4068-62-6

Basic information

• Product Name: 3-Chloro-5-fluorosalicylic acid
• Synonyms: 3-Chloro-5-fluorosalicylic acid;3-chloro-5-fluoro-2-hydroxy-;BENZOIC ACID, 3-CHLORO-5-FLUORO-2-HYDROXY
• CAS NO: 4068-62-6
• Molecular Formula: C₇H₄ClFO₃
• Molecular Weight: 190.56
• Product Categories: API intermediates
• Mol File: 4068-62-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 298.8°C at 760 mmHg
• Flash Point: 134.5°C
• Appearance: /
• Density: 1.634g/cm³
• Vapor Pressure: 0.000555mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: 3-Chloro-5-fluorosalicylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-5-fluorosalicylic acid(4068-62-6)
• EPA Substance Registry System: 3-Chloro-5-fluorosalicylic acid(4068-62-6)

Safety Data

• Hazardous Substances Data: 4068-62-6(Hazardous Substances Data)

Usage

General Description

3-Chloro-5-fluorosalicylic acid is a chemical compound with the molecular formula C7H4ClFO3. It is a derivative of salicylic acid and contains both chlorine and fluorine atoms. 3-Chloro-5-fluorosalicylic acid is often used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It can also be used as a reagent in organic chemical reactions. 3-Chloro-5-fluorosalicylic acid exhibits strong acidic properties, making it a useful building block in the production of various compounds for industrial and research purposes.

InChI:InChI=1/C7H4ClFO3/c8-5-2-3(9)1-4(6(5)10)7(11)12/h1-2,10H,(H,11,12)

Upstream product

• 345-16-4 5-fluoro-2-hydroxybenzoic acid 

Relevant articles and documents

Salicylate activity. 3. Structure relationship to systemic acquired resistance

Salicylic acid (2-hydroxybenzoic acid; SA) is a primary signal inducing plant defenses against pathogens. This plant disease resistance, known as systemic acquired resistance (SAR), is an attractive target for the development of new plant protection agents. SAR induction is a multistep process that includes accumulation of pathogenesis-related (PR) proteins. The structure-activity profile of salicylates and related compounds has been evaluated using an inducible PR protein (PR-1a) and plant resistance to tobacco mosaic virus (TMV) as markers. Among the 47 selected monosubstituted and multiple-substituted salicylate derivatives tested, all 8 derivatives that induced more PR-1a protein than SA were fluorinated or chlorinated in the 3- and/or 5-position (3,5-difluorosalicylate > 3-chlorosalicylate > 5-chlorosalicylate > 3,5-dichlorosalicylate > 3-chloro-5-fluorosalicylate > 3-fluorosalicylate > 3-fluoro-5-chlorosalicylate > 3,5-dichloro-6-hydroxysalicylate > SA). In general, substitutions for or on the 2-hydroxyl group or at the 4-position of the ring reduced or eliminated PR-1a protein induction. In contrast, substitutions in positions ortho (3-position) or para (5-position) to the hydroxyl group with electron-withdrawing groups other than chlorine or fluorine decreased induction, and electron-donating groups in these positions also had a deleterious effect on PR-1a induction. PR-1a protein accumulation and reduction in TMV lesion diameter exhibited a log-linear relationship. The seven salicylate derivatives that were the most active TMV resistance inducers were all halogenated in the 3- and/or 5-position (3-chlorosalicylate > 3,5-difluorosalicylate > 3,5-dichloro-6-hydroxysalicylate > 3,5,6-trichlorosalicylate > 5-chlorosalicylate > 5-fluorosalicylate > 3,5-dichlorosalicylate > 4-fluorosalicylate > 3-fluorosalicylate > 3-chloro-5-fluorosalicylate > 4-chlorosalicylate > SA). The correlation between PR-1a protein induction and resistance to TMV confirms the value of using PR-1a induction as a screening tool for developing new plant disease control agents.