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109-09-1

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High quality 2-Chloropyridine supplier in China
Cas No: 109-09-1
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2-chloropyridine
Cas No: 109-09-1
USD $ 1.0-2.0 / Metric Ton 1 Metric Ton 500 Metric Ton/Week Hebei yanxi chemical co.,LTD. Contact Supplier
2-Chloropyridine
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Amadis Chemical offer CAS#109-09-1;CAT#A801967
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2-Chloropyridine
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2-Chloropyridine
Cas No: 109-09-1
USD $ 4.0-4.0 / Kilogram 1 Kilogram 1-10 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
2-Chloropyridine
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USD $ 1.0-1.0 / Kilogram 1 Kilogram 1000 Metric Ton/Year Henan Sinotech Import&Export Corporation Contact Supplier
2-Chloropyridine
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USD $ 5.0-5.0 / Gram 1 Gram 100 Metric Ton/Month Jinan Finer Chemical Co., Ltd Contact Supplier
2-Chloropyridine 109-09-1
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No Data 1 Kilogram 10 Metric Ton/Month Henan Tianfu Chemical Co., Ltd. Contact Supplier
2-Chloropyridine
Cas No: 109-09-1
USD $ 10.0-1000.0 / Gram 10 Gram 8000 Kilogram/Month HUBEI AOKS BIO-TECH CO.,LTD Contact Supplier

109-09-1 Usage

Air & Water Reactions

Slightly soluble in water and denser than water.

Purification Methods

Dry 2-chloropyridine with NaOH for several days, then distil it from CaO under reduced pressure. [Beilstein 20/5 V 402.]

General Description

A colorless oily liquid. Toxic by ingestion and/or skin absorption. Used to make other chemicals.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Chemical Properties

Clear colourless to light yellow liquid

Uses

2-Chloropyridine (2-CPY) has been identified as a trace organic chemical in process streams, wastewater and even drinking water. Furthermore, it appears to be formed as a secondary pollutant during t he decomposition of specific insecticides.
InChI:InChI=1/C5H4ClN/c6-5-3-1-2-4-7-5/h1-4H

109-09-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (C69802)  2-Chloropyridine  99% 109-09-1 C69802-500G 1,285.83CNY Detail
Aldrich (C69802)  2-Chloropyridine  99% 109-09-1 C69802-100G 319.41CNY Detail
Aldrich (C69802)  2-Chloropyridine  99% 109-09-1 C69802-5G 297.18CNY Detail

109-09-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Chloropyridine

1.2 Other means of identification

Product number -
Other names Pyridine,2-chloro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:109-09-1 SDS

109-09-1Synthetic route

2-hydroxypyridin
142-08-5

2-hydroxypyridin

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With P,P-dichlorophenylphosphine oxide; phosphorus pentachloride at 160℃; for 5h;96.5%
With pyridine; trichlorophosphate at 180℃; under 150.015 - 900.09 Torr; for 2h; Neat (no solvent);90%
With dmap; thionyl chloride; bis(trichloromethyl) carbonate for 4h; Reflux; Green chemistry;89%
With N-chloro-succinimide; triphenylphosphine In 1,4-dioxane for 4h; Chlorination; substitution; Heating;43%
With trichloroacetonitrile; triphenylphosphine In toluene for 4h; Reflux;100 %Chromat.
2-chloropyridine N-oxide hydrochloride
20295-64-1

2-chloropyridine N-oxide hydrochloride

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With titanium In tetrahydrofuran for 0.25h; Ambient temperature;96%
2-aminopyridine
504-29-0

2-aminopyridine

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With hydrogenchloride; dinitrogen trioxide; tetrabutyl-ammonium chloride In dichloromethane for 2h; Ambient temperature;95%
With tert-Butyl thionitrate; copper dichloride In acetonitrile at 25℃; for 0.025h; Product distribution; Mechanism; other copper(II) halide, other reagent;64 % Chromat.
With hydrogenchloride; sodium nitrite
With tert-Butyl thionitrate; copper dichloride In acetonitrile at 25℃; for 0.025h;64 % Chromat.
2-chloropyridine-N-oxide
2402-95-1

2-chloropyridine-N-oxide

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With cerium(III) chloride heptahydrate; zinc In methanol at 20℃; for 0.5h;95%
With hydrogen; triethyl phosphite In isopropyl alcohol at 100℃; under 4500.45 Torr; for 18h; Glovebox; chemoselective reaction;90%
With polymethylhydrosiloxane; palladium on activated charcoal In ethanol at 20℃;87%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With trans-bis(glycinato)copper(II) monohydrate; tetramethlyammonium chloride In ethanol at 100℃; for 12h; Finkelstein Reaction; Schlenk technique; Inert atmosphere;92%
With copper(I) oxide; tetramethlyammonium chloride; L-proline In ethanol at 110℃; for 20h; Inert atmosphere;93 %Chromat.
pyridine N-oxide
694-59-7

pyridine N-oxide

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With oxalyl dichloride; triethylamine In dichloromethane at 5℃; for 1h; Temperature;91.2%
With triethylamine; trichlorophosphate In dichloromethane at 40℃; for 1h;90%
With diisopropylamine; trichloromethyl chloroformate In dichloromethane at -40 - 20℃;
Pyridin-Palladium(II)-chlorid-Komplex

Pyridin-Palladium(II)-chlorid-Komplex

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With chlorine In pyridine at 0 - 5℃; for 1h;90%
pyridine
110-86-1

pyridine

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With Fluoroacetic acid In dichloromethane at 25 - 60℃; under 675.068 Torr; for 5.5h; Temperature; Pressure;82.1%
With chlorine at 220℃; Product distribution / selectivity; UV-irradiation;29.7%
With sulfuryl dichloride at 350℃; Leiten durch Glasrohr;
With hydrogenchloride; sodium hypochlorite In water at 20 - 60℃; for 2h; Temperature; Reagent/catalyst;
2,2'-dipyridyldisulphide
2127-03-9

2,2'-dipyridyldisulphide

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With chlorine In chloroform; water; acetic acid at 15 - 17℃; for 0.5h;82%
C19H14N2O2
93845-11-5

C19H14N2O2

A

2-chloropyridine
109-09-1

2-chloropyridine

B

benzophenone
119-61-9

benzophenone

C

hexachloroethane
67-72-1

hexachloroethane

D

benzophenone azine
983-79-9

benzophenone azine

Conditions
ConditionsYield
With tetrachloromethane Ambient temperature; Irradiation; Yields of byproduct given;A 80%
B n/a
C n/a
D n/a
2,2'-dipyridyldisulphide
2127-03-9

2,2'-dipyridyldisulphide

A

2-chloropyridine
109-09-1

2-chloropyridine

B

pyridine-2-sulfonyl chloride
66715-65-9

pyridine-2-sulfonyl chloride

Conditions
ConditionsYield
With 1,3-dichloro-5,5-dimethylhydantoin; acetic acid In dichloromethane; water at 0 - 20℃; Inert atmosphere;A 20%
B 78%
2,6-dichloropyridine N-oxide
2587-00-0

2,6-dichloropyridine N-oxide

A

2-chloropyridine
109-09-1

2-chloropyridine

B

2,6-dichloropyridine
2402-78-0

2,6-dichloropyridine

Conditions
ConditionsYield
With copper(l) iodide; zinc In ethanol at 55 - 60℃; for 3h;A n/a
B 75%
pyridine
110-86-1

pyridine

acetyl hypofluorite
78948-09-1

acetyl hypofluorite

A

2-chloropyridine
109-09-1

2-chloropyridine

B

2-acetoxypyridine
3847-19-6

2-acetoxypyridine

Conditions
ConditionsYield
With dichloromethane Ambient temperature;A 70%
B 15%
In dichloromethane Mechanism; Ambient temperature; other N-heterocycles, other solvents;A 70%
B 15%
pyridine
110-86-1

pyridine

A

2-chloropyridine
109-09-1

2-chloropyridine

B

2-acetoxypyridine
3847-19-6

2-acetoxypyridine

Conditions
ConditionsYield
With dichloromethane; acetyl hypofluorite In trichlorofluoromethane Product distribution; Mechanism; Ambient temperature; var. halogenomethanes or primary alcohols; other substituted pyridines;A 70%
B 15%
2-chloropyridine-N-oxide
2402-95-1

2-chloropyridine-N-oxide

A

pyridine
110-86-1

pyridine

B

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With copper(l) iodide; zinc In ethanol at 55 - 60℃; for 3h;A n/a
B 70%
pyridine
110-86-1

pyridine

p-nitrophenyl isocyanide
1984-23-2

p-nitrophenyl isocyanide

A

2-chloropyridine
109-09-1

2-chloropyridine

B

pyridine-2-carboxylic acid (4-nitro-phenyl)amide
61349-99-3

pyridine-2-carboxylic acid (4-nitro-phenyl)amide

C

N-(4-nitro-phenyl)-2-oxo-2-pyridin-2-yl-acetamide

N-(4-nitro-phenyl)-2-oxo-2-pyridin-2-yl-acetamide

Conditions
ConditionsYield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃;
Stage #2: p-nitrophenyl isocyanide In dichloromethane at -50 - 0℃; for 4h;
A 11%
B 69%
C n/a
2-Picolinic acid
98-98-6

2-Picolinic acid

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With N-chloro-succinimide; tert-butylhypochlorite; potassium carbonate In dichloromethane at 150℃; for 10h; Schlenk technique;68%
With tert-butylhypochlorite; dichloromethane; sodium hydrogencarbonate at 60℃; for 20h; Green chemistry;73 %Spectr.
pyridine
110-86-1

pyridine

n-butyl isonitrile
2769-64-4

n-butyl isonitrile

A

2-chloropyridine
109-09-1

2-chloropyridine

B

N-butyl-pyridine-2-carboxylic acid amide
10354-51-5

N-butyl-pyridine-2-carboxylic acid amide

C

N-butyl-2-oxo-2-pyridin-2-yl-acetamide

N-butyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions
ConditionsYield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃;
Stage #2: n-butyl isonitrile In dichloromethane at -50 - 0℃; for 4h;
A 12%
B 64%
C n/a
N-fluoropyridinium triflate
107263-95-6

N-fluoropyridinium triflate

A

2-chloropyridine
109-09-1

2-chloropyridine

B

pyridin-2-yl trifluoromethanesulfonate
65007-00-3

pyridin-2-yl trifluoromethanesulfonate

C

2-fluoropyridine
372-48-5

2-fluoropyridine

Conditions
ConditionsYield
With dichloromethane; triethylamine for 0.0833333h; Product distribution; Ambient temperature; other time; various bases;A 62%
B 21%
C 5%
With dichloromethane; triethylamine for 0.0833333h; Ambient temperature; further bases;A 62 % Chromat.
B 21 % Chromat.
C 5 % Chromat.
With 2,6-di-tert-butyl-pyridine; dichloromethane for 48h; Ambient temperature;A 68 % Chromat.
B 3 % Chromat.
C 9 % Chromat.
With Benzotrichlorid; triethylamine for 0.0833333h; Ambient temperature;A 11 % Chromat.
B 58 % Chromat.
C 20 % Chromat.
With dichloromethane; diethylamine for 0.0833333h; Mechanism; Ambient temperature;A 63 % Chromat.
B 22 % Chromat.
C 6 % Chromat.
Pyridin-Palladium(II)-chlorid-Komplex

Pyridin-Palladium(II)-chlorid-Komplex

A

2-chloropyridine
109-09-1

2-chloropyridine

B

2,3-dichloro-pyridine
2402-77-9

2,3-dichloro-pyridine

C

2,3,5-trichloropyridine
16063-70-0

2,3,5-trichloropyridine

Conditions
ConditionsYield
With chlorine In cyclohexane at 75℃; for 1h;A 9%
B 62%
C 4.5%
pyridine
110-86-1

pyridine

Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

A

2-chloropyridine
109-09-1

2-chloropyridine

B

N-picolinoylcyclohexylamine
10354-50-4

N-picolinoylcyclohexylamine

C

N-cyclohexyl-2-oxo-2-pyridin-2-yl-acetamide

N-cyclohexyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions
ConditionsYield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃;
Stage #2: Cyclohexyl isocyanide In dichloromethane at -50 - 0℃; for 4h;
A 15%
B 62%
C n/a
pyridine
110-86-1

pyridine

1-Phenyl-2-(trimethylsilyl)acetylene
2170-06-1

1-Phenyl-2-(trimethylsilyl)acetylene

A

2-chloropyridine
109-09-1

2-chloropyridine

B

2-(2-phenylethynyl)pyridine
13141-42-9

2-(2-phenylethynyl)pyridine

C

2-fluoropyridine
372-48-5

2-fluoropyridine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; fluorine Mechanism; multistep reaction; other trimethylsilyl derivatives;A n/a
B 61%
C n/a
With tetrabutyl ammonium fluoride; fluorine 1.) CH2Cl2, -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;
pyridine
110-86-1

pyridine

3-trifluoromethylphenyl isonitrile

3-trifluoromethylphenyl isonitrile

A

2-chloropyridine
109-09-1

2-chloropyridine

B

N-[3-(trifluoromethyl)phenyl]-2-pyridinecarboxamide
61350-01-4

N-[3-(trifluoromethyl)phenyl]-2-pyridinecarboxamide

C

2-oxo-2-pyridin-2-yl-N-(3-trifluoromethyl-phenyl)-acetamide

2-oxo-2-pyridin-2-yl-N-(3-trifluoromethyl-phenyl)-acetamide

Conditions
ConditionsYield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃;
Stage #2: 3-trifluoromethylphenyl isonitrile In dichloromethane at -50 - 0℃; for 4h;
A 21%
B 61%
C n/a
pyridine
110-86-1

pyridine

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

A

2-chloropyridine
109-09-1

2-chloropyridine

B

pyridine-2-carboxylic acid N-tert-butylamide
71653-50-4

pyridine-2-carboxylic acid N-tert-butylamide

C

N-tert-butyl-2-oxo-2-pyridin-2-yl-acetamide

N-tert-butyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions
ConditionsYield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃;
Stage #2: tert-butylisonitrile In dichloromethane at -50 - 0℃; for 4h;
A 11%
B 60%
C n/a
pyridine
110-86-1

pyridine

phenyl isocyanate
1197040-29-1

phenyl isocyanate

A

2-chloropyridine
109-09-1

2-chloropyridine

B

N-phenylpicolinamide
10354-53-7

N-phenylpicolinamide

C

2-Oxo-N-phenyl-2-pyridin-2-yl-acetamide
57152-71-3

2-Oxo-N-phenyl-2-pyridin-2-yl-acetamide

Conditions
ConditionsYield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃;
Stage #2: phenyl isocyanate In dichloromethane at -50 - 0℃; for 4h;
A 24%
B 55%
C n/a
pyridine
110-86-1

pyridine

Ethyl isocyanoacetate
2999-46-4

Ethyl isocyanoacetate

A

2-chloropyridine
109-09-1

2-chloropyridine

B

N-(2-pyridinecarbonyl)-glycine ethyl ester
39484-31-6

N-(2-pyridinecarbonyl)-glycine ethyl ester

C

(2-oxo-2-pyridin-2-yl-acetylamino)-acetic acid ethyl ester

(2-oxo-2-pyridin-2-yl-acetylamino)-acetic acid ethyl ester

Conditions
ConditionsYield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃;
Stage #2: Ethyl isocyanoacetate In dichloromethane at -50 - 0℃; for 4h;
A 15%
B 46%
C n/a
pyridin-3-ylamine
462-08-8

pyridin-3-ylamine

chloroform
67-66-3

chloroform

A

pyridine
110-86-1

pyridine

B

3-Chloropyridine
626-60-8

3-Chloropyridine

C

2-chloropyridine
109-09-1

2-chloropyridine

D

pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
at 550℃;A 3%
B 24%
C 29%
D 44%
2-Pyridone
142-08-5

2-Pyridone

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With N-chloro-succinimide; triphenylphosphine In 1,4-dioxane for 4h; Heating;43%
With phosphorus pentachloride; trichlorophosphate at 130℃;
2-methoxypyridine
1628-89-3

2-methoxypyridine

2-chloropyridine
109-09-1

2-chloropyridine

Conditions
ConditionsYield
With N,N-dimethyl-formamide; trichlorophosphate at 80℃; for 2h;40%
With N,N-dimethyl-formamide; trichlorophosphate 0 deg C, 1 h; 80 deg C, 2 h;39%
pyridine
110-86-1

pyridine

Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

A

2-chloropyridine
109-09-1

2-chloropyridine

B

N-benzyl-2-pyridinecarboxamide
18904-38-6

N-benzyl-2-pyridinecarboxamide

C

N-benzyl-2-oxo-2-pyridin-2-yl-acetamide

N-benzyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions
ConditionsYield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃;
Stage #2: Benzyl isocyanide In dichloromethane at -50 - 0℃; for 4h;
A 20%
B 39%
C n/a
2-chloropyridine
109-09-1

2-chloropyridine

4-methoxy-aniline
104-94-9

4-methoxy-aniline

N-(4-methoxyphenyl)pyridin-2-amine
78644-78-7

N-(4-methoxyphenyl)pyridin-2-amine

Conditions
ConditionsYield
at 160℃; for 6h; Inert atmosphere; Neat (no solvent);100%
With palladium 10% on activated carbon; sodium t-butanolate; CyJohnPhos In tert-Amyl alcohol at 110℃; Buchwald-Hartwig amination; Inert atmosphere;73%
With sodium dispersion In tetrahydrofuran at 50℃; for 1h;65.6%
With zinc(II) chloride at 220 - 230℃;
morpholine
110-91-8

morpholine

2-chloropyridine
109-09-1

2-chloropyridine

4-(pyridin-2-yl)morpholine
24255-25-2

4-(pyridin-2-yl)morpholine

Conditions
ConditionsYield
With dichloro(3-chloropyridinyl)(1,3-(diisopropylphenyl)-4,5-bis(dimethylamino)imidazol-2-ylidene)palladium(II); caesium carbonate In 1,2-dimethoxyethane at 80℃; for 24h; Buchwald-Hartwig Coupling; Schlenk technique; Sealed tube; Inert atmosphere;100%
With tris(dibenzylideneacetone)dipalladium (0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃; for 3h;99%
With Pd-PEPPSI-IPrAn; potassium tert-butylate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere;99%
2-chloropyridine
109-09-1

2-chloropyridine

2-chloro-[6-(2)H]pyridine
395071-05-3

2-chloro-[6-(2)H]pyridine

Conditions
ConditionsYield
Stage #1: 2-chloropyridine With n-butyllithium; BuLi-LiDMAE In hexane at -78℃; for 1h; Metallation;
Stage #2: With deuteromethanol In tetrahydrofuran at -78 - 0℃; for 1h; Condensation;
100%
Stage #1: 2-chloropyridine With n-butyllithium; 2-(N,N-dimethylamino)ethanol In hexane at -78℃; for 1h;
Stage #2: With diclazuril; water-d2 In hexane at -78℃; for 0.25h; Further stages.;
65%
Stage #1: 2-chloropyridine With n-butyllithium; 2-(N,N-dimethylamino)ethanol In hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: With deuteromethanol In hexane at -78 - 0℃; for 0.666667h; Inert atmosphere; regioselective reaction;
33%
With Crabtree's catalyst; rhodium; deuterium In tetrahydrofuran; dichloromethane at 20℃; for 4h;
2-chloropyridine
109-09-1

2-chloropyridine

LiZnPh3

LiZnPh3

2-phenylpyridine
1008-89-5

2-phenylpyridine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride100%
2-chloropyridine
109-09-1

2-chloropyridine

phenylacetylene
536-74-3

phenylacetylene

2-(2-phenylethynyl)pyridine
13141-42-9

2-(2-phenylethynyl)pyridine

Conditions
ConditionsYield
With pyrrolidine; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine; 1-butyl-3-methylimidazolium Tetrafluoroborate at 100℃; for 4h; Heck alkynylation; Inert atmosphere;100%
With palladium 10% on activated carbon; potassium carbonate; XPhos In N,N-dimethyl acetamide at 110℃; for 2h; Sonogashira coupling; Inert atmosphere;99%
With piperidine; tetrabutylammomium bromide In water at 60℃; for 5h; Sonogashira coupling;96%
2-chloropyridine
109-09-1

2-chloropyridine

diphenylamine
122-39-4

diphenylamine

2-N,N-diphenylaminopyridine
50910-08-2

2-N,N-diphenylaminopyridine

Conditions
ConditionsYield
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0); P(i-BuNCH2CH2)3N In toluene at 100℃; for 20h; Buchwald-Hartwig amination;100%
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;99%
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;99%
2-chloropyridine
109-09-1

2-chloropyridine

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With C32H41N12Ni2O(3+)*3F6P(1-) In tetrahydrofuran at 25℃; for 5h; Inert atmosphere; Schlenk technique;100%
With N-heterocyclic carbene-based nickel(II) complex In tetrahydrofuran at 20℃; for 12h; Kumada reaction;99%
With chloro(1,3-bis(pyridin-2-ylmethyl)imidazolylidene)nickel(II) hexafluorophosphate In tetrahydrofuran at 20℃; for 12h; Kumada-Corriu coupling reaction; Inert atmosphere;99%
2-chloropyridine
109-09-1

2-chloropyridine

indole
120-72-9

indole

N-(2-pyridyl)indole
3419-91-8

N-(2-pyridyl)indole

Conditions
ConditionsYield
With potassium phosphate; CuI In toluene100%
2-chloropyridine
109-09-1

2-chloropyridine

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

4-fluorophenylpyridine
58861-53-3

4-fluorophenylpyridine

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane Suzuki Coupling; Inert atmosphere; Reflux;100%
With potassium phosphate tribasic trihydrate; (2-(anthracen-9-yl)-1H-inden-3-yl)dicyclohexylphosphine; palladium diacetate In water; isopropyl alcohol; toluene at 90℃; for 16h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;90%
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; tetrabutylammomium bromide; sodium hydrogencarbonate In water for 1h; Catalytic behavior; Suzuki-Miyaura Coupling; Reflux;82%
2-chloropyridine
109-09-1

2-chloropyridine

1,1-dimethoxy-1-(4-bromophenyl)methane
24856-58-4

1,1-dimethoxy-1-(4-bromophenyl)methane

2-(4-formylphenyl)pyridine
127406-56-8

2-(4-formylphenyl)pyridine

Conditions
ConditionsYield
Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 2.5h;
Stage #2: 2-chloropyridine With 1,4-di(diphenylphosphino)-butane; palladium diacetate; zinc(II) chloride In tetrahydrofuran at 70℃; for 3.5h; Conversion of starting material;
100%
Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 2.5h;
Stage #2: 2-chloropyridine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; zinc(II) chloride In tetrahydrofuran at 70℃; for 3.5h;
Stage #3: With hydrogenchloride; ammonia; water Conversion of starting material; more than 3 stages;
99.4%
Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 2.5h;
Stage #2: 2-chloropyridine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; zinc(II) chloride In tetrahydrofuran at 50℃; for 3.5h;
Stage #3: With hydrogenchloride; ammonia; water Conversion of starting material; more than 3 stages;
97%
2-chloropyridine
109-09-1

2-chloropyridine

4,4-ethylenedioxy-piperidine
177-11-7

4,4-ethylenedioxy-piperidine

(8-pyridin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane
264608-40-4

(8-pyridin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium tert-butylate In 1,2-dimethoxyethane at 20℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere;100%
With sodium carbonate In acetonitrile at 150℃; for 1.5h; Inert atmosphere;50%
2-chloropyridine
109-09-1

2-chloropyridine

1-tert-butyl-3-methyl-1H-pyrazol-5-amine
141459-53-2

1-tert-butyl-3-methyl-1H-pyrazol-5-amine

N-(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)pyridin-2-amine
1416439-41-2

N-(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)pyridin-2-amine

Conditions
ConditionsYield
Stage #1: 2-chloropyridine; 1-tert-butyl-3-methyl-1H-pyrazol-5-amine With tetrabutylammomium bromide; sodium hydroxide In water; toluene for 0.0833333h; Inert atmosphere;
Stage #2: With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In water; toluene at 87℃; for 24h; Inert atmosphere;
100%
2-chloropyridine
109-09-1

2-chloropyridine

L-proline
147-85-3

L-proline

(S)-1-(pyridin-2-yl)-pyrrolidine-2-carboxylic acid
1104077-35-1

(S)-1-(pyridin-2-yl)-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With caesium carbonate In toluene for 53h; Inert atmosphere; Reflux;100%
With caesium carbonate In toluene for 53h; Reflux;100%
2-chloropyridine
109-09-1

2-chloropyridine

4-cyanophenol
767-00-0

4-cyanophenol

4-(pyridin-2-yloxy)benzonitrile
270260-33-8

4-(pyridin-2-yloxy)benzonitrile

Conditions
ConditionsYield
With C45H65FeNO3P2PdS; caesium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Sealed tube;100%
2-chloropyridine
109-09-1

2-chloropyridine

para-bromotoluene
106-38-7

para-bromotoluene

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
Stage #1: para-bromotoluene With lithium
Stage #2: With zinc(II) chloride
Stage #3: 2-chloropyridine; nickel phosphine amido pincer complex In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70℃; for 12h; Negishi cross-coupling; Further stages.;
99.5%
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis;80%
2-aminopyridine
504-29-0

2-aminopyridine

2-chloropyridine
109-09-1

2-chloropyridine

di(pyridin-2-yl)amine
1202-34-2

di(pyridin-2-yl)amine

Conditions
ConditionsYield
With lithium amide; sodium t-butanolate In toluene at 100 - 110℃; for 1h; Buchwald-Hartwig amination; Inert atmosphere; Sealed vial;99%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 15h;94%
With potassium tert-butylate In toluene at 3120℃; for 36h; Inert atmosphere;75.5%
2-chloropyridine
109-09-1

2-chloropyridine

aniline
62-53-3

aniline

2-(phenylamino)pyridine
6631-37-4

2-(phenylamino)pyridine

Conditions
ConditionsYield
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;99%
With indium(III) chloride In acetonitrile at 120℃; for 0.5h; Microwave irradiation; regioselective reaction;98%
at 160℃; for 6h; Inert atmosphere; Neat (no solvent);95%
piperidine
110-89-4

piperidine

2-chloropyridine
109-09-1

2-chloropyridine

2-(piperidin-1-yl)pyridine
68654-52-4

2-(piperidin-1-yl)pyridine

Conditions
ConditionsYield
With (IPr)Ni(π-allyl)Cl; sodium t-butanolate In tetrahydrofuran at 25℃; for 1h; Buchwald-Hartwig reaction; Inert atmosphere;99%
With potassium tert-butylate; C50H75ClP2Pd In tetrahydrofuran at 20℃; for 6h; Schlenk technique; Inert atmosphere;99%
With potassium tert-butylate; ClPd[N,N-(2,6-iPr2C6H3)2-4,5-dihydroimidazol-2-yl](cinnamyl) In 1,2-dimethoxyethane at 20℃; for 0.0833333h; Buchwald-Hartwig cross-coupling reaction;98%
2-chloropyridine
109-09-1

2-chloropyridine

N-methylaniline
100-61-8

N-methylaniline

N-2-pyridyl-N-methylaniline
62093-17-8

N-2-pyridyl-N-methylaniline

Conditions
ConditionsYield
With sodium t-butanolate; palladium diacetate In toluene at 80℃; for 11h; Buchwald-Hartwig amination;99%
With tris-(dibenzylideneacetone)dipalladium(0); 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; sodium t-butanolate In toluene at 20 - 135℃; for 20h; Buchwald-Hartwig reaction; Inert atmosphere;99%
With [Pd(IPr*)(acac)Cl]; lithium hexamethyldisilazane In 1,4-dioxane at 20℃; for 3h; Buchwald-Hartwig cross coupling; Inert atmosphere;99%
2-chloropyridine
109-09-1

2-chloropyridine

(2-hydroxyethyl)(methyl)amine
109-83-1

(2-hydroxyethyl)(methyl)amine

2-(N-methyl-N-(pyridin-2-yl)amino)ethanol
122321-04-4

2-(N-methyl-N-(pyridin-2-yl)amino)ethanol

Conditions
ConditionsYield
for 9h; Reflux;99%
With triphenylmethyl sodium at 70℃; for 8h; Temperature;97%
at 140℃; for 0.333333h; Sealed vessel; Neat (no solvent);92%
pyrrolidine
123-75-1

pyrrolidine

2-chloropyridine
109-09-1

2-chloropyridine

2-pyrrolidinopyridine
54660-06-9

2-pyrrolidinopyridine

Conditions
ConditionsYield
With (IPr)Ni(π-allyl)Cl; sodium t-butanolate In tetrahydrofuran at 25℃; for 3h; Buchwald-Hartwig reaction; Inert atmosphere;99%
With sodium hydride; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; tert-butyl alcohol; bis(acetylacetonate)nickel(II) In tetrahydrofuran at 65℃; for 2h;95%
With [Pd(2-aminobiphenyl)(PCyp2ArXyl2)](OMs); sodium t-butanolate In tert-butyl alcohol at 80℃; for 19h; Reagent/catalyst; Inert atmosphere; Schlenk technique;93%
2-chloropyridine
109-09-1

2-chloropyridine

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylpyridine
1008-89-5

2-phenylpyridine

Conditions
ConditionsYield
With 4-di-tert-butylphosphanyl-1,5-diphenyl-1H-[1,2,3]triazole; potassium phosphate; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; for 12h; Suzuki-Miyaura coupling;99%
With 4-di-tert-butylphosphanyl-1,5-diphenyl-1H-[1,2,3]triazole; potassium phosphate; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; for 12h; Suzuki-Miyaura coupling;99%
With potassium phosphate; palladium diacetate In tetrahydrofuran at 100℃; for 24h; Suzuki-Miyaura coupling;99%
2-chloropyridine
109-09-1

2-chloropyridine

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

N-methyl-2-chloropyridinium trifluoromethanesulfonate

N-methyl-2-chloropyridinium trifluoromethanesulfonate

Conditions
ConditionsYield
In toluene at 20℃; for 1h;99%
In dichloromethane Schlenk technique; Inert atmosphere;95%
In dichloromethane at -78 - 20℃; for 16h; Methylation;94%
In dichloromethane at -78 - 23℃; for 12.1667h; Inert atmosphere;93%
In dichloromethane at 20℃; for 18h;88%
2-chloropyridine
109-09-1

2-chloropyridine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

N-benzyl-N-methyl-N-(2-pyridyl)amine
20173-75-5

N-benzyl-N-methyl-N-(2-pyridyl)amine

Conditions
ConditionsYield
With PdCl2(C3H3N2(CH3))(C3H2N2(C6H3(C3H7)2)2); potassium tert-butylate In 1,4-dioxane at 70℃; for 3h; Inert atmosphere;99%
With C36H45Cl2N3OPd; potassium tert-butylate In 1,4-dioxane at 90℃; for 1h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;99%
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4-(4-diphenylphosphinyl[2.2]paracyclophan-13-yl)morpholine; sodium t-butanolate In toluene at 110℃; for 3h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere;99%
2-chloropyridine
109-09-1

2-chloropyridine

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate In tetrahydrofuran at 100℃; for 24h; Suzuki-Miyaura coupling;99%
With potassium phosphate monohydrate; 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; palladium diacetate In 1,4-dioxane; 1,3,5-trimethyl-benzene at 135℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;98%
With 4-di-tert-butylphosphanyl-1-phenyl-5-(2,6-dimethoxyphenyl)-1H-[1,2,3]triazole; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 12h; Suzuki coupling; Inert atmosphere;97%
2-chloropyridine
109-09-1

2-chloropyridine

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2-(2-methylphenyl)pyridine
10273-89-9

2-(2-methylphenyl)pyridine

Conditions
ConditionsYield
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 16h; Suzuki-Miyaura coupling;99%
With [Pd(μ-Cl)Cl(IPr)]2; sodium methylate In ethanol at 20℃; Suzuki-Miyaura reaction;99%
With ethanol; [PdCl2(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(P(OMe)3)]; sodium hydroxide at 80℃; for 24h; Suzuki-Miyaura reaction; Inert atmosphere;99%
2-chloropyridine
109-09-1

2-chloropyridine

4-methoxyphenyl magnesium bromide
13139-86-1

4-methoxyphenyl magnesium bromide

4-(2-pyridinyl)anisole
5957-90-4

4-(2-pyridinyl)anisole

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)-imidazolium][Ni(PPh3)Cl3] In tetrahydrofuran at 30℃; for 5h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere;99%
With ((C6H4)(PPh2)(NCHPhP(O)Ph2))NiCl In diethyl ether at 25℃; for 12h; Kumada cross-coupling; Inert atmosphere;98%
Stage #1: 2-chloropyridine With Ni(PPh3)(1,3-di-tert-butylimidazol-2-ylidene)Br2 In tetrahydrofuran at 0℃; for 0.0333333h; Inert atmosphere; Schlenk technique;
Stage #2: 4-methoxyphenyl magnesium bromide In tetrahydrofuran at 0 - 25℃; for 3h; Inert atmosphere; Schlenk technique;
97%
2-chloropyridine
109-09-1

2-chloropyridine

benzophenone hydrazone
5350-57-2

benzophenone hydrazone

2-[2-(diphenylmethylene)hydrazinyl]pyridine
19848-68-1

2-[2-(diphenylmethylene)hydrazinyl]pyridine

Conditions
ConditionsYield
With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; sodium t-butanolate; palladium diacetate In 1,2-dimethoxyethane at 70℃; for 16h;99%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; palladium diacetate In toluene at 100℃; for 16h;70%
2-chloropyridine
109-09-1

2-chloropyridine

C24H20Zn(2-)*2Li(1+)

C24H20Zn(2-)*2Li(1+)

2-phenylpyridine
1008-89-5

2-phenylpyridine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride99%
2-chloropyridine
109-09-1

2-chloropyridine

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-(2-pyridinyl)anisole
5957-90-4

4-(2-pyridinyl)anisole

Conditions
ConditionsYield
With NHC-Pd(II)-Im; potassium tert-butylate In water at 80℃; for 12h; Suzuki-Miyaura coupling;99%
With potassium phosphate tribasic trihydrate; PdCl2(C3H3N2(CH3))(C3H2N2(C6H3(C3H7)2)2) In tetrahydrofuran; water at 20℃; for 24h; Suzuki-Miyaura coupling reaction; Inert atmosphere;99%
With potassium phosphate tribasic trihydrate; (2-mesityl-1H-inden-3-yl)dicyclohexyl phosphine; palladium diacetate; Aliquat 336 In water at 20 - 100℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;98%

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