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Merck
CN

79989

Sigma-Aldrich

四丁基氰化铵

technical, ≥80%

别名:

N,N,N-tributyl-1-butanaminium cyanide

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About This Item

线性分子式:
(CH3CH2CH2CH2)4N(CN)
CAS号:
分子量:
268.48
Beilstein:
3598808
EC 号:
MDL编号:
UNSPSC代码:
12352116
PubChem化学物质编号:
NACRES:
NA.22

等级

technical

质量水平

检测方案

≥80%

形式

crystals

mp

89-92 °C (lit.)

SMILES字符串

[C-]#N.CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.CN/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-2/h5-16H2,1-4H3;/q+1;-1

InChI key

KRRBFUJMQBDDPR-UHFFFAOYSA-N

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应用

氰化四丁基胺可用作催化剂:
  • 在质子溶剂存在下,用于脱保护脂肪族硫醋酸酯,以合成自由硫基
  • 在三甲基氰硅烷(TMSCN)存在下,用于羰基化合物的O-TMS 氰硅化反应,以合成氰丙烷三甲基硅醚.
  • 在乙腈的存在下,通过对β-内酰胺键裂合成γ内酰胺,进而实现β-内酰胺的环扩展.

象形图

Skull and crossbonesEnvironment

警示用语:

Danger

危险分类

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1

补充剂危害

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Tetrabutylammonium cyanide catalyzes the addition of TMSCN to aldehydes and ketones
Cordoba R, et al.
ARKIVOC (Gainesville, FL, United States), 4, 94-99 (2004)
Benito Alcaide et al.
Organic letters, 7(18), 3981-3984 (2005-08-27)
Tetrabutylammonium cyanide (20 mol %) catalyzes ring expansion of 4-(arylimino)methylazetidin-2-ones 2 to 5-aryliminopyrrolidin-2-ones 3 through a novel N1-C4 bond cleavage of the beta-lactam nucleus. New, efficient one-pot protocols to enantiopure succinimide derivatives 3 and 4 from beta-lactam aldehydes 1 have
Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide
Holmes B, et al.
Tetrahedron, 61, 12339-12342 (2005)
Jacek Cieślak et al.
Current protocols in nucleic acid chemistry, Chapter 4, Unit4-Unit4 (2012-09-08)
The conversion of 3',5'-disilylated 2'-O-(methylthiomethyl)ribonucleosides to 2'-O-(phthalimidooxymethyl)ribonucleosides is achieved in yields of 66% to 94%. Desilylation and dephtalimidation of these ribonucleosides by treatment with NH(4)F in MeOH produce 2'-O-aminooxymethylated ribonucleosides, which are efficient in producing stable and yet reversible 2'-conjugates
Purnandhu Bose et al.
Chemistry, an Asian journal, 7(10), 2373-2380 (2012-07-26)
A new series of tris(2-aminoethyl)amine (tren)-based L-alanine amino acid backboned tripodal hexaamide receptors (L1-L5) with various attached moieties based on electron-withdrawing fluoro groups and lipophilicity have been synthesized and characterized. Detailed binding studies of L1-L5 with different anions, such as

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