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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:
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

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.

signalword

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

supp_hazards

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

1.4 °F - closed cup - Solvent

flash_point_c

-17 °C - closed cup - Solvent

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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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)
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
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
Krause, N.; Gerold, A.
Angewandte Chemie (International Edition in English), 36, 186-186 (1997)

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