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Quality Control of [ 117-21-5 ] Purity: 95% SDS Specification

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Product Details of [ 117-21-5 ]

CAS No. :	117-21-5
Formula :	C₈H₃ClO₃
M.W :	182.56
SMILES Code :	O=C(C1=CC=CC(Cl)=C12)OC2=O
MDL No. :	MFCD00023107
InChI Key :	UERPUZBSSSAZJE-UHFFFAOYSA-N
Pubchem ID :	67014

Safety of [ 117-21-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 117-21-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 117-21-5 ]

[ 117-21-5 ] Synthesis Path-Downstream 1~32

1
[ 117-21-5 ]
[ 62-53-3 ]
[ 42899-83-2 ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid; for 3h;Reflux;	SYNTHESIS EXAMPLE 105-1 An acetic acid (200 mL) solution of <strong>[117-21-5]3-chlorophthalic anhydride</strong> (36.5 g) and aniline (18.6 g) was heated to reflux for 3 hours. After cooling to room temperature, the reaction mixture was poured into iced water, and the precipitated crystal was collected by filtration, washed with water and 5% isopropanol aqueous solution, and then dried. The resulting crude crystal was washed with a t-butylmethylether/petroleum ether mixed solvent to obtain 3-chloro-N-phenylphthalimide (50.1 g). 1H-NMR (CDCl3, δ ppm): 7.38-7.55 (5H, m), 7.69-7.74 (2H, m), 7.85-7.91 (1H, m).

References: [1]Organic Letters,2017,vol. 19,p. 6404 - 6407.
[2]Journal of Organic Chemistry,2019,vol. 84,p. 1898 - 1907.
[3]Journal of the Chemical Society,1939,p. 134,137.
[4]Journal of the Chemical Society,1939,p. 134,137.
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 751 - 754.
[6]Patent: US2011/184188,2011,A1 .Location in patent: Page/Page column 107.
[7]Organic Letters,2015,vol. 17,p. 2684 - 2687.

2
[ 117-21-5 ]
[ 108-90-7 ]
[ 92158-88-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With aluminum (III) chloride; at 90℃; for 2h;	General procedure: A mixture of the corresponding phthalic anhydride (1 mol. equiv.), the appropriate halobenzene (8 mol. equiv.), and aluminium chloride (2.4 mol. equiv.) was heated at 90 oC for 2h, then cooled to room temperature. Ice was added followed by conc. HCl (5 mL) and the mixture was extracted into DCM (3 x 50 mL) and washed with 10% Na2CO3 solution (2 x 50 mL). The Na2CO3 washings were combined and acidified to pH3 with conc. HCl acid. The resulting precipitate was collected by filtration and dried in a vacuum oven.

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5916 - 5919.
[2]Journal of Medicinal Chemistry,1964,vol. 7,p. 453,454,456.

3
[ 117-21-5 ]
[ 71-43-2 ]
[ 4889-73-0 ]

References: [1]Journal of the American Chemical Society,1956,vol. 78,p. 5004,5006.
[2]Journal of Medicinal Chemistry,1975,vol. 18,p. 177 - 182.

4
[ 117-21-5 ]
[ 3790-09-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrazine hydrate; acetic acid; at 0 - 125℃; for 2h;Inert atmosphere;	3-Chloro-phthalic anhydride (5a, purchased from TCI) (10 g, 54.95 mmol) was dissolved in glacial acetic acid (100 mL), and hydrazine hydrate (20 mL) was added dropwise at 0C, and then refluxed for two hours at 125C. When the reaction was completed, the solution was cooled down to room temperature, filtrated, and washed with water until the filtrate pH=6.0, and then dried to give 5-chloro-2,3-dihydrophthalazin-1,4-dione (5b), 10.08 g white solid (yield 93%).
93%	With hydrazine hydrate; acetic acid; In acetic acid; at 0 - 125℃; for 2h;	3-Chloro-phthalic anhydride (5a, purchased from TCI) (10 g, 54.95 mmol) was dissolved in glacial acetic acid (100 mL), and hydrazine hydrate (20 mL) was added dropwise at 0 C., and then refluxed for two hours at 125 C. When the reaction was completed, the solution was cooled down to room temperature, filtrated, and washed with water until the filtrate pH 6.0, and then dried to give 5-chloro-2,3-dihydrophthalazin-1,4-dione (5b), 10.08 g white solid (yield 93%).
	With hydrogenchloride; hydrazine hydrate; In quinoline; for 24h;Reflux;	General procedure: A stirred solution of phthalic anhydride (S1, 1.0 equiv), HCl (10 wt% aq), and N2H4*H2O (1.5 equiv) was refluxed in an oil bath for 24 hours under air. Then, the reaction mixture was cooled to room temperature and filtered through filter paper.The filter cake was washed with H2O and dried under reduced pressure to give 2,3-dihydrophthalazine-1,4-dione (S2). The crude material was used for the next step without further purification.

References: [1]Patent: EP2799435,2014,A1 .Location in patent: Paragraph 0077; 0078.
[2]Patent: US2015/51211,2015,A1 .Location in patent: Paragraph 0103; 0104.
[3]Synthesis,2021,vol. 53,p. 1760 - 1770.
[4]Patent: DE481650,1929,C .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 16,p. 541.
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 16,p. 541.
[5]Tetrahedron Letters,2020,vol. 61.

5
[ 641-70-3 ]
[ 117-21-5 ]

References: [1]Journal of Organic Chemistry,1983,vol. 48,p. 2465 - 2468.
[2]Journal of the American Chemical Society,1901,vol. 23,p. 751.
[3]Journal of the American Chemical Society,1956,vol. 78,p. 5004,5006.

6
[ 27563-65-1 ]
[ 117-21-5 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 129 - 134.
[2]Chemische Berichte,1885,vol. 18,p. 1759.
[3]Justus Liebigs Annalen der Chemie,1935,vol. 515,p. 23,28.
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 473 - 486.

7
[ 117-21-5 ]
[ 52010-22-7 ]
[ 70097-45-9 ]

References: [1]Canadian Journal of Chemistry,1987,vol. 65,p. 1214 - 1217.
[2]Journal of Organic Chemistry,1987,vol. 52,p. 129 - 134.
[3]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1985,vol. 34,p. 141 - 144.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1985,p. 151 - 155.
[4]Journal of Organic Chemistry,1987,vol. 52,p. 129 - 134.

8
[ 117-21-5 ]
[ 52010-22-7 ]
[ 70097-45-9 ]
[ 110706-48-4 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 129 - 134.

9
[ 117-21-5 ]
[ 4466-59-5 ]
[ 88389-98-4 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 5532 - 5535.

10
[ 117-21-5 ]
[ 107-95-9 ]
[ 202984-40-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With acetic acid; at 100℃; for 3h;	Add <strong>[117-21-5]3-chlorophthalic anhydride</strong> (365 mg, 2.0 mmol) and aminopropionic acid (190 mg, 2.1 mmol) to glacial acetic acid(10 mL), heated to 100 C for 3 h. The reaction was quenched with water (10 mL), and the pH of the solution was adjusted to NaOH solution (0.1 mol/L).6-8. Filtered and dried to give a yellow solid 425mg, LC-MS and 1H-NMR confirmed the expected intermediate compound, yield 96.0%.

References: [1]Patent: CN109867661,2019,A .Location in patent: Paragraph 0403; 0405.
[2]Russian Chemical Bulletin,1997,vol. 46,p. 1904 - 1908.

11
[ 117-21-5 ]
[ 15499-84-0 ]
4,4'-bis(3-chlorophthalimido)diphenyl-9-fluorenylidene [ No CAS ]