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752959 Sigma-Aldrich

(Tributylphosphoranylidene)acetonitrile solution

1 M in toluene

Synonym: CMBP solution, Cyanomethylene)tributylphosphorane, Tsunoda reagent

  • Empirical Formula (Hill Notation) C14H28NP

  • Molecular Weight 241.35

  •  MDL number MFCD01321151

  •  PubChem Substance ID 329766327

  •  NACRES NA.22

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Properties

Related Categories C-X Bond Formation (Non-Halogen), Chemical Synthesis, Mitsunobu, Synthetic Reagents
concentration   1 M in toluene
refractive index   n/D 1.500 (lit.)
  n20/D 1.501
density   0.886 g/mL at 25 °C
storage temp.   2-8°C
SMILES string   CCCCP(CCCC)(CCCC)=CC#N
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
InChI key   OZMLUMPWPFZWTP-UHFFFAOYSA-N

Description

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.

Packaging

1, 5 mL in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Target organs 
Central nervous system
RIDADR 
UN1294 - class 3 - PG 2 - Toluene, solution
WGK Germany 
WGK 3
Flash Point(F) 
44.6 °F - closed cup
Flash Point(C) 
7 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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