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33252-28-7

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33252-28-7 Usage

Uses

Different sources of media describe the Uses of 33252-28-7 differently. You can refer to the following data:
1. 2-Chloro-5-cyanopyridine (cas# 33252-28-7) is a compound useful in organic synthesis.
2. 6-Chloro-3-pyridinecarbonitrile (2-Chloro-5-cyanopyridine) may be used in the preparation of:(6-chloro-3-pyridyl)methylamine2-(N-methyl-N-isopropylamino)-5-cyanopyridineS-(5-cyano-2-pyridyl)thiouronium chloride

General Description

6-Chloro-3-pyridinecarbonitrile is a substituted pyridine.

Check Digit Verification of cas no

The CAS Registry Mumber 33252-28-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,2,5 and 2 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 33252-28:
(7*3)+(6*3)+(5*2)+(4*5)+(3*2)+(2*2)+(1*8)=87
87 % 10 = 7
So 33252-28-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H3ClN2/c7-6-2-1-5(3-8)4-9-6/h1-2,4H

33252-28-7 Well-known Company Product Price

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  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (A13291)  2-Chloro-5-cyanopyridine, 98%   

  • 33252-28-7

  • 1g

  • 754.0CNY

  • Detail
  • Alfa Aesar

  • (A13291)  2-Chloro-5-cyanopyridine, 98%   

  • 33252-28-7

  • 5g

  • 1816.0CNY

  • Detail
  • Alfa Aesar

  • (A13291)  2-Chloro-5-cyanopyridine, 98%   

  • 33252-28-7

  • 25g

  • 7267.0CNY

  • Detail
  • Aldrich

  • (510734)  6-Chloro-3-pyridinecarbonitrile  97%

  • 33252-28-7

  • 510734-5G

  • 558.09CNY

  • Detail
  • Aldrich

  • (510734)  6-Chloro-3-pyridinecarbonitrile  97%

  • 33252-28-7

  • 510734-25G

  • 2,204.28CNY

  • Detail

33252-28-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-chloropyridine-3-carbonitrile

1.2 Other means of identification

Product number -
Other names 6-Chloronicotionitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:33252-28-7 SDS

33252-28-7Synthetic 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;
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;
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%)

33252-28-7Relevant articles and documents

Studies on some glitazones having pyridine as the linker unit

Ramachandran, Uma,Mital, Alka,Bharatam, Prasad V.,Khanna, Smriti,Rao, Poduri Rama,Srinivasan, Krishnamoorthy,Kumar, Rakesh,Singh Chawla, Harmander Pal,Kaul, Chaman Lal,Raichur, Suryaprakash,Chakrabarti, Ranjan

, p. 655 - 662 (2004)

Molecular modeling on various well-known glitazones carrying a pyridine ring instead of benzene ring as the middle linker unit showed conformational rigidity as compared to their parent molecules. Blocking the lone pair of electrons on the pyridine N, made them flexible once again. A few representatives of these analogues were synthesized and their efficacy as PPARγ agonists evaluated.

Preparation method of 2-chloro-5-cyano nitrogen-containing six-membered heterocyclic compound

-

Paragraph 0069; 0070; 0071; 0074, (2019/01/08)

The invention provides a preparation method of a 2-chloro-5-cyano nitrogen-containing six-membered heterocyclic compound. The method comprises the following steps: using a 2-hydroxy-5-bromine nitrogen-containing six-membered heterocyclic compound as a raw material, under existence of a catalyst, in atmosphere of carbon monoxide gas, using methanol as a solvent, and performing a coupling reaction to obtain a methyl 2-hydroxyl nitrogen-containing six-membered heterocyclic ring-5-carboxylate, and sequentially performing an aminolysis reaction, a chlorination reaction with phosphorus oxychloride,and an oxidation reaction to obtain the 2-chloro-5-cyano nitrogen-containing six-membered heterocyclic compound. The preparation method has the advantages of short route and easily available raw material, a post-processing method is simple, no column chromatography is required after each reaction, the reaction product can be purified only by washing and extraction of a solvent, amplification is realized, industrial production is carried out, the method accords with environmental protection requirements, and has important value for actual production.

Cu-Catalyzed Cyanation of Arylboronic Acids with Acetonitrile: A Dual Role of TEMPO

Zhu, Yamin,Li, Linyi,Shen, Zengming

supporting information, p. 13246 - 13252 (2015/09/15)

The cyanation of arylboronic acids by using acetonitrile as the "CN" source has been achieved under a Cu(cat.)/TEMPO system (TEMPO=2,2,6,6-tetramethylpiperidine N-oxide). The broad substrate scope includes a variety of electron-rich and electron-poor arylboronic acids, which react well to give the cyanated products in high to excellent yields. Mechanistic studies reveal that TEMPO-CH2CN, generated in situ, is an active cyanating reagent, and shows high reactivity for the formation of the CN- moiety. Moreover, TEMPO acts as a cheap oxidant to enable the reaction to be catalytic in copper. The cyanation of arylboronic acids by using acetonitrile as the "CN" source has been achieved under a Cu(cat.)/TEMPO system. Electron-rich and electron-poor arylboronic acids react well to give the cyanated products in high to excellent yields. Mechanistic studies reveal that TEMPO-CH2CN, generated in situ, is an active cyanating reagent. Moreover, TEMPO, a cheap oxidant, enables the reaction to be catalytic in copper (see scheme; TEMPO=2,2,6,6-tetramethylpiperidine N-oxide).

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