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Synthetic route

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

A

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

B

cyanogen chloride
506-77-4

cyanogen chloride

C

S, SO2

S, SO2

Conditions
ConditionsYield
With thionyl chloride at 30 - 40℃; Product distribution; oth. reagent (SO2Cl2);A 100%
B 45%
C n/a
ethanedinitrile
460-19-5

ethanedinitrile

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In water (CN)2/Cl2 = 1:1, at 560°C, in 10% CaCl2 soln.; cool and crystn. at -10°C;100%
With chlorine In gas at 900K;93%
With chlorine In gas at 1100K;89%
sodium cyanide
773837-37-9

sodium cyanide

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In water continuous method, 15% NaCN soln.;98.4%
With chlorine In neat (no solvent) alkali cyanides, liquid Cl2 mixed in autoclave at -30°C;95%
With chlorine In hydrogenchloride at 0°C; distn.;90%
dipotassium tetracyanozincate(II)

dipotassium tetracyanozincate(II)

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In water byproducts: KCl, ZnCl2; in suspension, 60-90 min. at room temp.; drying above CaCl2 and freezing with ice/NaCl or CO2/acetone mixt.; >99.9% pure;98%
With chlorine In not given byproducts: ZnCl2, KCl; at 0-5°C; product sepd. below 45°C;
With Cl2 In not given byproducts: ZnCl2, KCl; at 0-5°C; product sepd. below 45°C;
With Cl2 In not given byproducts: ZnCl2, KCl; at 0-5°C; product sepd. below 45°C;
2Na(1+)*{Zn(CN)4}(2-)=Na2{Zn(CN)4}

2Na(1+)*{Zn(CN)4}(2-)=Na2{Zn(CN)4}

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In water byproducts: NaCl, ZnCl2; in suspension, 60-90 min. at room temp.; drying above CaCl2 and freezing with ice/NaCl or CO2/acetone mixt.; >99.9% pure;98%
With chlorine In not given byproducts: ZnCl2, NaCl; at 0-5°C; product sepd. below 45°;
With Cl2 In not given byproducts: ZnCl2, NaCl; at 0-5°C; product sepd. below 45°;
With Cl2 In not given byproducts: ZnCl2, NaCl; at 0-5°C; product sepd. below 45°;
Ca(2+)*Zn(CN)4(2-)=CaZn(CN)4

Ca(2+)*Zn(CN)4(2-)=CaZn(CN)4

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In water byproducts: CaCl2, ZnCl2; in suspension, 60-90 min. at room temp.; drying above CaCl2 and freezing with ice/NaCl or CO2/acetone mixt.; >99.9% pure;98%
With chlorine In not given byproducts: ZnCl2, CaCl2; at 0-5°C; product sepd. below 45°C;
With Cl2 In not given byproducts: ZnCl2, CaCl2; at 0-5°C; product sepd. below 45°C;
With Cl2 In not given byproducts: ZnCl2, CaCl2; at 0-5°C; product sepd. below 45°C;
cyanide(1-)
57-12-5

cyanide(1-)

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In tetrachloromethane with alkali cyanides, under 3°C;98%
With chlorine In neat (no solvent) alkali cyanides, at -18°C;85%
With chlorine In neat (no solvent) alkali cyanides mixed with sand at 3°C;80%
With chlorine In tetrachloromethane alkali cyanides, at 0°C;
With hydrogenchloride In not given
silver cyanide
330660-35-0

silver cyanide

hypochlorous anhydride
7791-21-1

hypochlorous anhydride

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
In neat (no solvent) in closed U-tube, at room temp., AgCN free from water; fract. distn. at -78°C; pure prod.;95%
hydrogen cyanide
74-90-8

hydrogen cyanide

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide; iron(III) In water at 50-65°C, continuous method;90%
With hydrogenchloride; dihydrogen peroxide; copper(II) ion In water at 50-65°C, continuous method;90%
With dihydrogen peroxide In water at 30°C;15%
cyanide(1-)
57-12-5

cyanide(1-)

A

hydrogen cyanide
74-90-8

hydrogen cyanide

B

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In hydrogenchloride alkali cyanides, pH=9;A n/a
B 90%
tetracyanomethane
24331-09-7

tetracyanomethane

A

Lithium-tricyan-methanid

Lithium-tricyan-methanid

B

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With lithium chloride In acetonitrile 2h in vacuum at room temp. with mixing; fract. cond.;A n/a
B 79%
perfluoro-(2-chloro-5-methyl-4-oxa-2,5-diazahexane)
78707-99-0

perfluoro-(2-chloro-5-methyl-4-oxa-2,5-diazahexane)

A

trifluoromethyl isocyanate
460-49-1

trifluoromethyl isocyanate

B

perfluoro-<1-(dimethylamino-oxy)-2-azapropene>
38592-11-9

perfluoro-<1-(dimethylamino-oxy)-2-azapropene>

C

2H-octafluoro-5-trifluoromethyl-4-oxa-2,5-diazahexane
38592-13-1

2H-octafluoro-5-trifluoromethyl-4-oxa-2,5-diazahexane

D

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With silver cyanide for 89h; Product distribution; Ambient temperature; other reagents;A n/a
B 54%
C 30%
D n/a

A

sulfur cyanate pentafluoride
106735-60-8

sulfur cyanate pentafluoride

B

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With mercury at 25℃; ultra sound;A 10%
B n/a
1,2-dichloro-1,1,2,2-tetranitroethane
2972-96-5

1,2-dichloro-1,1,2,2-tetranitroethane

potassium cyanide
151-50-8

potassium cyanide

cyanogen chloride
506-77-4

cyanogen chloride

2,4-dichloro-2-cyano-acetoacetic acid ethyl ester

2,4-dichloro-2-cyano-acetoacetic acid ethyl ester

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
Zersetzung;
Thiocyanate
302-04-5

Thiocyanate

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine
With chlorine In not given pH<11;
sodium cyanide
143-33-9

sodium cyanide

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With tetrachloromethane; chlorine; acetic acid at -10 - -5℃;
With tetrachloromethane; water; chlorine
With hydrogenchloride; water Electrolysis.an einer Graphitanode;
mercury fulminate
92114-96-0

mercury fulminate

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With aluminium trichloride in Gegenwart von aromatischen Kohlenwasserstoffen;
potassium cyanide
151-50-8

potassium cyanide

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With hydrogenchloride; water
With chlorine at 0℃;
With water; chlorine; zinc(II) sulfate at 0℃;
With chloroamine; water
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With tellurium chloride pentafluoride at -55 - 25℃;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

A

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

B

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With tellurium chloride pentafluoride at -55 - 25℃;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

A

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

B

thionyl cyanide
3313-35-7

thionyl cyanide

C

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With pentafluorosulfanyl chloride at -10℃; for 2h; Product distribution;
Phenylalanine
150-30-1

Phenylalanine

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With sodium hypochlorite; Ammonium In water for 1h; Product distribution; Ambient temperature; other aromatic amines;
(trifluoromethyl)chlorodicyanodifluorosulfur(VI)

(trifluoromethyl)chlorodicyanodifluorosulfur(VI)

A

cyan-trifluoromethylsulfane
690-24-4

cyan-trifluoromethylsulfane

B

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
at 25℃; for 42h;
formaldehyd
50-00-0

formaldehyd

A

N-chloroaminomethanol
245520-53-0

N-chloroaminomethanol

B

N-chlorodimethanolamine

N-chlorodimethanolamine

C

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chloroamine In phosphate buffer at 25℃; Kinetics; Equilibrium constant; Addition;
2-amino-1,9-dihydro-6H-purin-6-one
73-40-5

2-amino-1,9-dihydro-6H-purin-6-one

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In phosphate buffer for 0.5h; pH=7.0; Chlorination;
Conditions
ConditionsYield
With chlorine In phosphate buffer for 0.5h; pH=7.0; Chlorination;
ASPARAGINE
3130-87-8

ASPARAGINE

A

dichloroacetonitrile
3018-12-0

dichloroacetonitrile

B

N-chloroiminoacetonitrile

N-chloroiminoacetonitrile

C

dichloroaminoacetonitrile

dichloroaminoacetonitrile

D

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In phosphate buffer for 0.5h; pH=7.0; Chlorination;
Cytosine
71-30-7

Cytosine

A

dichloroacetonitrile
3018-12-0

dichloroacetonitrile

B

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In phosphate buffer for 0.5h; pH=7.0; Chlorination;
uracil
66-22-8

uracil

A

chloroform
67-66-3

chloroform

B

dichloroacetonitrile
3018-12-0

dichloroacetonitrile

C

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In phosphate buffer for 0.5h; pH=7.0; Chlorination;
malononitrile
109-77-3

malononitrile

cyanogen chloride
506-77-4

cyanogen chloride

sodium tricyanomethanide
36603-80-2

sodium tricyanomethanide

Conditions
ConditionsYield
With phosphoric acid; sodium hydroxide In methanol; water at 25 - 30℃; for 3.5h; pH=7.0 - 7.2; Product distribution / selectivity;100%
With ethanol; sodium
sodium 2-mercaptobenzothiazole
2492-26-4

sodium 2-mercaptobenzothiazole

cyanogen chloride
506-77-4

cyanogen chloride

benzo[d]thiazol-2-yl thiocyanate
6011-99-0

benzo[d]thiazol-2-yl thiocyanate

Conditions
ConditionsYield
Ambient temperature;100%
With water
With ethanol
With ethanol
With water
N-cyclohexylethylenediamine
5700-53-8

N-cyclohexylethylenediamine

cyanogen chloride
506-77-4

cyanogen chloride

1-cyclohexyl-2-iminoimidazolidine hydrochloride
51099-11-7

1-cyclohexyl-2-iminoimidazolidine hydrochloride

Conditions
ConditionsYield
In benzene for 3h;100%
p-toluidine
106-49-0

p-toluidine

cyanogen chloride
506-77-4

cyanogen chloride

N-(4-methylphenyl)cyanamide
10532-64-6

N-(4-methylphenyl)cyanamide

Conditions
ConditionsYield
With trimethylamine Ambient temperature;100%
4-chloro-aniline
106-47-8

4-chloro-aniline

cyanogen chloride
506-77-4

cyanogen chloride

N-(4-chlorophenyl)cyanamide
13463-94-0

N-(4-chlorophenyl)cyanamide

Conditions
ConditionsYield
With trimethylamine Ambient temperature;100%
With sodium hydroxide In water; acetic acid84%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

cyanogen chloride
506-77-4

cyanogen chloride

N-(4-methoxyphenyl)cyanamide
13519-16-9

N-(4-methoxyphenyl)cyanamide

Conditions
ConditionsYield
With trimethylamine Ambient temperature;100%
potassium p-methoxyphenolate
1122-93-6

potassium p-methoxyphenolate

cyanogen chloride
506-77-4

cyanogen chloride

4-methoxyphenyl cyanate
2983-74-6

4-methoxyphenyl cyanate

Conditions
ConditionsYield
Ambient temperature;100%
2-mercaptobenzoxazole sodium salt
15091-70-0

2-mercaptobenzoxazole sodium salt

cyanogen chloride
506-77-4

cyanogen chloride

2-thiocyanato-benzooxazole
5285-95-0

2-thiocyanato-benzooxazole

Conditions
ConditionsYield
Ambient temperature;100%
6-mercaptopurine sodium salt
1194-62-3

6-mercaptopurine sodium salt

cyanogen chloride
506-77-4

cyanogen chloride

6-thiocyanato-9H-purine
19447-73-5

6-thiocyanato-9H-purine

Conditions
ConditionsYield
Ambient temperature;100%
cyanogen chloride
506-77-4

cyanogen chloride

2-mercaptopyrimidine sodium salt
58289-71-7

2-mercaptopyrimidine sodium salt

2-thiocyanatopyrimidine
89283-87-4

2-thiocyanatopyrimidine

Conditions
ConditionsYield
Ambient temperature;100%
Potassium; 3,4-dimethoxy-phenolate

Potassium; 3,4-dimethoxy-phenolate

cyanogen chloride
506-77-4

cyanogen chloride

4-cyanato-1,2-dimethoxy-benzene
220075-82-1

4-cyanato-1,2-dimethoxy-benzene

Conditions
ConditionsYield
Ambient temperature;100%
acetonitrile
75-05-8

acetonitrile

cyanogen chloride
506-77-4

cyanogen chloride

2,4-dichloro-6-methyl-1,3,5-triazine
1973-04-2

2,4-dichloro-6-methyl-1,3,5-triazine

Conditions
ConditionsYield
With hydrogenchloride; aluminum (III) chloride In water; 1,2-dichloro-ethane at -5 - 5℃; for 8h; Reagent/catalyst; Solvent;99%
With hydrogenchloride; aluminum (III) chloride In dichloromethane at -5 - 5℃; under 750.075 Torr; for 12h;
4-hydroxybenzaldehyde potassium salt
58765-11-0

4-hydroxybenzaldehyde potassium salt

cyanogen chloride
506-77-4

cyanogen chloride

4-cyanatobenzaldehyde
1126-84-7

4-cyanatobenzaldehyde

Conditions
ConditionsYield
Ambient temperature;98%
silver hexafluoroantimonate

silver hexafluoroantimonate

cyanogen chloride
506-77-4

cyanogen chloride

bis(cyanogen chloride-N)silver(I) hexafluoroantimonate(V)
117504-97-9

bis(cyanogen chloride-N)silver(I) hexafluoroantimonate(V)

Conditions
ConditionsYield
In sulfur dioxide N2, exclusion of light, stirred for 12 h at room temp.;; filtrated, SO2 removed in vacuo, elem. anal.;98%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

cyanogen chloride
506-77-4

cyanogen chloride

6-(propylthio)-1H-benzo[d]imidazol-2-amine

6-(propylthio)-1H-benzo[d]imidazol-2-amine

Conditions
ConditionsYield
With sodium hydroxide In methanol at 3 - 45℃; for 2h; pH=4; pH-value; Temperature;95.21%
N-(methoxycarbonylmethyl)-N'-methoxydiazene-N-oxide
82385-77-1

N-(methoxycarbonylmethyl)-N'-methoxydiazene-N-oxide

cyanogen chloride
506-77-4

cyanogen chloride

(N'-methoxydiazene-N-oxido)cyanoacetic acid methyl ester

(N'-methoxydiazene-N-oxido)cyanoacetic acid methyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; hexane 1.) -10 - -5 deg C, 30 min, 2.) -50 deg C to 20 deg C, 1 h;95%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

cyanogen chloride
506-77-4

cyanogen chloride

2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 0 - 5℃; for 8h; pH=4 - 5; Diels-Alder Cycloaddition;95%
N'-((6-chloropyridin-3-yl)methyl)ethane-1,2-diamine
101990-44-7

N'-((6-chloropyridin-3-yl)methyl)ethane-1,2-diamine

cyanogen chloride
506-77-4

cyanogen chloride

Desnitro-imidacloprid
115970-17-7

Desnitro-imidacloprid

Conditions
ConditionsYield
In water at 20℃; for 3h;94.2%
CYANAMID
420-04-2

CYANAMID

cyanogen chloride
506-77-4

cyanogen chloride

A

sodium N-cyanoisourea
76989-89-4

sodium N-cyanoisourea

B

sodium dicyanamide
1934-75-4

sodium dicyanamide

C

sodium chloride
7647-14-5

sodium chloride

Conditions
ConditionsYield
With sodium hydroxide In water at 70 - 75℃; under 1050.11 Torr; pH=7.2 - 8.0; Purification / work up;A n/a
B 94%
C n/a
antimonypentachloride
7647-18-9

antimonypentachloride

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
In neat (no solvent) under N2, excess of CN-compd. was condensed onto SbCl5 at -196 °C, mixt. was allowed to warm to room temp.; recrystn. from SO2, elem. anal.;94%
(η5-C5H5)2Ti(AsF6)2

(η5-C5H5)2Ti(AsF6)2

cyanogen chloride
506-77-4

cyanogen chloride

(C5H5)2Ti(NCCl)2(2+)*2AsF6(1-)=(C5H5)2Ti(NCCl)2(AsF6)2

(C5H5)2Ti(NCCl)2(2+)*2AsF6(1-)=(C5H5)2Ti(NCCl)2(AsF6)2

Conditions
ConditionsYield
In sulfur dioxide (strictly anhydrous conditions, N2) SO2 was condensed in vessel with complex at -196°C, allowed to warm to room temp., cooled using liquid N2, 5-fold excess of ClCN was condensed in, warmed to room temp., stirred for 30 min; SO2 and ClCN were removed;94%
benzenesulfinic acid sodium dihydrate
25932-11-0

benzenesulfinic acid sodium dihydrate

cyanogen chloride
506-77-4

cyanogen chloride

benzenesulfonyl cyanide
24224-99-5

benzenesulfonyl cyanide

Conditions
ConditionsYield
In dichloromethane; water93.8%

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