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752959

Sigma-Aldrich

(Tributylphosphoranylidene)acetonitrile solution

1 M in toluene

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Synonym(s):
CMBP solution, Tsunoda reagent, Cyanomethylene)tributylphosphorane
Empirical Formula (Hill Notation):
C14H28NP
Molecular Weight:
241.35
MDL number:
MFCD01321151
UNSPSC Code:
12352001
PubChem Substance ID:
329766327
NACRES:
NA.22

form

liquid

Quality Level

100

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

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.

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

Target Organs

Central nervous system

WGK

WGK 3

Flash Point(F)

44.6 °F

Flash Point(C)

7 °C

Regulatory Information

易制毒化学品（3类）
危险化学品

Certificates of Analysis (COA)

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Application of Tsunoda Reagent to the Convenient Synthesis of Drug-Like Pyrazoles.
Mosallanejad A
Tetrahedron Letters, 59(18), 1708-1710 (2018)
Novel reactivity of stabilized methylenetributylphosphorane: a new Mitsunobu reagent.
Tsunoda T
Tetrahedron Letters, 35(28), 5081-5082 (1994)
Izumi Sakamoto et al.
Chemical & pharmaceutical bulletin, 53(11), 1508-1509 (2005-11-08)
(Cyanomethylene)tributylphosphorane (CMBP), which promoted the alkylation of various nucleophiles (HA) with alcohols (ROH) to give RA (Mitsunobu-type reaction), was prepared in two steps starting from chloroacetonitrile.

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