5-Chloroisatoic anhydride
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5-Chloroisatoic anhydride
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CAS No:
4743-17-3
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Formula:
C8H4ClNO3
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Chemical Name:
5-Chloroisatoic anhydride
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Synonyms:
2H-3,1-Benzoxazine-2,4(1H)-dione,6-chloro-;Isatoic anhydride,5-chloro-;6-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione;5-Chloroisatoic anhydride;6-Chloro-1,2-dihydro-4H-3,1-benzoxazine-2,4-dione;6-Chloro-1H-benzo[d][1,3]oxazine-2,4-dione;NSC 139890;NSC 75847;6-Chloro-2H-3,1-dihydrobenzoxazine-2,4-dione
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CAS No:
5-Chloroisatoic anhydride Basic Attributes
197.58
197.58
225-255-7
139890|75847
DTXSID3063592
2934999090
Safety Information
NONH for all modes of transport
3
R36/37/38
S26-S37/39
Xi:Irritant;
P261-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 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-Chloroisatoic anhydride Use and Manufacturing
Step 1 A 500 mL 3-necked round bottom flask was charged with 2-amino-5- chlorobenzoic acid (17 g, 0.1 mol) and 1 , 2-dichloroethane (200 mL). To the above was added dropwise a solution of triphosgene (21 g, 0.21 mol) in 1, 2- dichloroethane (100 mL) at 80 °C. The resulting mixture was heated at 80 °C for further 3 h then cooled in ice- water. The precipitate was collected by filtration and dried to afford 19 g (97percent) of the product as white solid. *H NMR (300 MHz, DMSO-d2-Amino-6-chlorobenzoic acid (30 g) was suspended in 1, 4-dioxane (225 ml) and ethyl chloroformate (75 ml) was added. The mixture was heated at reflux for 1 hour, then cooled to 50° C. and acetyl chloride (75 ml) was added. The mixture was stirred for 10 hours, after which the precipitated product was filtered off and washed with toluene. Drying in vacuum yields 5-chloroisatoic anhydride (33 g, 97percent yield). 5-Chloroisatoic anhydride (30 gram) was dissolved in dimethylacetamide (300 ml), and cooled to 5° C. over a nitrogen atmosphere. Sodium hydride (5.8 g, 70percent) was added portionwise, followed by addition of methyl iodide (11.5 ml). The reaction mixture was stirred at room temperature for 18 hours and the evacuated (40 mbar) for 1 hour in order to remove excess methyl iodide. Sodium hydride (5.8 g, 70percent) was added followed by addition of dimethyl malonate (20 ml), and the mixture was heated to 85° C. After 3 hours at 85° C., the mixture was cooled and diluted with cold water (2.4 litre). The product was precipitated by addition of 5 M HCl (aq) until pH=1.5-2. Filtration of the precipitated product and recrystallisation from methanol gave the title compound (29 g, 70percent yield).Trichloromethyl CHLOROFORMATE (4.8 mL, 300 mmol) was added to a stirred solution of Compound 57 (6.84 g, 40 mmol) in dry dioxane at room temperature and the solution was refluxed for 4 h. The solution was cooled in an ice bath and the solids formed were filtered. The solids were washed by ether and dried under vacuum at room temperature to yield 7.3 g (92percent) of white SOLIDS. H NMR (DMSO-D6) : d 7.47 (d, J= 8.6 Hz, 1H), 7.70 (dd, J= 8.6, 1.8 Hz, 1H), 7.82 (d, J= 1.1, 1H), 11.63 (S, 1H).
2H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-: ACTIVE
Computed Properties
Molecular Weight:197.57
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:196.9879707
Monoisotopic Mass:196.9879707
Topological Polar Surface Area:55.4
Heavy Atom Count:13
Complexity:256
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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