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Tetrabutylammonium cyanide

Name: Tetrabutylammonium cyanide
Brand: ALDRICH

technical, ≥80%

Synonyme(s) :

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

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About This Item

Formule linéaire :

(CH₃CH₂CH₂CH₂)₄N(CN)

Numéro CAS:

10442-39-4

Poids moléculaire :

268.48

Numéro Beilstein :

3598808

Numéro CE :

233-926-0

Numéro MDL:

MFCD00043221

Code UNSPSC :

12352116

ID de substance PubChem :

329768102

Nomenclature NACRES :

NA.22

Qualité

technical

Niveau de qualité

100

Pureté

≥80%

Forme

crystals

Pf

89-92 °C (lit.)

Chaîne SMILES

[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

Clé InChI

KRRBFUJMQBDDPR-UHFFFAOYSA-N

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Application

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.

Pictogrammes

GHS06,GHS09

Mention d'avertissement

Danger

Mentions de danger

H300 + H310 + H330,H410

Conseils de prudence

P262 - P264 - P273 - P280 - P302 + P352 + P310 - P304 + P340 + P310

Classification des risques

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

Risques supp

EUH032

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Organocatalytic ring expansion of beta-lactams to gamma-lactams through a novel N1-C4 bond cleavage. direct synthesis of enantiopure succinimide derivatives.

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)

Photoinduced ligand exchange and DNA binding of cis-[Ru(phpy)(phen)(CH3CN)2]+ with long wavelength visible light.

R Bryan Sears et al.

Journal of inorganic biochemistry, 121, 77-87 (2013-01-29)

The complex cis-[Ru(phpy)(phen)(CH3CN)2](+) (phpy=2-phenylpyridine, phen=1,10-phenanthroline) was investigated as a potential photodynamic therapy (PDT) agent. This complex presents desirable photochemical characteristics including a low energy absorption tail extending into the PDT window (600-850nm) and photoinduced exchange of the CH3CN ligands, generating

Small-angle neutron scattering study of temperature vs. salt dependence of clouding in charged micellar system.

A J Chinchalikar et al.

The European physical journal. E, Soft matter, 35(7), 55-55 (2012-07-06)

Clouding is studied by small-angle neutron scattering (SANS) on a charged micellar system of sodium dodecyl sulphate (SDS) and tetrabutylammonium bromide (TBAB) with varying temperature and salt NaCl. We show that the clouding occurs as a result of increase in

Ultrafast photo-induced charge transfer unveiled by two-dimensional electronic spectroscopy.

Oliver Bixner et al.

The Journal of chemical physics, 136(20), 204503-204503 (2012-06-07)

The interaction of exciton and charge transfer (CT) states plays a central role in photo-induced CT processes in chemistry, biology, and physics. In this work, we use a combination of two-dimensional electronic spectroscopy (2D-ES), pump-probe measurements, and quantum chemistry to

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