13100-05-5

Basic information

• Product Name: O-hydroxyphenyl acetone
• Synonyms: O-hydroxyphenyl acetone
• CAS NO: 13100-05-5
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150
• Mol File: 13100-05-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 15 °C
• Boiling Point: 274.2 °C at 760 mmHg
• Flash Point: 114.5 °C
• Appearance: /
• Density: 1.118 g/cm³
• Storage Temp.: 2-8°C
• PKA: 9.88±0.30(Predicted)
• CAS DataBase Reference: O-hydroxyphenyl acetone(CAS DataBase Reference)
• NIST Chemistry Reference: O-hydroxyphenyl acetone(13100-05-5)
• EPA Substance Registry System: O-hydroxyphenyl acetone(13100-05-5)

Safety Data

• Hazardous Substances Data: 13100-05-5(Hazardous Substances Data)

Usage

General Description

O-hydroxyphenyl acetone, also known as 3'-hydroxyacetophenone, is a chemical compound with the molecular formula C8H8O2. It is a colorless to pale yellow liquid with a sweet, floral odor, and it is commonly used in the fragrance industry as an ingredient due to its pleasant smell. O-hydroxyphenyl acetone is also used in the synthesis of various pharmaceuticals and as a chemical intermediate in the production of other compounds. It is considered to be relatively stable, but care should be taken to avoid contact with skin and eyes, as well as ingestion or inhalation, as it can cause irritation and other adverse effects.

Synthetic route

(E)-2-(2-nitroprop-1-en-1-yl) phenol (86029-73-4) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
With sodium hypophosphite; nickel In ethanol; water at 40 - 60℃; for 2h;	70%

2-(bromomethyl)phenyl acetate (704-65-4) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
With chromium dichloride In tetrahydrofuran Heating;	65%
With chromium dichloride; water; ammonium chloride 1.) THF, reflux, 5 h; 2.) ether/THF; Yield given. Multistep reaction;

3-acetylbenzofuran-2-ylacetic acid (93680-68-3) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
With sodium hydroxide In water at 90℃; for 2h;	58%

2-methylphenyl acetate (533-18-6) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
	57%

(E)-2-propenylphenol (23619-59-2) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In dichloromethane at 40℃; for 2h;	56%
With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium
Multi-step reaction with 2 steps 1: 2) m-chloroperbenzoic acid / 1) O-acetylation 2: 2 N Na2CO3 / Heating View Scheme

2-(prop-1-enyl)phenol (6380-21-8) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
With peracetic acid; diethyl ether
With peracetic acid; ethyl acetate

1-acetoxy-1-(2-hydroxy-phenyl)-propan-2-ol → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
at 230℃; ohne Loesungsmittel;

peracetic acid (79-21-0) + (E)-2-propenylphenol (23619-59-2) + ethyl acetate (141-78-6) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

1-(2-Hydroxyphenyl)-2-methyloxiran → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
With sodium carbonate Heating;

1-(2-methoxyphenyl)propan-2-one (5211-62-1) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
With chloro-trimethyl-silane; sodium iodide Yield given;

ortoquinone (583-63-1) + acetone (67-64-1) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
(i) Al2O3, (ii) Zn, AcOH; Multistep reaction;

2-Allylphenol (1745-81-9) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / [(HOCH2CH2NHCOCH2)2NCH2]2 / Pd(OCOCF3)2 / H2O; methanol / 24 h / 50 °C 2: VO(acac)2; t-BuOOH View Scheme

4-iodoanisol (529-28-2) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / tBuOK / liquid ammonia / -33 °C / Irradiation 2: ClSiMe3, NaI View Scheme

1-(2-hydroxyphenyl)-2-nitropropane → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
With sodium hydroxide In methanol; water for 0.0833333h; Nef reaction;

1-(2-methoxyphenyl)-2-nitropropene (6306-34-9) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; sodium hydroxide / ethanol / 1 h / 0 °C 2: boron tribromide / chloroform / -78 - 20 °C / Inert atmosphere 3: sodium hydroxide / methanol; water / 0.08 h View Scheme

1-(2'-methoxyphenyl)-2-nitropropane (34322-76-4) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: boron tribromide / chloroform / -78 - 20 °C / Inert atmosphere 2: sodium hydroxide / methanol; water / 0.08 h View Scheme

ortho-anisaldehyde (135-02-4) → 1-(2-hydroxyphenyl)propan-2-one (13100-05-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: ammonium acetate / Reflux 2: sodium tetrahydroborate; sodium hydroxide / ethanol / 1 h / 0 °C 3: boron tribromide / chloroform / -78 - 20 °C / Inert atmosphere 4: sodium hydroxide / methanol; water / 0.08 h View Scheme

1-(2-hydroxyphenyl)propan-2-one (13100-05-5) + benzoyl chloride (98-88-4) → o-benzoyloxyphenylacetone (86358-85-2)

Conditions	Yield
With pyridine; dmap In tetrahydrofuran at 0 - 20℃;	71%
With pyridine; dmap In tetrahydrofuran at 20℃;	71%

1-(2-hydroxyphenyl)propan-2-one (13100-05-5) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (E)-ethyl 3-(2-hydroxyphenyl)-2-methylacrylate (106929-19-5)

Conditions	Yield
In dichloromethane at 20℃; Sealed tube;	69%

1-(2-hydroxyphenyl)propan-2-one (13100-05-5) + lead(IV) tetraacetate (546-67-8) → (RS)-6-acetoxy-6-(2-oxopropyl)cyclohexa-2,4-dien-1-one (198201-05-7) + 4,4-dimethoxy-2-(2-oxopropyl)cyclohexa-2,5-dien-1-one + 6,6-diacetoxy-2-(2-oxopropyl)cyclohexa-2,4-dien-1-one

Conditions	Yield
With boron trifluoride diethyl etherate In methanol; ethyl acetate for 0.166667h;	A 39% B 8% C 12%

1-(2-hydroxyphenyl)propan-2-one (13100-05-5) → 2-methylbenzofuran (4265-25-2)

Conditions	Yield
bei 2-taegigen Aufbewahren ueber Schwefelsaeure in Exiccator.;
With trifluoroacetic acid In dichloromethane for 6h;

1-(2-hydroxyphenyl)propan-2-one (13100-05-5) + acetic anhydride (108-24-7) → 1-(2-acetoxyphenyl)-2-propanone (115144-87-1)

O-Methylhydroxylamin (67-62-9) + 1-(2-hydroxyphenyl)propan-2-one (13100-05-5) → (E)-1-(2-hydroxyphenyl)propan-2-one O-methyloxime (58484-61-0)

1-(2-hydroxyphenyl)propan-2-one (13100-05-5) → C9H13NO

Conditions	Yield
With NADH In aq. buffer at 25℃; pH=9.6; Kinetics;

1-(2-hydroxyphenyl)propan-2-one (13100-05-5) → 7-methyl-3-(tetrahydrothiophen-2-yl)-2H-chromen-2-one

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 20 °C / Sealed tube 2: 1,4-diaza-bicyclo[2.2.2]octane; tris(bipyridine)ruthenium(II) dichloride hexahydrate; tert.-butylhydroperoxide / acetonitrile; tetrahydrofuran; decane / 25 °C / Irradiation; Inert atmosphere View Scheme

1-(2-hydroxyphenyl)propan-2-one (13100-05-5) → 3-methylcoumarine (2445-82-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 20 °C / Sealed tube 2: 1,4-diaza-bicyclo[2.2.2]octane; tris(bipyridine)ruthenium(II) dichloride hexahydrate; tert.-butylhydroperoxide / acetonitrile; tetrahydrofuran; decane / 25 °C / Irradiation; Inert atmosphere View Scheme

Upstream product

• 79-21-0 peracetic acid 
• 23619-59-2 (E)-2-propenylphenol 
• 141-78-6 ethyl acetate 
• 533-18-6 2-methylphenyl acetate 
• 135-02-4 ortho-anisaldehyde 
• 34322-76-4 1-(2'-methoxyphenyl)-2-nitropropane 
• 6306-34-9 1-(2-methoxyphenyl)-2-nitropropene 
• 529-28-2 4-iodoanisol 
• 1745-81-9 o-Allylphenol 
• 583-63-1 ortoquinone 
• 67-64-1 acetone 
• 93680-68-3 3-acetylbenzofuran-2-ylacetic acid 
• 86029-73-4 (E)-2-(2-nitroprop-1-en-1-yl) phenol 
• 5211-62-1 1-(2-methoxyphenyl)propan-2-one 

Downstream Products

• 4265-25-2 2-methylbenzofuran 
• 2445-82-1 3-methylcoumarine 
• 106929-19-5 (E)-ethyl 3-(2-hydroxyphenyl)-2-methylacrylate 
• 58484-61-0 (E)-1-(2-hydroxyphenyl)propan-2-one O-methyloxime 
• 198201-05-7 (RS)-6-acetoxy-6-(2-oxopropyl)cyclohexa-2,4-dien-1-one 
• 115144-87-1 1-(2-acetoxyphenyl)-2-propanone 

Relevant articles and documents

Novel highly regioselective VO(acac)2/TBHP mediated oxidation of o-alkenyl phenols to o-hydroxybenzyl ketones

A novel mild methodology for the preparation of o-hydroxybenzyl ketones is described starting from o-alkenyl phenols and based on the VO(acac)2/TBHP (2 mol %/1.2 equiv) system. VO(acac)2 first catalyzes the epoxidation of o-alkenyl phenols and then the rearrangement of the epoxyphenols to ketones via the selective benzylic C-O cleavage and 1,2 hydride migration. The protocol has also been applied to set up a useful and easy one-pot conversion of o-alkenyl phenols to benzo[b]furans by means of the sequential addition of TFA, after the generation of the intermediate o-hydroxybenzyl ketones.

Mechanistic insights into the palladiumII-catalyzed hydroxyalkoxylation of 2-allylphenols

The Pd(OCOCF3)2/[(HOCH2CH 2NHCOCH2)2NCH2]2- catalyzed oxidation of o-allylphenol with H2O2 in water/methanol affords a syn and anti mixture of 2-(1,2-dihydroxypropyl)phenol and 2-(2-hydroxy-1-methoxypropyl)phenol. Mechanistic experiments and ESI-MS studies support a pathway wherein isomerization of the C=C bond followed by its epoxidation and oxirane opening led to the products. Recycling of the catalytic system led to gradual lost of activity.

Methods of treating conditions associated with an EDG-2 receptor

In one aspect, the present invention provides a method for modulating an Edg-2 receptor mediated biological activity in a cell. A cell expressing the Edg-2 receptor is contacted with an modulator of the Edg-2 receptor, which modulates the Edg-2 receptor mediated biological activity. In another aspect, the present invention provides a method for modulating Edg-2 receptor mediated biological activity in a subject. A therapeutically effective amount of an modulator of the Edg-2 receptor is administered to the subject.