| Identification | More | [Name]
2'-Hydroxypropiophenone | [CAS]
610-99-1 | [Synonyms]
2-HYDROXYPHENYL ETHYL KETONE
2'-HYDROXYPROPIOPHENONE
2-HYDROXYPROPIOPHENONE
ETHYL 2-HYDROXYPHENYL KETONE
O-HYDROXYPROPIOPHENONE
1-(2-Hydroxyphenyl)-1-propanone
1-(2-Hydroxy-phenyl)-propan-1-one
1-Propanone, 1-(2-hydroxyphenyl)-
2-Propionylphenol
o-Propiophenol
Propiophenone, 2'-hydroxy-
2-HYDROXYNITROBENZENE
2''-HYDROXYACETOPHENONEPROPAFENONE
2''-HYDROXYPROPRIOPHENONE
o-Hydroxylpropiophenone
Ethyl o-hydroxyphenyl ketone | [EINECS(EC#)]
210-244-1 | [Molecular Formula]
C9H10O2 | [MDL Number]
MFCD00002220 | [Molecular Weight]
150.17 | [MOL File]
610-99-1.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR BROWNISH LIQUID | [Melting point ]
20-22 °C | [Boiling point ]
115 °C15 mm Hg(lit.) | [density ]
1.094 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.548(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Oil | [pka]
8.33±0.35(Predicted) | [color ]
Colourless | [BRN ]
1860264 | [InChI]
1S/C9H10O2/c1-2-8(10)7-5-3-4-6-9(7)11/h3-6,11H,2H2,1H3 | [InChIKey]
KDUWXMIHHIVXER-UHFFFAOYSA-N | [SMILES]
CCC(=O)c1ccccc1O | [LogP]
2.540 | [CAS DataBase Reference]
610-99-1(CAS DataBase Reference) | [NIST Chemistry Reference]
ortho-Hydroxypropiophenone(610-99-1) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [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 . | [WGK Germany ]
3
| [REACH Registrations]
Active | [HS Code ]
29145090 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR BROWNISH LIQUID | [Definition]
ChEBI: 2'-hydroxypropiophenone is an aromatic ketone. | [Preparation]
Obtained by Fries rearrangement of phenyl propionate
with aluminium chloride in refluxing carbon disulfide ?, then at 130–150° for 2–3 h after solvent elimination (32–35%)
with aluminium chloride in chlorobenzene using microwave irradiation for 3 ? min at 106° (28%)
with aluminium chloride in nitrobenzene at 50° for 18 h (16%) or at ? 20° for 48 h (10%)
with aluminium chloride in nitromethane at 20° for 7 days (20%)
with aluminium chloride in heptane at 80–90° for 7 h (53%) or in tetrachlo-? roethane at 95° for 5 h (43%)
with aluminium chloride without solvent at 250° for 5 min or at 180–200° for ? 15 min (76–78%), at 140–160° (32–35%), at 140°
with zirconium chloride in o-dichlorobenzene at 120° for 3 h (83%)
with titanium tetrachloride in o-dichlorobenzene at 150° for 1 h (62%) ?, in nitromethane at 20° for 7 days (13%) or without solvent at 50° for 10 h (30%)
with titanium tetrabromide in o-dichlorobenzene at 150° for 1 h (60%)
with stannic chloride at 50° for 3 h (25%)
with boron trifluoride at 120–135° for 15 min (15%)
with zinc chloride at 180–200° for 15 min (10%)
with polyphosphoric acid at 100° (13%)
Also obtained by Friedel–Crafts acylation of phenol with propionyl chloride in the presence of aluminium chloride (40%), at 120–130° for 1 h (45%) according to the method
Also obtained by acylation of phenol with propionic acid
in the presence of boron trifluoride at 165° for 1 h (45%) or at 80° for ? 2 h (8%)
in the presence of polyphosphoric acid at 100° for 10 min (by-product)
in the presence of zinc chloride at 160° for 1 h
Also obtained by isomerization of 4-hydroxypropiophenone with aluminium chloride (1.5 equiv) at 165° for 1 h (40%) or at 180–200° for 15 min (55%)
Also obtained by demethylation of 2-propionylanisole with fuming hydrochloric acid (d = 1.19) in a sealed tube at 110° for 6 h
Also obtained (by-product) by heating 3-tert-butyl-4-hydroxypropiophenone with aluminium chloride at 170° for 15 min (13%)
Also obtained by treatment of 2,3-dimethylchromone with sodium ethoxide in boiling ethanol for 30 h according to the method
Also obtained from 2-allylphenol by treatment with perbenzoic acid in ethyl ether, first at 0°, then between 0° and 25° for 24 h (78%)
Also obtained by reaction of 2-bromophenyl propionate in a ethyl ether/hexane/THF mixture at low temperature (?78 to ?95°) with sec-butyllithium to give, after hydrolysis, the titled ketone (metal-promoted Fries rearrangement) (17%)
Also obtained by reaction of ethylmagnesium bromide
with 2-hydroxybenzamide in boiling benzene, followed by hydrolysis ? (30%)
with 2-hydroxy-N,N-diethylbenzamide in boiling benzene, followed by ? hydrolysis (82–84%)
Also isolated by heating of 1-(o-hydroxyphenyl)cyclopropyltrimethylam-monium iodide for 1 h at 140° with 1.5 equiv of N,N-diisopropylethylamine (not water-free) (38%)
Also obtained by hydrolysis of 2-(1-methyliminopropyl)phenol (4aa) with aqueous acetic acid/THF at 40° for 4 h (86%)
Also obtained by photolysis of phenyl propionate in water or in solution containing b-cyclodextrine (254 nm) at 25° for 2 h
Also obtained by treatment of 2-(1-hydroxypropyl)phenol with MnO2 in methylene chloride for 7 h at r.t. |
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