CAS 157141-27-0 Cyanomethylenetributylphosphorane (HCID 4622928)

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Basic information

CAS: 157141-27-0
Standard SMILES: CCCCP(=CC#N)(CCCC)CCCC
InChIKey: OZMLUMPWPFZWTP-UHFFFAOYSA-N
Molecular formula: C14H28NP
Average molar mass: 241.35 g/mol
Monoisotopic mass: 241.19593653

Names & identifiers

Preferred name: Cyanomethylenetributylphosphorane
IUPAC: 2-(tributyl-λ5-phosphanylidene)acetonitrile
English name: Cyanomethylenetributylphosphorane
Molecular formula: C14H28NP
Molecular weight: 241.35

Names & synonyms

157141-27-0CyanomethylenetributylphosphoraneDTXSID90404992RefChem:334883DTXCID60355846679-660-22-(Tributylphosphoranylidene)acetonitrile(Tributylphosphoranylidene)acetonitrileMFCD013211512-(tributyl-lambda5-phosphanylidene)acetonitrile2-tributylphosphoranylideneacetonitrileAcetonitrile, (tributylphosphoranylidene)-

Show more names

CMBPTsunoda Reagent2-(tributyl-l5-phosphanylidene)acetonitrileCyanomethyltributylphosphoraneCynoMethylenetributyl phosphorane

Acetonitrile, 2-(tributylphosphoranylidene)-cyanomethylenetribuylphosphorane(cyanomethylene)tributylphosphoranecyanomethylene tributyl phosphoranecyanomethylenetri-n-butylphosphoraneSY025792CS-0046100A50071

Database identifiers

CAS: 157141-27-0
PubChem CID: 4622928
DTXSID: DTXSID90404992
EC Number: 679-660-2
Nikkaji: J1.882.895B、J726.653G

Properties

Computed structural properties

XLogP: 2.9
Topological polar surface area: 23.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 9
Heavy atoms: 16
Formal charge: 0
Complexity: 231

Physicochemical properties

Boiling point: 339.1 · 339.1±25.0 °C(Predicted)
Density: 0.921 g/mL · 0.921 g/mL at 25 °C
refractive index: 20 · n20/D1.500(lit.)
Flash point: 7 °C · 7 °C
storage temp.: 2 · 2-8°C
form: clear liquid
color: Yellow to Amber to Dark purple
InChI: InChI=1S/C14H28NP/c1-4-7-11-16(14-10-15,12-8-5-2)13-9-6-3/h14H,4-9,11-13H2,1-3H3
InChIKey: OZMLUMPWPFZWTP-UHFFFAOYSA-N
SMILES: C(#N)C=P(CCCC)(CCCC)CCCC
UNSPSC Code: 12352001 · 12352001
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319
Precautionary statements: 264 · P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301+H311 (20%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

P260, P261, P262, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P320, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (40%)

Safety data

wgk: 3
ridadr: 3275
hs_code: 2931499090
risk_code: 10-23/24/25-67-65-48/20-38-11-63
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: F,Xn
safety_code: 16-26-36/37/39-62-36/37
hazard_class: 3
Storage Class: 10 - Combustible liquids
Hazard statements: H302-H315-H319
Limited Quantities: 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Precautionary statements: P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501

Chemistry & industry

Applications · 2 items

Uses(Tributylphosphoranylidene)acetonitrile can be utilized as a reagent in the: Stereoselective synthesis of skytanthine and other O- and N-containing heterocycles by Mitsunobu intramolecular cycloalkylation.Wittig olefination of esters, lactones, N-Boc lactam, and cyclic imide to corresponding Wittig products.

General Description(Tributylphosphoranylidene)acetonitrile is a stabilized trialkylphosphorane that can act as a substitute to the diethyl azodicarboxylate and triphenylphosphine (DEAD-TPP) system for Mitsunobu reaction between nucleophiles (HA) and alcohols (ROH) to form RA. It is highly useful when the pKa of the nucleophiles are higher than 11.