2-Chloro-3′,4′-dihydroxyacetophenone
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2-Chloro-3′,4′-dihydroxyacetophenone
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CAS No:
99-40-1
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Formula:
C8H7ClO3
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Chemical Name:
2-Chloro-3′,4′-dihydroxyacetophenone
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Synonyms:
Ethanone,2-chloro-1-(3,4-dihydroxyphenyl)-;Acetophenone,2-chloro-3′,4′-dihydroxy-;Acetophenone,α-chloro-3,4-dihydroxy-;2-Chloro-1-(3,4-dihydroxyphenyl)ethanone;3,4-Dihydroxyphenacyl chloride;α-Chloro-3′,4′-dihydroxyacetophenone;2-Chloro-3′,4′-dihydroxyacetophenone;1-Chloroacetyl-3,4-dihydroxybenzene;2-Chloro-1-(3,4-dihydroxyphenyl)-1-ethanone;4-(Chloroacetyl)catechol;NSC 13905;NSC 17869;3,4-Dihydroxy-α-chloroacetophenone
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CAS No:
Description
Off-White Solid
2-chloro-3',4'-dihydroxyacetophenone is an alpha-chloroketone, a member of acetophenones and an aromatic ketone.
2-Chloro-3′,4′-dihydroxyacetophenone Basic Attributes
186.59
186.59
202-754-8
FN6949L56Q
17869|13905
DTXSID90243929
2914700090
Characteristics
57.5
2.1
1.4±0.1 g/cm3
173 °C (decomp)
418.7ºC at 760 mmHg
207.0±25.9 °C
1.612
Refrigerator
Safety Information
NONH for all modes of transport
3
R36/37/38
S26-S37/39
Xi:Irritant;
P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 51 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Chloro-3′,4′-dihydroxyacetophenone Use and Manufacturing
To a cooled solution of 1, 2-dichloroethane (20mL) at about 5–10°C, aluminum chloride (6.0g, 45mmol) was added, then the mixture solution was stirred at 5–10°C for about 30min. Then catechol (1) (2.0g, 18.1mmol) was added portion wise to the stirred reaction mixture within about 10min and the reaction mixture was further stirred for 20min. To the above solution, chloroacetyl chloride (2.2g, 19.3mmol) was added at 5–10°C. Then the temperature was raised to room temperature and with further stirring for about 20h. After completion of the reaction, the reaction was quenched with dilute hydrochloric acid solution (40mL) at 5–10°C and stirred for 2–3h at room temperature. The obtained solid was filtered and washed with water. The wet solid was suspended in dilute acetic acid and heated to get a clear solution. To this clear solution, carbon (0.1g) was added and stirred for 30min. The reaction mixture was filtered in hot. The filtrate was cooled and the formed solid was filtered and washed with water. It was dried to obtain the product 2-chloro-1-(3, 4-dihydroxyphenyl)ethanone (2). Yield: 2.5g, 74percent; M.P. 175–177°C.Preparation of 4-chloroacetyl-catecholSimilar to the procedures of R. W. Schayer (J. Am. Chem. Soc. 74, 2441 [1952]) and N. Levin et al. (J. Org. Chem. 7, 408-415 [1942]), but without an additional solvent, a mixture of 100 g catechol, 750 g (450 ml) of phosporus oxychloride and 206 g (145 ml) of chloracetyl chloride was stirred at reflux temperature (ca. 125°C) in an argon atmosphere for 4.5 hours. Then most of the volatiles were distilled off at 80 °C (bath temperature) and, finally, under reduced pressure. To the nearly intractable dark mass were added at ca 80°C 200 ml of water upon which the mixture became stirabel again. 600 ml of cold (0°C) water were added in portions to control the exothermic reaction. When all of the water was added and the exothermic reaction had ceased the mixture was stirred for 2 hours under reflux. Catechol (2, 200 g) was added lot-wise to the mixture of aluminium chloride (606 g)and dichloromethane (1800 ml) at 0-10°C followed by gradual addition ofchloroacetyl chloride (3, 217.3 g) in 200 ml dichloromethane at 0-10°C. The reactionmixture was stined at 25-35°C till completion of the reaction as monitored by HPLC. The reaction mass was quenched with aqueous hydrochloric acid followed by filtration to isolate the crude product. Isolation from aqueous acetic acid gave the desired compound, 2-chloro-3, 4-dihydroxy acetophenone (4).Yield: 210 g; (62percent).
Computed Properties
Molecular Weight:186.59
XLogP3:2.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:186.0083718
Monoisotopic Mass:186.0083718
Topological Polar Surface Area:57.5
Heavy Atom Count:12
Complexity:172
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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2-Chloro-3′,4′-dihydroxyacetophenone
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