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ChemicalBook--->CAS DataBase List--->67818-41-1

67818-41-1

67818-41-1 Structure

67818-41-1 Structure
IdentificationBack Directory
[Name]

1-(2-CHLORO-4-NITROPHENYL)ETHAN-1-ONE
[CAS]

67818-41-1
[Synonyms]

NSC 231605
2'-CHLORO-4'-NITROACETOPHENONE
1-(2-chloro-4-nitrophenyl)ethanone
1-(2-CHLORO-4-NITROPHENYL)ETHAN-1-ONE
Ethanone, 1-(2-chloro-4-nitrophenyl)-
1-(2-CHLORO-4-NITROPHENYL)ETHAN-1-ONE ISO 9001:2015 REACH
[Molecular Formula]

C8H6ClNO3
[MDL Number]

MFCD00017340
[MOL File]

67818-41-1.mol
[Molecular Weight]

199.59
Chemical PropertiesBack Directory
[Melting point ]

43.0 to 47.0 °C
[Boiling point ]

270.9±20.0 °C(Predicted)
[density ]

1.378±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[form ]

powder to crystal
[color ]

Light yellow to Yellow to Orange
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
[HS Code ]

2914790090
Hazard InformationBack Directory
[Uses]

1-(2-Chloro-4-nitrophenyl)ethanone is used in the preparation of Propiconazole (P770100) as haptens in manufacture of antibodies with hybridomas for immunoassay.
[Synthesis]

2-CHLORO-4-NITROBENZOYL CHLORIDE

7073-36-1

Diethyl malonate

105-53-3

1-(2-CHLORO-4-NITROPHENYL)ETHAN-1-ONE

67818-41-1

Step 5: Synthesis of 1-(2-chloro-4-nitrophenyl)ethanone (7) Anhydrous magnesium chloride (47 g, 0.214 mol, 0.7 eq.) was suspended in toluene (300 mL) under dry conditions, followed by the addition of triethylamine (75.04 mL, 0.535 mol, 2.5 eq.) and diethyl malonate (41.09 g, 0.257 mol, 1.2 eq.). The reaction mixture was stirred at room temperature for 1.5 hours. 2-Chloro-4-nitrobenzoyl chloride (6) (47 g, 0.214 mol, 1 eq.) was slowly added dropwise, and an exothermic increase in temperature to 50 °C was observed during the dropwise addition. Flush with toluene (50 mL) to ensure complete transfer of 2-chloro-4-nitrobenzoyl chloride to the reaction system. The reaction mixture was continued to be stirred at room temperature for 18 h. The reaction progress was monitored by thin layer chromatography (TLC) and nuclear magnetic resonance (NMR). After complete consumption of the feedstock, 35% concentrated hydrochloric acid (300 mL) was added to separate the toluene layer. The toluene layer was concentrated under reduced pressure (temperature below 50 °C). Dimethyl sulfoxide (DMSO) (200 mL) and water (10 mL) were added to the residue and the mixture was heated at 160 °C for 12 h. The reaction progress was followed by TLC and NMR. After the reaction mixture was cooled to room temperature, water (40 mL) was added and extracted with ethyl acetate (EtOAc) (3 x 200 mL). The organic phases were combined, washed with saturated brine (3 × 300 mL) and dried over anhydrous sodium sulfate. The EtOAc layer was concentrated under reduced pressure to give a yellow liquid 1-(2-chloro-4-nitrophenyl)ethanone (7) (43 g, 84% yield), which was cooled and solidified. 1H NMR (400 MHz, CDCl3): δ (ppm): 8.29 (d, J = 2.2 Hz, 1H), 8.17 (dd, J = 8.5, 2.1 Hz, 1H), 7.65 (d, J = 8.4 Hz, 1H), 2.66 (s, 3H).

[References]

[1] Patent: WO2015/31650, 2015, A1. Location in patent: Paragraph 0189
[2] Patent: US2018/28518, 2018, A1. Location in patent: Paragraph 0432; 0471; 0476
Spectrum DetailBack Directory
[Spectrum Detail]

1-(2-CHLORO-4-NITROPHENYL)ETHAN-1-ONE(67818-41-1)1HNMR
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