88349-88-6

Basic information

• Product Name: Cloquintocet
• Synonyms: Cloquintocet PESTANAL;5-chloro-8-quinolinoxyacetic acid;cloquintocet (free acid);Herbicide Safener Cloquintocet;(5-Chloro-8-quinolyloxy)acetic acid;Cloquintocet;[(5-Chloro-8-quinolinyl)oxy]acetic acid;Cloquintocet [iso]
• CAS NO: 88349-88-6
• Molecular Formula: C11H8ClNO3
• Molecular Weight: 237.64
• Mol File: 88349-88-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 435 °C at 760 mmHg
• Flash Point: 216.9 °C
• Appearance: off-white to light yellow crystalline powder
• Density: 1.450
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.653
• PKA: 2.87±0.40(Predicted)
• CAS DataBase Reference: Cloquintocet(CAS DataBase Reference)
• NIST Chemistry Reference: Cloquintocet(88349-88-6)
• EPA Substance Registry System: Cloquintocet(88349-88-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 88349-88-6(Hazardous Substances Data)

Usage

Uses

Cloquintocet is a herbicidal composition that contains Pinoxaden(P469505).

InChI:InChI=1/C11H8ClNO3/c12-8-3-4-9(16-6-10(14)15)11-7(8)2-1-5-13-11/h1-5H,6H2,(H,14,15)

Upstream product

• 99607-70-2 cloquintocet-mexyl 
• 130-16-5 5-Chloro-8-hydroxyquinoline 
• 79-11-8 chloroacetic acid 
• 88349-90-0 ethyl ((5-chloroquinolin-8-yl)oxy)acetate 

Downstream Products

• 1346981-39-2 C₂₃H₁₆ClN₃O₃S 
• 1346981-41-6 C₂₄H₁₈ClN₃O₃S 
• 1346981-47-2 C₂₅H₁₈ClN₃O₃ 

Relevant articles and documents

Process Development for the Crop Safener Cloquintocet Acid

A practical one-pot process was developed for (5-chloroquinolin-8-yloxy)acetic acid (CQC acid), known commercially as cloquintocet, a crop safener that is added to various herbicide formulations to reduce crop damage. The process consists of (1) conversion of 5-chloro-8-hydroxyquinoline (5-ChQ) to its corresponding sodium salt 5-ChQ-Na with 50 wt % NaOH in dimethyl sulfoxide (DMSO), (2) alkylation of 5-ChQ-Na with methyl 2-chloroacetate to generate CQC methyl ester (CQC-Me) after removal of water by distillation under reduced pressure, and (3) hydrolysis of CQC-Me with a catalytic amount of 0.1 N HCl (0.5 mol %) or 0.1 N H2SO4 (0.25 mol %) to afford CQC acid in >90% yield with >98% purity. All of the steps were carried out in one pot with only one isolation. Recovery and reuse of DMSO were also demonstrated. Each step/stage of the process was subjected to reactive chemical evaluation by differential scanning calorimetry and/or accelerating rate calorimetry for identification of potential safety hazards.

PROCESS FOR THE PREPARATION OF A QUINOLINE CARBOXYLIC ACID

The invention provides a process for the preparation of a carboxylic acid of formula (IV) (which is useful as a safener for herbicides): wherein R1 is hydrogen or chlorine, comprising the steps of: (i) subjecting a compound of formula (V) wherein: R1 is as defmed above; and R2 is C1-C18 alkyl; C1-C6 alkoxyC1-C8 alkyl-; optionally substituted phenyl; or optionally substituted benzyl; to hydrolysis under acidic conditions to give a solution of a quinolinium salt; and (ii) addingbase to the solution obtained in step (i) to give the free carboxylic acid (IV). The invention also provides a solid (e.g. particulate) form of one quinoline carboxylic acid compound within formula (IV) defmed by R1 being chlorine;and novel intermediates useable in the above process.

Synthesis and antimicrobial activities of novel 8-(1-alkyl//alkylsulphonyl/ alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinolines

The synthesis of a series of novel 8-(1-alkyl/alkylsulphonyl/ alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinoline derivatives is reported. These derivatives were prepared by the condensation of o-phenylenediamine with [(5-chloroquinolin-8-yl)oxy]ac