
- Hygroscopic
- InChI
- 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
- InChIKey
- KRRBFUJMQBDDPR-UHFFFAOYSA-N
- SMILES
- [N+](CCCC)(CCCC)(CCCC)CCCC.N#[C-]
- EPA Substance Registry System
- 1 · 1-Butanaminium, N,N,N-tributyl-, cyanide (10442-39-4)
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information1-Butanaminium, N,N,N-tributyl-, cyanide: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryAn irritant; Readily absorbed through skin; Targets CNS, blood, lungs, thyroid, and cardiovascular system; May cause cyanosis and CNS depression; [MSDSonline] See CYANIDES.
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Safety & protection
Exposure Control and Personal Protection2.0 [mg/m3], inhalable fraction, as CN[German Research Foundation (DFG)]
Permissible Exposure Limit (PEL)5.0 [mg/m3], as CN
Immediately Dangerous to Life or Health (IDLH)25.0 [mg/m3], as CN
Toxicology
Adverse EffectsOther Poison - Chemical Asphyxiant
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties.
Uses & manufacturing
General Manufacturing Information1-Butanaminium, N,N,N-tributyl-, cyanide (1:1): ACTIVE
Applications
UsesTetrabutylammonium 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.
UsesTetrabutylammonium cyanide is commonly used as a catalyst for the synthesis of organic compounds such as multisubstituted dihydrofurans and pyrrolo[2,1-a]isoquinolines.
Upstream & downstream products
Downstream products
Related reactions
122 records
Compound notes
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