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1702-17-6

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1702-17-6 Usage

Description

Clopyralid is an herbicide that selectively inhibits the growth of the broadleaf weed L. palustris over a panel of 17 New Zealand native non-broadleaf plant species when applied at a concentration of 1.5 mg/L. It does not inhibit growth of human pluripotent stem cells (IC50 = >100 μM) or decrease nuclear translocation of the transcription factor SOX17, a marker of teratogenic risk. In vivo, clopyralid induces brain defects in rabbits, but not rats, when administered at a dose of 250 mg/kg.

Chemical Properties

Different sources of media describe the Chemical Properties of 1702-17-6 differently. You can refer to the following data:
1. White Crystalline Solid
2. Odorless and colorless crystalline solid. Odorless. Available as a soluble concentrate that is usually mixed with water. Combustible

Uses

Systemic post-emergence herbicide for use in food crops and mesquite.

Definition

ChEBI: An organochlorine pesticide having a 3,6-dichlorinated picolinic acid structure.

Agricultural Uses

Herbicide: Clopyralid is used to control annual and perennial broadleaf weeds on rangeland, pastures, turf and lawns, rights-of-way and a few agricultural products such as sugar beets, oats, barley, mint and wheat.

Trade name

ACCENT?; CONFRONT?; CURTAIL?; CURTAIL M?; DOWCO?-290; HORNET?; LONTREL?; LONTREL? 3; LONTRIL? F; LONTRIL? T; MATRIGON?; MILLENNIUM?; NAF?-280; PARADIGM?; RECLAIM?; REDEEM?; RIVERDALE?; SCORPION?; STINGER?; TRANSLINE?; WIDEMATCH?; XRM-3972?

Pharmacology

Clopyralid is systemic herbicides that is actively absorbed by foliage and, is also readily absorbed through root tissues. Once absorbed, it is translocated, primarily in the phloem, throughout the entire plant. At normal field doses, this herbicide controls many broadleaf species and are selective in pasturelands and most grass crops. The exact weed spectrum and use is specific to the compound.

Potential Exposure

Clopyralid is a pyralid herbicide used to control annual and perennial broadleaf weeds on rangeland, pastures, turf, and lawns, rights-of-way and a few agricultural products such as sugarbeets, oats, barley, mint, and wheat.

Environmental Fate

Clopyralid is a relatively strong acid and water soluble, making it susceptible to leaching. Most studies, however, indicate that it is metabolized relatively quickly by soilmicrobes, significantly decreasing the amount of clopyralid that is available for this process. Clopyralid is dissociated in soil because of its low pKa, and thus, its adsorption to most soils is weak and governed by the anion exchange capacity. Soils with relatively large anion exchange capacities will bind relatively large quantities of clopyralid,making it biologically unavailable. Clopyralid is not volatile.

Metabolism

Chemical. Clopyralid is stable to hydrolytic decomposition in acidic conditions becoming unstable above pH 5. It does not undergo significant photolytic degradation. Clopyralid decomposes above its melting point. Plant. Hall and Vanden Born (29) showed that clopyralid underwent substantial metabolism in tolerant Brasica napus; i.e., 70% of applied clopyralid was metabolized 144 hours after application. Themetabolites were not fully characterized. Relatively little metabolism is thought to occur in susceptible plants. Soil. Clopyralid is readily degraded by soil microbes, e.g., the field dissipation DT50 ranges from 8 to 66 days. The major metabolic pathway in soil microbes is decarboxylation.

Shipping

UN3077 Environmentally Hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

Toxicity evaluation

Mammalian Toxicity. Limited studies have been conducted, but, from what data exist, it appears that clopyralid is quickly excreted, unmodified, in the urine of animals. The acute oral LD50 of clopyralid in male and female rat is 3738 mg/kg and 2775 mg/kg, respectively. Weed Resistance/Modified Crop Tolerance. Fuerst et al. (48) reported clopyralid resistance in yellow starthistle (Centaurea solstitialis). No crops with modified tolerance toward clopyralid are currently in production.

Incompatibilities

May react violently with strong oxidizers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders, or dust. Incompatible with silver compounds. Mixture with some silver compounds forms explosive salts of silver oxalate. Keep away from oxidizers, sulfuric acid, caustics, ammonia, aliphatic amines, alkanolamines, isocyanates, alkylene oxides, epichlorohydrin. Solutions are strong acids; corrosive to aluminum, iron, and tin. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water, and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates, and dithionites (releasing hydrogen sulfate and oxides of sulfur).

Waste Disposal

Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an Clopyralid 877 afterburner and scrubber. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.

Check Digit Verification of cas no

The CAS Registry Mumber 1702-17-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,0 and 2 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1702-17:
(6*1)+(5*7)+(4*0)+(3*2)+(2*1)+(1*7)=56
56 % 10 = 6
So 1702-17-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H4ClNO2/c7-4-2-1-3-8-5(4)6(9)10/h1-3H,(H,9,10)

1702-17-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (H27146)  3,6-Dichloropyridine-2-carboxylic acid, 96%   

  • 1702-17-6

  • 1g

  • 739.0CNY

  • Detail
  • Alfa Aesar

  • (H27146)  3,6-Dichloropyridine-2-carboxylic acid, 96%   

  • 1702-17-6

  • 5g

  • 3628.0CNY

  • Detail

1702-17-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name clopyralid

1.2 Other means of identification

Product number -
Other names 3,6-DCP

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:1702-17-6 SDS

1702-17-6Synthetic route

3,6-dichloro-2-pyridinecarbonitrile
1702-18-7

3,6-dichloro-2-pyridinecarbonitrile

Clopyralid
1702-17-6

Clopyralid

Conditions
ConditionsYield
With ethanol; sodium hydroxide Reflux;94.8%
With sodium carbonate In sulfuric acid; water86.6%
2,5 dichloropyridine
16110-09-1

2,5 dichloropyridine

carbon dioxide
124-38-9

carbon dioxide

Clopyralid
1702-17-6

Clopyralid

Conditions
ConditionsYield
Stage #1: 2,5 dichloropyridine With tert.-butyl lithium In diethyl ether; pentane at -75℃; for 2h;
Stage #2: carbon dioxide at -78℃;
58%
3,5,6-trichloro-4-hydrazinopicolinic acid
32889-74-0

3,5,6-trichloro-4-hydrazinopicolinic acid

Clopyralid
1702-17-6

Clopyralid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In dichloromethane; water
3,4,5,6-tetrachloropyridinecarboxylic acid
10469-09-7

3,4,5,6-tetrachloropyridinecarboxylic acid

Clopyralid
1702-17-6

Clopyralid

Conditions
ConditionsYield
With sodium hydroxide In water at 24.84℃; Mechanism; Electrochemical reaction;
2,3,6-trichloropyridine
6515-09-9

2,3,6-trichloropyridine

Clopyralid
1702-17-6

Clopyralid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; molybdenum(VI) oxide; dihydrogen peroxide / 80 °C
2: N,N-dimethyl-formamide / 80 - 90 °C
3: trichlorophosphate / 75 °C
4: sodium hydroxide; ethanol / Reflux
View Scheme
2,3,6-trichloropyridine-1-oxide

2,3,6-trichloropyridine-1-oxide

Clopyralid
1702-17-6

Clopyralid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 80 - 90 °C
2: trichlorophosphate / 75 °C
3: sodium hydroxide; ethanol / Reflux
View Scheme
ethanol
64-17-5

ethanol

Clopyralid
1702-17-6

Clopyralid

ethyl 3,6-dichloropyridine-2-carboxylate

ethyl 3,6-dichloropyridine-2-carboxylate

Conditions
ConditionsYield
With thionyl chloride at 0 - 90℃; for 2h;100%
With thionyl chloride at 0 - 90℃;100%
With sulfuric acid for 2h; Reflux;83.6%
Clopyralid
1702-17-6

Clopyralid

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-butyl 3,6-dichloro-2-pyridinecarboxylate
211122-64-4

tert-butyl 3,6-dichloro-2-pyridinecarboxylate

Conditions
ConditionsYield
With pyridine; p-toluenesulfonyl chloride at 0 - 20℃;98%
Stage #1: Clopyralid; tert-butyl alcohol With sulfuric acid; magnesium sulfate In dichloromethane at 20℃; for 15.3333h;
Stage #2: With sodium carbonate In dichloromethane; water at 0℃;
66%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

Clopyralid
1702-17-6

Clopyralid

potassium 3-chloro-6-(4-methylpiperazin-1-yl)pyridine-2-carboxylate
503555-19-9

potassium 3-chloro-6-(4-methylpiperazin-1-yl)pyridine-2-carboxylate

Conditions
ConditionsYield
Stage #1: 1-methyl-piperazine; Clopyralid In N,N-dimethyl acetamide at 95℃; for 72h;
Stage #2: With potassium carbonate Saturated solution;
96%
C22H37ClNO3(1+)*Br(1-)

C22H37ClNO3(1+)*Br(1-)

Clopyralid
1702-17-6

Clopyralid

C22H37ClNO3(1+)*C6H2Cl2NO2(1-)

C22H37ClNO3(1+)*C6H2Cl2NO2(1-)

Conditions
ConditionsYield
Stage #1: Clopyralid With sodium hydroxide In water Heating;
Stage #2: C22H37ClNO3(1+)*Br(1-) In water; isopropyl alcohol
96%
Clopyralid
1702-17-6

Clopyralid

dimethyl sulfate
77-78-1

dimethyl sulfate

methyl 3,6-dichloro-2-pyridinecarboxylate
1532-24-7

methyl 3,6-dichloro-2-pyridinecarboxylate

Conditions
ConditionsYield
With potassium carbonate In acetone at 40℃; for 8h;90.1%
With potassium carbonate In acetone at 20℃; for 4h;89.2%
With potassium carbonate In acetone at 40℃; for 8h;
Clopyralid
1702-17-6

Clopyralid

3,6-dichloropyridine-2-carboxylic acid chloride
16866-53-8

3,6-dichloropyridine-2-carboxylic acid chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane for 5h; Reflux;90%
With thionyl chloride; N,N-dimethyl-formamide In toluene for 2h; Reflux;
With thionyl chloride In chloroform at 0℃; for 3h; Inert atmosphere;
C23H39ClNO3(1+)*Br(1-)

C23H39ClNO3(1+)*Br(1-)

Clopyralid
1702-17-6

Clopyralid

C23H39ClNO3(1+)*C6H2Cl2NO2(1-)

C23H39ClNO3(1+)*C6H2Cl2NO2(1-)

Conditions
ConditionsYield
Stage #1: Clopyralid With sodium hydroxide In water Heating;
Stage #2: C23H39ClNO3(1+)*Br(1-) In water; isopropyl alcohol
90%
C18H15FN4O
503555-51-9

C18H15FN4O

Clopyralid
1702-17-6

Clopyralid

8-{[(3,6-dichloropyridin-2-yl)carbonyl]amino}-1-(4-fluorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide
1204588-05-5

8-{[(3,6-dichloropyridin-2-yl)carbonyl]amino}-1-(4-fluorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

Conditions
ConditionsYield
With triethylamine; HATU In N,N-dimethyl-formamide at 20℃;89%
methanol
67-56-1

methanol

Clopyralid
1702-17-6

Clopyralid

3-chloro-6-methoxypyridine-2-carboxylic acid
856836-44-7

3-chloro-6-methoxypyridine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: methanol With sodium at 25℃; for 1h;
Stage #2: Clopyralid at 100℃; for 36h;
87.14%
4-(2-(2-pyridinyloxy)ethoxy)benzaldehyde oxime

4-(2-(2-pyridinyloxy)ethoxy)benzaldehyde oxime

Clopyralid
1702-17-6

Clopyralid

4-(2-(2-pyridinyloxy)ethoxy)benzaldehyde-O-((3,6-dichloro-2-pyridinyl)carbonyl)oxime

4-(2-(2-pyridinyloxy)ethoxy)benzaldehyde-O-((3,6-dichloro-2-pyridinyl)carbonyl)oxime

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 10h;87%
sodium methylate
124-41-4

sodium methylate

Clopyralid
1702-17-6

Clopyralid

3-chloro-6-methoxypyridine-2-carboxylic acid
856836-44-7

3-chloro-6-methoxypyridine-2-carboxylic acid

Conditions
ConditionsYield
In methanol at 100℃; for 20h; Sealed tube; regioselective reaction;84%
In 1,4-dioxane; methanol at 85℃; for 14h;
Clopyralid
1702-17-6

Clopyralid

ethanethiol
75-08-1

ethanethiol

S-ethyl 3,6-dichloropyridine-2-thiocarboxylate

S-ethyl 3,6-dichloropyridine-2-thiocarboxylate

Conditions
ConditionsYield
Stage #1: Clopyralid With thionyl chloride; N,N-dimethyl-formamide In toluene at 110℃; for 2h;
Stage #2: ethanethiol at 20℃; for 1h;
81%
Stage #1: Clopyralid With thionyl chloride In N,N-dimethyl-formamide; toluene at 80℃; for 1h; Inert atmosphere;
Stage #2: ethanethiol In toluene at 0 - 50℃; for 1.25h; Inert atmosphere;
61.49 g
Stage #1: Clopyralid With thionyl chloride In N,N-dimethyl-formamide; toluene at 80℃; for 2h; Inert atmosphere;
Stage #2: ethanethiol In N,N-dimethyl-formamide; toluene at 20 - 60℃; for 1.25h; Inert atmosphere;
C19H16N4O3
503554-60-7

C19H16N4O3

Clopyralid
1702-17-6

Clopyralid

1-(1,3-benzodioxol-5-yl)-8-{[(3,6-dichloropyridin-2-yl)carbonyl]amino}-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide
503555-17-7

1-(1,3-benzodioxol-5-yl)-8-{[(3,6-dichloropyridin-2-yl)carbonyl]amino}-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

Conditions
ConditionsYield
With triethylamine; HATU In N,N-dimethyl-formamide at 20℃;80%
(2-aminophenyl)diphenylphosphane oxide
23081-74-5

(2-aminophenyl)diphenylphosphane oxide

Clopyralid
1702-17-6

Clopyralid

3,6-dichloro-N-[2-(diphenylphosphoryl)phenyl]pyridine-2-carboxamide
1439353-39-5

3,6-dichloro-N-[2-(diphenylphosphoryl)phenyl]pyridine-2-carboxamide

Conditions
ConditionsYield
With thionyl chloride; triethylamine79%
Clopyralid

Clopyralid

3,6-bis(n-hexylthio)-2-pyridinecarboxylic acid

3,6-bis(n-hexylthio)-2-pyridinecarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In water; dimethyl sulfoxide68%
With sodium hydroxide In water; dimethyl sulfoxide68%
Clopyralid
1702-17-6

Clopyralid

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

3,6-bis-methylthiopyridine-2-carboxylic acid
85330-61-6

3,6-bis-methylthiopyridine-2-carboxylic acid

Conditions
ConditionsYield
In dimethyl sulfoxide at 130 - 135℃; for 2h;65%
4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Clopyralid
1702-17-6

Clopyralid

3,6-dichloro-N-(4-methyl-thiazole-2-yl)-2-pyridine carboxamide

3,6-dichloro-N-(4-methyl-thiazole-2-yl)-2-pyridine carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 24h;64%
Clopyralid
1702-17-6

Clopyralid

(2-aminophenyl)diphenylphosphine sulfide

(2-aminophenyl)diphenylphosphine sulfide

3,6-dichloro-N-[2-(diphenylthiophosphoryl)phenyl]pyridine-2-carboxamide
1439353-43-1

3,6-dichloro-N-[2-(diphenylthiophosphoryl)phenyl]pyridine-2-carboxamide

Conditions
ConditionsYield
With thionyl chloride; triethylamine63%
europium(III) chloride hexahydrate

europium(III) chloride hexahydrate

Clopyralid
1702-17-6

Clopyralid

Eu(3,5-dichloropicolinate)3*3H2O

Eu(3,5-dichloropicolinate)3*3H2O

Conditions
ConditionsYield
With NaOH In ethanol soln. of ligand in EtOH added dropwise to soln. of EuCl3*6H2O in EtOH under stirring, heated at 60°C for 24 h, pH adjusted to 6 by aq. soln. of NaOH; filtered, washed with EtOH, dried in vac. for 48 h; elem. anal.;60%
morpholine
110-91-8

morpholine

Clopyralid
1702-17-6

Clopyralid

3-chloro-6-(morpholin-4-yl)-2-pyridinecarboxylic acid hydrochloride

3-chloro-6-(morpholin-4-yl)-2-pyridinecarboxylic acid hydrochloride

Conditions
ConditionsYield
Stage #1: morpholine; Clopyralid In N,N-dimethyl acetamide at 80℃;
Stage #2: In diethyl ether; water pH=2;
53%
Clopyralid
1702-17-6

Clopyralid

bis(3,6-dichloropicolinato) cobalt(II)
118963-43-2

bis(3,6-dichloropicolinato) cobalt(II)

Conditions
ConditionsYield
In ethanol; water addn. of ethanolic soln. of acid to water soln. of Co salt, stirred, 70-100°C (color change); cooled; pptn.; filtered; washed (acetone, water); dried; elem. anal.;50%
copper diacetate
142-71-2

copper diacetate

Clopyralid
1702-17-6

Clopyralid

bis(3,6-dichloropicolinato)copper(II)

bis(3,6-dichloropicolinato)copper(II)

Conditions
ConditionsYield
In methanol; water addn. of methanolic 3,6-dichloropicolinic acid to aq. Cu(OAc)2 (stirring, 70°C), pptn.; collection (filtn.), washing (acetone, water), drying; elem. anal.;50%
Clopyralid
1702-17-6

Clopyralid

benzene
71-43-2

benzene

3,6-dichloro-2-phenylpyridine
84333-73-3

3,6-dichloro-2-phenylpyridine

Conditions
ConditionsYield
With dipotassium peroxodisulfate; silver sulfate In acetonitrile at 120℃; for 24h; Glovebox; Schlenk technique; Sealed tube; Inert atmosphere;50%
Clopyralid
1702-17-6

Clopyralid

phenol
108-95-2

phenol

3,6-dichloro-2-pyridinecarboxylic acid phenyl ester
324028-93-5

3,6-dichloro-2-pyridinecarboxylic acid phenyl ester

Conditions
ConditionsYield
With sodium bicarbonate; triethylamine; N,N-dimethyl-formamide In thionyl chloride; dichloromethane; water46.7%
2,2'-bipyridinedichlorocopper(II)
220632-01-9, 22393-36-8

2,2'-bipyridinedichlorocopper(II)

Clopyralid
1702-17-6

Clopyralid

bis(3,6-dichloropicolinato)(α,α'-dipyridyl)copper(II)

bis(3,6-dichloropicolinato)(α,α'-dipyridyl)copper(II)

Conditions
ConditionsYield
In ethanol; water addn. of ethanolic 3,6-dichloropicolinic acid to aq. Cu-complex (stirring, 80°C), pptn.; collection (filtn.), washing (alcohol, water, acetone), drying; elem. anal.;40%
Clopyralid
1702-17-6

Clopyralid

N-methyl-1,2-phenylenediamine
4760-34-3

N-methyl-1,2-phenylenediamine

2-(3,6-dichloropyridin-2-yl)-1-methyl-1H-benzimidazole
1269771-40-5

2-(3,6-dichloropyridin-2-yl)-1-methyl-1H-benzimidazole

Conditions
ConditionsYield
With triphenyl phosphite In pyridine at 160℃; for 0.5h; Irradiation;37%
tryptophan ethyl ester hydrochloride salt

tryptophan ethyl ester hydrochloride salt

Clopyralid
1702-17-6

Clopyralid

(3,6-dichloropicolinoyl)-L-tryptophan

(3,6-dichloropicolinoyl)-L-tryptophan

Conditions
ConditionsYield
Stage #1: Clopyralid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 0.166667h;
Stage #2: tryptophan ethyl ester hydrochloride salt With triethylamine In N,N-dimethyl-formamide at 20℃;
Stage #3: With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; for 12h;
30%
Clopyralid
1702-17-6

Clopyralid

sodium thioethylate
811-51-8

sodium thioethylate

3,6-bis-ethylthio-2-pyridinecarboxylic acid
85331-31-3

3,6-bis-ethylthio-2-pyridinecarboxylic acid

Conditions
ConditionsYield
In dimethyl sulfoxide at 130℃; for 6h;273 g

1702-17-6Relevant articles and documents

In situ FTIR studies on the electrochemical hydrodechlorination of 3,4,5,6-tetrachloropicolinic acid on Ag cathode

Ma, Chun An,Li, Mei Chao,Liu, Yan Na,Xu, Ying Hua

, p. 3171 - 3174 (2010)

The electrochemical hydrodechlorination reaction from starting material 3,4,5,6-tetrachloropicolinic acid (3,4,5,6-TCP) to the end product 3,6-dichloropicolinic acid (3,6-DCP) was investigated by cyclic voltammetry and in situ Fourier transform infrared spectroscopy (in situ FTIR). Compared with copper and glassy carbon, Ag cathode showed a high electrocatalytic activity for the irreversible reduction process of 3,4,5,6-TCP in NaOH aqueous solution. In situ FTIR results suggested that electrochemical hydrodechlorination took place in the 4- or 5-position of 3,4,5,6-TCP on Ag cathode after receiving an electron to get mixed trichloropicolinic acid free radical, which could receive another electron and give 3,5,6-trichloropicolinic acid (3,5,6-TCP) and 3,4,6-trichloropicolinic acid (3,4,6-TCP) at the potential more positive than -1000 mV afterwards. Finally, 3,5,6-TCP and 3,4,6-TCP were further dechlorinated to produce 3,6-dichloropicolinic acid (3,6-DCP) at the potential more negative than -1000 mV. Further studies of preparative electrolysis experiments by constant current electrolysis were carried out. The results were in good agreement with those from in situ FTIR investigations.

Preparation method of 3,6-dichloro-2-pyridinecarboxylic acid

-

, (2017/08/25)

The invention discloses a preparation method of 3,6-dichloro-2-pyridinecarboxylic acid. The preparation method comprises following steps: 2,3,6-trichloropyridine is dissolved in acetic acid, a catalyst is added, an obtained mixture is heated, hydrogen peroxide is added dropwise for oxidation, after reaction, the catalyst is removed via filtering, and concentration desolvation is carried out so as to obtain a 2,3,6-trichloropyridine oxynitride; the 2,3,6-trichloropyridine oxynitride is dissolved in solvent DMF, sodium cyanide is added, an obtained mixed material is heated for cyanation, after cyanation, rotary evaporateion desolvation is carried out, and a 2-cyano-3,6-trichloropyridine oxynitride is obtained via ethyl alcohol recrystallization; the 2-cyano-3,6-trichloropyridine oxynitride is mixed with phosphorus trichloride, an obtained product is heated for deoxygenation, after deoxygenation, desolvation is carried out, a left product is added into ice-water mixture so as to obtain a solid material via precipitation, and 2-cyano-3,6-dichloropyridine is obtained via filtering; the 2-cyano-3,6-dichloropyridine is added into an ethyl alcohol-sodium hydroxide solution for hydrolysis reaction, after hydrolysis reaction, system pH value is adjusted to 2 to 3, and the finished product 3,6-dichloro-2-pyridinecarboxylic acid is obtained via desolvation crystallization. The total yield of the preparation method is high, and generation of a large amount of salt-bearing wastewater in conventional route is avoided.

Strategies for the selective functionalization of dichloropyridines at various sites

Marzi, Elena,Bigi, Anna,Schlosser, Manfred

, p. 1371 - 1376 (2007/10/03)

Whereas 2,3-dichloropyridine and 2,5-dichloro-4-(lithiooxy)-pyridine undergo deprotonation exclusively at the 4- and 2-positions, respectively, optional site selectivity can be implemented with 2,5- and 3,4-dichloropyridine (which are attacked, depending on the choice of the reagents, at either the 4- or 6- and either the 2- and 5-positions, respectively). Upon treatment with lithium diisopropylamide, 2,4-dichloro-3-iodopyridine, 3,5-dichloro-4-bromopyridine and 2,6-dichloro-3-iodopyridine afford 5-, 2- and 4-lithiated intermediates, but the latter isomerize instantaneously to species in which lithium and iodine have swapped places, the driving force being the low basicity of C-Li bonds when flanked by two neighboring halogens.

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