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544-92-3

Basic Information
CAS No.: 544-92-3
Name: Copper(I) cyanide
Molecular Structure:
Molecular Structure of 544-92-3 (Copper(I) cyanide)
Formula: CuCN
Molecular Weight: 89.56
Synonyms: Copper cyanide (Cu(CN));AI3-28745;Copper cyanide;Copper(+1) cyanide;Cupricin;Cuprous cyanide;HSDB 1438;RCRA waste number P029;
EINECS: 208-883-6
Density: 2.92 g/mL at 25 °C(lit.)
Melting Point: 474 °C(lit.)
Boiling Point: 25.7 °C at 760 mmHg
Flash Point:
Solubility: Insoluble in water
Appearance: off-white / pale yellow powder
Hazard Symbols: VeryT+,DangerousN,ToxicT
Risk Codes: 26/27/28-32-50/53
Safety: 7-28-29-45-60-61
Transport Information: UN 1587 6.1/PG 2
PSA: 23.79000
LogP: 0.01428
Synthetic route
143-33-9

sodium cyanide

copper(l) chloride

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In water at 100℃; for 1h;94.2%
143-33-9

sodium cyanide

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
With sodium hydroxide; water; copper(II) sulfate; sodium sulfite
With water; sodium hydrogensulfite; copper(II) sulfate at 60℃;
151-50-8

potassium cyanide

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
With water; copper(II) sulfate
With ethanol; water; copper(II) sulfate
K

K

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
With water; nitric acid
151-50-8

potassium cyanide

7758-99-8

copper(II) sulfate

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In water; toluene at 0 - 60℃;
7681-65-4

copper(l) iodide

592-04-1

mercury(II) cyanide

544-92-3

copper(I) cyanide

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

potassium cyanide

copper(ll) sulfate pentahydrate

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
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;;

potassium tetracyanocuprate (I)

A

74-90-8

hydrogen cyanide

B

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
With NH4-salt In water
With NH4-salt In water

potassium tetracyanocuprate (I)

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
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.;;
592-04-1

mercury(II) cyanide

7787-70-4

copper(I) bromide

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In water byproducts: HgI2; in heat;;
In water
592-04-1

mercury(II) cyanide

copper(l) chloride

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In water0%
In water
592-04-1

mercury(II) cyanide

copper(II) nitrate

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In not given in coldness or in heat;;0%
592-04-1

mercury(II) cyanide

7758-99-8

copper(II) sulfate

544-92-3

copper(I) cyanide

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

K(1+)*2Cu(1+)*3CN(1-)*H2O=K{Cu2(CN)3}*H2O

A

potassium cyanide

B

544-92-3

copper(I) cyanide

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

2Cu(1+)*Na(1+)*3CN(1-)*2H2O=Cu2Na(CN)3*2H2O

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In water decompn.;;
In water decompn.;;

potassium cyanide

3Cu(1+)*18Na(1+)*Br(1-)*10S2O3(2-)=Cu3Na18Br(S2O3)10

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In hydrogenchloride pptn.;;

3Cu(1+)*5Hg(2+)*3Cl(1-)*10CN(1-)=Cu3Hg5Cl3(CN)10

A

544-92-3

copper(I) cyanide

B

copper(l) chloride

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

potassium cyanide copper (I)-cyanide (1:1)

A

74-90-8

hydrogen cyanide

B

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
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)

A

74-90-8

hydrogen cyanide

B

201230-82-2

carbon monoxide

C

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
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)

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
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)

A

Kalium-kupfer(I)-cyanid

B

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In water

Cu(1+)*Na(1+)*2CN(1-)*2H2O=CuNa(CN)2*2H2O

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In water decompn.;;
In water decompn.;;

2Cu(1+)*3Hg(2+)*2Cl(1-)*6CN(1-)=Cu2Hg3Cl2(CN)6

544-92-3

copper(I) cyanide

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

copper (I) mercury (II) bromide cyanide

544-92-3

copper(I) cyanide

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

Rb(1+)*Cu(1+)*2CN(1-)=RbCu(CN)2

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In water pptn.;;
In water pptn.;;
In water

copper (I) strontium cyanide * 8 H2O

544-92-3

copper(I) cyanide

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

3Cu(1+)*2K(1+)*5CN(1-)=Cu3K2(CN)5

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
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

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In water pptn.;;
In water pptn.;;
In water

potassium cyanide

2Cu(1+)*11Na(1+)*I(1-)*6S2O3(2-)=Cu2Na11I(S2O3)6

544-92-3

copper(I) cyanide

Conditions
ConditionsYield
In water pptn.;;
2943-42-2

di(4-methyl)phenylthiosulfonate

544-92-3

copper(I) cyanide

A

5285-74-5

4-tolyl thiocyanate

B

824-79-3

sodium 4-methylbenzenesulfinate

Conditions
ConditionsYield
In acetonitrile at 100℃; for 12h;A 93%
B 100%
452-74-4

4-bromo-3-fluorotoluene

544-92-3

copper(I) cyanide

85070-67-3

2-fluoro-4-methylbenzonitrile

Conditions
ConditionsYield
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%
5111-65-9

2-Bromo-6-methoxynaphthalene

544-92-3

copper(I) cyanide

67886-70-8

2-cyano-6-methoxynaphthalene

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 4h; Heating;100%
Substitution;
544-92-3

copper(I) cyanide

444119-25-9

2,6-diiodo-N,N,N',N'-tetramethyl-p-phenylenediamine

2,6-dicyano-N,N,N',N'-tetramethyl-p-phenylenediamine

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 20h; Heating;100%
102308-43-0

4-bromoisobenzofuran-1(3H)-one

544-92-3

copper(I) cyanide

90483-95-7

3-cyano-phthalide

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 12h; Rosenmund-von Braun reaction; Heating;100%
951231-87-1

1-bromo-5-methoxy-2-nitro-4-trifluoromethyl-benzene

544-92-3

copper(I) cyanide

951231-88-2

5-methoxy-2-nitro-4-trifluoromethyl-benzonitrile

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 150℃; for 0.5h;100%
22190-38-1

5-bromo-N-acetylindoline

544-92-3

copper(I) cyanide

15861-29-7

1-acetyl-2,3-dihydro-indole-5-carbonitrile

Conditions
ConditionsYield
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

544-92-3

copper(I) cyanide

755754-46-2

4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one for 2h; Heating / reflux;100%
850341-06-9

5-bromo-7-fluoro-6-methylamino-2-(4-nitro-phenyl)-2H-isoquinolin-1-one

544-92-3

copper(I) cyanide

850341-12-7

7-fluoro-6-methylamino-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinoline-5-carbonitrile

Conditions
ConditionsYield
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

544-92-3

copper(I) cyanide

1-(2,4-dimethoxybenzyl)-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile

Conditions
ConditionsYield
In DMF (N,N-dimethyl-formamide) for 34h; Heating / reflux;100%
15126-06-4

methyl 3-iodo-4-hydroxybenzoate

143-33-9

sodium cyanide

544-92-3

copper(I) cyanide

156001-68-2

methyl 3-cyano-4-hydroxybenzoate

Conditions
ConditionsYield
In DMF (N,N-dimethyl-formamide) at 105℃; for 18h;100%
349-03-1

1-bromo-4-trifluoromethyl-2-nitrobenzene

544-92-3

copper(I) cyanide

778-94-9

2-nitro-4-trifluoromethyl-benzonitrile

Conditions
ConditionsYield
at 130℃; for 6h; Product distribution / selectivity;100%
928324-97-4

5-(2-fluorophenyl)-4-iodo-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde

544-92-3

copper(I) cyanide

928325-00-2

2-(2-fluorophenyl)-4-formyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbonitrile

Conditions
ConditionsYield
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane for 3h; Heating / reflux;100%
5433-01-2

1-bromo-3-isopropylbenzene

544-92-3

copper(I) cyanide

40751-59-5

3-isopropyl benzonitrile

Conditions
ConditionsYield
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%
19099-54-8

2-isopropyliodobenzene

13435-20-6

tetraethylammoniumcyanide

544-92-3

copper(I) cyanide

40751-52-8

2-Isopropyl-1-benzonitrile

Conditions
ConditionsYield
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran for 1.5h; Heating / reflux;100%
1029434-01-2

N,N'-bis(4-n-butylbenzyl)-1,7-dibromoperylene-3,4:9,10-bis(dicarboximide)

544-92-3

copper(I) cyanide

1029433-75-7

N,N'-bis(4-n-butylbenzyl)-1,7-dicyanoperylene-3,4:9,10-bis(dicarboximide)

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

1-[4-{2-(4-pyridyl)ethynyl}phenyl]-1,1-bis(4-iodophenyl)-3-ethylheptane

544-92-3

copper(I) cyanide

1-[4-{2-(4-pyridyl)ethynyl}phenyl]-1,1-bis(4-cyanophenyl)-3-ethylheptane

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

1,1-bis[4-{2-(4-pyridyl)ethynyl}phenyl]-1-(4-iodophenyl)-3-ethylheptane

544-92-3

copper(I) cyanide

1067461-95-3

1,1-bis[4-{2-(4-pyridyl)ethynyl}phenyl]-1-(4-cyanophenyl)-3-ethylheptane

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 140℃; for 8h;100%
544-92-3

copper(I) cyanide

83341-63-3

2,2'-(6-Brom-1,4-naphthylen)dibenzoxazol

83341-64-4

5,8-Di(benzoxazol-2-yl)naphthalin-2-carbonitril

Conditions
ConditionsYield
In various solvent(s)99%
544-92-3

copper(I) cyanide

156536-84-4

(6-Iodo-dibenzofuran-4-yl)-acetic acid ethyl ester

156536-85-5

(6-Cyano-dibenzofuran-4-yl)-acetic acid ethyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 2.5h; Heating;99%
3609-87-8

Ν-benzyl-4-bromobenzenesulfonamide

544-92-3

copper(I) cyanide

56768-47-9

Ν-benzyl-4-cyanobenzenesulfonamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 150℃; for 18h;99%
3972-65-4

1-bromo-4-tert-butylbenzene

544-92-3

copper(I) cyanide

4210-32-6

4-tert-butyl benzonitrile

Conditions
ConditionsYield
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%
544-92-3

copper(I) cyanide

162637-29-8

2-Bromo-3-((R)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester

162637-30-1

3-((R)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-2-cyano-indole-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 85℃; for 1h;99%
6825-20-3

3,6-dibromo-9H-carbazole

544-92-3

copper(I) cyanide

57103-03-4

9H-carbazole-3,6-dicarbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 70h; Heating;99%
544-92-3

copper(I) cyanide

80360-14-1

3-iodo-1-phenylsulfonyl-1H-indole

99532-56-6

1-(benzenesulfonyl)-1H-indole-3-carbonitrile

Conditions
ConditionsYield
With (diphenylphosphin)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane for 4h; Substitution; Cyanation; Heating;99%
544-92-3

copper(I) cyanide

927896-38-6

(E)-1-(2-iodo-4-methylphenyl)-2-phenyldiazene

5-methyl-2-(phenylazo)benzonitrile

Conditions
ConditionsYield
In propan-1-ol Heating;99%
544-92-3

copper(I) cyanide

(E)-1-(4-chloro-2-iodophenyl)-2-phenyldiazene

5-chloro-2-(phenylazo)benzonitrile

Conditions
ConditionsYield
In propan-1-ol Heating;99%
544-92-3

copper(I) cyanide

(4-bromophenyl)-(2-iodo-4-methoxyphenyl)diazene

2-(4-bromophenylazo)-5-methoxybenzonitrile

Conditions
ConditionsYield
In propan-1-ol Heating;99%
544-92-3

copper(I) cyanide

(2-iodo-4-methoxyphenyl)(4-nitrophenyl)diazene

5-methoxy-2-(4-nitrophenylazo)benzonitrile

Conditions
ConditionsYield
In propan-1-ol Heating;99%
544-92-3

copper(I) cyanide

(4-carbomethoxyphenyl)-(2-iodo-4-methoxyphenyl)diazene

2-(4-carbomethoxyphenylazo)-5-methoxybenzonitrile

Conditions
ConditionsYield
In propan-1-ol Heating;99%
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    cupric cyanide

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    Copper(I) cyanide

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    Cuprous cyanide

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    Copper(I) cyanide CAS NO.544-92-3

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Consensus Reports

Reported in EPA TSCA Inventory. Cyanide and its compounds, as well as copper and its compounds, are on the Community Right-To-Know List.

Standards and Recommendations

ACGIH TLV: TWA 1 mg(Cu)/m3
DOT Classification:  6.1; Label: Poison

Specification

The Copper(I) cyanide, with the CAS registry number 544-92-3, is also known as Cuprous cyanide. It belongs to the product categories of Inorganics; Classes of Metal Compounds; Cu (Copper) Compounds; Transition Metal Compounds. Its EINECS registry number is 208-883-6. This chemical's molecular formula is CuCN and molecular weight is 89.563. Its IUPAC name is called copper(1+) cyanide. 

Physical properties of Copper(I) cyanide: (1)ACD/LogP: -0.25; (2)ACD/LogD (pH 5.5): -0.25; (3)ACD/LogD (pH 7.4): -0.25; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 17.42; (7)ACD/KOC (pH 7.4): 17.42; (8)#H bond acceptors: 1; (9)Enthalpy of Vaporization: 27.18 kJ/mol; (10)Boiling Point: 25.7 °C at 760 mmHg; (11)Vapour Pressure: 740 mmHg at 25°C.

Preparation: It can be prepared by the reduction of copper(II) sulfate with sodium bisulphite at 60 °C, followed by the addition of sodium cyanide to precipitate pure LT-CuCN as a pale yellow powder.

2 CuSO4 + NaHSO3 + H2O + 2 NaCN → 2 CuCN + 3 NaHSO4

Uses: The compound is useful as a catalyst, in electroplating copper, and as a reagent in the preparation of nitriles. Copper(I) cyanide is used for electroplating copper. The compound is useful reagent in organic synthesis, for example in the regioselective and stereoselective allylation and conjugate addition of N-Boc-2-lithiopyrrolidine and N-Boc-2-lithiopiperidine, or the copper cyanide catalyzed palladium coupling of α-lithio amines and aryl iodides.

When you are using this chemical, please be cautious about it as the following:
This chemical is very toxic and is dangerous for the environment. It is very toxic by inhalation, in contact with skin and if swallowed. In addition, it is very toxic to aquatic organisms which may cause long-term adverse effects in the aquatic environment. After contact with skin, you should wash immediately with plenty of ... (to be specified by the manufacturer). In case of accident or if you feel unwell seek medical advice immediately (show the label where possible). This material and its container must be disposed of as hazardous waste.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: [C-]#N.[Cu+]
(2)InChI: InChI=1S/CN.Cu/c1-2;/q-1;+1
(3)InChIKey: DOBRDRYODQBAMW-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 1265mg/kg (1265mg/kg)   Toxicologist. Vol. 3, Pg. 170, 1983.