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3-Chloropropiophenone

3-Chloropropiophenone structure

CAS No:
936-59-4
Formula:
C9H9ClO
Chemical Name:
3-Chloropropiophenone
Synonyms:
1-Propanone,3-chloro-1-phenyl-;Propiophenone,3-chloro-;3-Chloro-1-phenyl-1-propanone;β-Chloroethyl phenyl ketone;β-Chloropropiophenone;3-Chloropropiophenone;ω-Chloropropiophenone;2-Chloroethyl phenyl ketone;NSC 227202;NSC 37238;1-Phenyl-3-chloro-1-propanone;3-Chloro-1-phenylpropan-1-one;β-Chloropropanophenone
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

faintly yellow to tan crystalline powder

3-Chloropropiophenone Basic Attributes

Molecular Weight：

168.62

Exact Mass：

168.62

EC Number：

213-317-6

NSC Number：

227202|37238

DSSTox ID：

DTXSID5061324

HScode：

2914700090

Characteristics

PSA：

17.1

XLogP3：

2.2

Appearance：

faintly yellow to tan crystalline powder

Density：

1.0983 g/cm³ @ Temp: 20 °C

Melting Point：

57 °C

Boiling Point：

255-265 °C

Flash Point：

127.0±13.7 °C

Refractive Index：

1.527

Water Solubility：

H2O: Insoluble

Storage Conditions：

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S37/39-S26

Marks：

Xi:Irritant;

Stability/Shelf Life：

Stable. Incompatible with strong bases, strong oxidizing agents.

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (53.85%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 14 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

3-chloro-1-phenylpropan-1-one

3-Chloropropiophenone Use and Manufacturing

Methods of Manufacturing

General procedure: Under nitrogen atmosphere, to a solution of substrate alcohol (0.5 mmol) in aceticacid (1.0 mL) was added a stock-solution of aqueous NaBr solution (1.94 M, 25 μL)and 30percent aqueous H2O2 (50 μL, 0.5 mmol). After stirring the mixture for one hour at60 °C, additional 30percent aqueous H2O2 (50 μL, 0.5 mmol) was added, and stirring wascontinued for another one hour. After cooling, the mixture was poured into a saturatedaqueous NaHCO3 solution (ca. 30 mL) with the aid of CH2Cl2, and resulting mixturewas extracted with CH2Cl2. The combined organic layers were dried over anhydrousMgSO4, filtered and concentrated in vacuo. The residue was chromatographed onsilica gel (flash column or preparative TLC) to afford the corresponding ketone.3-Chloropropionyl chloride (0.151 g; 1.19 mmol) followed by anhydrous benzene (0.084 g; 1.08 mmol) were added in a dropwise fashion to a solution of aluminum trichloride(0.173 g; 1.30 mmol) dissolved in anhydrous CHTo a solution of 3-chloropropanoic acid (17.5 g, 189.8 mmol) in benzene (100 mL) was added thionyl chloride (45.2 g, 379.6 mmol, 28 mL) at room temperature. The resulting mixture was heated at 80-90°C for 4h. Excess thionyl chloride was removed by azeotropic distillation with dry benzene. 3-Chloropropionyl chloride thus obtained was diluted with benzene (150 mL). Anhydrous aluminum chloride (45 g, 340.0 mmol) was added slowly into flask over a period of 6h at 0-5°C under stirring. The reaction mixture was further stirred at 0-5°C for 2h. Excess aluminum chloride was decomposed carefully in ice-water and the reaction mixture was extracted with ethyl acetate (30 mL x 3). Combined organic layer was washed with water (10 mL x 5) to neutral pH and dried over sodium sulfate. Sodium sulfate was filtered off, washed with ethyl acetate (10 mL x 2) and the filtrate was concentrated under reduced pressure to give crude product, which was purified by column chromatography (5percent ethyl acetate/hexane) to provide 21.0 g of compound 2. Brown solid; Yield 69percent; Mp 46-49°C; IR (KBr): 3110, 2922, 1670 cmIn a 25 mL reaction flask, ferric chloride (0.05 mmol), ene 1ag (0.5 mmol), tetraphenyl disilane (2.0 mmol) and tert-butanol (2.0 mL) were added successively to the 25 mL reaction flask.After mixing at room temperature, the reaction mixture was reacted at 80 ° C for 24 h.The reaction was completed, aqueous ammonia (0.5 mL) was added and stirred for 1 h.Then, 5 mL of water was added and extracted with ether (5 mL x 3). The organic phases were combined and the solvent was evaporated under reduced pressure. Column chromatography gave 90percent yield.

Uses

3-Chloropropiophenone is an Impurity of Fluoxetine (F597100).

Manufacturing Info：

1-Propanone, 3-chloro-1-phenyl-: ACTIVE

Computed Properties

Molecular Weight:168.62
XLogP3:2.2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:168.0341926
Monoisotopic Mass:168.0341926
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:128
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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