15707-31-0

Basic information

• Product Name: 2,5-Cyclohexadiene-1,4-dione, 2,3-dichloro-5,6-dimethyl-
• Synonyms: 2,3-Dichlor-5,6-dimethyl-1,4-benzochinon;2,3-dichloro-5,6-dimethyl-1,4-benzoquinone;2,5-Cyclohexadiene-1,4-dione,2,3-dichloro-5,6-dimethyl;2,3-dichloroxyloquinone;5.6-Dichlor-o-xylo-p-chinon
• CAS NO: 15707-31-0
• Molecular Formula: C8H6Cl2O2
• Molecular Weight: 205.04
• Mol File: 15707-31-0.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadiene-1,4-dione, 2,3-dichloro-5,6-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadiene-1,4-dione, 2,3-dichloro-5,6-dimethyl-(15707-31-0)
• EPA Substance Registry System: 2,5-Cyclohexadiene-1,4-dione, 2,3-dichloro-5,6-dimethyl-(15707-31-0)

Safety Data

• Hazardous Substances Data: 15707-31-0(Hazardous Substances Data)

Usage

General Description

2,5-Cyclohexadiene-1,4-dione, 2,3-dichloro-5,6-dimethyl- is a chemical compound with the molecular formula C8H8Cl2O2. It is a yellowish crystalline solid that is used as a pesticide and herbicide. The compound is toxic to aquatic organisms and may cause long-term adverse effects in the environment. It is a chlorinated aromatic compound that is classified as a potential environmental hazard. Proper handling and disposal of this chemical are necessary to prevent harmful effects on the environment and human health.

Synthetic route

1,2,3,4-tetrachloro-5,6-dimethyl-benzene (877-08-7) → tetrachlorophthalonitrile (1953-99-7) + carbon monoxide (201230-82-2) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + tetrachloro-o-tolunitrile (113791-92-7)

Conditions	Yield
With ammonia; oxygen; vanadium-tin oxide at 330 - 360℃; for 8.33333E-05h; Yield given. Further byproducts given. Title compound not separated from byproducts;	A n/a B n/a C n/a D 30%

1,2,3,4-tetrachloro-5,6-dimethyl-benzene (877-08-7) → tetrachlorophthalonitrile (1953-99-7) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + 3,4-Dichloro-5,6-dimethyl-[1,2]benzoquinone + tetrachloro-o-tolunitrile (113791-92-7)

Conditions	Yield
With ammonia; oxygen; vanadium-tin oxide at 330 - 360℃; for 8.33333E-05h; Yield given. Further byproducts given. Title compound not separated from byproducts;	A n/a B n/a C n/a D 30%

1,2,3,4-tetrachloro-5,6-dimethyl-benzene (877-08-7) → tetrachlorophthalonitrile (1953-99-7) + 3,4,5,6-tetrachlorophthalimide (1571-13-7) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + tetrachloro-o-tolunitrile (113791-92-7)

Conditions	Yield
With ammonia; oxygen; vanadium-tin oxide at 375 - 405℃; for 8.33333E-05h; Yield given. Further byproducts given. Title compound not separated from byproducts;	A n/a B n/a C n/a D 30%

1,2,3,4-tetrachloro-5,6-dimethyl-benzene (877-08-7) → 3,4,5,6-tetrachlorophthalimide (1571-13-7) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + 3,6-Dichloro-4,5-dimethyl-[1,2]benzoquinone + tetrachloro-o-tolunitrile (113791-92-7)

Conditions	Yield
With ammonia; oxygen; vanadium-tin oxide at 400℃; for 8.33333E-05h; Yield given. Further byproducts given. Title compound not separated from byproducts;	A n/a B n/a C n/a D 30%

1,2,3,4-tetrachloro-5,6-dimethyl-benzene (877-08-7) → 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + 3,6-Dichloro-4,5-dimethyl-[1,2]benzoquinone + 3,4-Dichloro-5,6-dimethyl-[1,2]benzoquinone + tetrachloro-o-tolunitrile (113791-92-7)

Conditions	Yield
With ammonia; oxygen; vanadium-tin oxide at 330 - 360℃; for 8.33333E-05h; Yield given. Further byproducts given. Title compound not separated from byproducts;	A n/a B n/a C n/a D 30%

2,3-dimethylhydroquinone (74894-42-1, 74894-43-2) → 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0)

Conditions	Yield
With hydrogenchloride; nitric acid at 80 - 90℃; for 1h;	25%
With hydrogenchloride; nitric acid In water at 90℃; for 0.166667h;

2,3-dichloro-5,6-dimethyl-p-phenylenediamine (858012-57-4) → 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0)

Conditions	Yield
With chromium(VI) oxide; acetic acid

1,2,3,4-tetrachloro-5,6-dimethyl-benzene (877-08-7) → tetrachlorophthalonitrile (1953-99-7) + carbon dioxide (124-38-9) + 3,4,5,6-tetrachlorophthalimide (1571-13-7) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + 3,4-Dichloro-5,6-dimethyl-[1,2]benzoquinone + tetrachloro-o-tolunitrile (113791-92-7)

Conditions	Yield
With ammonia; oxygen; vanadium-tin oxide at 375 - 405℃; for 8.33333E-05h; Product distribution; other temperature,;

2,3-dichloro-5,6-dimethyl-p-phenylenediamine (858012-57-4) + acetic acid (64-19-7) + CrO3 → 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0)

Conditions	Yield

2,3-dimethyl-1,4-dihydroxybenzene (608-43-5) → 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0)

Conditions	Yield
With hydrogenchloride; nitric acid
With hydrogenchloride; nitric acid In water
With hydrogenchloride; nitric acid at 90℃; for 0.166667h;
With hydrogenchloride; nitric acid at 90℃; for 0.166667h;
With hydrogenchloride; nitric acid at 80 - 90℃; for 0.166667h;

o-xylene (95-47-6) → 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: man fuehrt das durch Chlorierung in Gegenwart von Jod erhaltene fluessige Dichlor-o-xylol in eine Dinitroderivat ueber und reduziert dieses in verduennt-alkoholischer Loesung durch Erwaermen mit Zinnchloruer und konz.Salzsaeure 2: CrO3; glacial acetic acid View Scheme

ethyleneimine (151-56-4) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → 2-aziridinyl-3-chloroxyloquinone

Conditions	Yield
In diethyl ether at 0℃; for 0.333333h;	85%

2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + disodium maleonitriledithiolato → 5,8-dihydroxy-6,7-dimethyl-1,4-benzodithiine-2,3-dicarbonitrile (23433-11-6)

Conditions	Yield
With water; acetic acid In N,N-dimethyl-formamide for 0.5h; Cooling with ice;	71.4%

2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + aniline (62-53-3) → 2‐chloro‐5,6‐dimethyl‐3‐(phenylamino)‐1,4‐benzoquinone

Conditions	Yield
In ethanol Reflux;	71%

4-phenyl-1-piperazine (92-54-6) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → 2-chloro-5,6-dimethyl-3-(4-phenylpiperazin-1-yl)-1,4-benzoquinone

Conditions	Yield
In water at 50 - 60℃;	70%

1-(4-Nitrophenyl)piperazine (6269-89-2) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → 2-Chloro-5,6-dimethyl-3-(4-(4-nitrophenyl)piperazin-1-yl)-1,4-benzoquinone

Conditions	Yield
In water at 50 - 60℃;	67%

2,4-dimethyl-thiophenol (13616-82-5) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → 2-chloro-3-(2,4-dimethylphenylthio)-5,6-dimethyl-1,4-benzoquinone + 2,3-bis(2,4-dimethylphenylthio)-5,6-dimethyl-1,4-benzoquinone

Conditions	Yield
In ethanol at 20℃;	A 65% B 21%

2,5-dimethylthiophenol (4001-61-0) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → 2-chloro-3-(2,5-dimethylphenylthio)-5,6-dimethyl-1,4-benzoquinone + 2,3-bis(2,5-dimethylphenylthio)-5,6-dimethyl-1,4-benzoquinone

Conditions	Yield
In ethanol at 20℃;	A 65% B 33%

2,6-dimethylbenzene-1-thiol (118-72-9) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → 2-chloro-3-(2,6-dimethylphenylthio)-5,6-dimethyl-1,4-benzoquinone + 2,3-bis(2,6-dimethylphenylthio)-5,6-dimethyl-1,4-benzoquinone

Conditions	Yield
In ethanol at 20℃;	A 63% B 5%

4-ethoxycarbonylpiperazine (120-43-4) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → ethyl 4-(2-chloro-4,5-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)piperazine-1-carboxylate

Conditions	Yield
In water at 50 - 60℃;	60%

2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + 3-trifluoromethylaniline (98-16-8) → 2‐chloro‐5,6‐dimethyl‐3‐((3‐(trifluoromethyl)phenyl)amino)‐1,4-benzoquinone

Conditions	Yield
In ethanol Reflux;	56%

2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + 2-isopropylaniline (643-28-7) → 2‐chloro‐3‐((2‐isopropylphenyl)amino)‐5,6‐dimethyl‐1,4‐benzoquinone

Conditions	Yield
In ethanol Reflux;	54%

tert-butyl 3-aminobenzoate (92146-82-2) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → tert-butyl 3-((2-chloro-4,5-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)amino)benzoate

Conditions	Yield
In ethanol Reflux;	51%

4-isopropoxy-3-(prop-1-en-1-yl)aniline + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → 2-chloro-3-{[4-isopropoxy-3-(prop-1-en-1-yl)phenyl]amino}-5,6-dimethylcyclohexa-2,5-diene-1,4-dione

Conditions	Yield
In ethanol at 0 - 25℃; for 24h; Inert atmosphere;	50%

2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + 4,4-ethylenedioxy-piperidine (177-11-7) → 2-chloro-5,6-dimethyl-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-1,4-benzoquinone

Conditions	Yield
In water at 50 - 60℃;	50%

3-Aminomethylpyridine (3731-52-0) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → 2-chloro-5,6-dimethyl-3-((pyridin-3-ylmethyl)amino)cyclohexa-2,5-diene-1,4-dione

Conditions	Yield
In ethanol at 0 - 20℃; for 24h; Inert atmosphere;	49%

(2-aminomethylpyridine) (3731-51-9) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → 2‐chloro‐5,6‐dimethyl‐3‐((pyridin‐2‐ylmethyl)amino)‐1,4-benzoquinone

Conditions	Yield
In ethanol at 0 - 20℃; for 24h; Inert atmosphere;	47%
In ethanol for 6h; Reflux;	35%

Methyl 3-aminobenzoate (4518-10-9) + 2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) → methyl 3-((2-chloro-4,5-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)amino)benzoate

Conditions	Yield
In ethanol Reflux;	47%

2,3‐dichloro-5,6‐dimethyl‐1,4‐benzoquinone (15707-31-0) + methyl 2-cyanoacetate (105-34-0) → (2-chloro-4,5-dimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-cyano-acetic acid methyl ester (883902-87-2)

Conditions	Yield
With ammonium hydroxide In ethanol at 20℃; for 0.166667h; Michael-type addition;	45%
With ammonium hydroxide In ethanol at 20℃; for 0.166667h;	31%

Upstream product

• 858012-57-4 2,3-dichloro-5,6-dimethyl-p-phenylenediamine 
• 877-08-7 1,2,3,4-tetrachloro-5,6-dimethyl-benzene 
• 95-47-6 o-xylene 
• 608-43-5 2,3-dimethyl-1,4-dihydroxybenzene 
• 74894-42-1 2,3-dimethylhydroquinone 
• 64-19-7 acetic acid 

Downstream Products

• 926013-25-4 (2-chloro-4,5-dimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-cyano-acetic acid ethyl ester 

Relevant articles and documents

Synthesis of thianthrene and dienzothiophene skeletons from some 5,6-dichloro-benzoquinones

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Design, synthesis, characterization, and antimicrobial activity of novel piperazine substituted 1,4-benzoquinones

Recently, amine substituted and halogen containing 1,4-benzoquinone molecules have attracted a significant attention because of the efficient biological activities. Thus, novel chlorinated/unchlorinated and piperazine substituted dimethyl-1,4-benzoquinone derivatives (4a-h and 5a-h) were designed, synthesized and characterized in the present paper. Furthermore, antibacterial and antifungal activity performances of the new products were compared and evaluated employing the MIC (Minimum Inhibitory Concentrations) values of reference antimicrobial substances. The compounds of 4a and 4b were highly potent with the MIC values of 4.88 μg/mL and 78.12 μg/mL compared to Cefuroxime (MIC = 9.8 μg/mL against S. epidermidis) and Amikacin (MIC = 128.0 μg/mL against E. faecalis), respectively. The presence of the chlorine atom in the structure appeared essential, since most of the chlorinated compounds exhibited more improved activity in comparison to those of unchlorinated products. On the other side, an opposite tendency was observed for the antifungal activity that the MIC values of the unchlorinated derivatives were lower in most cases than those of chlorinated ones. According to the obtained results, while chlorinated derivatives, in particular 4a and 4b, can be proposed as potential antibacterial agents with nearly two fold lower MIC values compared to reference drugs, unchlorinated compounds might be suggested as a relatively active antifungal agents which are needed further improvements due to the higher MIC values than those of reference antifungal materials.

Novel plastoquinone analogs containing benzocaine and its analogs: structure‐based design, synthesis, and structural characterization

Introducing new biologically active organic molecules or their analogs into the pharmaceutically important molecules significantly enables the discovery and development of the medicines that improve the health of patients. Chemical synthesis has a key role in pharmaceutical research and development, aiming to design and build molecules with the essential biological activity needed in drugs. For that reason, herein, three series of novel PQ analogs (the nonhalogenated (PQ1-6) and the halogenated PQ analogs (BrPQ1-6 and ClPQ1-6)) containing benzocaine and its analogs were designed and synthesized starting from the commercially available dimethylhydroquinone (1) with benzocaine and its analogs. The structures of all synthesized analogs were characterized by using spectroscopic methods. The in vitro antibacterial and antifungal activities were evaluated for the PQ analogs.