| Identification | More | [Name]
1-(5-Chloro-2-hydroxyphenyl)ethanone | [CAS]
1450-74-4 | [Synonyms]
1-(5-CHLORO-2-HYDROXYPHENYL)-1-ETHANONE
1-(5-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE
1-(5-CHLORO-2-HYDROXYPHENYL)ETHANONE
2'-HYDROXY-5'-CHLORO ACETOPHENONE
2-HYDROXY-5-CHLORO ACETOPHENONE
5'-CHLORO-2'-HYDROXYACETOPHENONE
5-CHLORO-2-HYDROXYACETOPHENONE
AKOS BB-6937
ASISCHEM D38764
SALOR-INT L497495-1EA
2-Acetyl-4-chlorophenol
Acetophenone, 5'-chloro-2'-hydroxy-
Acetophenone,5-chloro-2-hydroxy-
5'-Chloro-2'-Hydroxy Acetophenone 2'-Hydorxy-5'-Chloro Acetophenone
2'-Hydorxy-5'-ChloroAcetophenone | [EINECS(EC#)]
215-916-8 | [Molecular Formula]
C8H7ClO2 | [MDL Number]
MFCD00067788 | [Molecular Weight]
170.59 | [MOL File]
1450-74-4.mol |
| Chemical Properties | Back Directory | [Appearance]
slightly yellow crystalline powder or chunks | [Melting point ]
54-56 °C(lit.) | [Boiling point ]
126-128 °C28 mm Hg(lit.) | [density ]
1.2315 (rough estimate) | [refractive index ]
1.5590 (estimate) | [Fp ]
107-109°C/12mm | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Solid | [pka]
9.72±0.18(Predicted) | [BRN ]
1365589 | [InChI]
InChI=1S/C8H7ClO2/c1-5(10)7-4-6(9)2-3-8(7)11/h2-4,11H,1H3 | [InChIKey]
XTGCUDZCCIRWHL-UHFFFAOYSA-N | [SMILES]
C(=O)(C1=CC(Cl)=CC=C1O)C | [CAS DataBase Reference]
1450-74-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethanone, 1-(5-chloro-2-hydroxyphenyl)-(1450-74-4) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29147000 |
| Hazard Information | Back Directory | [Chemical Properties]
slightly yellow crystalline powder or chunks | [Uses]
5′-Chloro-2′-hydroxyacetophenone (5-chloro-2- hydroxyacetophenone) may be used in the synthesis of:
- 6-chloro-2-methyl-4H-chrome-4-one
- 1-(2-hydroxyphenyl)-5-phenyl-2,4-pentadien-1-ones
- 1-(2-hydroxyphenyl)-5-phenyl-2,4-pentadien-1-ones
- 2-styrenyl allyl ether
| [Preparation]
Preparation by Fries rearrangement of 4-chlorophenyl acetate with aluminium chloride without solvent between 110° and 200°(90–100% yield). | [General Description]
5′-Chloro-2′-hydroxyacetophenone (5-chloro-2- hydroxyacetophenone) on condensation with salicylhydrazide yields Schiff base, which is reported to form copper(II) complexes. Dipole moment of 5-chloro-2- hydroxyacetophenone has been evaluated in benzene solution. | [Synthesis]
General procedure for the synthesis of 5'-chloro-2'-hydroxyacetophenone from acetic acid-4-chlorophenyl ester: Acetic acid-4-chlorophenyl ester (10 g, 0.091 mol) was placed in a 500 ml round-bottomed flask with aluminum chloride (14.56 g, 0.11 mol). The mixture was heated in an oil bath at 140-150°C for 5-6 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) using ethyl acetate:hexane as the unfolding agent. Upon completion of the reaction, the reaction mixture was quenched with crushed ice and the solid product was extracted with ethyl acetate (2 x 50 mL). The organic phases were combined, washed with saturated brine solution (2 x 15 mL) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by recrystallization from aqueous solution. The yield is 90% and the melting point is 54-56°C. | [References]
[1] Chinese Chemical Letters, 2016, vol. 27, # 7, p. 1058 - 1063
[2] Synthesis, 1985, # 9, p. 901 - 902
[3] Tetrahedron, 2011, vol. 67, # 3, p. 641 - 649
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 2, p. 184 - 185
[5] Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 151 - 156 |
|
|