AMINOPYRALID Chemical Properties

Melting point:

>166°C (dec.)

Boiling point:

432.0±45.0 °C(Predicted)

Density 

1.705

vapor pressure 

0Pa at 25℃

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

2.22±0.25(Predicted)

color 

Off-White to Light Pink

Water Solubility 

2.48g/L at 18℃

BRN 

12065018

Stability:

Hygroscopic

InChI

InChI=1S/C6H4Cl2N2O2/c7-3-1-2(9)4(8)5(10-3)6(11)12/h1H,(H2,9,10)(H,11,12)

InChIKey

NIXXQNOQHKNPEJ-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC(Cl)=CC(N)=C1Cl

LogP

0.201 at 19℃

EPA Substance Registry System

Aminopyralid (150114-71-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

Hazardous Substances Data

150114-71-9(Hazardous Substances Data)

AMINOPYRALID Usage And Synthesis

Uses

Aminopyralid

Definition

ChEBI: An organochlorine pesticide having a 3,6-dichlorinated 4-aminopicolinic acid structure.

Flammability and Explosibility

Non flammable

Agricultural Uses

Herbicide: A systemic, post-emergence herbicide for industrial vegetation and pastures. Used to control woody plants, clovers, and thistles. This herbicide is absorbed by roots and leaves. Not listed for use in EU countries.

Trade name

BANISH®; FOREFRONT®; HALCYON®; MILESTONE® VM; PHARAOH®; PRO-BANISH®; RUNWAY®; SYNERO®; UPFRONT®

Synthesis

General procedure for the synthesis of 4-amino-3,6-dichloropyridine-2-carboxylic acid from 4-amino-3,5,6-trichloropyridine-2-carboxylic acid: 50.8 g of 4-amino-3,5,6-trichloropyridine-2-carboxylic acid was mixed with 500 ml of water, and 66.7 g of 30% sodium hydroxide solution was added homogeneously, and then after filtration the filtrate was transferred to a 1000 ml high-pressure reactor fitted with a magnetic stirrer, a thermometer, and an exhaust pipe. After filtration, the filtrate was transferred to a 1000-mL high-pressure reactor equipped with a magnetic stirrer, thermometer and exhaust pipe. 2 g of 5% Pd/C catalyst was added to the reactor, the reactor was sealed, replaced with nitrogen three times, and then filled with hydrogen to a pressure of 0.2 MPa. Stirring was initiated and the temperature was raised to 50°C, and the pressure was further increased to 0.3 MPa by filling with hydrogen, and the reaction was confirmed to be complete by HPLC after 20 hours, and then cooled down to room temperature. The reaction solution was decanted out, filtered to recover the catalyst, and the filtrate was adjusted to pH 1-2 with 30% hydrochloric acid, cooled to crystallize and centrifuged, and the precipitate was washed with hot water to obtain 38.8 g of 4-amino-3,6-dichloro-pyridine-2-carboxylic acid, with the product purity of 97.5% and the yield of 91.4%.

References

[1] Patent: CN105461622, 2016, A. Location in patent: Paragraph 0024-0027
[2] Patent: WO2008/42429, 2008, A1. Location in patent: Page/Page column 9-10
[3] Patent: WO2008/42429, 2008, A1. Location in patent: Page/Page column 10-11; 11-12

AMINOPYRALID(150114-71-9)Related Product Information

• AMINOPYRALID
• PENTYL 4-AMINO-3,5,6-TRICHLOROPYRIDINE-2-CARBOXYLATE
• ETHYL 3,5,6-TRICHLORO-4-[(4-FLUOROPHENYL)AMINO]PYRIDINE-2-CARBOXYLATE
• Picloram
• 4,5-DIAMINO-3,6-DICHLORO-2-PICOLINIC ACID
• ISOBUTYL 4-AMINO-3,5,6-TRICHLOROPYRIDINE-2-CARBOXYLATE
• PICLORAM METHYL ESTER
• RARECHEM AL BO 1991
• 2-Pyridinecarboxylic acid, 4-amino-3,5,6-trichloro-, isooctyl ester
• 3,5,6-TRICHLORO-4-HYDRAZINO-PYRIDINE-2-CARBOXYLIC ACID
• 2-Pyridinecarboxylic acid, 4-amino-3,6-dichloro-, monopotassium salt
• TORDON101R
• Aminopyralid-13C3-15N