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6285-05-8

Basic Information
CAS No.: 6285-05-8
Name: 4'-Chloropropiophenone
Article Data: 81
Molecular Structure:
Molecular Structure of 6285-05-8 (4'-Chloropropiophenone)
Formula: C9H9ClO
Molecular Weight: 168.623
Synonyms: Propiophenone,4'-chloro- (6CI,7CI,8CI);1-(4-Chlorophenyl)-1-propanone;4-Chloropropiophenone;Ethyl p-chlorophenyl ketone;NSC5600;p-Chloropropiophenone;4'-Chloropropiophenone;
EINECS: 228-511-6
Density: 1.128 g/cm3
Melting Point: 34-37 °C
Boiling Point: 276.6 °C at 760 mmHg
Flash Point: 123.5 °C
Solubility: insoluble in water
Appearance: crystalline mass
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 37/39-26
PSA: 17.07000
LogP: 2.93270
Synthetic route
1745-18-2

1-allyl-4-chlorobenzene

6285-05-8

4'-chloropropiophenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; palladium diacetate; toluene-4-sulfonic acid In water; acetonitrile at 20℃; for 6h; Wacker Oxidation; chemoselective reaction;98%
79-03-8

propionyl chloride

108-90-7

chlorobenzene

6285-05-8

4'-chloropropiophenone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 10 - 25℃; for 2h; Solvent; Temperature; Reagent/catalyst;96.5%
With aluminum (III) chloride at 0 - 60℃; Inert atmosphere;87%
With aluminium trichloride for 3h; Friedel-Crafts acylation; cooling;74%
56962-09-5

1-(4-chlorophenyl)-N-hydroxypropan-1-imine

6285-05-8

4'-chloropropiophenone

Conditions
ConditionsYield
With cetyltrimethylammonium peroxodisulphate In acetonitrile for 0.366667h; Reflux;94%
58824-54-7

p-chlorophenylvinylcarbinol

6285-05-8

4'-chloropropiophenone

Conditions
ConditionsYield
With 2C25H28N2OP(1-)*2Cl(1-)*2Ru(2+) In tetrahydrofuran at 80℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;93%
With tetrapropylammonium perruthennate; undecan-2-ol In fluorobenzene Isomerization; Heating;87%
With C13H21Cl2N3PRu(1+)*Cl(1-); potassium carbonate In tetrahydrofuran at 75℃; for 20h; Catalytic behavior; Inert atmosphere; Sealed tube;80%
99360-14-2

C10H12ClN3O

6285-05-8

4'-chloropropiophenone

Conditions
ConditionsYield
With cetyltrimethylammonium peroxodisulphate In acetonitrile for 0.466667h; Reflux;90%
67-56-1

methanol

3391-10-4

1-(p-chlorophenyl)ethyl alcohol

6285-05-8

4'-chloropropiophenone

Conditions
ConditionsYield
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; potassium hydroxide In water at 80℃; Schlenk technique; Inert atmosphere;90%
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; potassium hydroxide In water at 80℃; for 14h; Schlenk technique; Inert atmosphere; chemoselective reaction;90%

C10H13ClO

6285-05-8

4'-chloropropiophenone

Conditions
ConditionsYield
With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 24h;89%
13856-85-4

1-(4-chlorophenyl)-1-propanol

6285-05-8

4'-chloropropiophenone

Conditions
ConditionsYield
With peracetic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In acetonitrile at 20℃; for 10h;88%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium acetate; (S)-3-phenyl-2-(phenylamino)propionic acid; copper(ll) bromide In water for 24h; Reflux; Schlenk technique;87%
With diisopropoxyaluminium trifluoroacetate; 4-nitrobenzaldehdye In benzene for 0.75h; Ambient temperature;85%
122-01-0

4-chloro-benzoyl chloride

EtMgX

EtMgX

6285-05-8

4'-chloropropiophenone

Conditions
ConditionsYield
With iron(III)-acetylacetonate In tetrahydrofuran at -78℃;87%
1021934-07-5

C9H10BrClO

A

6285-05-8

4'-chloropropiophenone

B

5586-88-9

1-(4-chlorophenyl)propan-2-one

Conditions
ConditionsYield
With diethylzinc In dichloromethane at 20℃; for 2h;A 5%
B 86%
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    CAS No. 6285-05-8 Chemical Name: 4'-Chloropropiophenone Synonyms 1-(4-CHLOROPHENYL)PROPAN-2-ONE;4-CHLOROPROPIOPHENONE;chloropropiophenone;1-(4-CHLORO-PHENYL)-PROPAN-1-ONE;usafek-5296;USAF ek-5296;AKOS B028567;ART-CHEM-BB B028567;4'-Chlorop

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The p-Chloropropiophenone with CAS registry number of 6285-05-8 belongs to the classes of Acetophenone Series; Aromatic Propiophenones (substituted); Ketones; Adehydes, Acetals & Ketones; Chlorine Compounds; Carbonyl Compounds. Its EINECS registry number is 228-511-6. This chemical is also known as 1-(4-Chlorophenyl)-1-propanone. Its IUPAC name and systematic name are the same which is called 1-(4-chlorophenyl)propan-1-one.

Physical properties about this chemical are: (1)ACD/LogP: 2.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.88; (4)ACD/LogD (pH 7.4): 2.88; (5)ACD/BCF (pH 5.5): 91.16; (6)ACD/BCF (pH 7.4): 91.16; (7)ACD/KOC (pH 5.5): 879.94; (8)ACD/KOC (pH 7.4): 879.94; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 17.07 Å2; (13)Index of Refraction: 1.525; (14)Molar Refractivity: 45.8 cm3; (15)Molar Volume: 149.4 cm3; (16)Surface Tension: 36.8 dyne/cm; (17)Density: 1.128 g/cm3; (18)Flash Point: 123.5 °C; (19)Enthalpy of Vaporization: 51.52 kJ/mol; (20)Boiling Point: 276.6 °C at 760 mmHg; (21)Vapour Pressure: 0.00475 mmHg at 25°C; (22)Refractive index: 1.5325-1.5345.

Preparation: this chemical can be prepared by 1-(4-chloro-phenyl)-2-nitro-propan-1-one. This reaction will need reagent Bu3SnH, catalyst AIBN and solvent benzene. The reaction time is 90 min with reaction temperature of 80 °C. The yield is about 78%.

4--Chloropropiophenone can be prepared by 1-(4-chloro-phenyl)-2-nitro-propan-1-one

Uses of p-Chloropropiophenone: it can be used to produce 2-bromo-1-(4-chloro-phenyl)-propan-1-one at temperature of 5 - 20 °C. This reaction is a kind of Bromination. It will need reagent bromine and solvent acetic acid with reaction time of 1.5 hours. The yield is about 95%.

When you are using this chemical, please be cautious about it as the following:
Poison by intraperitoneal and intravenous routes. When heated to decomposition it emits toxic fumes of Cl-. This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c1ccc(Cl)cc1)CC
(2)InChI: InChI=1/C9H9ClO/c1-2-9(11)7-3-5-8(10)6-4-7/h3-6H,2H2,1H3
(3)InChIKey: ADCYRBXQAJXJTD-UHFFFAOYAE

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 100mg/kg (100mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04477,