2-Chloro-5-acetylpyridine
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2-Chloro-5-acetylpyridine
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CAS No:
55676-22-7
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Formula:
C7H6ClNO
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Chemical Name:
2-Chloro-5-acetylpyridine
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Synonyms:
1-(6-CHLORO-3-PYRIDINYL)-1-ETHANONE;1-(6-CHLOROPYRIDIN-3-YL)ETHANONE;2-CHLORO-5-ACETYLPYRIDINE;6-CHLORO-3-ACETYLPYRIDINE;1-(6-CHLOROPYRIDIN-3-YL)ETHANONE ,97%;1-(6-Chloropyridin-3-yl)ethan-1-one;5-Acetyl-2-chloropyridine;3-Acetyl-6-chloropyridine
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CAS No:
Safety Information
IRRITANT
22-36
26
Xn
Harmful
P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
H301
|Danger|H301 (33.33%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Chloro-5-acetylpyridine Use and Manufacturing
Step 3 1-(6-Chloropyridin-3-yl)ethanone: A solution of dimethyl 2-(6-chloronicotinoyl)malonate (89.8 g, 331 mmol) in DMSO (445 mL) and water (11 mL) was heated at 130° C. for 2.5 hours. The reaction mixture was cooled and poured into HA suspension of dimethyl malonate (7.8 mL, 68.3 mmol), MgCI2 (3.872 g, 40.7 mmol), Et3N (19.1 mL, 136.9 mmol) in toluene (15 mL) at room temperature under nitrogen was stirred for 2 h. To this mixture a suspension of 6-chloro-nicotinoyl chloride (3.872 g, 40.7 mmol) and Et3N (4.25 mL, 30.5 mmol) in toluene (46 mL) was added via canula. The resultant reaction mixture was stirred overnight, quenched with 1N HCI (100 mL) and water (100 mL) and extracted with EtOAc. The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated to give white crystalline material (6.5 g) which was dissolved in a mixture DMSO (9 mL) and H20 (0.37 mL), heated at 130ex for 5 h, cooled down to room temperature and treated with water (10 mL). A precipitate formed which was collected by filtration, rinsed with water and dried to afford the title compound 32 (1.8 g, 28percent yield) as pale yellow crystalline solid.A round bottomed flask was charged with 5-bromo-2-chloropyridine (5.30 g, 27.6 mmol) in THF under NCH3MgBr (10 mL of a 3M soln.) was added dropwise to a solution of the product of Step 1 (5.7 g, 28 mmol) in 25 mL of dry THF at 0°C, generating a yellow precipitate. After stirring 1 h at RT, the reaction was quenched with saturated NH4CI solution and the product isolated by extracting with CH2CI2. The product was purified by flash silica gel chromatography and isolated 3.7g (84percent) as white solid. TLC: Rf = 0.6 in 25percentEtOAc/CH2CI2.The BL02 compound dispersed in 1.6kg 8L methyl tertiary ether, 3L of methyl chloride was added dropwise.1 hour.The reaction was stopped, the reaction solution was poured into 10L water and extracted with dichloromethane.The organic phase was washed with water, saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure, to give compound 1.2kg BL03.Preparation 11 1 -(6-Chloropyridin-3 -yl)ethanolAdd sodium tetrahydroborate (1.01 g, 26.35 mmol) slowly to a solution of l-(6- chloro-pyridin-3-yl)-ethanone (10 g, 64.27 mmol) in methanol (100 mL). Stir at RT for 15 min. Pour the reaction mixture into a beaker containing saturated nuaHCtheta3 (40 mL) and then extract between water (100 mL) and DCM (400 mL). Wash the organic layers with saturated aqueous sodium chloride, dry over sodium sulfate and concentrate. Purify by normal phase column chromatography (20 % ethyl acetate in hexanes -> 70 % ethyl acetate in hexanes) to afford the title compound (7 g, 69 %). MS (ES) m/z 158 [M+l]+.
Computed Properties
Molecular Weight:155.58
XLogP3:1.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:155.0137915
Monoisotopic Mass:155.0137915
Topological Polar Surface Area:30
Heavy Atom Count:10
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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