Product Name

  • Name

    6-Chloronicotinonitrile

  • EINECS -0
  • CAS No. 33252-28-7
  • Article Data19
  • CAS DataBase
  • Density 1.33 g/cm3
  • Solubility Insoluble in water, soluble in carbon tetrachloride, toluene and other solvents
  • Melting Point 113-116 °C
  • Formula C6H3ClN2
  • Boiling Point 236.4 °C at 760 mmHg
  • Molecular Weight 138.556
  • Flash Point 96.8 °C
  • Transport Information
  • Appearance Yellow to brown crystal
  • Safety 26-36-36/37/39-37
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 33252-28-7 (6-Chloronicotinonitrile)
  • Hazard Symbols HarmfulXn,ToxicT,IrritantXi
  • Synonyms Nicotinonitrile,6-chloro- (8CI);2-Chloro-5-cyanopyridine;2-Chloro-5-pyridinecarbonitrile;5-Cyano-2-chloropyridine;6-Chloro-3-cyanopyridine;6-Chloro-3-pyridinecarbonitrile;6-chloropyridine-3-carbonitrile;
  • PSA 36.68000
  • LogP 1.60668

Synthetic route

6-chloronicotinylaldehyde
23100-12-1

6-chloronicotinylaldehyde

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide at 100℃;96%
6-hydroxy-3-pyridinecarbonitrile
94805-52-4

6-hydroxy-3-pyridinecarbonitrile

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide Chlorination;95%
6-chloro-3-pyridinecarboxamide
6271-78-9

6-chloro-3-pyridinecarboxamide

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
With trichlorophosphate In chloroform for 2.5h; Heating;88%
With chloroform; trichlorophosphate
With trichlorophosphate In chloroform; water10.3 g (83 %)
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 0℃; for 2h;
6-chloronicotinaldehyde oxime
170727-01-2

6-chloronicotinaldehyde oxime

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
With pyridinium chlorochromate In chloroform for 3h; Reflux;88%
2-(6-chloropyridin-3-yl)acetic acid
39891-13-9

2-(6-chloropyridin-3-yl)acetic acid

urea
57-13-6

urea

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
With oxygen; copper(II) trifluoroacetate In dimethyl sulfoxide at 110℃; for 19h; Sealed tube; Green chemistry;80%
trans-3-dimethylaminoacrylonitrile
35520-41-3

trans-3-dimethylaminoacrylonitrile

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
In hydrogenchloride; water; N,N-dimethyl-formamide77.7%
2-(6-chloropyridin-3-yl)acetic acid
39891-13-9

2-(6-chloropyridin-3-yl)acetic acid

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 110℃; for 19h; Green chemistry;75%
5-bromo-2-chloropyridine
53939-30-3

5-bromo-2-chloropyridine

N-cyano-N-phenyl-p-toluenesulfonamide
55305-43-6

N-cyano-N-phenyl-p-toluenesulfonamide

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
Stage #1: 5-bromo-2-chloropyridine With TurboGrignard In tetrahydrofuran at 0℃; for 1.33333h; Inert atmosphere;
Stage #2: N-cyano-N-phenyl-p-toluenesulfonamide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;		70%
acetonitrile
75-05-8

acetonitrile

6-chloropyridin-3-ylboronic acid
444120-91-6

6-chloropyridin-3-ylboronic acid

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
With N-iodo-succinimide; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,1,1,2,2,2-hexamethyldisilane; oxygen; copper diacetate; diisopropylamine at 20 - 150℃; Schlenk technique;56%
3-cyanopyridine N-oxide
14906-64-0

3-cyanopyridine N-oxide

A

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

B

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

C

4-chloro-nicotinonitrile
89284-61-7

4-chloro-nicotinonitrile

Conditions
ConditionsYield
With trichlorophosphate at 110℃; for 2h; Yield given. Yields of byproduct given;
...Expand
nicotinamide N-oxide
1986-81-8

nicotinamide N-oxide

A

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

B

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

C

4-chloro-nicotinonitrile
89284-61-7

4-chloro-nicotinonitrile

Conditions
ConditionsYield
With trichlorophosphate for 3.5h; Heating; Yield given. Yields of byproduct given;
...Expand
diazotized 6-chloro-<3>pyridylamine

diazotized 6-chloro-<3>pyridylamine

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
With potassium cyanide; water; copper(II) sulfate
6-Chloronicotinoyl chloride
58757-38-3

6-Chloronicotinoyl chloride

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 9 g / NH3 gas / diethyl ether
2: 88 percent / POCl3 / CHCl3 / 2.5 h / Heating
View Scheme
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2 / 4 h / Heating
2: 9 g / NH3 gas / diethyl ether
3: 88 percent / POCl3 / CHCl3 / 2.5 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 0 - 25 °C
2: ammonia / water / 0.5 h / 0 °C
3: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 2 h / 0 °C
View Scheme
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / Microbiological reaction
2: 95 percent / SOCl2 / DMF
View Scheme
6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: POCl3 / Behandeln des Reaktionsprodukts in Aceton mit wss. NH3
2: POCl3; CHCl3
View Scheme
5-bromopyridin-2-ol
13466-38-1

5-bromopyridin-2-ol

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / 90 h / 100 °C / 3750.38 Torr / Autoclave; Large scale
2.1: ammonium hydroxide / 90 h / 30 °C / Sealed tube; Large scale
3.1: trichlorophosphate / 2 h / 50 °C / Large scale
3.2: 20 h / 75 °C / Large scale
View Scheme
6-hydroxynicotinamide
3670-59-5

6-hydroxynicotinamide

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
ConditionsYield
Stage #1: 6-hydroxynicotinamide With trichlorophosphate at 50℃; for 2h; Large scale;
Stage #2: With N-ethyl-N,N-diisopropylamine at 75℃; for 20h; Large scale;		0.52 kg
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

sodium methylate
124-41-4

sodium methylate

6-methoxynicotinonitrile
15871-85-9

6-methoxynicotinonitrile

Conditions
ConditionsYield
In methanol for 20h; Heating / reflux;100%
With 1,4-dioxane; methanol
In methanol Reflux;8.8 g
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

6-(methylthio)nicotinonitrile
408350-80-1

6-(methylthio)nicotinonitrile

Conditions
ConditionsYield
In tetrahydrofuran for 9h; Heating / reflux;100%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

4-Ethylphenol
123-07-9

4-Ethylphenol

6-(4-ethylphenoxy)nicotinonitrile
620608-67-5

6-(4-ethylphenoxy)nicotinonitrile

Conditions
ConditionsYield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 100℃; for 4h;100%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

benzyl alcohol
100-51-6

benzyl alcohol

6-(benzyloxy)nicotinonitrile
876516-71-1

6-(benzyloxy)nicotinonitrile

Conditions
ConditionsYield
Stage #1: benzyl alcohol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 6-chloronicotinonitrile In N,N-dimethyl-formamide at 20℃; for 0.5h;		100%
Stage #1: benzyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h;
Stage #2: 6-chloronicotinonitrile In tetrahydrofuran; mineral oil at 25℃; for 17h;		92%
Stage #1: benzyl alcohol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 6-chloronicotinonitrile In N,N-dimethyl-formamide at 20℃; for 2h;		40%
With sodium hydride In tetrahydrofuran at 0℃; for 0.25h;
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

3(S)-(tert-butoxycarbonylamino)pyrrolidine
122536-76-9

3(S)-(tert-butoxycarbonylamino)pyrrolidine

(S)-tert-butyl (1-(5-cyanopyridin-2-yl)pyrrolidin-3-yl)carbamate

(S)-tert-butyl (1-(5-cyanopyridin-2-yl)pyrrolidin-3-yl)carbamate

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 20℃;100%
With sodium carbonate In N,N-dimethyl-formamide at 20℃;100%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

4-Benzyloxyphenol
103-16-2

4-Benzyloxyphenol

6-[(4-benzyloxy)phenoxy]nicotinonitrile
639091-30-8

6-[(4-benzyloxy)phenoxy]nicotinonitrile

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 100℃; for 3.5h;99%
With potassium carbonate In N,N-dimethyl-formamide at 100℃;
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

3-Hydroxybenzyl alcohol
620-24-6

3-Hydroxybenzyl alcohol

6-(3-hydroxymethyl-phenoxy)-nicotinonitrile

6-(3-hydroxymethyl-phenoxy)-nicotinonitrile

Conditions
ConditionsYield
With potassium carbonate In ISOPROPYLAMIDE at 100℃; for 4h;99%
With potassium carbonate In N,N-dimethyl acetamide at 100℃;
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

(piperidin-4-yl)carbamic acid tert-butyl ester
73874-95-0

(piperidin-4-yl)carbamic acid tert-butyl ester

(1-(5-cyanopyridin-2-yl)piperidin-4-yl)carbamic acid tert-butyl ester
252577-86-9

(1-(5-cyanopyridin-2-yl)piperidin-4-yl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 90℃; for 4h;99%
With sodium carbonate In N,N-dimethyl-formamide at 90℃; for 4h;99%
With sodium carbonate In N,N-dimethyl-formamide at 90℃; for 4h;99%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.5h;78%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h;
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

t-butyl piperidin-3-ylcarbamate
184637-48-7

t-butyl piperidin-3-ylcarbamate

(1-(5-cyanopyridin-2-yl)piperidin-3-yl)carbamic acid tert-butyl ester

(1-(5-cyanopyridin-2-yl)piperidin-3-yl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;99%
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 10h;96%
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 10h;96%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

6-chloro-3-pyridinecarboxamide
6271-78-9

6-chloro-3-pyridinecarboxamide

Conditions
ConditionsYield
With manganese(IV) oxide; water In isopropyl alcohol at 50℃; under 5171.62 Torr; for 0.166667h;99%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

thiophenol
108-98-5

thiophenol

6-phenylsulfanylpyridine-3-carbonitrile

6-phenylsulfanylpyridine-3-carbonitrile

Conditions
ConditionsYield
Stage #1: thiophenol With sodium hydride In N,N-dimethyl-formamide for 0.5h;
Stage #2: 6-chloronicotinonitrile In N,N-dimethyl-formamide at 50℃; for 1h;		99%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

phenylboronic acid
98-80-6

phenylboronic acid

2-phenyl-5-cyanopyridine
39065-54-8

2-phenyl-5-cyanopyridine

Conditions
ConditionsYield
With potassium phosphate; C46H52Cl3N3O2Pd In tetrahydrofuran; water at 60℃; for 4h; Suzuki-Miyaura Coupling;98%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 16h;94%
With palladium on activated charcoal; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 80℃; for 9h; Suzuki-Miyaura coupling;90%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

benzyl 4-(2-hydroxypropyl)-1-piperidinecarboxylate
99198-80-8

benzyl 4-(2-hydroxypropyl)-1-piperidinecarboxylate

benzyl 4-[3-[(5-cyano-2-pyridyl)oxy]propyl]piperidine-1-carboxylate

benzyl 4-[3-[(5-cyano-2-pyridyl)oxy]propyl]piperidine-1-carboxylate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;98%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

N-methylpropan-2-amine
4747-21-1

N-methylpropan-2-amine

2-(N-methyl-N-isopropylamino)-5-cyanopyridine

2-(N-methyl-N-isopropylamino)-5-cyanopyridine

Conditions
ConditionsYield
Stage #1: 6-chloronicotinonitrile; N-methylpropan-2-amine In 1,4-dioxane at 90℃; for 12h;
Stage #2: With sodium hydroxide In water		97%
In 1,4-dioxane for 12h; Heating;60%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

3,3-difluoropyrrolidine hydrochloride
163457-23-6

3,3-difluoropyrrolidine hydrochloride

6-(3,3-difluoropyrrolidin-1-yl)nicotinonitrile

6-(3,3-difluoropyrrolidin-1-yl)nicotinonitrile

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 85℃; for 22h; Inert atmosphere;97%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

(R)-tert-butyl 3-methylpiperazine-1-carboxylate
163765-44-4

(R)-tert-butyl 3-methylpiperazine-1-carboxylate

tert-butyl (3R)-4-(5-cyano-2-pyridyl)-3-methylpiperazine-1-carboxylate
912556-68-4

tert-butyl (3R)-4-(5-cyano-2-pyridyl)-3-methylpiperazine-1-carboxylate

Conditions
ConditionsYield
With potassium carbonate; tetrakis(acetonitrile)copper(I) hexafluorophosphate In dimethyl sulfoxide at 140℃; for 4h;96%
With tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium carbonate In dimethyl sulfoxide at 20 - 140℃; for 4h;55%
With tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium carbonate In dimethyl sulfoxide at 140℃; for 3h;
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

6-(2,2,2-trifluoroethoxy)nicotinonitrile
159981-18-7

6-(2,2,2-trifluoroethoxy)nicotinonitrile

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h;96%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

tert-butyl hexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate

tert-butyl hexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate

tert-butyl 4-(5-cyanopyridin-2-yl)-octahydropyrrolo[3,2-b]pyrrole-1-carboxylate

tert-butyl 4-(5-cyanopyridin-2-yl)-octahydropyrrolo[3,2-b]pyrrole-1-carboxylate

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 2h;96%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol
1018297-63-6

[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol

6-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinonitrile
1431329-33-7

6-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran95%
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Concentration; Temperature;91%
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h;91%
2-hydroxy-N,N-dimethylacetamide
14658-93-6

2-hydroxy-N,N-dimethylacetamide

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

6-chloroniconitrile
1539303-85-9

6-chloroniconitrile

Conditions
ConditionsYield
Stage #1: 2-hydroxy-N,N-dimethylacetamide With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: 6-chloronicotinonitrile In N,N-dimethyl-formamide at 10 - 20℃; for 16h; Inert atmosphere;		95%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

6-(4-tert-butylphenyl)nicotinonitrile
1268140-34-6

6-(4-tert-butylphenyl)nicotinonitrile

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; nixantphos In tetrahydrofuran; water at 20℃; for 6h; Suzuki-Miyaura Coupling;95%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

Pyridine-2,5-dicarbonitrile
20730-07-8

Pyridine-2,5-dicarbonitrile

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; [Pd(cinnamyl)Cl]2; N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 80℃; for 2h; Inert atmosphere;95%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

1,4-Phenyldiboronic acid
4612-26-4

1,4-Phenyldiboronic acid

1,4-bis-(5'-cyanopyridin-2'-yl)phenylene
910547-33-0

1,4-bis-(5'-cyanopyridin-2'-yl)phenylene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; toluene at 80℃; Suzuki coupling;94%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

t-butyl 4-hydroxy piperidine-1-carboxylate
109384-19-2

t-butyl 4-hydroxy piperidine-1-carboxylate

4-(5-cyano-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester
194668-38-7

4-(5-cyano-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: t-butyl 4-hydroxy piperidine-1-carboxylate With sodium hydride In DMF (N,N-dimethyl-formamide) at 20 - 50℃; for 1.41667h;
Stage #2: 6-chloronicotinonitrile In DMF (N,N-dimethyl-formamide) at 60℃;		94%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1.75h;89%
Stage #1: t-butyl 4-hydroxy piperidine-1-carboxylate With sodium hydride In N,N-dimethyl-formamide at 80℃; for 1h;
Stage #2: 6-chloronicotinonitrile In N,N-dimethyl-formamide at 80℃; for 16h;
Stage #3: With water; ammonium chloride In N,N-dimethyl-formamide
Thien-3-ylboronic acid
6165-69-1

Thien-3-ylboronic acid

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

6-(thiophen-3-yl)nicotinonitrile
937601-80-4

6-(thiophen-3-yl)nicotinonitrile

Conditions
ConditionsYield
With potassium phosphate; C43H37ClFeNiP2*C4H8O In 1,4-dioxane at 80℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;94%
With C84H64Cl3N3Pd; potassium carbonate In ethanol at 80℃; for 2h; Suzuki-Miyaura Coupling;85%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

4-chloro-phenol
106-48-9

4-chloro-phenol

6-(4-chlorophenoxy)-3-pyridinecarbonitrile
99902-70-2

6-(4-chlorophenoxy)-3-pyridinecarbonitrile

Conditions
ConditionsYield
Stage #1: 4-chloro-phenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h;
Stage #2: 6-chloronicotinonitrile In N,N-dimethyl-formamide at 100℃; for 10h;		93%
With sodium hydride In dimethyl sulfoxide at 120℃;
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(6-chloropyridin-3-ylmethyl)carbamic acid tert-butyl ester
285119-72-4

(6-chloropyridin-3-ylmethyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In methanol at 0 - 20℃; for 1h;93%
Stage #1: 6-chloronicotinonitrile; di-tert-butyl dicarbonate With sodium tetrahydroborate; nickel dichloride In methanol at 0 - 20℃; for 1.5h;
Stage #2: With 3-azapentane-1,5-diamine In methanol for 0.5h;		67%
With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; Reduction;25%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

6-chloro-N-hydroxypyridine-3-carboxamidine
468068-39-5

6-chloro-N-hydroxypyridine-3-carboxamidine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; potassium tert-butylate In dimethyl sulfoxide at 20℃;93%
With sodium hydroxide; hydroxylamine hydrochloride In ethanol at 20℃;53%
With hydroxylamine hydrochloride In ethanol275 mg (53%)

6-Chloronicotinonitrile Specification

The IUPAC name of 2-Chloro-5-cyanopyridine is 6-chloropyridine-3-carbonitrile. With the CAS registry number 33252-28-7, it is also named as 3-Pyridinecarbonitrile, 6-chloro-. The product's categories are Blocks; Carboxes; Pyridines; Pyridine Derivative; Pyridine Series; Halides; Aromatics Compounds; Chloropyridines; Halopyridines; Aromatics; Heterocycles. It is yellow to brown crystal which is insoluble in water, soluble in carbon tetrachloride, toluene and other solvents. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.12; (4)ACD/LogD (pH 7.4): 1.12; (5)ACD/BCF (pH 5.5): 4.18; (6)ACD/BCF (pH 7.4): 4.18; (7)ACD/KOC (pH 5.5): 96.94; (8)ACD/KOC (pH 7.4): 96.94; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.565; (13)Molar Refractivity: 33.94 cm3; (14)Molar Volume: 104.1 cm3; (15)Polarizability: 13.45×10-24 cm3; (16)Surface Tension: 56.6 dyne/cm; (17)Enthalpy of Vaporization: 47.32 kJ/mol; (18)Vapour Pressure: 0.0474 mmHg at 25°C; (19)Exact Mass: 137.998476; (20)MonoIsotopic Mass: 137.998476; (21)Topological Polar Surface Area: 36.7; (22)Heavy Atom Count: 9; (23)Complexity: 137.

Preparation of 2-Chloro-5-cyanopyridine: It can be obtained by 6-hydroxy-nicotinonitrile. This reaction which is a kind of chlorination needs reagent SOCl2 and catalytic agent DMF. The yield is 95%.

Uses of 2-Chloro-5-cyanopyridine: It is used as intermediate of pesticides imidacloprid and acetaniprid. It also can react with di-tert-butyl dicarbonate to get (6-chloro-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester. This reaction needs reagent NiCl2*6H2O, NaBH4 and solvent methanol at temperature of 0-20 °C. The reaction time is 1 hours. The yield is 93%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:c1cc(ncc1C#N)Cl
2. InChI:InChI=1/C6H3ClN2/c7-6-2-1-5(3-8)4-9-6/h1-2,4H
3. InChIKey:ORIQLMBUPMABDV-UHFFFAOYAQ

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