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Merck
모든 사진(1)

주요 문서

79989

Sigma-Aldrich

Tetrabutylammonium cyanide

technical, ≥80%

동의어(들):

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

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(CN)
CAS Number:
Molecular Weight:
268.48
Beilstein:
3598808
EC Number:
MDL number:
UNSPSC 코드:
12352116
PubChem Substance ID:
NACRES:
NA.22

grade

technical

Quality Level

분석

≥80%

형태

crystals

mp

89-92 °C (lit.)

SMILES string

[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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애플리케이션

Tetrabutylammonium cyanide can be used as a catalyst:
  • For the deprotection of aliphatic thioacetate to synthesize free thiols in the presence of a protic solvent.
  • In the O-TMS cyanosilylation of carbonyl compounds to synthesize cyanohydrin trimethylsilyl ethers in the presence of trimethylsilyl cyanide (TMSCN).
  • For the ring expansion of β-lactams to synthesize γ-lactams through a bond cleavage of the β-lactam in the presence of acetonitrile.

픽토그램

Skull and crossbonesEnvironment

신호어

Danger

유해 및 위험 성명서

Hazard Classifications

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

보충제 위험성

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

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


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시험 성적서(COA)

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문서 라이브러리 방문

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
Tetrabutylammonium cyanide catalyzes the addition of TMSCN to aldehydes and ketones
Cordoba R, et al.
ARKIVOC (Gainesville, FL, United States), 4, 94-99 (2004)
Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide
Holmes B, et al.
Tetrahedron, 61, 12339-12342 (2005)
Matt Petrowsky et al.
The journal of physical chemistry. B, 116(33), 10098-10105 (2012-07-31)
Onsager's model of the dielectric constant is used to provide a molecular-level picture of how the dielectric constant affects mass and charge transport in organic liquids and organic liquid electrolytes. Specifically, the molecular and system parameters governing transport are the
Erbo Shi et al.
Organic letters, 14(13), 3384-3387 (2012-06-27)
A metal-free C-H oxidation for the construction of allylic esters has been developed. The use of a commercially available and inexpensive catalyst and oxidant, and readily available starting materials, coupled with the operational simplicity of the reaction, renders the methodology

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