153505-32-9|2-Chloro-4-fluoro-6-nitroaniline| Ambeed

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Quality Control of [ 153505-32-9 ] Purity: 96% SDS Specification

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Product Details of [ 153505-32-9 ]

CAS No. :	153505-32-9
Formula :	C₆H₄ClFN₂O₂
M.W :	190.56
SMILES Code :	NC1=C([N+]([O-])=O)C=C(F)C=C1Cl
MDL No. :	MFCD22571067
InChI Key :	COJJQULUJYCZEP-UHFFFAOYSA-N
Pubchem ID :	19958561

Safety of [ 153505-32-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H320-H335
Precautionary Statements:	P264-P270-P301+P312-P330

Application In Synthesis of [ 153505-32-9 ]

* 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 [ 153505-32-9 ]

[ 153505-32-9 ] Synthesis Path-Downstream 1~24

2
[ 364-78-3 ]
[ 153505-32-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide; In N,N-dimethyl-formamide;	2-Chloro-4-fluoro-6-nitroaniline 2-Chloro-4-fluoro-6-nitroaniline was prepared using an adaptation of the method of Mitchell, et al. (Mitchell, R. H. et al., J. Org. Chem. 44:4733 (1979)). To a solution of 4-fluoro-2-nitroaniline (500 mg, 3.2 mmol) in dry DMF (10 mL) under N2 was added dropwise a solution of N-chlorosuccinimide (426 mg, 3.2 mmol) in dry DMF (16 mL). The reaction was allowed to stir overnight. The solution was then poured into 100 mL H2 O and the resulting cloudy suspension extracted with 425 mL ethyl acetate. The combined organic phases were washed with 425 mL H2 O and 25 mL saturated NaCl solution and dried (MgSO4). The MgSO4 was vacuum filtered and the solvent rotary evaporated to yield a brown crystalline solid which was purified further by flash chromatography (2:1 hexanes:ethyl acetate) to yield 424 mg of an orange crystalline solid (69.5%) 1 H NMR (CDCl3) δ6.46 (br s, 2H, NH2), 7.42 (dd, JH5-3 =3 Hz, JH3-F =7.2 Hz, H-4), 7.85 (dd, JH5-3 =3 Hz, JH5-F =8.7 Hz, H-5)

References: [1]Patent: US5514680,1996,A .

3
SnCl₂ 2H₂ O [ No CAS ]
[ 153505-32-9 ]
3-chloro-5-fluoro-1,2-phenylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In ethanol; ethyl acetate;	1,2-Diamino-3-chloro-5-fluorobenzene 1,2-Diamino-3-chloro-5-fluorobenzene was prepared using an adaptation of the method of Bellamy, et al., (Bellamy, F. D. et al., Tetrahedron Lett. 25:839 (1984)). A mixture of <strong>[153505-32-9]2-chloro-4-fluoro-6-nitroaniline</strong> (424 mg, 2.22 mmol) and SnCl2 2H2 O (2.50 g, 11.1 mmol) dissolved in 7 mL ethyl acetate and 3 mL absolute ethanol under N2 was heated at 70 C. for 2.5 h. All the starting material had reacted as evidenced by TLC (silica gel, 2:1 hexanes:ethyl acetate). The reaction was allowed to cool to room temperature and poured into 20 mL crushed ice. Sufficient solid NaHCO3 was added (foaming) to bring the pH to 6. The thick yellow white emulsion was then extracted with 3*25 mL ethyl acetate and the combined organic extracts washed with sat'd NaCl solution. The organic phase was dried (MgSO4), vacuum filtered and the solvent rotary evaporated to yield a dark brown oil which crystallized on standing to yield 290 mg (82%). 1 H NMR (CDCl3) δ3.59 (br s, 4H, 2(NH2)); 6.37 (dd, 1H, H5, J4-5 =2.7, JH-F =9.3); 6.55 (dd, 1H, H4, J4-5 =2.7, JHF =8.4).

References: [1]Patent: US5514680,1996,A .

4
[ 153505-32-9 ]
[ 1253789-92-2 ]

References: [1]Patent: WO2011/154298,2011,A1 .
[2]Patent: US2013/85136,2013,A1 .

5
[ 153505-32-9 ]
[ 1352144-76-3 ]

References: [1]Patent: WO2011/154298,2011,A1 .
[2]Patent: US2013/85136,2013,A1 .

6
[ 153505-32-9 ]
[ 1352144-77-4 ]

References: [1]Patent: WO2011/154298,2011,A1 .
[2]Patent: US2013/85136,2013,A1 .

7
[ 153505-32-9 ]
[ 1352144-58-1 ]

References: [1]Patent: WO2011/154298,2011,A1 .
[2]Patent: US2013/85136,2013,A1 .

8
[ 153505-32-9 ]
copper(l) cyanide [ No CAS ]
[ 1253789-63-7 ]

Yield	Reaction Conditions	Operation in experiment
41%		Example A; 5a) Preparation of intermediate; Tert-butyl nitrite (25 g, 242 mmol) was added to a suspension of CuCN (21.5 g,242 mmol) in CH3CN (500 ml). The mixture was heated to 70 C and was stirred for 15 min. Subsequently, a mixture of 2-chloro-4-fluoro-6-nitro-benzenamine (23 g,121 mmol) and CH3CN (q.s.) was added, and the resulting brown solution was heated overnight at 70 C. The solvent was removed in vacuo. Water (q.s.) was added to the residue and the aqueous mixture was extracted with EtOAc. The separated organic layer was dried (MgS04), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: EtO Ac/petroleum ether 1/4). The desired fractions were collected and the solvent was evaporated. Yield: 10 g of intermediate 10 (41% yield; yellow solid).
41%		Tert-butyl nitrite (25 g, 242 mmol) was added to a suspension of CuCN (21.5 g, 242 mmol) in CH3CN (500 ml). The mixture was heated to 70 C. and was stirred for 15 mm. Subsequently, a mixture of 2-chioro-4-fluoro-6-nitro-benze- namine (23 g, 121 mmol) and CH3CN (q.s.) was added, and the resulting brown solution was heated overnight at 70 C. The solvent was removed in vacuo. Water (q.s.) was added to the residue and the aqueous mixture was extracted with EtOAc. The separated organic layer was dried (Mg504), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: EtOAc/petroleum ether 1/4). The desired fractions were collected and the solvent was evaporated. Yield: 10 g of intermediate 10 (41% yield; yellow solid).

References: [1]Patent: WO2011/154298,2011,A1 .Location in patent: Page/Page column 35.
[2]Patent: US2013/85136,2013,A1 .Location in patent: Paragraph 0270; 0271.

9
[ 2106-02-7 ]
[ 153505-32-9 ]

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548.
[2]Patent: CN108503593,2018,A .
[3]Journal of Enzyme Inhibition and Medicinal Chemistry,2022,vol. 37,p. 844 - 856.

10
[ 399-35-9 ]
[ 153505-32-9 ]

References: [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2022,vol. 37,p. 844 - 856.
[2]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548.
[3]Patent: CN108503593,2018,A .

11
N-(2-chloro-4-fluoro-6-nitrophenyl)acetamide [ No CAS ]
[ 153505-32-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogenchloride; In water; at 120℃; for 1.25h;	Add N-(2-chloro-4-fluoro-6-nitrophenyl)acetamide (2.58 g, 11.11 mmol) to a 100 ml flaskIt was reacted with 30 ml of concentrated hydrochloric acid at 120 C for 1.25 h.Concentrated under reduced pressure, ethyl acetate was dissolved, and the organicColumn chromatography gave 1.904 g of solid, yield: 90.0%.

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548.
[2]Patent: CN108503593,2018,A .Location in patent: Paragraph 0072; 0075; 0082; 0083.

12
[ 153505-32-9 ]
N-(3-chloro-2-((5-((2,6-dichloro-3,5-dimethoxybenzyl)oxy)pyrimidin-2-yl)amino)-5-fluorophenyl)acrylamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548.
[2]Patent: CN108503593,2018,A .

13
[ 153505-32-9 ]
tert-butyl (2-amino-3-chloro-5-fluorophenyl)carbamate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548.
[2]Patent: CN108503593,2018,A .

14
[ 153505-32-9 ]
tert-butyl (3-chloro-2((5-((2,6-dichloro-3,5-dimethoxybenzyl)oxy)pyrimidin-2-yl)amino)-5-fluorophenyl)carbamate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548.
[2]Patent: CN108503593,2018,A .

15
[ 153505-32-9 ]
6-chloro-N₁-(5-((2,6-dichloro-3,5-dimethoxybenzyl)oxy)pyrimidin-2-yl)-4-fluorobenzene-1,2-diamine [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548.
[2]Patent: CN108503593,2018,A .

16
[ 153505-32-9 ]
3-chloro-5-fluoro-1,2-phenylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.77%	With iron; ammonium chloride; In methanol; water; at 75℃; for 3h;	2-Chloro-4-fluoro-6-nitroaniline (1.904 g, 9.91 mmol) was added sequentially to a 250 ml flask.Ammonium chloride (3.21 g), reduced iron powder (2.234 g), methanol (70 ml) and water (30 ml) were reacted at 75 C for 3 h.The mixture was filtered with Celite, washed with methanol, and evaporated.Washed, concentrated,Column chromatography gave 1.376 g of a solid, yield: 85.77%.

References: [1]Patent: CN108503593,2018,A .Location in patent: Paragraph 0072; 0075; 0084; 0085.
[2]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548.

17
[ 153505-32-9 ]
5-chloro-7-fluoro-1,4-dihydroquinoxaline-2,3-dione [ No CAS ]

References: [1]Patent: US5514680,1996,A .

18
[ 153505-32-9 ]
5-chloro-6-nitro-7-fluoro-1,4-dihydro-2,3-quinoxalinedione [ No CAS ]

References: [1]Patent: US5514680,1996,A .

19
[ 153505-32-9 ]
C₁₇H₁₈BrF₂NO₃ [ No CAS ]
C₂₃H₂₁ClF₃N₃O₅ [ No CAS ]