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Clopyralid

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Name

Clopyralid

EINECS 216-935-4
CAS No. 1702-17-6 Density 1.612 g/cm3
PSA 50.19000 LogP 2.08660
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;

Article Data 13

Clopyralid Synthetic route

1702-18-7

3,6-dichloro-2-pyridinecarbonitrile

1702-17-6

Clopyralid

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

2,5 dichloropyridine

124-38-9

carbon dioxide

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%
32889-74-0

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

1702-17-6

Clopyralid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In dichloromethane; water
10469-09-7

3,4,5,6-tetrachloropyridinecarboxylic acid

1702-17-6

Clopyralid

Conditions
ConditionsYield
With sodium hydroxide In water at 24.84℃; Mechanism; Electrochemical reaction;
6515-09-9

2,3,6-trichloropyridine

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

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
64-17-5

ethanol

1702-17-6

Clopyralid

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%
1702-17-6

Clopyralid

75-65-0

tert-butyl alcohol

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%
109-01-3

1-methyl-piperazine

1702-17-6

Clopyralid

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-)

1702-17-6

Clopyralid

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 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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