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| | 2-CHLORO-1,4-BENZOQUINONE Basic information |
| | 2-CHLORO-1,4-BENZOQUINONE Chemical Properties |
| 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) |
| Hazard Codes | Xi,Xn,F | | Risk Statements | 36/37/38-15-10 | | Safety Statements | 26-37/39-43-36-7/8 | | WGK Germany | 3 | | HS Code | 29147000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2-CHLORO-1,4-BENZOQUINONE Usage And Synthesis |
| 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 |
| | 2-CHLORO-1,4-BENZOQUINONE Preparation Products And Raw materials |
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