ChemicalBook >> CAS DataBase List >>2,6-Dichloroisonicotinic acid

2,6-Dichloroisonicotinic acid

CAS No.
5398-44-7
Chemical Name:
2,6-Dichloroisonicotinic acid
Synonyms
2,6-DICHLOROPYRIDINE-4-CARBOXYLIC ACID;CGA-41396;BUTTPARK 43\57-46;AKOS BBS-00006615;RARECHEM AL BO 0824;TIMTEC-BB SBB003621;2,6-dichloroisonicotinicaci;2,6-DICHLOROISONICOTINIC ACID;Dichloropyridinecarboxylicacid;2,6-DichloroisonicotinicAcid>
CBNumber:
CB6110923
Molecular Formula:
C6H3Cl2NO2
Molecular Weight:
192
MDL Number:
MFCD00234147
MOL File:
5398-44-7.mol
MSDS File:
SDS
Last updated:2024-03-06 09:46:37

2,6-Dichloroisonicotinic acid Properties

Melting point 209-212 °C(lit.)
Boiling point 437.8±40.0 °C(Predicted)
Density 1.612±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility soluble in Methanol
form powder to crystal
pka 2.63±0.10(Predicted)
color White to Brown
Water Solubility insoluble
InChI InChI=1S/C6H3Cl2NO2/c7-4-1-3(6(10)11)2-5(8)9-4/h1-2H,(H,10,11)
InChIKey SQSYNRCXIZHKAI-UHFFFAOYSA-N
SMILES C1(Cl)=NC(Cl)=CC(C(O)=O)=C1
CAS DataBase Reference 5398-44-7(CAS DataBase Reference)
NIST Chemistry Reference 4-Pyridinecarboxylic acid, 2,6-dichloro-(5398-44-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36-37/39
WGK Germany  3
HazardClass  IRRITANT
HS Code  29333990
NFPA 704
1
2 0

2,6-Dichloroisonicotinic acid price More Price(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 456543 2,6-Dichloropyridine-4-carboxylic acid 98% 5398-44-7 1g $14.56 2024-03-01 Buy
Sigma-Aldrich 456543 2,6-Dichloropyridine-4-carboxylic acid 98% 5398-44-7 5g $133 2024-03-01 Buy
TCI Chemical D3345 2,6-Dichloroisonicotinic Acid >98.0%(GC)(T) 5398-44-7 1g $29 2024-03-01 Buy
TCI Chemical D3345 2,6-Dichloroisonicotinic Acid >98.0%(GC)(T) 5398-44-7 5g $82 2024-03-01 Buy
Alfa Aesar B20541 2,6-Dichloropyridine-4-carboxylic acid, 98% 5398-44-7 5g $121.65 2024-03-01 Buy
Product number Packaging Price Buy
456543 1g $14.56 Buy
456543 5g $133 Buy
D3345 1g $29 Buy
D3345 5g $82 Buy
B20541 5g $121.65 Buy

2,6-Dichloroisonicotinic acid Chemical Properties,Uses,Production

Chemical Properties

off-white to beige or light brownish powder

Uses

2,6-Dichloroisonicotinic acid is a derivative of isonicotinic acid (I821760). Treatment of oat cultivars using 2,6-dichloroisonicotinic acid results in an increased accumulation of avenathramide. 2,6-Dichloroisonicotinic acid is a well known inducer of plant resistance and induces the transcription of ZmNAC100 transcription factor.

Definition

ChEBI: A member of the class of pyridines that is isonicotinic acid which is substituted by chlorine at positions 2 and 6.

Agricultural Uses

The best characterized synthetic inducer of resistance, 2,6-dichloroisonicotinic acid and its methyl ester (both are referred to as INA) were the first synthetic compounds reported to activate a phenocopy of bonafide systemic acquired resistance (SAR). 2,6-dichloroisonicotinic acid was used as an abiotic resistance inducer against bacterial spot disease of tomato caused by Xanthomonas perforans. INA was found to protect cucumber, tobacco, arabidopsis, sugar beet, bean, rose, barley, and rice from several pathogens[1].

Mode of action

In tobacco, salicylic acid (SA) and 2,6-dichloroisonicotinic acid (INA) induce the same nine classes of genes (including the PR genes) that are expressed systemically after tobacco mosaic virus (TMV) infection. In contrast to many other abiotic inducers of PR gene expression and enhanced disease resistance, such as polyacrylic acid and thiamine, INA does not stimulate the accumulation of SA or its glucoside in treated tobacco plants. The strong correlation between biological activity and the ability to bind and inhibit catalase suggests that the physiological effects of INA, SA, and their active analogs are mediated by the same mechanism of action: inhibition of catalase's ability to degrade H202[2].

References

[1] S. Chandrashekar, S. Umesha. “2,6-Dichloroisonicotinic acid enhances the expression of defense genes in tomato seedlings against Xanthomonas perforans.” Physiological and Molecular Plant Pathology 86 (2014): Pages 49-56.
[2] Uwe Conrath. “Two inducers of plant defense responses, 2,6-dichloroisonicotinec acid and salicylic acid, inhibit catalase activity in tobacco.” Proceedings of the National Academy of Sciences of the United States of America 92 16 1 (1995): 7143–7.

99-11-6
5398-44-7
Synthesis of 2,6-Dichloroisonicotinic acid from Citrazinic acid
Global( 349)Suppliers
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Enki Biopharmaceuticals (Shanghai) Limited
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View Lastest Price from 2,6-Dichloroisonicotinic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2,6-Dichloroisonicotinic acid pictures 2024-05-13 2,6-Dichloroisonicotinic acid
5398-44-7
US $0.00-0.00 / kg 5kg 99.0% 1000 Enki Biopharmaceuticals (Shanghai) Limited
2,6-Dichloroisonicotinic acid  pictures 2021-10-26 2,6-Dichloroisonicotinic acid
5398-44-7
US $1.10 / g 1g 99.00% 100 Tons Min Dideu Industries Group Limited
2,6-Dichloroisonicotinic acid pictures 2019-07-12 2,6-Dichloroisonicotinic acid
5398-44-7
US $1.00 / KG 1KG 99% 1ton Career Henan Chemical Co
2,6-Dichloroisonicotinic acid ,98% CGA-41396 2,6-Dichloropyridine-4-carboxylic acid,2,6-Dichloroisonicotinic acid 2,6-Dichloropyridine-4-carboxylic acid, 4-Carboxy-2,6-dichloropyridine 2,6-Dichloropyridine-4-carboxylic acid 98% 2,6-Dichloropyrdine-4-carboxylic acid 4-Pyridinecarboxylic acid, 2,6-dichloro- BUTTPARK 43\57-46 2,6-DICHLOROISONICOTINIC ACID 2,6-DICHLORO-4-PYRIDINECARBOXYLIC ACID 2,6-DICHLORO-4-PYRIDINYL CARBOXYLIC ACID RARECHEM AL BO 0824 TIMTEC-BB SBB003621 AKOS BBS-00006615 Pyridine-4-carboxilic acid, 2, 6-dichloro- Pyridine-4-carboxylic acid, 2,6-dichloro- Dichloropyridinecarboxylicacid 2,6-DichloroisonicotinicAcid> 2,6-Dichloroisonicotinic acid (2,6-Dichloropyridine-4-carboxylic acid) 2,6-dichloroisonicotinicaci 2,6-Dichloroisonicotinic acid ISO 9001:2015 REACH 2,6-DICHLOROPYRIDINE-4-CARBOXYLIC ACID 5398-44-7 C6H3Cl2NO2 Building Blocks Heterocyclic Building Blocks Halogenated Heterocycles Pyridines Halopyridines Chloropyridines Intermediate of Irinotecan Pyridines Pyridine Chloropyridines Halopyridines Carboxylic Acids pharmacetical Carboxylic Acids