| Identification | Back Directory | [Name]
CYANOMETHYLENETRIBUTYLPHOSPHORANE | [CAS]
157141-27-0 | [Synonyms]
CMBP
Tsunoda Reagent
Cyanomethyltributylphosphorane
CynoMethylenetributyl phosphorane
CYANOMETHYLENETRIBUTYLPHOSPHORANE
CYANOMETHYLENETRI-N-BUTYLPHOSPHORANE
Cyanomethylenetributylphosphorane>
(Tributylphosphoranylidene)acetonitrile
2-(tributylphosphoranylidene)acetonitrile
cyanomethylenetri-n-butylphosphorane90+%n
2-(tributyl-l5-phosphanylidene)acetonitrile
Acetonitrile,2-(tributylphosphoranylidene)-
(Tributylphosphoranylidene)acetonitrile solution
{[Tri(but-1-yl)]phosphoranylidene}acetonitrile 97% | [Molecular Formula]
C14H28NP | [MDL Number]
MFCD01321151 | [MOL File]
157141-27-0.mol | [Molecular Weight]
241.35 |
| Questions And Answer | Back Directory | [Synthesis]
At 0 °C, a solution of 27.0 g (97.6 mmol) of ST913 in 100 mL of anhydrous tetrahydrofuran was added together with a solution of 44.4 mL (97.6 mmol) of 2,2 N-butyllithium in hexane. After stirring at room temperature for 1 hour, the reaction mixture was evaporated, and the residue was dissolved in toluene petroleum ether. The precipitated lithium chloride was filtered off, and the res solution was evaporated. The residue was purified by short-path distillation under high vacuum (220–230 °C/0.1 mbar). 15.3 g of cyanomethylenetri-n-butylphosphine (65% of the theoretical value) was given as a colorless liquid.  Figure: Synthetic Route of CYANOMETHYLENETRIBUTYLPHOSPHORANE |
| Chemical Properties | Back Directory | [Boiling point ]
339.1±25.0 °C(Predicted) | [density ]
0.921 g/mL at 25 °C | [refractive index ]
n20/D1.500(lit.) | [Fp ]
7 °C | [storage temp. ]
Refrigerator | [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 |
| Hazard Information | Back Directory | [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. |
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| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 18918157536; |
| Website: |
http://www.energy-chemical.com |
| Company Name: |
Adamas Reagent, Ltd.
|
| Telephone: |
4006009262 13023226327 |
| Website: |
http://www.tansoole.com |
| Company Name: |
Aemon Chemical
|
| Telephone: |
0086-755-86198205 |
| Website: |
www.aemonchem.com |
| Company Name: |
Sigma-Aldrich
|
| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
|