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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 characterized by a sweet, floral odor. O-hydroxyphenyl acetone is recognized for its stability and is widely utilized in various industries due to its distinctive properties.

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  • 13100-05-5 Structure
  • Basic information

    1. Product Name: O-hydroxyphenyl acetone
    2. Synonyms: O-hydroxyphenyl acetone
    3. CAS NO:13100-05-5
    4. Molecular Formula: C9H10O2
    5. Molecular Weight: 150
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 13100-05-5.mol
  • Chemical Properties

    1. Melting Point: 15 °C
    2. Boiling Point: 274.2 °C at 760 mmHg
    3. Flash Point: 114.5 °C
    4. Appearance: /
    5. Density: 1.118 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. PKA: 9.88±0.30(Predicted)
    10. CAS DataBase Reference: O-hydroxyphenyl acetone(CAS DataBase Reference)
    11. NIST Chemistry Reference: O-hydroxyphenyl acetone(13100-05-5)
    12. EPA Substance Registry System: O-hydroxyphenyl acetone(13100-05-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 13100-05-5(Hazardous Substances Data)

13100-05-5 Usage

Uses

Used in the Fragrance Industry:
O-hydroxyphenyl acetone is used as a fragrance ingredient for its pleasant smell, contributing to the creation of various scent profiles in perfumes, cosmetics, and other scented products.
Used in Pharmaceutical Synthesis:
O-hydroxyphenyl acetone is used as a chemical intermediate in the synthesis of various pharmaceuticals, playing a crucial role in the development of new medications and therapeutic agents.
Used as a Chemical Intermediate in Compound Production:
Beyond its applications in the fragrance and pharmaceutical sectors, O-hydroxyphenyl acetone is also utilized in the production of other compounds, highlighting its versatility as a key component in chemical processes.
It is important to handle O-hydroxyphenyl acetone with care to avoid skin and eye contact, as well as ingestion or inhalation, due to its potential to cause irritation and other adverse effects.

Check Digit Verification of cas no

The CAS Registry Mumber 13100-05-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,1,0 and 0 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 13100-05:
(7*1)+(6*3)+(5*1)+(4*0)+(3*0)+(2*0)+(1*5)=35
35 % 10 = 5
So 13100-05-5 is a valid CAS Registry Number.

13100-05-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(2-hydroxyphenyl)propan-2-one

1.2 Other means of identification

Product number -
Other names o-hydroxyphenylacetone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13100-05-5 SDS

13100-05-5Synthetic route

(E)-2-(2-nitroprop-1-en-1-yl) phenol
86029-73-4

(E)-2-(2-nitroprop-1-en-1-yl) phenol

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
With sodium hypophosphite; nickel In ethanol; water at 40 - 60℃; for 2h;70%
2-(bromomethyl)phenyl acetate
704-65-4

2-(bromomethyl)phenyl acetate

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
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

3-acetylbenzofuran-2-ylacetic acid

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 90℃; for 2h;58%
2-methylphenyl acetate
533-18-6

2-methylphenyl acetate

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
57%
(E)-2-propenylphenol
23619-59-2

(E)-2-propenylphenol

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
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

2-(prop-1-enyl)phenol

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
With peracetic acid; diethyl ether
With peracetic acid; ethyl acetate
1-acetoxy-1-(2-hydroxy-phenyl)-propan-2-ol

1-acetoxy-1-(2-hydroxy-phenyl)-propan-2-ol

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
at 230℃; ohne Loesungsmittel;
peracetic acid
79-21-0

peracetic acid

(E)-2-propenylphenol
23619-59-2

(E)-2-propenylphenol

ethyl acetate
141-78-6

ethyl acetate

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

1-(2-hydroxyphenyl)propan-2-one

1-(2-Hydroxyphenyl)-2-methyloxiran

1-(2-Hydroxyphenyl)-2-methyloxiran

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
With sodium carbonate Heating;
1-(2-methoxyphenyl)propan-2-one
5211-62-1

1-(2-methoxyphenyl)propan-2-one

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide Yield given;
ortoquinone
583-63-1

ortoquinone

acetone
67-64-1

acetone

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
(i) Al2O3, (ii) Zn, AcOH; Multistep reaction;
2-Allylphenol
1745-81-9

2-Allylphenol

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
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

4-iodoanisol

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
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)-2-nitropropane

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
With sodium hydroxide In methanol; water for 0.0833333h; Nef reaction;
1-(2-methoxyphenyl)-2-nitropropene
6306-34-9

1-(2-methoxyphenyl)-2-nitropropene

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
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'-methoxyphenyl)-2-nitropropane

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
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

ortho-anisaldehyde

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

1-(2-hydroxyphenyl)propan-2-one

Conditions
ConditionsYield
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

1-(2-hydroxyphenyl)propan-2-one

benzoyl chloride
98-88-4

benzoyl chloride

o-benzoyloxyphenylacetone
86358-85-2

o-benzoyloxyphenylacetone

Conditions
ConditionsYield
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

1-(2-hydroxyphenyl)propan-2-one

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

(E)-ethyl 3-(2-hydroxyphenyl)-2-methylacrylate
106929-19-5

(E)-ethyl 3-(2-hydroxyphenyl)-2-methylacrylate

Conditions
ConditionsYield
In dichloromethane at 20℃; Sealed tube;69%
1-(2-hydroxyphenyl)propan-2-one
13100-05-5

1-(2-hydroxyphenyl)propan-2-one

lead(IV) tetraacetate
546-67-8

lead(IV) tetraacetate

A

(RS)-6-acetoxy-6-(2-oxopropyl)cyclohexa-2,4-dien-1-one
198201-05-7

(RS)-6-acetoxy-6-(2-oxopropyl)cyclohexa-2,4-dien-1-one

B

4,4-dimethoxy-2-(2-oxopropyl)cyclohexa-2,5-dien-1-one

4,4-dimethoxy-2-(2-oxopropyl)cyclohexa-2,5-dien-1-one

C

6,6-diacetoxy-2-(2-oxopropyl)cyclohexa-2,4-dien-1-one

6,6-diacetoxy-2-(2-oxopropyl)cyclohexa-2,4-dien-1-one

Conditions
ConditionsYield
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

1-(2-hydroxyphenyl)propan-2-one

2-methylbenzofuran
4265-25-2

2-methylbenzofuran

Conditions
ConditionsYield
bei 2-taegigen Aufbewahren ueber Schwefelsaeure in Exiccator.;
With trifluoroacetic acid In dichloromethane for 6h;
1-(2-hydroxyphenyl)propan-2-one
13100-05-5

1-(2-hydroxyphenyl)propan-2-one

acetic anhydride
108-24-7

acetic anhydride

1-(2-acetoxyphenyl)-2-propanone
115144-87-1

1-(2-acetoxyphenyl)-2-propanone

O-Methylhydroxylamin
67-62-9

O-Methylhydroxylamin

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

1-(2-hydroxyphenyl)propan-2-one

(E)-1-(2-hydroxyphenyl)propan-2-one O-methyloxime
58484-61-0

(E)-1-(2-hydroxyphenyl)propan-2-one O-methyloxime

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

1-(2-hydroxyphenyl)propan-2-one

C9H13NO

C9H13NO

Conditions
ConditionsYield
With NADH In aq. buffer at 25℃; pH=9.6; Kinetics;
1-(2-hydroxyphenyl)propan-2-one
13100-05-5

1-(2-hydroxyphenyl)propan-2-one

7-methyl-3-(tetrahydrothiophen-2-yl)-2H-chromen-2-one

7-methyl-3-(tetrahydrothiophen-2-yl)-2H-chromen-2-one

Conditions
ConditionsYield
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

1-(2-hydroxyphenyl)propan-2-one

3-methylcoumarine
2445-82-1

3-methylcoumarine

Conditions
ConditionsYield
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

13100-05-5Relevant articles and documents

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

Lattanzi, Alessandra,Senatore, Antonello,Massa, Antonio,Scettri, Arrigo

, p. 3691 - 3694 (2003)

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.

Primary kinetic hydrogen isotope effects in deprotonations of a nitroalkane by intramolecular phenolate groups

Backstroma, Nicholas,Burtona, Neil A.,Watta, C. Ian F.

, p. 711 - 722 (2010)

Rate constants and kinetic isotope effects have been determined for the formation of nitronate anions from the ethers 1-(2-methoxyphenyl)-2- nitropropane, 7(X=H, L=H and D) and 1-(2-methoxy-5-nitrophenyl)-2-nitropropane, 7(X=NO2, L=H and D), and from the corresponding phenols, 1-(2-hydroxyphenyl)-2-nitropropane, 3(X=H, L=H and D), and 1-(2-hydroxy-5- nitrophenyl)-2-nitropropane, 3(X=NO2, L=H and D), in aqueous basic medium. For the ethers 7, rates of deprotonation by hydroxide are comparable with those found for deprotonations of 2-nitropropane, with kH/k D (25 °C)=7.7 and 7.8, respectively. In both the cases, the isotope effects are conventionally temperature dependent. For the corresponding phenols 3, conditions have been established under which the deprotonations of the nitroalkane are dominated by intramolecular deprotonation by the kinetically first-formed phenolate anion, with an estimated effective molarity EM ~ 250. For 3 (X=H, L=H or D), kH/kD (25 °C)=7.8, with EaD - EaH =6.9 kJ mol-1 and AH/AD=0.5. For 3(X=NO2, L=H or D), rates of intramolecular deprotonation are reduced 30-fold, and an elevated kinetic isotope effect is found (kH/kD (25 °C)=10.7). Activation parameters (EaD - EaH =17.8 kJ mol-1 and AH/AD=0.008) are compatible with an enhanced tunnelling contribution to reactivity in the H-isotopomer. Copyright

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

Thiery, Emilie,Chevrin, Carole,Le Bras, Jean,Harakat, Dominique,Muzart, Jacques

, p. 1859 - 1862 (2007/10/03)

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

-

Page/Page column 23, (2008/06/13)

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.

Methods of treating conditions associated with an Edg-2 receptor

-

Page/Page column 11; 17, (2008/06/13)

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.

Mass spectrometric investigations on phenylacetic acid derivatives, IV: Loss of ortho-substituents from ionized phenyl-2-propanones upon electron impact

Striegel,Mayer,Wiegrebe,Schlunegger,Siegrist,Aebi

, p. 751 - 760 (2007/10/02)

In the gas phase, the phenyl-2-propanone molecules 2a-4a lose upon electron impact chloro-, bromo-, and iodo-radicals specifically at the orthopOsition of the phenyl group giving rise to strong (M-Hal.)+-ions (70/12 eV; 1st and 2nd FFR) of identical structure as confirmed by their MIKE-CAD-spectra. The daughter ions at m/z 133 from o-chlorophenyl-2-propanone (2a) and 2,2-dimethyl-2,3-dihydro[b]furane (11) are structurally similar but not identical (similarity index 99.8). The collisionally activated (2nd FFR) (M-Br.)+-ions from o-bromophenyl-2-propanone (3a) and 1-bromo-1-phenyl-2-propanone (12) produce virtually congruent spectra. The most impOrtant subsequent fragmentation of the (M-Hal-)+-ions from 2a-4a is the loss of CO which incorporates the C-atom of the carbonyl group exclusively (13C labelling). Mechanistic aspects of the fragmentation sequences are discussed (Figs. 5 and 8).

REDUCTION PAR LES SELS CHROMEUX DE BROMURES BENZYLIQUES ORTHO-O-ACYLES AVEC TRANSPOSITION DU GROUPEMENT ACYLE DE L'ESTER: ACCES AUX ORTHO-HYDROXYBENZYL CETONES NON MASQUEES ET UNE NOUVELLE PREPARATION DE BENZO(B)FURANNES SUBSTITUES EN POSITION-2

Ledoussal, B.,Gorgues, A.,Coq, A. Le

, p. 5841 - 5852 (2007/10/02)

The ?-bonded organochromium (III) complexes resulting from the reduction of ortho-O-acyl benzylic bromides 1 with CrCl2 undergo an 1,5-transposition of the ester acyl functional group which allows, through selected experimental conditions either a selective access to the unmasked ortho-hydroxybenzyl ketones 2 or a new preparation of the 2-substituted benzofurans 3.The scope and limitations of the method are presented.

Process for producing phenylacetones

-

, (2008/06/13)

A phenylacetone or its derivative having the general formula (I): STR1 wherein X, Y, and Z are independently a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group, an amino group, a lower alkyl group having 1 to 6 carbon atoms, a lower alkoxy group having 1 to 6 carbon atoms, or a benzyloxy group and any two substituents of X, Y, and Z may form, together with the benzene ring, a heterocycling ring having 5 to 7 members including 1 or 2 oxygen atoms is produced at a high yield and a high selectivity by reacting a 3-phenylpropylene or its derivative having the general formula (II): STR2 wherein X, Y, and Z are as defined above, with an alkyl nitrite having the general formula (III): wherein R is an aliphatic, aromatic, or alicyclic saturated or unsaturated hydrocarbon group in the presence of (a) water, (b) an alcohol, (c) a palladium catalyst, and (d) an optional amine or copper compound, or by reacting the above-mentioned 3-phenylpropylene or its derivative with the above-mentioned alkyl nitrite in the presence of (a) an alcohol, (b) a palladium catalyst and (c) an optional amine or copper compound to form 1-phenyl-2,2-dialkoxypropane or it derivative having the general formula (IV): STR3 wherein X, Y, Z and R are as defined above, followed by hydrolyzing the reaction product.

Chromium(II) Salt mediated Reductive Transposition of an Ester Acyl Group in ortho-O-Acyl Benzylic Bromides: a Ready Access to Unmasked ortho-Hydroxybenzyl Ketones and a New Route to Benzofurans

Ledoussal, Benoit,Gorgues, Alain,Coq, Andre Le

, p. 171 - 172 (2007/10/02)

The mono-ο-bonded organochromium(III) complexes (A) derived from (1) rearrange internally into (B) through an acyl ester group transposition, selected experimental conditions allowing either a good access to the unmasked ortho-hydroxybenzyl ketones (2) or a new route to the 2-substituted benzofurans (3).

Naturally Occurring Dibenzofurans. Part 4. Synthesis of Dibenzofurandiols by Annelation of Benzofurans

Carvalho, Christopher F.,Sargent, Melvyn V.

, p. 1605 - 1612 (2007/10/02)

Methyl 3-acetylbenzofuran-2-ylacetate (8) undergoes C-methylation affording methyl 2-(3-acetylbenzofuran-2-yl)propionate (13).These compounds and similar oxo esters undergo ready cyclization to dibenzofurandiols on treatment with sodium methoxide in boiling methanol.A convenient synthesis of dimethyl furan-2,5-diylacetate (30) is described, as are attempts to synthesize 1,3,7,9-tetramethoxy-2,8-dimethyldibenzofuran (3).

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