| Identification | More | [Name]
2-CHLORO-1,4-BENZOQUINONE | [CAS]
695-99-8 | [Synonyms]
2-CHLORO-1,4-BENZOQUINONE
2,5-Cyclohexadiene-1,4-dione, 2-chloro-
2-Chloro-2,5-cyclohexadien-1,4-dione
2-Chlorobenzo-1,4-quinone
2-Chloro-p-benzoquinone
2-Chloroquinone
benzoquinone,2-chloro-
Chloro-1,4-benzoquinone
Chloro-p-benzoquinone
Chloroquinone
Monochloro-p-benzoquinone
Monochloroquinone
p-Benzoquinone, 2-chloro-
Monochlorobenzoquinone
2-Chloro-1,4-benzoquinone,95%
2-CHLORO-PARA-BENZOQUINONE
2-chlorocyclohexa-2,5-diene-1,4-dione
2-Chloro-2,5-cyclohexadiene-1,4-dione | [Molecular Formula]
C6H3ClO2 | [MDL Number]
MFCD00075260 | [Molecular Weight]
142.54 | [MOL File]
695-99-8.mol |
| Chemical Properties | Back Directory | [Appearance]
YELLOW TO BROWN CRYSTALS | [Melting point ]
52-57 °C | [Boiling point ]
210℃ | [density ]
1.40 | [refractive index ]
1.4620 (estimate) | [Fp ]
83℃ | [storage temp. ]
Storage temp. 2-8°C | [form ]
Crystals | [color ]
Yellow to brown | [InChI]
1S/C6H3ClO2/c7-5-3-4(8)1-2-6(5)9/h1-3H | [InChIKey]
WOGWYSWDBYCVDY-UHFFFAOYSA-N | [SMILES]
ClC1=CC(=O)C=CC1=O | [CAS DataBase Reference]
695-99-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn,F | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R15:Contact with water liberates extremely flammable gases.
R10:Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S36:Wear suitable protective clothing .
S7/8:Keep container tightly closed and dry . | [WGK Germany ]
3
| [HS Code ]
29147000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
YELLOW TO BROWN CRYSTALS | [Uses]
2-Chloro-1,4-benzoquinone may be used in the preparation of chloro derivatives of prenylnaphthohydroquinone. | [General Description]
2-Chloro-1,4-benzoquinone is a quinone derivative. It is one of the intermediate formed during the degradation of 3,4-dichloroaniline in a dielectric barrier discharge plasma reactor. It is formed during lignin peroxidase catalyzed oxidation of 2-chloro-1,4-dimethoxybenzene. 2-Chloro-1,4-benzoquinone on dechlorination yields 1,2,4-trihydroxybenzene. | [Synthesis]
GENERAL METHOD: Diacetoxyiodobenzene (5 mmol, 1.61 g) and NaHSO4-H2O (1 mmol, 0.138 g) were stirred in an aqueous acetonitrile solution (5 mL of water and 5 mL of acetonitrile) for 10-15 minutes at room temperature. To this reaction mixture, 2-chlorobenzamide (1 mmol) was added and stirring was continued until the reaction was complete (monitored by TLC). Upon completion of the reaction, the reaction mixture was quenched with ice water and subsequently extracted with chloroform (3 x 10 mL). The chloroform layers were combined, washed with water (3 x 20 mL), dried with anhydrous Na2SO4 and concentrated on a rotary evaporator to give the crude product. The crude product was further purified by silica gel column chromatography using ethyl acetate: hexane (1:9, v/v) as eluent to give pure 2-chloro-1,4-benzoquinone. | [References]
[1] Organic Letters, 2010, vol. 12, # 20, p. 4644 - 4647
[2] Synthetic Communications, 2014, vol. 44, # 4, p. 468 - 473 |
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