Product Name

  • Name

    Clopyralid

  • EINECS 216-935-4
  • CAS No. 1702-17-6
  • Article Data13
  • CAS DataBase
  • Density 1.612 g/cm3
  • Solubility 1.0 g/L in water
  • Melting Point 151-152 °C
  • Formula C6H3Cl2NO2
  • Boiling Point 323.718 °C at 760 mmHg
  • Molecular Weight 192.001
  • Flash Point 149.579 °C
  • Transport Information UN 3077
  • Appearance white crystalline solid
  • Safety 26-30-61-39
  • Risk Codes 41-51/53
  • Molecular Structure Molecular Structure of 1702-17-6 (Clopyralid)
  • Hazard Symbols IrritantXi,DangerousN
  • Synonyms Picolinicacid, 3,6-dichloro- (7CI,8CI);3,6-Dichloro-2-pyridinecarboxylic acid;3,6-Dichloropicolinic acid;Cirtoxin;Dichloro pyridine acid;Dowco 290;IWD 3523;Lontrel;Lontrel 100;Lontrel 300;Lontrel L;Matrigon;Transline;Versatill;
  • PSA 50.19000
  • LogP 2.08660

Synthetic 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%
cobalt(II) acetate
71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7

cobalt(II) acetate

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

Clopyralid Specification

The 3,6-Dichloro-2-pyridinecarboxylic acid, with the CAS registry number 1702-17-6, is also known as . It belongs to the product categories of Pharmacetical; rganic acids; Agro Products; Herbicide; Agro-Products; Heterocycles; Alphabetic; Analytical Standards. Its EINECS registry number is 216-935-4. Its IUPAC name is called 3,6-dichloropyridine-2-carboxylic acid. This chemcial is white crystalline solid which can be used as systemic post-emergence herbicide for use in food crops and mesquite. In addition, its classification codes are Agricultural Chemical; Herbicide; Reproductive Effect.

Physical properties of 3,6-Dichloro-2-pyridinecarboxylic acid: (1)ACD/LogP: 1.59; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 3; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.606; (11)Molar Refractivity: 41.064 cm3; (12)Molar Volume: 119.088 cm3; (13)Surface Tension: 62.834 dyne/cm; (14)Density: 1.612 g/cm3; (15)Melting Point: 151-152 °C; (16)Flash Point: 149.579 °C; (17)Enthalpy of Vaporization: 59.716 kJ/mol; (18)Boiling Point: 323.718 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,5-dichloro-pyridine and carbon dioxide. This reaction will need reagent tert-butyllithium and solvent pentane, diethyl ether. The reaction time is 2 hours with reaction temperature of -75--78 ℃. The yield is about 58%.

Uses of 3,6-Dichloro-2-pyridinecarboxylic acid: it can be used to produce 3,6-bis-methylsulfanyl-pyridine-2-carboxylic acid at temperature of 130-135 °C. This reaction will need solvent dimethylsulfoxide with reaction time of 2 hours. The yield is about 65%.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes and may present an immediate or delayed danger to one or more components of the environment. There will be a risk of serious damage to eyes when you will contact it. It is toxic to aquatic organisms which may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should never add water to this product. Whenever you will contact it, please wear eye/face protection. You should avoid releasing it to the environment. When you will use it, please refer to special instructions/safety data sheet.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC(=NC(=C1Cl)C(=O)O)Cl
(2)InChI: InChI=1S/C6H3Cl2NO2/c7-3-1-2-4(8)9-5(3)6(10)11/h1-2H,(H,10,11)
(3)InChIKey: HUBANNPOLNYSAD-UHFFFAOYSA-N

The toxicity data is as follows:
 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
duck LD50 oral 1465mg/kg (1465mg/kg)   Pesticide Manual. Vol. 9, Pg. 182, 1991.
mouse LD50 oral > 5gm/kg (5000mg/kg)   Defense des Vegetaux. Vol. 31, Pg. 387, 1977.
rabbit LD50 skin > 2gm/kg (2000mg/kg)   Defense des Vegetaux. Vol. 31, Pg. 387, 1977.
rat LD50 intraperitoneal 900mg/kg (900mg/kg)   Defense des Vegetaux. Vol. 31, Pg. 387, 1977.
rat LD50 oral 4300mg/kg (4300mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A433, Pg. 1985,

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