| Identification | More | [Name]
2,5-Dichlorobenzophenone | [CAS]
16611-67-9 | [Synonyms]
2,5-DICHLOROBENZOPHENONE
2,5-Dichlorobenzophenone 98%
(2,5-Dichlorophenyl)-(phenyl)methanone
2,5-Dichlorophenylphenyl ketone | [EINECS(EC#)]
605-427-1 | [Molecular Formula]
C13H8Cl2O | [MDL Number]
MFCD00079746 | [Molecular Weight]
251.11 | [MOL File]
16611-67-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
87-88°C | [Boiling point ]
240-260 °C | [density ]
1.311±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
crystals | [color ]
Off-white to brown | [InChI]
InChI=1S/C13H8Cl2O/c14-10-6-7-12(15)11(8-10)13(16)9-4-2-1-3-5-9/h1-8H | [InChIKey]
FAVKIHMGRWRACA-UHFFFAOYSA-N | [SMILES]
C(C1=CC(Cl)=CC=C1Cl)(C1=CC=CC=C1)=O | [CAS DataBase Reference]
16611-67-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
2,5-Dichlorobenzophenones can be used as starting materials for general, pharmaceutical and polymer synthesis. For example, using such compounds to prepare substituted para-polyphenylenes should proceed readily by metal-catalyzed aryl coupling of the 2,5-dichlorophenyl group of these compounds. Polyphenylenes formed from these compounds will have pendant side groups comprising the carbonyl, and the aryl or pyridyl group bonded thereto. | [Synthesis]
To a 22 L, three-necked flask fitted with a thermometer, mechanical stirrer and a Vigreux column connected to an aqueous NaOH scrubbing tower, was added 1,4-dichlorobenzene (3 Kg, 26.4 mol) and benzoyl chloride (2.6 Kg, 18.55 mol). The mixture was heated to 80° C. to give a homogeneous solution. Aluminum chloride (5.5 Kg, 41.25 mol) was added over 12 min. with stirring. (The molar ratio of reactants was 2.2:1.4:1.0 (AlCl3 : Dichlorobenzene: Benzoyl Chloride)). The resulting mixture was heated to 140° C. over 60 min, followed by heating to 175° C. over 30 min. The heating was stopped at 175° C. The mixture was allowed to cool to 80° C. over two hours and poured into a well-stirred mixture of ice and water (ca. 25 L water and 15 Kg of ice) over 30 min. The organic solid was collected by filtration and dissolved in 7 L of toluene. The solution was washed with aqueous sodium bicarbonate and dried. Toluene was removed by distillation. Pure 2,5-dichlorobenzophenone was isolated in 80% yield after recrystallization from hexane and toluene.
| [References]
[1] Patent: US5210313, 1993, A
[2] Patent: US5210313, 1993, A
[3] Recueil des Travaux Chimiques des Pays-Bas, 1931, vol. 50, p. 753,779
[4] Journal fuer Praktische Chemie (Leipzig), 1933, vol. <2> 138, p. 311 |
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