544-92-3

Usage

Uses

Used in Electroplating Industry:
Copper(I) cyanide is used as a plating agent for depositing a thin layer of copper onto various surfaces. Its ability to form complexes with different molecules makes it suitable for this application, enhancing the quality and durability of the plated surfaces.
Used in Metallurgy:
In the metallurgical industry, copper(I) cyanide is used as a reagent in the extraction and refining of copper. Its complex-forming properties aid in the separation and purification processes, contributing to the production of high-purity copper.
Used as a Catalyst in Chemical Reactions:
Copper(I) cyanide is employed as a catalyst in various chemical reactions due to its ability to form stable complexes with reactants. This enhances the reaction rates and selectivity, making it a valuable component in the synthesis of certain compounds.
Production Method:
The production of copper(I) cyanide involves the reaction between copper(I) salts and cyanide. This process results in the formation of the desired compound, which can then be used in its various applications.

InChI:InChI=1/CN.Cu/c1-2;/rCCuN/c2-1-3

Synthetic route

sodium cyanide (143-33-9) + copper(l) chloride → copper(I) cyanide (544-92-3)

Conditions	Yield
In water at 100℃; for 1h;	94.2%

sodium cyanide (143-33-9) → copper(I) cyanide (544-92-3)

Conditions	Yield
With sodium hydroxide; water; copper(II) sulfate; sodium sulfite
With water; sodium hydrogensulfite; copper(II) sulfate at 60℃;

potassium cyanide (151-50-8) → copper(I) cyanide (544-92-3)

Conditions	Yield
With water; copper(II) sulfate
With ethanol; water; copper(II) sulfate

K → copper(I) cyanide (544-92-3)

Conditions	Yield
With water; nitric acid

potassium cyanide (151-50-8) + copper(II) sulfate (7758-99-8) → copper(I) cyanide (544-92-3)

Conditions	Yield
In water; toluene at 0 - 60℃;

copper(l) iodide (7681-65-4) + mercury(II) cyanide (592-04-1) → copper(I) cyanide (544-92-3)

Conditions	Yield
In water byproducts: HgI2; excess CuI;;	>99
In water byproducts: HgI2; in coldness or in heat;;
In water

potassium cyanide + copper(ll) sulfate pentahydrate → copper(I) cyanide (544-92-3)

Conditions	Yield
In diethyl ether; ethanol treatment of CuSO4*5H2O crystals with a soln. of KCN;;
In ethanol treatment of CuSO4*5H2O crystals with a soln. of KCN;;
In diethyl ether; ethanol treatment of CuSO4*5H2O crystals with a soln. of KCN;;
In ethanol treatment of CuSO4*5H2O crystals with a soln. of KCN;;

water (7732-18-5) + potassium tetracyanocuprate (I) → hydrogen cyanide (74-90-8) + copper(I) cyanide (544-92-3)

Conditions	Yield
With NH4-salt In water
With NH4-salt In water

potassium tetracyanocuprate (I) → copper(I) cyanide (544-92-3)

Conditions	Yield
With acids In water decompn. in dild. acids;;
With acids In water decompn. in dild. acids;;
With HCl In water decompn. in excess of HCl;; pptn.;;

mercury(II) cyanide (592-04-1) + copper(I) bromide (7787-70-4) → copper(I) cyanide (544-92-3)

Conditions	Yield
In water byproducts: HgI2; in heat;;
In water

mercury(II) cyanide (592-04-1) + copper(l) chloride → copper(I) cyanide (544-92-3)

Conditions	Yield
In water	0%
In water

mercury(II) cyanide (592-04-1) + copper(II) nitrate → copper(I) cyanide (544-92-3)

Conditions	Yield
In not given in coldness or in heat;;	0%

mercury(II) cyanide (592-04-1) + copper(II) sulfate (7758-99-8) → copper(I) cyanide (544-92-3)

Conditions	Yield
In not given in coldness or heat;;	0%

K(1+)*2Cu(1+)*3CN(1-)*H2O=K{Cu2(CN)3}*H2O → potassium cyanide + copper(I) cyanide (544-92-3)

Conditions	Yield
In water decompn. in hot water;;
In water decompn. in hot water;;

2Cu(1+)*Na(1+)*3CN(1-)*2H2O=Cu2Na(CN)3*2H2O → copper(I) cyanide (544-92-3)

Conditions	Yield
In water decompn.;;
In water decompn.;;

potassium cyanide + 3Cu(1+)*18Na(1+)*Br(1-)*10S2O3(2-)=Cu3Na18Br(S2O3)10 → copper(I) cyanide (544-92-3)

Conditions	Yield
In hydrogenchloride pptn.;;

3Cu(1+)*5Hg(2+)*3Cl(1-)*10CN(1-)=Cu3Hg5Cl3(CN)10 → copper(I) cyanide (544-92-3) + copper(l) chloride

Conditions	Yield
With water In hydrogenchloride addn. of water to soln.;;
With H2O In hydrogenchloride

potassium cyanide copper (I)-cyanide (1:1) → hydrogen cyanide (74-90-8) + copper(I) cyanide (544-92-3)

Conditions	Yield
With acids In water decompn. in acids;; CuCN as ppt.;;
With acids In water decompn. in acids;; CuCN as ppt.;;

potassium cyanide copper (I)-cyanide (1:1) → hydrogen cyanide (74-90-8) + carbon monoxide (201230-82-2) + copper(I) cyanide (544-92-3)

Conditions	Yield
With sulfuric acid In sulfuric acid byproducts: SO2; decompn. in dild. H2SO4; depending on H2SO4 concn.;;	A n/a B n/a C >99
With H2SO4 In sulfuric acid byproducts: SO2; aq. H2SO4; decompn. in dild. H2SO4; depending on H2SO4 concn.;;	A n/a B n/a C >99

potassium cyanide copper (I)-cyanide (1:1) → copper(I) cyanide (544-92-3)

Conditions	Yield
In water decompn. in cold water;; pptn.;;
In water decompn. in water;; pptn.;;
In water decompn. in cold water;; pptn.;;
In water decompn. in water;; pptn.;;

potassium cyanide copper (I)-cyanide (1:1) → Kalium-kupfer(I)-cyanid + copper(I) cyanide (544-92-3)

Conditions	Yield
In water

Cu(1+)*Na(1+)*2CN(1-)*2H2O=CuNa(CN)2*2H2O → copper(I) cyanide (544-92-3)

Conditions	Yield
In water decompn.;;
In water decompn.;;

2Cu(1+)*3Hg(2+)*2Cl(1-)*6CN(1-)=Cu2Hg3Cl2(CN)6 → copper(I) cyanide (544-92-3)

Conditions	Yield
In water decompn. in hot water;;
In water

copper (I) mercury (II) bromide cyanide → copper(I) cyanide (544-92-3)

Conditions	Yield
In water decompn. in water on heating;;
In water

Rb(1+)*Cu(1+)*2CN(1-)=RbCu(CN)2 → copper(I) cyanide (544-92-3)

Conditions	Yield
In water pptn.;;
In water pptn.;;
In water

copper (I) strontium cyanide * 8 H2O → copper(I) cyanide (544-92-3)

Conditions	Yield
In water decompn. in water;; pptn.;;
In water decompn. in water;; pptn.;;

3Cu(1+)*2K(1+)*5CN(1-)=Cu3K2(CN)5 → copper(I) cyanide (544-92-3)

Conditions	Yield
With acids In water decompn. in acids;;
With acids In water decompn. in acids;;

Cs(1+)*Cu(1+)*2CN(1-)*1.5H2O=CsCu(CN)2*1.5H2O → copper(I) cyanide (544-92-3)

Conditions	Yield
In water pptn.;;
In water pptn.;;
In water

potassium cyanide + 2Cu(1+)*11Na(1+)*I(1-)*6S2O3(2-)=Cu2Na11I(S2O3)6 → copper(I) cyanide (544-92-3)

Conditions	Yield
In water pptn.;;

di(4-methyl)phenylthiosulfonate (2943-42-2) + copper(I) cyanide (544-92-3) → 4-tolyl thiocyanate (5285-74-5) + sodium 4-methylbenzenesulfinate (824-79-3)

Conditions	Yield
In acetonitrile at 100℃; for 12h;	A 93% B 100%

4-bromo-3-fluorotoluene (452-74-4) + copper(I) cyanide (544-92-3) → 2-fluoro-4-methylbenzonitrile (85070-67-3)

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Heating;	100%
In N,N-dimethyl-formamide for 5h; Heating;	94%
In N,N-dimethyl-formamide for 24h; Heating / reflux;	88%

2-Bromo-6-methoxynaphthalene (5111-65-9) + copper(I) cyanide (544-92-3) → 2-cyano-6-methoxynaphthalene (67886-70-8)

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Heating;	100%
Substitution;

copper(I) cyanide (544-92-3) + 2,6-diiodo-N,N,N',N'-tetramethyl-p-phenylenediamine (444119-25-9) → 2,6-dicyano-N,N,N',N'-tetramethyl-p-phenylenediamine

Conditions	Yield
In N,N-dimethyl-formamide for 20h; Heating;	100%

4-bromoisobenzofuran-1(3H)-one (102308-43-0) + copper(I) cyanide (544-92-3) → 3-cyano-phthalide (90483-95-7)

Conditions	Yield
In N,N-dimethyl-formamide for 12h; Rosenmund-von Braun reaction; Heating;	100%

1-bromo-5-methoxy-2-nitro-4-trifluoromethyl-benzene (951231-87-1) + copper(I) cyanide (544-92-3) → 5-methoxy-2-nitro-4-trifluoromethyl-benzonitrile (951231-88-2)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 150℃; for 0.5h;	100%

5-bromo-N-acetylindoline (22190-38-1) + copper(I) cyanide (544-92-3) → 1-acetyl-2,3-dihydro-indole-5-carbonitrile (15861-29-7)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one for 4h; Heating;	100%

3-bromo-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine + copper(I) cyanide (544-92-3) → 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile (755754-46-2)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one for 2h; Heating / reflux;	100%

5-bromo-7-fluoro-6-methylamino-2-(4-nitro-phenyl)-2H-isoquinolin-1-one (850341-06-9) + copper(I) cyanide (544-92-3) → 7-fluoro-6-methylamino-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinoline-5-carbonitrile (850341-12-7)

Conditions	Yield
Stage #1: 5-bromo-7-fluoro-6-methylamino-2-(4-nitro-phenyl)-2H-isoquinolin-1-one; copper(I) cyanide In 1-methyl-pyrrolidin-2-one at 200℃; for 2h; Stage #2: With potassium cyanide In 1-methyl-pyrrolidin-2-one; water at 50℃;	100%

5-bromo-1-(2,4-dimethoxybenzyl)-7-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one + copper(I) cyanide (544-92-3) → 1-(2,4-dimethoxybenzyl)-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile

Conditions	Yield
In DMF (N,N-dimethyl-formamide) for 34h; Heating / reflux;	100%

methyl 3-iodo-4-hydroxybenzoate (15126-06-4) + sodium cyanide (143-33-9) + copper(I) cyanide (544-92-3) → methyl 3-cyano-4-hydroxybenzoate (156001-68-2)

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 105℃; for 18h;	100%

1-bromo-4-trifluoromethyl-2-nitrobenzene (349-03-1) + copper(I) cyanide (544-92-3) → 2-nitro-4-trifluoromethyl-benzonitrile (778-94-9)

Conditions	Yield
at 130℃; for 6h; Product distribution / selectivity;	100%

5-(2-fluorophenyl)-4-iodo-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (928324-97-4) + copper(I) cyanide (544-92-3) → 2-(2-fluorophenyl)-4-formyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbonitrile (928325-00-2)

Conditions	Yield
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane for 3h; Heating / reflux;	100%

1-bromo-3-isopropylbenzene (5433-01-2) + copper(I) cyanide (544-92-3) → 3-isopropyl benzonitrile (40751-59-5)

Conditions	Yield
With pyridine at 150℃; for 13h;	100%
With pyridine at 180℃; for 24h;	100%
Stage #1: 1-bromo-3-isopropylbenzene; copper(I) cyanide With pyridine at 180℃; for 24h; Stage #2: With ammonia In water; toluene	100%

2-isopropyliodobenzene (19099-54-8) + tetraethylammoniumcyanide (13435-20-6) + copper(I) cyanide (544-92-3) → 2-Isopropyl-1-benzonitrile (40751-52-8)

Conditions	Yield
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran for 1.5h; Heating / reflux;	100%

N,N'-bis(4-n-butylbenzyl)-1,7-dibromoperylene-3,4:9,10-bis(dicarboximide) (1029434-01-2) + copper(I) cyanide (544-92-3) → N,N'-bis(4-n-butylbenzyl)-1,7-dicyanoperylene-3,4:9,10-bis(dicarboximide) (1029433-75-7)

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 5h;	100%

1-[4-{2-(4-pyridyl)ethynyl}phenyl]-1,1-bis(4-iodophenyl)-3-ethylheptane + copper(I) cyanide (544-92-3) → 1-[4-{2-(4-pyridyl)ethynyl}phenyl]-1,1-bis(4-cyanophenyl)-3-ethylheptane

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 8h;	100%

1,1-bis[4-{2-(4-pyridyl)ethynyl}phenyl]-1-(4-iodophenyl)-3-ethylheptane + copper(I) cyanide (544-92-3) → 1,1-bis[4-{2-(4-pyridyl)ethynyl}phenyl]-1-(4-cyanophenyl)-3-ethylheptane (1067461-95-3)

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 8h;	100%

copper(I) cyanide (544-92-3) + 2,2'-(6-Brom-1,4-naphthylen)dibenzoxazol (83341-63-3) → 5,8-Di(benzoxazol-2-yl)naphthalin-2-carbonitril (83341-64-4)

Conditions	Yield
In various solvent(s)	99%

copper(I) cyanide (544-92-3) + (6-Iodo-dibenzofuran-4-yl)-acetic acid ethyl ester (156536-84-4) → (6-Cyano-dibenzofuran-4-yl)-acetic acid ethyl ester (156536-85-5)

Conditions	Yield
In N,N-dimethyl-formamide for 2.5h; Heating;	99%

Ν-benzyl-4-bromobenzenesulfonamide (3609-87-8) + copper(I) cyanide (544-92-3) → Ν-benzyl-4-cyanobenzenesulfonamide (56768-47-9)

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 18h;	99%

1-bromo-4-tert-butylbenzene (3972-65-4) + copper(I) cyanide (544-92-3) → 4-tert-butyl benzonitrile (4210-32-6)

Conditions	Yield
Stage #1: 1-bromo-4-tert-butylbenzene; copper(I) cyanide In N,N-dimethyl-formamide for 8h; Heating; Stage #2: With hydrogenchloride; iron(III) chloride In water; N,N-dimethyl-formamide at 70℃; for 0.5h;	99%
In N,N-dimethyl-formamide for 5h; Heating;	71%

copper(I) cyanide (544-92-3) + 2-Bromo-3-((R)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester (162637-29-8) → 3-((R)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-2-cyano-indole-1-carboxylic acid tert-butyl ester (162637-30-1)

Conditions	Yield
In N,N-dimethyl-formamide at 85℃; for 1h;	99%

3,6-dibromo-9H-carbazole (6825-20-3) + copper(I) cyanide (544-92-3) → 9H-carbazole-3,6-dicarbonitrile (57103-03-4)

Conditions	Yield
In N,N-dimethyl-formamide for 70h; Heating;	99%

copper(I) cyanide (544-92-3) + 3-iodo-1-phenylsulfonyl-1H-indole (80360-14-1) → 1-(benzenesulfonyl)-1H-indole-3-carbonitrile (99532-56-6)

Conditions	Yield
With (diphenylphosphin)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane for 4h; Substitution; Cyanation; Heating;	99%

copper(I) cyanide (544-92-3) + (E)-1-(2-iodo-4-methylphenyl)-2-phenyldiazene (927896-38-6) → 5-methyl-2-(phenylazo)benzonitrile

Conditions	Yield
In propan-1-ol Heating;	99%

copper(I) cyanide (544-92-3) + (E)-1-(4-chloro-2-iodophenyl)-2-phenyldiazene → 5-chloro-2-(phenylazo)benzonitrile

Conditions	Yield
In propan-1-ol Heating;	99%

copper(I) cyanide (544-92-3) + (4-bromophenyl)-(2-iodo-4-methoxyphenyl)diazene → 2-(4-bromophenylazo)-5-methoxybenzonitrile

Conditions	Yield
In propan-1-ol Heating;	99%

copper(I) cyanide (544-92-3) + (2-iodo-4-methoxyphenyl)(4-nitrophenyl)diazene → 5-methoxy-2-(4-nitrophenylazo)benzonitrile

Conditions	Yield
In propan-1-ol Heating;	99%

copper(I) cyanide (544-92-3) + (4-carbomethoxyphenyl)-(2-iodo-4-methoxyphenyl)diazene → 2-(4-carbomethoxyphenylazo)-5-methoxybenzonitrile

Conditions	Yield
In propan-1-ol Heating;	99%

Upstream product

• 143-33-9 sodium cyanide 
• 151-50-8 potassium cyanide 
• 7758-99-8 copper(II) sulfate 
• 7681-65-4 copper(l) iodide 
• 592-04-1 mercury(II) cyanide 
• 7732-18-5 water 
• 7787-70-4 copper(I) bromide 

Downstream Products

• 67588-10-7 4-methoxy-2-oxazolo[4,5-b]pyridin-2-yl-benzonitrile 
• 93326-18-2 4-[5-(4-cyano-phenyl)-2-methyl-oxazol-4-yl]-benzenesulfonamide 
• 1452-16-0 thiazole-2-carbonitrile 
• 3912-37-6 4-Cyanoisothiazol 
• 54286-59-8 5-Methylbenzofurazan-4-carbonitril 
• 14208-30-1 3-phenyl-isothiazole-5-carbonitrile 
• 54286-60-1 4,5-dicyanobenzofurazan 
• 61463-62-5 3-allyl benzonitrile 
• 61463-61-4 2-allylbenzonitrile 
• 53399-38-5 thieno[2,3-b]pyridine-3-carbonitrile 
• 19762-74-4 3-(4-methoxyphenyl)-5-methyl-4-isothiazolecarbonitrile 
• 55368-59-7 4,4'-(oxazole-2,5-diyl)dibenzonitrile 
• 55368-75-7 1,3-bis(4-cyanophenyl)isoxazole 
• 57439-07-3 4-(3-Ethyl-1-pentyl)benzoesaeure 

Relevant academic research and scientific papers

METHOD FOR PREPARING LAMOTRIGINE AND ITS INTERMEDIATE 2,3-DICHLOROBENZOYL CHLORIDE

The invention relates to an improved method for preparing 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine, also commonly known as lamotrigine. The present invention also relates to a method for preparing the intermediate 2,3-dichlorobenzoyl chloride, which comprises the synthesis by photochlorination of 2,3-dichlorobenzotrichloride followed by hydrolysis thereof. Said 2,3-dichlorobenzoyl chloride intermediate is useful for preparing lamotrigine.

THERAPEUTIC USE OF ARYL AMINO ACID DERIVATIVES

The compounds of formula (I) are useful in the treatment of faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, neuropathic pain, neuropathological disorders and sleep disorders. Processes for the preparation of the final products and intermediates useful in the process are included. Pharmaceutical compositions containing one or more of the compounds are also included.

Electrochemistry of cyanocopper thiomolybdates and thiotungstates: Redox-based interconversion of species

[MoS4]2- and its 1:1 and 1:2 CuCN adducts [(CN)CuS2MoS2]2- and [(CN)CuS2MoS2Cu(CN)]2- each exhibit electrochemically reversible one-electron reductions in MeCN at fast scan rates (>500 mV s-1). At lower scan rates, the reduced adduct species are unstable to dissociation of CuCN, leading to interconversion of the three anions. The tungsten analogues show similar properties.