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5326-23-8

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5326-23-8 Usage

Chemical Properties

Off-white to beige crystalline powder

Uses

Different sources of media describe the Uses of 5326-23-8 differently. You can refer to the following data:
1. 6-Chloronicotinic acid is used as building block for different chemical synthesis. Product Data Sheet
2. 6-Chloropyridine-3-carboxylic acid (6-chloronicotinic acid/6-CNA) has been used to study its photolytic and photocatalytic degradation. The product has been used as a media component during the isolation of 6-CNA degrading bacterial strain from imidacloprid-exposed soil samples.
3. 6-Chloropyridine-3-carboxylic acid (6-chloronicotinic acid/6-CNA) has been used to study its photolytic and photocatalytic degradation. 6-CNA is a degradation product of neonicotinoid insecticides imidacloprid and acetamiprid and is known to appear in different environmental matrices. The product has been used as a media component during the isolation of 6-CNA degrading bacterial strain from imidacloprid-exposed soil samples.

General Description

6-Chloropyridine-3-carboxylic acid is a metabolite of the neonicotinoid pesticides, imidacloprid and acetamiprid and occurs in different environmental matrices.(3) It is widely used in agricultural crop protection, domestic insect control and environmental pest management.

Purification Methods

Purify it by recrystallisation from hot H2O and sublime it in a vacuum. [Pechmann & Welsch Chem Ber 17 2384 1884, Herz & Murty J Org Chem 26 122 1961, Beilstein 22/2 V 177.]

Check Digit Verification of cas no

The CAS Registry Mumber 5326-23-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,2 and 6 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5326-23:
(6*5)+(5*3)+(4*2)+(3*6)+(2*2)+(1*3)=78
78 % 10 = 8
So 5326-23-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H4ClNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3H,(H,9,10)/p-1

5326-23-8 Well-known Company Product Price

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  • Alfa Aesar

  • (A15620)  6-Chloronicotinic acid, 99%   

  • 5326-23-8

  • 5g

  • 225.0CNY

  • Detail
  • Alfa Aesar

  • (A15620)  6-Chloronicotinic acid, 99%   

  • 5326-23-8

  • 25g

  • 743.0CNY

  • Detail
  • Alfa Aesar

  • (A15620)  6-Chloronicotinic acid, 99%   

  • 5326-23-8

  • 100g

  • 2494.0CNY

  • Detail
  • Sigma-Aldrich

  • (68678)  6-Chloropyridine-3-carboxylicacid  analytical standard

  • 5326-23-8

  • 68678-100MG

  • 450.45CNY

  • Detail
  • Aldrich

  • (156353)  6-Chloropyridine-3-carboxylicacid  99%

  • 5326-23-8

  • 156353-5G

  • 452.79CNY

  • Detail
  • Aldrich

  • (156353)  6-Chloropyridine-3-carboxylicacid  99%

  • 5326-23-8

  • 156353-25G

  • 1,503.45CNY

  • Detail
  • Aldrich

  • (156353)  6-Chloropyridine-3-carboxylicacid  99%

  • 5326-23-8

  • 156353-100G

  • 4,924.53CNY

  • Detail

5326-23-8SDS

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 6-Chloronicotinic acid

1.2 Other means of identification

Product number -
Other names 6-chloropyridine-3-carboxylic acid

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:5326-23-8 SDS

5326-23-8Synthetic route

6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride pH=2; pH-value;98%
With phosphorus pentachloride; trichlorophosphate at 120 - 130℃;
2-chloro-5-(Trichloromethyl)-pyridine
69045-78-9

2-chloro-5-(Trichloromethyl)-pyridine

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
In sulfuric acid94%
With sulfuric acid; lithium acetate; water; silver; fluorosulphonic acid; acetic acid In methanol at 30 - 35℃; Solvent; Temperature; Electrolysis;84%
2-chloro-5-methylpyridine
18368-64-4

2-chloro-5-methylpyridine

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate In chlorobenzene at 80℃; for 4h; Temperature;79.7%
With potassium permanganate In water for 5h; Heating;60.1%
2-choro-5-iodopyridine
69045-79-0

2-choro-5-iodopyridine

H2O*CHLiO2

H2O*CHLiO2

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
With formic acid; 1,3-bis-(diphenylphosphino)propane; nickel(II) acetate tetrahydrate; acetic anhydride In tetrahydrofuran at 100℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;60%
Ac2 O

Ac2 O

dichloromethane
75-09-2

dichloromethane

triethylamine
121-44-8

triethylamine

A

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

B

2-hydroxy-5-pyridine carboxylic acid (6-hydroxynicotinic acid)

2-hydroxy-5-pyridine carboxylic acid (6-hydroxynicotinic acid)

Conditions
ConditionsYield
With sodium hydroxideA n/a
B 54.2%
A n/a
B 53.8%
A n/a
B 40.8%
6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
at 120 - 130℃; eintragen des Reaktionsprodukts in Eiswasser;
3-(1-methylpyrrolidin-2-yl)-6-chloropyridine
112091-17-5

3-(1-methylpyrrolidin-2-yl)-6-chloropyridine

permanganate solution

permanganate solution

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
(+-)-Py 6-chloro-nicotine;
1-(6-chloronicotinyl)-2-nitroiminoimidazoline
105827-78-9

1-(6-chloronicotinyl)-2-nitroiminoimidazoline

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
With potassium permanganate In ethanol for 0.333333h; Oxidation; reflux;
nicotinic acid
59-67-6

nicotinic acid

phenyl-β-pyridyl ketone

phenyl-β-pyridyl ketone

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / 30percent H2O2 / acetic acid / 3 h / 90 °C
2: PCl5, POCl3
View Scheme
2-nitro-5-methylpyridine
1074-38-0

2-nitro-5-methylpyridine

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KMnO4; H2O
2: aqueous HCl
View Scheme
6-chloro-3-pyridinecarboxylic acid ethyl ester
49608-01-7

6-chloro-3-pyridinecarboxylic acid ethyl ester

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran
1-(6-chloronicotinyl)-2-nitroiminoimidazoline
105827-78-9

1-(6-chloronicotinyl)-2-nitroiminoimidazoline

A

2-pyrrolidinon
616-45-5

2-pyrrolidinon

B

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

C

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

6-chloro-3-pyridinecarboxamide

D

6-chloronicotinylaldehyde
23100-12-1

6-chloronicotinylaldehyde

E

n-Amyl nitrite
463-04-7

n-Amyl nitrite

F

1-nitroisobutane
625-74-1

1-nitroisobutane

G

1-[(6-chloro-3-pyridinyl)-methyl]-imidazolidin-2-one
120868-66-8

1-[(6-chloro-3-pyridinyl)-methyl]-imidazolidin-2-one

Conditions
ConditionsYield
With phosphotungstic acid supported on mesoporous sieve MCM-41 In water for 14h; Irradiation;
acetamiprid
135410-20-7

acetamiprid

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Conditions
ConditionsYield
With Er doped Ti/SnO2-Sb electrode for 3h; Kinetics; Electrochemical reaction;
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

6-iodo-nicotinic acid
13054-02-9

6-iodo-nicotinic acid

Conditions
ConditionsYield
With sodium iodide In butanone at 110℃; for 12h; Inert atmosphere;100%
With hydrogen iodide; sodium iodide for 24h; Heating;45%
With butanone; potassium iodide
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

6-Chloronicotinoyl chloride
58757-38-3

6-Chloronicotinoyl chloride

Conditions
ConditionsYield
With thionyl chloride at 90℃; Inert atmosphere;100%
With oxalyl dichloride at 63℃; for 20h;98%
With phosphorus pentachloride; trichlorophosphate for 4h; Heating;95%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

methyl 2-amino-3-phenylpropanoate hydrochloride
5619-07-8

methyl 2-amino-3-phenylpropanoate hydrochloride

2-[(6-chloropyridine-3-carbonyl)amino]-3-phenylpropionic acid methyl ester

2-[(6-chloropyridine-3-carbonyl)amino]-3-phenylpropionic acid methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Stirring overnight;100%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

5-(azetidin-1-ylcarbonyl)-2-chloropyridine
720693-14-1

5-(azetidin-1-ylcarbonyl)-2-chloropyridine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; Inert atmosphere;100%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

1-(piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea

1-(piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea

1-(1-(6-chloronicotinoyl)piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea
1246188-56-6

1-(1-(6-chloronicotinoyl)piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;100%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

6-chloronicotinic acid trimethylsilyl ester
1233246-15-5

6-chloronicotinic acid trimethylsilyl ester

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane at 78℃; for 3h; Inert atmosphere;100%
4-((5S,9R)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro-[4.4]nonan-9-yl)benzonitrile
509083-73-2

4-((5S,9R)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro-[4.4]nonan-9-yl)benzonitrile

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

BMS-688521
893397-44-9

BMS-688521

Conditions
ConditionsYield
Stage #1: 6-Chloro-3-pyridinecarboxylic acid With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE for 3h; Heating / reflux;
Stage #2: 4-((5S,9R)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro-[4.4]nonan-9-yl)benzonitrile In ISOPROPYLAMIDE at 95℃; for 30h;
Stage #3: With water In ISOPROPYLAMIDE at 0℃; Product distribution / selectivity;
98%
With N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE at 110℃; for 30h; Product distribution / selectivity;54%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

6-chloro-N-(4-methoxy-benzyl)-nicotinamide
805303-96-2

6-chloro-N-(4-methoxy-benzyl)-nicotinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;97%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 2-chloro-5-pyridinecarboxylate
115309-57-4

tert-butyl 2-chloro-5-pyridinecarboxylate

Conditions
ConditionsYield
With dmap In tetrahydrofuran for 4.5h; Reflux;97%
Stage #1: 6-Chloro-3-pyridinecarboxylic acid With dmap In tetrahydrofuran for 3h; Reflux;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran for 3h; Reflux;
94%
With dmap In tetrahydrofuran at 62.5℃; for 5.6h; Product distribution / selectivity;
With dmap In tetrahydrofuran at 62.5℃; Large scale reaction;
With dmap In tetrahydrofuran at 70℃; for 1h; Large scale;
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

tert-butylamine
75-64-9

tert-butylamine

N-tert-butyl-6-chloro-nicotinamide
115309-58-5

N-tert-butyl-6-chloro-nicotinamide

Conditions
ConditionsYield
Stage #1: 6-Chloro-3-pyridinecarboxylic acid With thionyl chloride
Stage #2: tert-butylamine
97%
Stage #1: 6-Chloro-3-pyridinecarboxylic acid With thionyl chloride for 2h; Heating;
Stage #2: tert-butylamine In dichloromethane at 20℃; for 20h; Further stages.;
88%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

3-fluorophenylboronic acid
768-35-4

3-fluorophenylboronic acid

6-(3-fluorophenyl)-3-pyridinecarboxylic acid
582325-22-2

6-(3-fluorophenyl)-3-pyridinecarboxylic acid

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In water; toluene for 20h; Product distribution / selectivity; Heating / reflux;97%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 90℃; Product distribution / selectivity;
Stage #1: 6-Chloro-3-pyridinecarboxylic acid; 3-fluorophenylboronic acid With tetrabutylammomium bromide; potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 20h; Reflux;
Stage #2: With hydrogenchloride In water; toluene pH=3;
quinolin-7-ylamine
580-19-8

quinolin-7-ylamine

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

C15H10ClN3O
582325-21-1

C15H10ClN3O

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;97%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

oxalyl dichloride
79-37-8

oxalyl dichloride

2-chloro-1-(6-chloropyridin-3-yl)ethanone
136592-00-2

2-chloro-1-(6-chloropyridin-3-yl)ethanone

Conditions
ConditionsYield
Stage #1: 6-Chloro-3-pyridinecarboxylic acid; oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide for 2.5h;
Stage #2: With diazomethyl-trimethyl-silane In dichloromethane; N,N-dimethyl-formamide for 2h;
97%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

6-hydrazinylnicotinic acid
133081-24-0

6-hydrazinylnicotinic acid

Conditions
ConditionsYield
With hydrazine hydrate at 100℃; for 4h; Inert atmosphere;96%
With hydrazine hydrate In ethanol Reflux;91%
With hydrazine hydrate In water for 6h; Heating;90%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

6-chloro-N-methoxy-N-methylpyridine-3-carboxamide
149281-42-5

6-chloro-N-methoxy-N-methylpyridine-3-carboxamide

Conditions
ConditionsYield
96%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20 - 60℃;93%
Stage #1: 6-Chloro-3-pyridinecarboxylic acid With oxalyl dichloride In tetrahydrofuran at 20℃; for 1h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 20℃; for 1h;
73.8%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

6-Chloronicotinic acid methyl ester
73781-91-6

6-Chloronicotinic acid methyl ester

Conditions
ConditionsYield
95%
In tetrahydrofuran
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

6-Chloronicotinic acid methyl ester
73781-91-6

6-Chloronicotinic acid methyl ester

Conditions
ConditionsYield
In methanol; diethyl ether; toluene at 0℃; for 0.75h; Inert atmosphere;95%
In methanol; diethyl ether; toluene at 0℃; for 0.5h; Inert atmosphere;95%
In methanol
In methanol; diethyl ether; toluene at 20℃; for 0.5h;
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

6-chloronicotinic acid 1-oxide
90327-03-0

6-chloronicotinic acid 1-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 45℃; for 24h;93%
With dihydrogen peroxide; trifluoroacetic acid at 0 - 45℃;64%
With dihydrogen peroxide; trifluoroacetic acid
Multi-step reaction with 3 steps
1.1: diethyl ether; toluene; methanol / 0.75 h / 0 °C / Inert atmosphere
2.1: dihydrogen peroxide; methyltrioxorhenium(VII) / water; ethanol / 24 h / 20 °C
3.1: sodium hydroxide / methanol / 1 h / Reflux
3.2: 0 °C / pH 4-5
View Scheme
Multi-step reaction with 3 steps
1: diethyl ether; toluene; methanol / 0.5 h / 0 °C / Inert atmosphere
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 20 °C
3: potassium hydroxide; water / 3 h / 100 °C
View Scheme
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

6-chloronicotinic acid chloride hydrochloride

6-chloronicotinic acid chloride hydrochloride

Conditions
ConditionsYield
With thionyl chloride for 2h; Heating / reflux;93%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

4-bromo-aniline
106-40-1

4-bromo-aniline

N-(4-bromophenyl)-6-chloronicotinamide
1002796-95-3

N-(4-bromophenyl)-6-chloronicotinamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux;93%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

6-chloro-3-pyridinecarboxylic acid ethyl ester
49608-01-7

6-chloro-3-pyridinecarboxylic acid ethyl ester

Conditions
ConditionsYield
In toluene92.3%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

tert–butyl (2–aminophenyl)carbamate
146651-75-4

tert–butyl (2–aminophenyl)carbamate

t-butyl (2-(6-chloronicotinamido)phenyl)carbamate
623588-14-7

t-butyl (2-(6-chloronicotinamido)phenyl)carbamate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 18h;92%
With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In acetonitrile at 20℃;
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

cyclohexanol
108-93-0

cyclohexanol

6-(cyclohexyloxy)pyridine-3-carboxylic acid

6-(cyclohexyloxy)pyridine-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 6-Chloro-3-pyridinecarboxylic acid; cyclohexanol With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 4h; Heating / reflux;
Stage #2: With acetic acid In DMF (N,N-dimethyl-formamide); water pH=5;
92%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 130℃; Inert atmosphere;76%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

6,6-difluoro-5-methyl-5-hexenol
509101-24-0

6,6-difluoro-5-methyl-5-hexenol

6,6-difluoro-5-methyl-5-hexenyl 6-chloronicotinate

6,6-difluoro-5-methyl-5-hexenyl 6-chloronicotinate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h;92%
4-(2-AMINOETHYL)MORPHOLINE
2038-03-1

4-(2-AMINOETHYL)MORPHOLINE

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

6-chloro-N-(2-morpholinoethyl)nicotinamide
446269-58-5

6-chloro-N-(2-morpholinoethyl)nicotinamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux;92%
methanol
67-56-1

methanol

6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

6-Chloronicotinic acid methyl ester
73781-91-6

6-Chloronicotinic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid at 0 - 60℃;91%
Stage #1: 6-Chloro-3-pyridinecarboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide at 20℃; for 16h;
Stage #2: methanol In dichloromethane at 40℃; for 0.25h;
91%
With sulfuric acid for 8h; Reflux; Large scale;84.6%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

C12H11BrN4O3

C12H11BrN4O3

1-(4-bromophenyl)-2-(2-methyl-4-nitro-1H-imidazol-1-yl)ethanone-(6-chloronicotinoyl)oxime

1-(4-bromophenyl)-2-(2-methyl-4-nitro-1H-imidazol-1-yl)ethanone-(6-chloronicotinoyl)oxime

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;91%
6-Chloro-3-pyridinecarboxylic acid
5326-23-8

6-Chloro-3-pyridinecarboxylic acid

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

6-aminopyridine-3-carboxylic acid
165901-22-4

6-aminopyridine-3-carboxylic acid

Conditions
ConditionsYield
With acetic acid for 24h; Heating;90%

5326-23-8Relevant articles and documents

Synthesis and Herbicidal Activity of (Z)-Ethoxyethyl 2-Cyano-3-(2-methylthio-5-pyridylmethylamino)acrylates

Wang, Qing Min,Sun, Hui Kai,Huang, Run Qiu

, p. 67 - 70 (2004)

2-Methylthio-5-pyridinemethylene amine was prepared from 2-chloro-5-methylpyridine. Ethoxyethyl 2-cyano-3,3-dimethylthioacrylate was prepared from ethoxyethyl cyanoacetate, carbon disulfide, and dimethyl sulfate in 86.2% yield. Its reaction with 2-methylthio-5-pyridinemethylene amine yielded (Z)-ethoxyethyl 2-cyano-3-methylthio-3-(2-methylthio-5-pyridylmethylamino)acrylate. Ethoxyethyl (Z+E)-2-cyano-3-ethoxyacrylate was synthesized from ethoxyethyl 2-cyanoacetate and triethyl orthoacetate in 90.7% yield, and its reaction with 2-methylthio-5-pyridinemethylene amine yielded (Z)-ethoxyethyl 2-cyano-3-methyl-3-(2-methylthio-5-pyridylmethylamino)acrylate. The structures of all of the products were confirmed by 1H NMR, elemental analysis, IR, and mass spectroscopy. The herbicidal activities of the products were evaluated, and the results of bioassay showed that (Z)-ethoxyethyl 2-cyano-3-methyl-3-(2-methylthio-5-pyridylmethylamino) acrylate exhibits good herbicidal activity on rape (Brassica napus) at a dose of 1.5 kg/ha.

Nickel-catalyzed carboxylation of aryl iodides with lithium formate through catalytic CO recycling

Fu, Ming-Chen,Fu, Yao,Shang, Rui,Wu, Ya-Nan

supporting information, p. 4067 - 4069 (2020/04/20)

A protocol for the Ni-catalyzed carboxylation of aryl iodides with formate has been developed with good functional group compatibility for the synthesis of a variety of aromatic carboxylic acids under mild conditions. The reaction tolerates other functionalities for cross-coupling, such as aryl bromide, aryl chloride, aryl tosylate, and aryl pinacol boronate. The reaction proceeds through a carbonylation process with in situ generated carbon monoxide in the presence of a catalytic amount of acetic anhydride and lithium formate, avoiding the use of gaseous CO. The strategy of CO recycling in catalytic amounts is critical for the success of the reaction.

Method for preparing aldehyde and acid by electrochemical dehydrochlorination of polychloromethylpyridine derivatives

-

Paragraph 0035-0037; 0044-0046; 0053-0056, (2020/08/27)

The invention discloses a method for preparing aldehyde and an acid by electrochemical dechlorination of a polychloromethylpyridine derivative, the method comprises the following steps: dissolving thepolychloromethylpyridine derivative in an acetic acid and acetate- containing buffer solution to obtain an electrolytic reaction solution; taking the electrolytic reaction solution as a cathode liquid, performing electrolytic reduction dechlorination reaction at a cathode, and hydrolyzing in the solution to obtain a polychlorinated pyridylaldehyde or acid derivative. The polychloromethylpyridinederivative is shown in formula (I), and the product polychlorinated pyridylaldehyde or acid derivative is shown in formula (II): in the formula (I), m is 0, 1, 2, 3 or 4, n is 0 or 1, and R' is an easy-to-oxidize or easy-to-hydrolyze substituent. The m and the R' in the formula (II) are same as that in the formula (I), R is H or OH, no waste acid is generated in the preparation process, the easy-to-oxidize or easy-to-hydrolyze substituent contained in the polychloromethylpyridine derivative and carbon-chlorine bonds on pyridine rings are not affected, and the recovery conversion rate is high.

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