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697257

Sigma-Aldrich

Copper(I) cyanide di(lithium chloride) complex solution

in anhydrous tetrahydrofuran

Synonym(s):

Copper(I) cyanide di(lithium chloride)

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About This Item

Linear Formula:
CuCN · 2LiCl
Molecular Weight:
174.35
UNSPSC Code:
12161600
PubChem Substance ID:
329761902
NACRES:
NA.22

form

liquid

reaction suitability

core: copper
reagent type: catalyst

concentration

in anhydrous tetrahydrofuran

density

0.999 g/mL at 25 °C

SMILES string

[Li]Cl.[Li]Cl.[Cu]C#N

InChI

1S/CN.2ClH.Cu.2Li/c1-2;;;;;/h;2*1H;;;/q;;;;2*+1/p-2

InChI key

QGXKBLXNBYNHBV-UHFFFAOYSA-L

Related Categories

Application

Copper(I) cyanide di(lithium chloride) complex can be used for the synthesis of organocopper(I) reagents by transmetalation with organozinc and Grignard reagents. It is also a useful precursor to prepare organocuprate(I) reagents.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

1.4 °F - closed cup - Solvent

Flash Point(C)

-17 °C - closed cup - Solvent

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Regioselective functionalization of trisubstituted pyridines using a bromine-magnesium exchange.
Ren H and Knochel P
Chemical Communications (Cambridge, England), 11(7), 726-728 (2006)
TMPZnCl?LiCl: A new active selective base for the directed zincation of sensitive aromatics and heteroaromatics.
Mosrin M and Knochel P
Organic Letters, 11(8), 1837-1840 (2009)
Joel M Harris et al.
The Journal of organic chemistry, 68(11), 4371-4381 (2003-05-24)
2,5,6-Trisubstituted piperidines are readily prepared by a combination of an aza-Achmatowicz oxidation of a furyl-substituted benzenesulfonamide followed by a conjugate addition to the resulting 2H-pyridone and subsequent addition of various nucleophiles to a transient N-sulfonyliminium ion. The stereochemistry of the
Tomas Hudlicky et al.
The Journal of organic chemistry, 67(25), 8726-8743 (2002-12-07)
Biocatalytic approaches have yielded efficient total syntheses of the major Amaryllidaceae alkaloids, all based on the key enzymatic dioxygenation of suitable aromatic precursors. This paper discusses the logic of general synthetic design for lycoricidine, narciclasine, pancratistatin, and 7-deoxypancratistatin. Experimental details
Krause, N.; Gerold, A.
Angewandte Chemie (International Edition in English), 36, 186-186 (1997)
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