752959
(Tributylphosphoranylidene)acetonitrile solution
1 M in toluene
Synonym(s):
CMBP solution, Tsunoda reagent, Cyanomethylene)tributylphosphorane
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About This Item
Empirical Formula (Hill Notation):
C14H28NP
Molecular Weight:
241.35
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352001
MDL number:
Form:
liquid
form
liquid
Quality Level
concentration
1 M in toluene
refractive index
n/D 1.500 (lit.), n20/D 1.501
density
0.886 g/mL at 25 °C
functional group
nitrile, phosphine
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.
signalword
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
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
44.6 °F - closed cup
flash_point_c
7 °C - closed cup
Regulatory Information
危险化学品
易制毒化学品（3类）
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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.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 752959-5ML | 04061832907505 |
| 752959-1ML | 04061838136671 |