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6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE is a quinoxaline derivative with the molecular formula C15H9ClN2O2. It features a chlorine atom and a hydroxyphenyl group attached to the quinoxaline ring, which endows it with potential pharmacological activities. 6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE has been the subject of research for its possible applications in treating a range of diseases, such as cancer and infectious diseases. Its unique structure and properties make it a significant candidate for medicinal chemistry research and drug development.

76578-79-5

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76578-79-5 Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE is used as a pharmaceutical agent for its potential therapeutic effects on various diseases. Its specific application reason is due to its pharmacological activities, which are currently under investigation for efficacy in treating conditions such as cancer and infectious diseases.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE is utilized as a research compound to explore its structure-activity relationships and optimize its properties for drug development. The reason for its use in this context is to understand how its unique chemical structure contributes to its potential medicinal properties and to improve upon these for more effective treatments.
Used in Drug Development:
6-CHLORO-2-[(4-HYDROXYPHENYL)OXY]QUINOXALINE is also used in drug development as a lead compound. The application reason is to leverage its pharmacological potential and chemical properties to create new drugs that can address unmet medical needs, particularly in the areas of cancer treatment and infectious disease management.

Check Digit Verification of cas no

The CAS Registry Mumber 76578-79-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,6,5,7 and 8 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 76578-79:
(7*7)+(6*6)+(5*5)+(4*7)+(3*8)+(2*7)+(1*9)=185
185 % 10 = 5
So 76578-79-5 is a valid CAS Registry Number.
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

76578-79-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(6-chloroquinoxalin-2-yl)oxyphenol

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:76578-79-5 SDS

76578-79-5Synthetic route

2,6-dichloroquinoxaline
18671-97-1

2,6-dichloroquinoxaline

hydroquinone
123-31-9

hydroquinone

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

Conditions
ConditionsYield
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

2,6-dichloroquinoxaline

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

Conditions
ConditionsYield
With potassium hydroxide; hydroquinone In water92%
2,6-dichloroquinoxaline
18671-97-1

2,6-dichloroquinoxaline

phenol
108-95-2

phenol

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

Conditions
ConditionsYield
Yield given. Multistep reaction;
ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate
57057-80-4

ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

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

(R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester

Conditions
ConditionsYield
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

(+)-ethyl 2-chloropropionate

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

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

(R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester

Conditions
ConditionsYield
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

ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

quizalofop-p
94051-08-8

quizalofop-p

Conditions
ConditionsYield
In toluene for 5h; Reflux;92.9%
ethyl (S)-α-(4-methyl-phenylsulphonyloxy)-propionate
33798-77-5

ethyl (S)-α-(4-methyl-phenylsulphonyloxy)-propionate

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

quizalofop ethyl

quizalofop ethyl

Conditions
ConditionsYield
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

dichloromethane

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

cyanomethyl bromide
590-17-0

cyanomethyl bromide

2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}acetonitrile

2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}acetonitrile

Conditions
ConditionsYield
With potassium carbonate In acetonitrile80%
6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

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

(R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester

Conditions
ConditionsYield
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

2-thiophenylmethyl 2-bromopropanoate

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

A

2-thiophenylmethyl 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propanoate

2-thiophenylmethyl 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propanoate

B

2-thiophenylmethyl 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxyl]propanoate

2-thiophenylmethyl 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxyl]propanoate

Conditions
ConditionsYield
With potassium carbonateA 65.3%
B n/a
ethyl (S)-2-{[(prop-2-yn-1-ylthio)carbonothioyl]oxy}propanoate

ethyl (S)-2-{[(prop-2-yn-1-ylthio)carbonothioyl]oxy}propanoate

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

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

(R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester

Conditions
ConditionsYield
In benzonitrile at 130℃; Inert atmosphere; enantioselective reaction;35%
1,4,7,10,13-pentaoxycyclopentadecane

1,4,7,10,13-pentaoxycyclopentadecane

L-2-[(isopropylideneamino)oxy]ethyl-2-[(p-toluenesulphonyl)oxy]propionate

L-2-[(isopropylideneamino)oxy]ethyl-2-[(p-toluenesulphonyl)oxy]propionate

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

2-[(isopropylideneamino)oxy]ethyl D-2-[p-[(6-chloro-2-quinoxalinyl)oxy]-phenoxy]propionate

2-[(isopropylideneamino)oxy]ethyl D-2-[p-[(6-chloro-2-quinoxalinyl)oxy]-phenoxy]propionate

Conditions
ConditionsYield
In N-methyl-acetamide; hexane; water; mineral oil
(-)-lactic acid [[(isopropylideneamino)-oxy]methyl]ester

(-)-lactic acid [[(isopropylideneamino)-oxy]methyl]ester

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

[(isopropylideneamino)oxy]methyl D-1-[p-[(6-chloro-2-quinoxalinyl)-oxy]-phenoxy]propionate

[(isopropylideneamino)oxy]methyl D-1-[p-[(6-chloro-2-quinoxalinyl)-oxy]-phenoxy]propionate

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; water
2-chloro-N-(2-fluorophenyl)acetamide
347-66-0

2-chloro-N-(2-fluorophenyl)acetamide

6-chloro-2-(4-hydroxyphenoxy)quinoxaline
76578-79-5

6-chloro-2-(4-hydroxyphenoxy)quinoxaline

2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]-N-(2-fluorophenyl)acetamide

2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]-N-(2-fluorophenyl)acetamide

Conditions
ConditionsYield
With potassium carbonate In butanone

76578-79-5Relevant academic research and scientific papers

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

Babu, T. S. S.,Srinivasu, N.

, p. 647 - 652 (2021/06/01)

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 spore and intermediate 4 - (6 - chloro - 2 kuikui oh linlin oxygen radical) phenol synthesis method (by machine translation)

-

Paragraph 0021; 0025, (2018/04/28)

The invention relates to a synthesis method of spore, characterized in that the first hydroquinone with sodium hydroxide 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 spore. The synthesizing process to optimize the original process, advantage lies in 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, follow-up synthesis reaction the yield of 90% or more. (by machine translation)

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

-

Paragraph 0023; 0027; 0031; 0035; 0039, (2018/04/03)

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)

Evaluation of the Elbs Persulfate Oxidation Reaction for the Preparation of Aryloxyphenoxypropionate Herbicides

Watson, Keith G.,Serban, Alexander

, p. 1503 - 1510 (2007/10/02)

A new, simple method for the preparation of several 4-(aryloxy)phenols (2a-d) and alkyl 2-(4-hydroxyphenoxy)propionates (3a,b) is described.These compounds are key precursors for the synthesis of important aryloxyphenoxypropionate herbicides (1a-d).The method uses the Elbs persulfate oxidation to convert phenol into 4-hydroxyphenyl sulfate (5).The free hydroxy group is then reacted with various aryl halides and alkyl 2-halopropionates.Mild hydrolysis of the sulfate group with boiling acetic acid then gives the products (2a-d) and (3a,b), generally in modest to good yield.

4-quinoxalinyloxyphenoxyalkylinitrile herbicides

-

, (2008/06/13)

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.

THE FACILE SYNTHESIS OF QUINOXALINYL-2-OXYPHENOLS

Sakata, Gozyo,Makino, Kenzi,Hashiba, Isao

, p. 2581 - 2585 (2007/10/02)

Facile synthesis of quinoxalinyl-2-oxyphenols are described.The condensation of 2-chloroquinoxalines with three molar equivalent of dihydroxybenzene in basic medium gave preferentially quinoxalinyl-2-oxyphenols, which involves nucleophilic cleavage of the initially formed bis(quinoxalinyl-2-oxy)benzenes by an excess of dihydroxybenzene.

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