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Key Documents

752959

Sigma-Aldrich

(Tributylphosphoranylidene)acetonitrile solution

1 M in toluene

同義詞:

CMBP solution, Tsunoda reagent, Cyanomethylene)tributylphosphorane

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About This Item

經驗公式(希爾表示法):
C14H28NP
分子量::
241.35
MDL號碼:
分類程式碼代碼:
12352001
PubChem物質ID:
NACRES:
NA.22

形狀

liquid

品質等級

濃度

1 M in toluene

折射率

n/D 1.500 (lit.)
n20/D 1.501

密度

0.886 g/mL at 25 °C

官能基

nitrile
phosphine

儲存溫度

2-8°C

SMILES 字串

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 密鑰

OZMLUMPWPFZWTP-UHFFFAOYSA-N

一般說明

(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.

訊號詞

Danger

危險分類

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

標靶器官

Central nervous system

儲存類別代碼

3 - Flammable liquids

水污染物質分類(WGK)

WGK 3

閃點(°F)

44.6 °F - closed cup

閃點(°C)

7 °C - closed cup


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分析證明 (COA)

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Novel reactivity of stabilized methylenetributylphosphorane: a new Mitsunobu reagent.
Tsunoda T
Tetrahedron Letters, 35(28), 5081-5082 (1994)
Application of Tsunoda Reagent to the Convenient Synthesis of Drug-Like Pyrazoles.
Mosallanejad A
Tetrahedron Letters, 59(18), 1708-1710 (2018)
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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