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Merck
CN

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:
329766327
UNSPSC Code:
12352001
MDL number:
MFCD01321151
Form:
liquid

Key Documents

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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

100

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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Certificates of Analysis (COA)

Lot/Batch Number
MKDB2366
MKCX9214
MKCW4284
MKCV5260
MKCT6979

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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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