76578-79-5

Basic information

• Product Name: 6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE
• Synonyms: 6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE;4-(6-Chloroquinoxalin-2-yloxy)phenol;4-[(6-chloro-2-quinoxalinyl)oxy]Phenol
• CAS NO: 76578-79-5
• Molecular Formula: C₁₄H₉ClN₂O₂
• Molecular Weight: 272.68646
• Product Categories: Miscellaneous
• Mol File: 76578-79-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 459.952 °C at 760 mmHg
• Flash Point: 231.971 °C
• Appearance: /
• Density: 1.428 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.696
• CAS DataBase Reference: 6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE(76578-79-5)
• EPA Substance Registry System: 6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE(76578-79-5)

Safety Data

• Hazardous Substances Data: 76578-79-5(Hazardous Substances Data)

Usage

General Description

6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE is a chemical compound with the molecular formula C15H9ClN2O2. It is a quinoxaline derivative with a chlorine atom and a hydroxyphenyl group attached to the quinoxaline ring. 6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE has potential pharmacological activities and has been studied for its potential use in treating various diseases, including cancer and infectious diseases. Its structure and properties make it a valuable compound for medicinal chemistry research and drug development.

InChI:InChI=1/C14H9ClN2O2/c15-9-1-6-12-13(7-9)16-8-14(17-12)19-11-4-2-10(18)3-5-11/h1-8,18H

Synthetic route

2,6-dichloroquinoxaline (18671-97-1) + hydroquinone (123-31-9) → 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5)

Conditions	Yield
Stage #1: hydroquinone With sodium hydroxide In toluene at 85℃; for 0.5h; Inert atmosphere; Stage #2: 2,6-dichloroquinoxaline In toluene at 100℃; for 7h; Temperature; Inert atmosphere;	93.5%
Stage #1: hydroquinone With sodium hydroxide In toluene at 85℃; for 0.5h; Inert atmosphere; Stage #2: 2,6-dichloroquinoxaline In toluene at 100℃; for 7h; Temperature; Inert atmosphere;	93.5%
With potassium carbonate 1.) DMF, 100 deg C, 1 h, 2.) DMF, 120 deg C, 3 h; Yield given. Multistep reaction;

2,6-dichloroquinoxaline (18671-97-1) → 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5)

Conditions	Yield
With potassium hydroxide; hydroquinone In water	92%

2,6-dichloroquinoxaline (18671-97-1) + phenol (108-95-2) → 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5)

Conditions	Yield
Yield given. Multistep reaction;

ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate (57057-80-4) + 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) → (R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester (76578-14-8)

Conditions	Yield
With potassium carbonate In methyl cyclohexane for 3h; Solvent; Inert atmosphere; Reflux;	95.9%
In toluene for 5h; Solvent; Reflux;	92.9%
With potassium carbonate In cyclohexane for 18h; Heating / reflux;	91%

(+)-ethyl 2-chloropropionate (74497-15-7) + 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) → (R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester (76578-14-8)

Conditions	Yield
With tetrabutylammomium bromide; triethylamine In toluene at 60℃; for 4h; Solvent; Temperature; Reflux;	95.1%

ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate (57057-80-4) + 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) → quizalofop-p (94051-08-8)

Conditions	Yield
In toluene for 5h; Reflux;	92.9%

ethyl (S)-α-(4-methyl-phenylsulphonyloxy)-propionate (33798-77-5) + 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) → quizalofop ethyl

Conditions	Yield
Stage #1: 6-chloro-2-(4-hydroxyphenoxy)quinoxaline With potassium carbonate; toluene-4-sulfonic acid Inert atmosphere; Stage #2: ethyl (S)-α-(4-methyl-phenylsulphonyloxy)-propionate for 11h; Time; Reflux;	91.9%
With potassium carbonate In toluene for 11h; Inert atmosphere; Reflux;	91.9%

dichloromethane (75-09-2) + 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) + cyanomethyl bromide (590-17-0) → 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}acetonitrile

Conditions	Yield
With potassium carbonate In acetonitrile	80%

6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) → (R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester (76578-14-8)

Conditions	Yield
With potassium carbonate In acetonitrile for 5h; Heating / reflux;	66%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80 - 90℃; for 4h;	63%
With potassium carbonate In butanone for 5h; Heating / reflux;	59%

2-thiophenylmethyl 2-bromopropanoate + 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) → 2-thiophenylmethyl 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propanoate + 2-thiophenylmethyl 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxyl]propanoate

Conditions	Yield
With potassium carbonate	A 65.3% B n/a

ethyl (S)-2-{[(prop-2-yn-1-ylthio)carbonothioyl]oxy}propanoate + 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) → (R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester (76578-14-8)

Conditions	Yield
In benzonitrile at 130℃; Inert atmosphere; enantioselective reaction;	35%

1,4,7,10,13-pentaoxycyclopentadecane + L-2-[(isopropylideneamino)oxy]ethyl-2-[(p-toluenesulphonyl)oxy]propionate + 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) → 2-[(isopropylideneamino)oxy]ethyl D-2-[p-[(6-chloro-2-quinoxalinyl)oxy]-phenoxy]propionate

Conditions	Yield
In N-methyl-acetamide; hexane; water; mineral oil

(-)-lactic acid [[(isopropylideneamino)-oxy]methyl]ester + 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) + diethylazodicarboxylate (1972-28-7) → [(isopropylideneamino)oxy]methyl D-1-[p-[(6-chloro-2-quinoxalinyl)-oxy]-phenoxy]propionate

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; water

2-chloro-N-(2-fluorophenyl)acetamide (347-66-0) + 6-chloro-2-(4-hydroxyphenoxy)quinoxaline (76578-79-5) → 2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]-N-(2-fluorophenyl)acetamide

Conditions	Yield
With potassium carbonate In butanone

Upstream product

• 18671-97-1 2,6-dichloroquinoxaline 
• 123-31-9 hydroquinone 
• 108-95-2 phenol 

Downstream Products

• 111479-05-1 2-[(isopropylideneamino)oxy]ethyl D-2-[p-[(6-chloro-2-quinoxalinyl)oxy]-phenoxy]propionate 
• 94051-08-8 quizalofop-p 
• 76578-14-8 (R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester 
• 100646-51-3 quizalofop ethyl 

Relevant articles and documents

Nucleophilic Substitution in 6-Chloro-2-(2-cyano-phenoxy)quinoxalines and Antibacterial Activity of Phenoxychloroquinoxaline Derivatives

Abstract: Ullmann reaction of 2-[(6-chloroquinoxalin-2-yl)oxy]benzonitrile with 4-tert-butylphenol unexpect-edly afforded 2-(4-tert-butylphenoxy)-6-chloroquinoxaline instead of the corresponding 6-substituted deriva-tive. Different phenols were used to check the nucleofugality of 2-cyanophenoxy group in the 2-position of quinoxalines, so that 2-cyanophenoxy group can be regarded as an alternative to halogens for nucleophilic substitution. A series of new substituted 6-chloro-2-phenoxyquinoxaline derivatives were synthesized from 4-[(6-chloroquinoxalin-2-yl)oxy]phenol and different heteroaryl and sulfonyl chlorides. The synthesized com-pounds were characterized by IR, 1H and 13C NMR and mass spectra and evaluated for their antibacterial activity.

A method for producing quizalofop-P-ethyl environment-friendly process (by machine translation)

The present invention relates to a method for producing quizalofop-P-ethyl environment-friendly process, characterized in that the first hydroquinone with sodium hydroxide reaction to prepare the sodium salt of hydroquinone, with 2, 6 - dichloro quinozaline reaction, to obtain 4 - (6 - chloro - 2 kuikui oh linlin oxygen radical) phenol, then with paratoluene sulfonic acid ethyl lactate reaction to obtain the quizalofop-P-ethyl, herbicide then the grease of the alkaline hydrolysis, acidification, recovery 6 - chloro - 2 - hydroxy-quinoxaline. The synthesis process is advantageous in that the organic solvent in the reaction and post-processing, the system reduces the response of the alkaline, avoids the strong alkaline aqueous phase reactions the drawback of easy to produce impurities, reduces the raw material 2, 6 - dichloro quinozaline hydrolysis, so that the 4 - (6 - chloro - 2 kuikui oh linlin oxygen radical) to the phenol content of 98% or more, the yield of 92% or more, the recovery of the herbicide of the grease in the 6 - chloro - 2 - hydroxy-quinoxaline, not only reduces the discharge capacity of the solid waste, the protection of the environment, reduces the quizalofop-P-ethyl intermediate cost. (by machine translation)

4-quinoxalinyloxyphenoxyalkylinitrile herbicides

Herbicidal methods utilizing compounds having the structure STR1 wherein: n is 0, 1, 2, or 3; R is H or alkyl; and R1 is halogen, nitro, methyl, halomethyl, methoxy, halomethoxy or ethoxy are disclosed which control the growth of undesirable weeds but are substantially innocuous to corn. Herbicidal compositions comprising the compounds and a carrier are also disclosed.