| Identification | Back Directory | [Name]
3,4-DICHLOROPHENETHYL ALCOHOL | [CAS]
35364-79-5 | [Synonyms]
3,4-Dichlorobenzeneethanol
2-(3,4-DICHLOROPHENYL)ETHANOL
3,4-DICHLOROPHENETHYL ALCOHOL
3,4-DICHLOROPHENETHYLALCOHOL 97%
3,4-Dichlorophenethyl alcohol,97%
3,4-Dichlorophenethyl alcohol, 97% 5GR | [Molecular Formula]
C8H8Cl2O | [MDL Number]
MFCD00800673 | [MOL File]
35364-79-5.mol | [Molecular Weight]
191.05 |
| Chemical Properties | Back Directory | [Appearance]
clear colorless liquid | [Boiling point ]
165 °C / 14mmHg | [density ]
1.32 | [refractive index ]
1.562-1.568
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Dichloromethane, Ethyl Acetate | [form ]
Liquid | [color ]
Clear colorless | [InChI]
InChI=1S/C8H8Cl2O/c9-7-2-1-6(3-4-11)5-8(7)10/h1-2,5,11H,3-4H2 | [InChIKey]
GITOMJDYNUMCOV-UHFFFAOYSA-N | [SMILES]
C1(CCO)=CC=C(Cl)C(Cl)=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless liquid | [Uses]
Intermediate in the synthesis of σ receptor ligands. | [Synthesis]
General procedure for the synthesis of 2-(3,4-dichlorophenyl)ethanol from 3,4-dichlorophenylacetic acid: 97% lithium aluminum hydride (LiAlH4, 5.54 g, 141.63 mmol) was added batchwise to an ice-bath-cooled solution of 2-(3,4-dichlorophenyl)acetic acid (19.36 g, 94.42 mmol) in tetrahydrofuran (THF, 200 mL). After the addition was completed, the reaction mixture was stirred at room temperature for 5 hours. Upon completion of the reaction, the mixture was slowly poured into ice water (150 mL) and stirring was continued for 0.5 hours. Subsequently, THF was evaporated under reduced pressure and extracted by adding dichloromethane (DCM, 200 mL). The organic layer was separated, washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/5, v/v) to afford the target compound 2-(3,4-dichlorophenyl)ethanol (17.14 g, 95% yield) as a colorless oil. | [References]
[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2818 - 2841
[2] Journal of Medicinal Chemistry, 1990, vol. 33, # 11, p. 3100 - 3110
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 24, p. 5420 - 5423
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 3, p. 756 - 760
[5] Journal of the American Chemical Society, 1956, vol. 78, p. 5612 |
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