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121-71-1

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121-71-1 Usage

Description

3’-Hydroxyacetophenone is a chemical compound and it is a component of castoreum, the exudate from the castor sacs of the mature beaver. It is used in the synthesis and preparation of chalcones and flavonoids as anti-tuberculosis agents, as well as antileishmanial chaocones.

Chemical Properties

beige-brown crystalline powder

Uses

Different sources of media describe the Uses of 121-71-1 differently. You can refer to the following data:
1. 3’Hydroxyacetophenone is a chemical reagent used in the synthesis and preparation of chalcones and flavonoids as anti-tuberculosis agents, as well as antileishmanial chaocones.
2. Useful in the preparation of chalcones, flavonoids, and phenylephrine. It is an active component of castoreum, which is used as a tincture in some perfumes and as a food additive.
3. 3?Hydroxyacetophenone is used in the preparation of chalcones and flavonoids, which finds application as an anti-tuberculosis agent and antileishmanial chaocones. It is also involved in the preparation of phenylephrine. Further, it is an active component of castoreum, which is used as a tincture in some perfumes and as a food additive.

Preparation

Preparation by diazotization of 3-aminoacetophenone, followed by hydrolysis of the obtained diazonium salt (78–82%).

General Description

3′-Hydroxyacetophenone is an hydroxy-substituted alkyl phenyl ketone.

Flammability and Explosibility

Nonflammable

Check Digit Verification of cas no

The CAS Registry Mumber 121-71-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 1 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 121-71:
(5*1)+(4*2)+(3*1)+(2*7)+(1*1)=31
31 % 10 = 1
So 121-71-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O2/c1-6(9)7-3-2-4-8(10)5-7/h2-5,10H,1H3

121-71-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A12547)  3'-Hydroxyacetophenone, 98%   

  • 121-71-1

  • 100g

  • 735.0CNY

  • Detail
  • Alfa Aesar

  • (A12547)  3'-Hydroxyacetophenone, 98%   

  • 121-71-1

  • 500g

  • 2776.0CNY

  • Detail

121-71-1SDS

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 3'-Hydroxyacetophenone

1.2 Other means of identification

Product number -
Other names 1-(3-hydroxyphenyl)ethanone

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:121-71-1 SDS

121-71-1Synthetic route

3-hydroxy phenylacetylene
10401-11-3

3-hydroxy phenylacetylene

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With gold(III) tribromide; water at 200℃; for 0.333333h; microwave irradiation;100%
With tropylium tetrafluoroborate; water; acetic acid at 130℃; for 1h; Catalytic behavior; Temperature; Microwave irradiation; Inert atmosphere;92%
With trifluorormethanesulfonic acid; water In 2,2,2-trifluoroethanol at 25℃; for 24h; Sealed tube; regioselective reaction;87%
With water at 60℃; for 20h; Sealed tube;63%
With methanesulfonic acid; iron(II) chloride tetrahydrate In 1,2-dichloro-ethane at 60℃; for 2h; Inert atmosphere;49%
1-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanone
124414-07-9

1-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanone

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With lithium acetate In water; N,N-dimethyl-formamide at 25℃; for 7h; Inert atmosphere;99%
With dichloro bis(acetonitrile) palladium(II) In water; acetone at 75℃; for 16h;88%
With KF-Al2O3 (acidic) In acetonitrile for 48h; Ambient temperature;82%
1-(3-Bromophenyl)ethanone
2142-63-4

1-(3-Bromophenyl)ethanone

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Inert atmosphere;99%
With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 80℃; for 14h;96%
With bis(η3-allyl-μ-chloropalladium(II)); t-BuBrettPhos; p-methylbenzaldehyde oxime; caesium carbonate In N,N-dimethyl-formamide at 90℃; for 5h; Catalytic behavior; Solvent; Reagent/catalyst; Inert atmosphere;90%
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;88%
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;72%
1-(3-ethoxyphenyl)ethan-1-one
52600-91-6

1-(3-ethoxyphenyl)ethan-1-one

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 200 - 220℃; for 0.5h; Microwave irradiation; Inert atmosphere;99%
3-acetylphenyl acetate
2454-35-5

3-acetylphenyl acetate

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With water; sodium acetate In ethanol for 5h; Reflux;98%
With potassium hydrogensulfate; silica gel In methanol at 20℃; for 1h;94%
With sodium hydroxide
3'-iodoacetophenone
14452-30-3

3'-iodoacetophenone

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; potassium hydroxide In water; dimethyl sulfoxide at 60℃; for 24h; Schlenk technique; Inert atmosphere;98%
With water; ethylene glycol; potassium hydroxide; copper dichloride In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;95%
With copper(I) oxide; water; potassium carbonate; Sucrose at 140℃; for 6h; Sealed tube; Inert atmosphere;90%
3-acetyl phenyltrifluoromethanesulfonate
138313-22-1

3-acetyl phenyltrifluoromethanesulfonate

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With tetraethylammonium hydroxide In 1,4-dioxane at 20℃; for 1h;97%
3-acetylphenyl benzenesulfonate

3-acetylphenyl benzenesulfonate

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere;97%
3-acetylphenylboronic acid

3-acetylphenylboronic acid

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With water; caesium carbonate; hydrazine hydrate at 80℃; for 48h;95%
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 24h; Green chemistry;68%
With recombinant phenylacetone monooxygenase from Thermobifida fusca, M446G mutant; NADPH In dimethyl sulfoxide at 25℃; pH=9; Kinetics; Tris/HCl buffer; Enzymatic reaction; chemoselective reaction;
Multi-step reaction with 2 steps
1: tetrahydrofuran / 40 °C / Reduced pressure
2: recombinant phenylacetone monooxygenase from Thermobifida fusca; NADPH / dimethyl sulfoxide / 25 °C / pH 9 / Tris/HCl buffer; Enzymatic reaction
View Scheme
With oxygen; N-ethyl-N,N-diisopropylamine; [5,6]fullerene-C70 In chloroform; toluene at 20℃; for 12h; Irradiation;
acetonitrile complex of hypofluorous acid

acetonitrile complex of hypofluorous acid

3-acetylphenylboronic acid

3-acetylphenylboronic acid

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
In dichloromethane at 20℃;95%
methyllithium
917-54-4

methyllithium

3-Carboxyphenol
99-06-9

3-Carboxyphenol

A

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

B

meta-hydroxy-α,α-dimethylbenzyl alcohol
7765-97-1

meta-hydroxy-α,α-dimethylbenzyl alcohol

Conditions
ConditionsYield
With chloro-trimethyl-silane In tetrahydrofuran; diethyl ether at 0℃; for 2h; Yields of byproduct given;A 94%
B n/a
With chloro-trimethyl-silane In tetrahydrofuran; diethyl ether at 0℃; for 2h; Yield given;A 94%
B n/a
1-(3-Methoxyphenyl)ethanone
586-37-8

1-(3-Methoxyphenyl)ethanone

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 220℃; for 0.666667h; Inert atmosphere; Microwave irradiation;92%
With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 220℃; for 0.5h;83%
With 1-N-ferrocenylmethyl benzimidazole tagged polymer In N,N-dimethyl-formamide Reflux;76%
With sodium thioethylate In N,N-dimethyl-formamide at 80℃; for 3.5h;18%
1-(3-(methoxymethoxy)phenyl)ethan-1-one
124414-06-8

1-(3-(methoxymethoxy)phenyl)ethan-1-one

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at 0℃; for 0.0333333h;92%
acetic acid 3-aminophenyl ester
42758-84-9

acetic acid 3-aminophenyl ester

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
Stage #1: acetic acid 3-aminophenyl ester With sulfuric acid at 20℃; Cooling with ice;
Stage #2: With sodium nitrite In water Reflux;
92%
1-(3-(allyloxy)phenyl)ethanone
58621-54-8

1-(3-(allyloxy)phenyl)ethanone

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride In benzene for 20h; Heating;90%
1-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one
16162-70-2

1-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at 0℃; for 0.0333333h;90%
1-(3-aminophenyl)ethanone
99-03-6

1-(3-aminophenyl)ethanone

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
Stage #1: 1-(3-aminophenyl)ethanone With sulfuric acid In water at 45 - 50℃; for 0.5h;
Stage #2: With water; urea; sodium nitrite In water at 0 - 5℃; for 0.5h;
Stage #3: With sulfuric acid In 5,5-dimethyl-1,3-cyclohexadiene; water at 90℃; for 2h;
88.3%
Stage #1: 1-(3-aminophenyl)ethanone With sodium nitrite In water at 20℃; Milling; Green chemistry;
Stage #2: With water at 80℃; for 0.5h; Neutral conditions; Green chemistry;
80%
With uranyl nitrate hydrate; water; trifluoroacetic acid for 48h; Irradiation; Inert atmosphere;58%
With sulfuric acid; water Diazotization;
C14H14O7

C14H14O7

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With water In dimethyl sulfoxide at 155℃; for 0.5h;85%
3'-Chloroacetophenone
99-02-5

3'-Chloroacetophenone

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 130℃; for 24h; Concentration; Schlenk technique; Inert atmosphere;82%
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation;81%
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;54%
1-[3-(phenylmethoxy)phenyl]ethan-1-one
34068-01-4

1-[3-(phenylmethoxy)phenyl]ethan-1-one

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With sodium hydrogen sulfate; silica gel; methoxybenzene at 115℃; for 3h;81%
3-acetoxybenzoylmalonate diethyl ester

3-acetoxybenzoylmalonate diethyl ester

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With acetic acid In water at 90℃; for 4h; Reagent/catalyst; Temperature;77.6%
3-acetyl-2-cyclohexen-1-one
15040-96-7

3-acetyl-2-cyclohexen-1-one

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); 6,6'-dimethyl-2,2'-bipyridine; sodium anthraquinone-2-sulfonate; oxygen In water; dimethyl sulfoxide at 80℃; under 760.051 Torr; for 24h;77%
octakis(m-acetylphenyl)octasilsesquioxane

octakis(m-acetylphenyl)octasilsesquioxane

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With potassium fluoride; dihydrogen peroxide; sodium hydrogencarbonate In tetrahydrofuran; methanol at 40℃;76%
5-acetyl-2-cyclohexen-1-one
70550-16-2

5-acetyl-2-cyclohexen-1-one

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With lithium bromide; copper(ll) bromide In acetonitrile for 1h; Heating;75%
tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

4-iodoanisol
529-28-2

4-iodoanisol

1-(3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)ethanone
443777-09-1

1-(3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)ethanone

A

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

B

1,1'-(biphenyl-3,3'-diyl)bis(ethan-1-one)
94113-07-2

1,1'-(biphenyl-3,3'-diyl)bis(ethan-1-one)

C

tert-butyl (E)-3-(2-methoxyphenyl)prop-2-enoate
474097-69-3

tert-butyl (E)-3-(2-methoxyphenyl)prop-2-enoate

D

tert-butyl (E)-3-(3-acetylphenyl)-acrylate

tert-butyl (E)-3-(3-acetylphenyl)-acrylate

Conditions
ConditionsYield
With oxygen; palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 50℃; for 6h; Further byproducts given;A 6%
B 5%
C 26%
D 71%
3-hydroxy phenylacetylene
10401-11-3

3-hydroxy phenylacetylene

acetic acid
64-19-7

acetic acid

A

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

B

3-acetylphenyl acetate
2454-35-5

3-acetylphenyl acetate

Conditions
ConditionsYield
With iron(III) sulfate hydrate at 95℃; for 24h; Schlenk technique;A 71%
B 6%
3-(1-hydroxyethyl)phenol
2415-09-0

3-(1-hydroxyethyl)phenol

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

Conditions
ConditionsYield
With iodine; hydrazine hydrate; dimethyl sulfoxide In water; acetonitrile at 80℃; for 7.5h;64.7%
With chromium(VI) oxide
3-(1-hydroxyethyl)phenol
2415-09-0

3-(1-hydroxyethyl)phenol

A

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

B

(R)‐(+)‐3‐(1‐hydroxyethyl)phenol

(R)‐(+)‐3‐(1‐hydroxyethyl)phenol

Conditions
ConditionsYield
With Candida albicans CCT 0776 In water at 30℃; for 144h; Resolution of racemate; Enzymatic reaction; enantioselective reaction;A 42%
B 42%
With immobilized Candida albicans CCT 0776 cells in calcium alginate beads In water at 30℃; for 16h; Reagent/catalyst;A n/a
B n/a
acetophenone
98-86-2

acetophenone

A

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

B

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

C

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

Conditions
ConditionsYield
With (difluoroboryl)dimethylglyoximatocobalt(II) bis(acetonitrile); water; 3-cyano-1-methylquinolinium cation In acetonitrile at 20℃; for 5h; Inert atmosphere; Irradiation; Green chemistry;A 6%
B 38%
C 14%
With hydroxyl radical; potassium hexacyanoferrate(III) Rate constant; Ambient temperature; also without K3Fe(CN)6;
With air; carbon monoxide; sodium acetate; palladium on activated charcoal; phosphovanadomolybdic acid In water; acetic acid at 120℃; under 15200 Torr; for 4h; Title compound not separated from byproducts;
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

1-iodo-propane
107-08-4

1-iodo-propane

3-(prop-1-yloxy)acetophenone
121704-77-6

3-(prop-1-yloxy)acetophenone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide100%
With NaH In N,N-dimethyl-formamide98%
With sodium ethanolate
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

allyl bromide
106-95-6

allyl bromide

1-(3-(allyloxy)phenyl)ethanone
58621-54-8

1-(3-(allyloxy)phenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; Reflux;100%
With potassium carbonate In acetone for 8h; Heating;95%
With potassium carbonate In ethanol for 3h; Reflux; Inert atmosphere;93%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

3-(1-hydroxyethyl)phenol
2415-09-0

3-(1-hydroxyethyl)phenol

Conditions
ConditionsYield
Stage #1: 3-Hydroxyacetophenone With sodium tetrahydroborate at 60℃; for 0.5h; Ball milling; neat (no solvent);
Stage #2: With water regiospecific reaction;
100%
With formic acid; C18H24ClIrN3 In water at 80℃; for 4h; Schlenk technique; Inert atmosphere; chemoselective reaction;99%
With sodium tetrahydroborate; nickel(II) phthalocyanine In PEG-400 at 20℃; for 0.416667h; chemoselective reaction;86%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

sodium 3-acetylphenoxide
3019-87-2

sodium 3-acetylphenoxide

Conditions
ConditionsYield
With sodium hydride In benzene for 0.5h;100%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

benzyl bromide
100-39-0

benzyl bromide

1-[3-(phenylmethoxy)phenyl]ethan-1-one
34068-01-4

1-[3-(phenylmethoxy)phenyl]ethan-1-one

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux; Inert atmosphere;100%
With potassium carbonate; potassium iodide In acetone for 24h; Heating / reflux;98%
In N,N-dimethyl-formamide; mineral oil97%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

(E)-1-(3,4-dimethoxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one
178445-80-2

(E)-1-(3,4-dimethoxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 0 - 20℃; for 16h;100%
With potassium hydroxide In ethanol; water at 0 - 20℃;92%
With potassium hydroxide In ethanol at 20℃; for 16h; Condensation;91%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

(Z)-ethyl 2-hydroxy-4-(3-hydroxyphenyl)-4-oxobut-2-enoate

(Z)-ethyl 2-hydroxy-4-(3-hydroxyphenyl)-4-oxobut-2-enoate

Conditions
ConditionsYield
With sodium ethanolate In tetrahydrofuran at 25℃; for 0.00277778h; microwave irradiation;100%
With potassium tert-butylate In tetrahydrofuran at 20℃; Claisen Condensation;88%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanone
124414-07-9

1-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanone

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h;93%
With dmap; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 2.5h;91%
N-ethyl-N-methylcarbamoyl chloride
42252-34-6

N-ethyl-N-methylcarbamoyl chloride

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

1-(N-ethyl-N-methylaminocarbonyloxy)-3-acetylbenzene
855300-09-3

1-(N-ethyl-N-methylaminocarbonyloxy)-3-acetylbenzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 20 - 55℃; for 5h; Product distribution / selectivity; Heating / reflux;100%
With potassium carbonate In acetone for 4h; Reflux;100%
With potassium carbonate In acetone at 60℃; for 0.4h; Reagent/catalyst; Temperature; Solvent;100%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

1-[3-(2-methylallyloxy)phenyl]ethanone
1017048-68-8

1-[3-(2-methylallyloxy)phenyl]ethanone

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃;100%
With potassium carbonate In acetonitrile for 17h; Reflux;
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

propargyl bromide
106-96-7

propargyl bromide

1-(3-(prop-2-yn-1-yloxy)phenyl)ethan-1-one
34264-13-6

1-(3-(prop-2-yn-1-yloxy)phenyl)ethan-1-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; toluene at 25℃; for 24h;100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
Stage #1: 3-Hydroxyacetophenone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 0 - 25℃; for 16h;
pyridine
110-86-1

pyridine

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

1-(3-hydroxy-phenacyl)-pyridinium; iodide

1-(3-hydroxy-phenacyl)-pyridinium; iodide

Conditions
ConditionsYield
With iodine at 140℃; for 3h;100%
With iodine at 140℃; for 3h;100%
With iodine at 140℃; for 3h;100%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

(R)‐(+)‐3‐(1‐hydroxyethyl)phenol

(R)‐(+)‐3‐(1‐hydroxyethyl)phenol

Conditions
ConditionsYield
With C38H46ClIrN2P; hydrogen; sodium t-butanolate In ethanol at 0 - 50℃; under 1500.15 - 75007.5 Torr; Reagent/catalyst; Solvent; Inert atmosphere; Autoclave;100%
With 1,1,1,3',3',3'-hexafluoro-propanol; C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; enantioselective reaction;99%
With formic acid; triethylamine; [Ru(η6-p-cymene)(HNC(Ph)C(Ph)NTs)] In ethanol at 60 - 70℃; for 5h; Product distribution / selectivity; Inert atmosphere;90%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

dimethyl sulfate
77-78-1

dimethyl sulfate

1-(3-Methoxyphenyl)ethanone
586-37-8

1-(3-Methoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: 3-Hydroxyacetophenone With potassium carbonate In acetone for 0.166667h;
Stage #2: dimethyl sulfate In acetone at 45℃; for 2h;
99.73%
With potassium carbonate In acetone at 45℃; for 2h; Large scale reaction;95%
Stage #1: 3-Hydroxyacetophenone With sodium hydroxide In water for 0.5h; Large scale;
Stage #2: dimethyl sulfate In water at 30 - 38℃; for 9.15h; pH=> 13; Temperature; pH-value; Microwave irradiation; Large scale;
91.1%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

acetic anhydride
108-24-7

acetic anhydride

3-acetylphenyl acetate
2454-35-5

3-acetylphenyl acetate

Conditions
ConditionsYield
With magnesium(II) perchlorate at 20℃; for 1h;99%
With sodium hydroxide In water at 0℃; for 1.5h; pH=7 - 8;94%
copper(II) bis(tetrafluoroborate) at 20℃; for 0.5h;92%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

benzoyl chloride
98-88-4

benzoyl chloride

3-acetylphenyl benzoate
139-28-6

3-acetylphenyl benzoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 4h; Inert atmosphere;99%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

3-acetyl phenyltrifluoromethanesulfonate
138313-22-1

3-acetyl phenyltrifluoromethanesulfonate

Conditions
ConditionsYield
With 2,6-dimethylpyridine; dmap In dichloromethane for 2h; Ambient temperature;99%
With pyridine In dichloromethane at 0 - 20℃;96%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;96%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

ethylene glycol
107-21-1

ethylene glycol

2-(3-hydroxyphenyl)-2-methyl-1,3-dioxolane

2-(3-hydroxyphenyl)-2-methyl-1,3-dioxolane

Conditions
ConditionsYield
With Triisopropoxymethan; cerium triflate In hexane at 25℃; for 1h;99%
With zeolite HSZ-360 In toluene for 11h; Heating;88%
With toluene-4-sulfonic acid In benzene Heating / reflux;36%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

3-acetylphenyl p-toluenesulfonate
58297-34-0

3-acetylphenyl p-toluenesulfonate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 2h; Green chemistry;99%
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 0 - 20℃; Inert atmosphere;91%
With dmap; triethylamine In dichloromethane
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

diethyl dicarbonate
1609-47-8

diethyl dicarbonate

ethyl 3-acetylphenyl carbonate

ethyl 3-acetylphenyl carbonate

Conditions
ConditionsYield
With magnesium(II) perchlorate at 40℃; for 4.5h;99%
n-propanesulfonyl chloride
10147-36-1

n-propanesulfonyl chloride

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

3-acetylphenyl propane-1-sulfonate
937079-67-9

3-acetylphenyl propane-1-sulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 5h;99%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

triphenylbismuthane
603-33-8

triphenylbismuthane

3'-phenoxyacetophenone
32852-92-9

3'-phenoxyacetophenone

Conditions
ConditionsYield
With copper diacetate; triethylamine In dichloromethane at 50℃; for 3h; Reagent/catalyst; Time; Sealed tube;99%
triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

1-(3-((triisopropylsilyl)oxy)phenyl)ethanone
1569974-52-2

1-(3-((triisopropylsilyl)oxy)phenyl)ethanone

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 6h;99%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

1-O-acetyl-6-O-chloracetylbritannilactone

1-O-acetyl-6-O-chloracetylbritannilactone

1-O-acetyl-6-O-(2-(3-acetylphenoxy)acetyl)britannilactone

1-O-acetyl-6-O-(2-(3-acetylphenoxy)acetyl)britannilactone

Conditions
ConditionsYield
With triethanolamine; N-benzyl-N,N,N-triethylammonium chloride; sodium iodide In acetone at 25℃;99%
4-chloro-2-(trichloromethyl)quinazoline
3137-63-1

4-chloro-2-(trichloromethyl)quinazoline

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

1-(3-(2-(trichloromethyl)quinazolin-4-yloxy)phenyl)ethanone

1-(3-(2-(trichloromethyl)quinazolin-4-yloxy)phenyl)ethanone

Conditions
ConditionsYield
With dmap In toluene at 130℃; for 1h; Microwave irradiation; Sealed tube;99%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

4-Hydrazino-5,6-tetramethylenethieno<2,3-d>pyrimidine
40106-45-4

4-Hydrazino-5,6-tetramethylenethieno<2,3-d>pyrimidine

3-{1-[(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)hydrazono]ethyl}phenol

3-{1-[(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)hydrazono]ethyl}phenol

Conditions
ConditionsYield
In ethanol for 24h; Reflux;99%

121-71-1Relevant articles and documents

Preparation and trapping of 3-lithium-O-lithiophenoxide

Selnick,Bourgeois,Butcher,Radzilowski

, p. 2043 - 2046 (1993)

3-Bromophenol and 3-bromothiophenol are converted into the title compounds by proton abstraction followed by halogen-metal exchange with tert-butyllithium. The resulting dianions are then trapped on carbon with various electrophiles.

Letsinger,Colb

, p. 3665 (1972)

Efficient microwave-assisted Pd-catalyzed hydroxylation of aryl chlorides in the presence of carbonate

Yu, Chao-Wu,Chen, Grace S.,Huang, Chen-Wei,Chern, Ji-Wang

, p. 3688 - 3691 (2012)

An efficient microwave-assisted, palladium-catalyzed hydroxylation of aryl chlorides in the presence of a weak base carbonate was developed, which rapidly converts aryl and heteroaryl chlorides to phenols, and can be used when the aryl chloride is functionalized with a ketone, aldehyde, ester, nitrile, or amide.

Aryl phenol compound as well as synthesis method and application thereof

-

Paragraph 0100-0102, (2021/05/12)

The invention discloses a synthesis method of an aryl phenol compound shown as a formula (3). All systems are carried out in an air or nitrogen atmosphere, and visible light is utilized to excite a photosensitizer for catalyzation. In a reaction solvent, ArNR1R2 as shown in a formula (1) and water as shown in a formula (2) are used as reaction raw materials and react under the auxiliary action of acid to obtain the aryl phenol compound as shown in a formula (3). The ArNR1R2 in the formula (1) can be primary amine and tertiary amine, can also be steroid and amino acid derivatives, and can also be drugs or derivatives of propofol, paracetamol, ibuprofen, oxaprozin, indomethacin and the like. The synthesis method has the advantages of cheap and easily available raw materials, simple reaction operation, mild reaction conditions, high reaction yield and good compatibility of substrate functional groups. The fluid reaction not only can realize amplification of basic chemicals, but also can realize amplification of fine chemicals, such as synthesis of drugs propofol and paracetamol. The invention has wide application prospect and use value.

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei

supporting information, p. 5905 - 5908 (2021/06/18)

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.

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