752959
(Tributylphosphoranylidene)acetonitrile solution
1 M in toluene
别名:
CMBP solution, Tsunoda reagent, Cyanomethylene)tributylphosphorane
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关于此项目
经验公式（希尔记法）:
C14H28NP
分子量:
241.35
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352001
MDL number:
产品名称
(Tributylphosphoranylidene)acetonitrile solution, 1 M in toluene
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
SMILES string
CCCCP(CCCC)(CCCC)=CC#N
InChI key
OZMLUMPWPFZWTP-UHFFFAOYSA-N
form
liquid
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
Quality Level
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
存储类别
3 - Flammable liquids
wgk
WGK 3
flash_point_f
44.6 °F - closed cup
flash_point_c
7 °C - closed cup
法规信息
危险化学品
易制毒化学品（3类）
此项目有
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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