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752959

Sigma-Aldrich

(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
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

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.

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

44.6 °F - closed cup

Flash Point(C)

7 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

752959-5ML:4548173327488
752959-BULK:
752959-1ML:4548173327471
752959-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW4284
MKCV5260
MKCT6979
MKCT8726
MKCR2618

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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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