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| CAS No.: | 2648-61-5 |
|---|---|
| Name: | 2,2-DICHLOROACETOPHENONE |
| Article Data: | 112 |
| Molecular Structure: | |
|
|
|
| Formula: | C8H6 Cl2 O |
| Molecular Weight: | 189.041 |
| Synonyms: | Acetophenone,2,2-dichloro- (6CI,7CI,8CI); 2,2-Dichloro-1-phenylethanone;2,2-Dichloroacetophenone; NSC 53617; Phenacylidene dichloride; a,a-Dichloroacetophenone; w,w-Dichloroacetophenone |
| Density: | 1.34 g/mL at 25 °C(lit.) |
| Melting Point: | 21oC |
| Boiling Point: | 132-134 °C13 mm Hg(lit.) |
| Flash Point: | >230 °F |
| Appearance: | CLEAR COLOURLESS TO SLIGHTLY PINK LIQUID |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | R36/37/38; |
| Safety: | Poison by intravenous route. Moderately toxic by inhalation. When heated to decomposition it emits toxic fumes of Cl−. |
| PSA: | 17.07000 |
| LogP: | 2.67300 |
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N-(2,2-dichloro-3-oxo-1,3-diphenylpropyl)phenylsulfonamide
- 2648-61-5
2,2-dichloroacetophenone
| Conditions | Yield |
|---|---|
| With potassium hydroxide In tetrahydrofuran; water at 20℃; for 4h; retro-aldol reaction; | 100% |
| Conditions | Yield |
|---|---|
| With chlorine In methanol at 40℃; under 760.051 - 1520.1 Torr; Solvent; Temperature; | 99.1% |
| With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; N-chloro-succinimide at 70℃; Green chemistry; | 96% |
| With chlorine In acetic acid at 51 - 56℃; for 4.5h; | 95.5% |
| Conditions | Yield |
|---|---|
| With Oxone; potassium chloride In water; acetonitrile at 20℃; for 0.166667h; Reagent/catalyst; | 98% |
| With trichloroisocyanuric acid; p-methylphenylthiourea; water at 20℃; for 0.333333h; Reagent/catalyst; Temperature; Sealed tube; Sonication; Green chemistry; chemoselective reaction; | 92% |
| With hydrogenchloride; sulfuric acid; lithium perchlorate In water; acetonitrile at 10 - 20℃; for 4.25h; Mechanism; Reagent/catalyst; Electrochemical reaction; Electrolysis; Green chemistry; | 92% |
| Conditions | Yield |
|---|---|
| With methanol; triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Appel Halogenation; Inert atmosphere; chemoselective reaction; | 97% |
| With 10% Pt/activated carbon; hydrogen In N,N-dimethyl acetamide at 25℃; under 760.051 Torr; for 0.7h; Catalytic behavior; chemoselective reaction; | 89% |
| With palladium 10% on activated carbon; hydrogen In N,N-dimethyl acetamide at 25℃; under 760.051 Torr; for 0.7h; chemoselective reaction; | 88% |
| Conditions | Yield |
|---|---|
| With methyllithium lithium bromide; diisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; chemoselective reaction; | 90% |
- 95-68-1
2,4-Xylidine
- 160663-32-1
benzoyl(dichloro)acetaldehyde
A
- 2648-61-5
2,2-dichloroacetophenone
B
- 60397-77-5
N-(2,4-dimethylphenyl)formamide
| Conditions | Yield |
|---|---|
| In tetrachloromethane for 12h; Ambient temperature; | A 80% B 89% |
- 160663-32-1
benzoyl(dichloro)acetaldehyde
A
- 2648-61-5
2,2-dichloroacetophenone
B
- 60397-77-5
N-(2,4-dimethylphenyl)formamide
| Conditions | Yield |
|---|---|
| With 2,4-Xylidine In tetrachloromethane for 12h; Ambient temperature; | A 80% B 89% |
| Conditions | Yield |
|---|---|
| With trichloroisocyanuric acid; p-methylphenylthiourea; water at 20℃; for 0.333333h; Sealed tube; Sonication; Green chemistry; chemoselective reaction; | 88% |
- 20718-17-6
2-(dimethyl(oxo)-λ6-sulfaneylidene)-1-phenylethan-1-one
- 2648-61-5
2,2-dichloroacetophenone
| Conditions | Yield |
|---|---|
| With trichloroisocyanuric acid; tetrabutyl-ammonium chloride In tetrahydrofuran at 0 - 25℃; for 24h; Sealed tube; | 87% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; dihydrogen peroxide In ethanol at 91 - 93℃; for 0.25h; Product distribution; Further Variations:; Solvents; Temperatures; time; | A 85% B 4.5% |
| With N-chloro-succinimide; 1-(n-butyl)-3-methylimidazolium triflate at 70℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Concentration; Green chemistry; | A n/a B 74% |
| With N-chloro-succinimide; toluene-4-sulfonic acid at 20℃; for 24h; | A 4% B 70% |
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Chemistry
IUPAC Name: 2,2-Dichloro-1-phenylethanone
Product Name: 2,2-Dichloro-1-phenylethanone
The MF of 2,2-Dichloro-1-phenylethanone (CAS NO.2648-61-5) is C8H6Cl2O.
The MW of 2,2-Dichloro-1-phenylethanone (CAS NO.2648-61-5) is 189.04.
Synonyms of 2,2-Dichloro-1-phenylethanone (CAS NO.2648-61-5): 2,2-Dichloroacetophenone ; alpha,alpha-Dichloroacetophenone ; Phenacylidene chloride
Product Categories: C7 to C8;Carbonyl Compounds;Ketones
Form: clear colourless to slightly pink liquid
Index of Refraction: 1.55
EINECS: 202-783-6
Density: 1.311 g/ml
Flash Point: 103.6 °C
Boiling Point: 252.3 °C
Melting Point: 20-21 °C
BRN: 1864186
Uses
2,2-Dichloro-1-phenylethanone (CAS NO.2648-61-5) is used as organic intermediates.
Production
The acetophenone dissolved in glacial acetic acid, which leads to dry chlorine to control the reaction temperature does not exceed 60 ℃, until the reaction solution changed yellow.Chlorination process would take about 4-5h. The reactants with the ice water treatment, oil-like 2,2 - dichloro-acetophenone that is separated from the water.
Toxicity Data With Reference
| 1. | ihl-mus LCLo:940 mg/m3/10M | NDRC** National Defense Research Committee, Office of Scientific Research and Development, Progress Report NDCrc-132,Aug ,1942. | ||
| 2. | ivn-mus LD50:100 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#03021 . |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Poison by intravenous route. Moderately toxic by inhalation. When heated to decomposition it emits toxic fumes of Cl−.Safety information of 2,2-Dichloro-1-phenylethanone (CAS NO.2648-61-5):
Hazard Codes 
Xn,Xi
Risk Statements
36/37/38 Irritating to eyes, respiratory system and skin
Safety Statements
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
27 Take off immediately all contaminated clothing
28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
36/37/39 Wear suitable protective clothing, gloves and eye/face protection
7/9 Keep container tightly closed and in a well-ventilated place
RIDADR UN 2810 6.1/PG 2
WGK Germany 3
RTECS AM7175000
PackingGroup II