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2196-99-8 Usage

Chemical Properties

Pale yellow to beige crystalline powder

Preparation

Obtained by treatment of 4-methoxyacetophenone with 1,3-dichloro-5,5-dime-thylhydantoin (DCDMH) and p-toluenesulfonic acid in methanol at 30–35° (94%).

Check Digit Verification of cas no

The CAS Registry Mumber 2196-99-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,9 and 6 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 2196-99:
(6*2)+(5*1)+(4*9)+(3*6)+(2*9)+(1*9)=98
98 % 10 = 8
So 2196-99-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H9ClO2/c1-12-8-4-2-7(3-5-8)9(11)6-10/h2-5H,6H2,1H3

2196-99-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-chloro-1-(4-methoxyphenyl)ethanone

1.2 Other means of identification

Product number -
Other names 4-Methoxyphenacyl chloride

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:2196-99-8 SDS

2196-99-8Synthetic route

N-methyl-N-nitrosotoluene-p-sulfonamide
80-11-5

N-methyl-N-nitrosotoluene-p-sulfonamide

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: N-methyl-N-nitrosotoluene-p-sulfonamide With potassium hydroxide In methanol; water; N,N-dimethyl-formamide Flow reactor;
Stage #2: 4-methoxy-benzoyl chloride In methanol; diethyl ether; water; N,N-dimethyl-formamide at 0 - 30℃; for 1.5h; Sonication;
Stage #3: With hydrogenchloride In methanol; diethyl ether; water; N,N-dimethyl-formamide for 1h;
99%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With hydrogenchloride; ammonium nitrate; iodine; oxygen In water; acetonitrile at 60℃; for 72h; Solvent; Green chemistry; Large scale; chemoselective reaction;98%
With N,N,N-trimethylbenzenemethanaminium dichloroiodate In methanol; 1,2-dichloro-ethane for 5h; Heating;97%
With 1,3-dichloro-5,5-dimethylhydantoin; toluene-4-sulfonic acid In methanol at 30 - 35℃; for 8h;94%
4-(2-chloroethynyl)anisole
33491-06-4

4-(2-chloroethynyl)anisole

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With tetrafluoroboric acid; water In 2,2,2-trifluoroethanol at 80℃; for 10h;95%
2,2,2-trichloro-1-(4-methoxyphenyl)ethan-1-ol
14337-31-6

2,2,2-trichloro-1-(4-methoxyphenyl)ethan-1-ol

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper(l) chloride In 1,2-dichloro-ethane for 3h; Heating;90%
Multi-step reaction with 4 steps
1: 90 percent / NaH / tetrahydrofuran / 1 h / 0 °C
2: 0.2M ammonium nitrate / methanol; H2O / cathodic reduction
3: 5M KOH / ethanol / Heating
4: cond. H2SO4 / H2O; dioxane / 3 h / Ambient temperature
View Scheme
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate In toluene at 20℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere;88%
With mono(1-benzyl-3-(1-benzyl-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium)monopalladium(II) tetrachloride; potassium carbonate In chloroform at 20℃; for 0.75h;91 %Chromat.
[1-(4-methoxyphenyl)vinyloxy]trimethylsilane
55991-65-6

[1-(4-methoxyphenyl)vinyloxy]trimethylsilane

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With tris(triphenylphosphine)ruthenium(II) chloride; trifluoromethane sulfonyl chloride In benzene at 120℃; for 7h;85%
Trichloromethanesulfonyl chloride
2547-61-7

Trichloromethanesulfonyl chloride

[1-(4-methoxyphenyl)vinyloxy]trimethylsilane
55991-65-6

[1-(4-methoxyphenyl)vinyloxy]trimethylsilane

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With ruthenium(II) In benzene at 120℃; for 7h; sealed;80%
methoxybenzene
100-66-3

methoxybenzene

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane for 2h; Ambient temperature;78.5%
With carbon disulfide; aluminium trichloride
With carbon disulfide; aluminium trichloride
4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With hydrogenchloride; iodine In dimethyl sulfoxide at 20℃; for 16h;76%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With magnesium(II) chloride hexahydrate; oxygen; lithium perchlorate; manganese(ll) chloride In dichloromethane; acetone at 40℃; for 40h; Electrochemical reaction;71%
With magnesium(II) chloride hexahydrate; cobalt(II) chloride hexahydrate; sulfuric acid; oxygen; lithium perchlorate In dichloromethane; acetone at 40℃; for 12h; Electrolysis; Sealed tube; chemoselective reaction;65%
With iron(III) chloride; potassium chloride; oxygen; toluene-4-sulfonic acid In tert-butyl methyl ether at 20℃; Irradiation; Green chemistry;43%
Multi-step reaction with 3 steps
1: thionyl chloride / chloroform / 20 °C
2: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water / 24 h / 70 °C
3: iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen / 1,2-dichloro-ethane / 16 h / 75 °C / 760.05 Torr / Green chemistry
View Scheme
methoxybenzene
100-66-3

methoxybenzene

chloroacetic acid
79-11-8

chloroacetic acid

A

2-chloro-1-(2-methoxy-phenyl)-ethanone
53688-19-0

2-chloro-1-(2-methoxy-phenyl)-ethanone

B

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With P2O5/silica gel In 1,2-dichloro-ethane for 3h; Friedel Crafts acylation; Reflux;A 12 %Spectr.
B 70%
1-(1-chloroethenyl)-4-methoxybenzene
40811-01-6

1-(1-chloroethenyl)-4-methoxybenzene

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In 1,2-dichloro-ethane at 75℃; under 760.051 Torr; for 16h; Solvent; Green chemistry; chemoselective reaction;70%
2-diazo-1-(4-methoxyphenyl)ethanone
6832-17-3

2-diazo-1-(4-methoxyphenyl)ethanone

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With iron(III) chloride; silica gel In dichloromethane at 20℃; for 0.166667h;65%
chloroacetonitrile
107-14-2

chloroacetonitrile

methoxybenzene
100-66-3

methoxybenzene

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With trifluorormethanesulfonic acid for 264h; Ambient temperature;63%
(Z)-2-chloro-1-ethoxy-p-methoxystyrene

(Z)-2-chloro-1-ethoxy-p-methoxystyrene

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With hydrogenchloride; ethanol In 1,2-dichloro-ethane at 20℃;62%
2-chloro-1-(4-methoxyphenyl)-2-(phenylsulfinyl)-1-ethanone
162147-95-7

2-chloro-1-(4-methoxyphenyl)-2-(phenylsulfinyl)-1-ethanone

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With ethylmagnesium bromide In tetrahydrofuran at -70 - -40℃; for 2h;60%
2,2,2-trichloro-1-(4-methoxyphenyl)ethan-1-one
36458-91-0

2,2,2-trichloro-1-(4-methoxyphenyl)ethan-1-one

A

(Z)-2,3-dichloro-1,4-bis(4-methoxyphenyl)but-2-ene-1,4-dione

(Z)-2,3-dichloro-1,4-bis(4-methoxyphenyl)but-2-ene-1,4-dione

B

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper(l) chloride In 1,2-dichloro-ethane; benzene for 1h; Inert atmosphere; Schlenk technique; Reflux; diastereoselective reaction;A 60%
B 18%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

N-chloro-N-fluoro-benzenesulfonamide

N-chloro-N-fluoro-benzenesulfonamide

A

(Z)-N-(2-chloro-1-(4-methoxyphenyl)vinyl)benzenesulfonamide

(Z)-N-(2-chloro-1-(4-methoxyphenyl)vinyl)benzenesulfonamide

B

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: 4-Methoxystyrene; N-chloro-N-fluoro-benzenesulfonamide In dichloromethane at 35℃; for 12h;
Stage #2: With triethylamine In dichloromethane at 35℃; for 1h;
A 48%
B 38%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

A

2-chloro-1-(3-chloro-4-methoxyphenyl)-ethanone
79881-25-7

2-chloro-1-(3-chloro-4-methoxyphenyl)-ethanone

B

4-acetyl-2-chloroanisole
37612-52-5

4-acetyl-2-chloroanisole

C

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With aluminum oxide; sodium chlorite; manganese(III) acetylacetonate In dichloromethane at 20℃; for 3.16667h;A 25%
B 22%
C 30%
With chlorine In acetic acid for 0.5h; Ambient temperature;A 14%
B 19%
C 29%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

A

2,2-dichloro-4'-methoxyacetophenone
29003-60-9

2,2-dichloro-4'-methoxyacetophenone

B

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With hydrogenchloride; potassium permanganate In acetonitrile at 60℃;A 16%
B 28%
With aluminum (III) chloride; oxygen; vanadium(V) oxytriisopropoxide; tetra-(n-butyl)ammonium iodide In acetonitrile at 80℃; for 24h;A 13 %Spectr.
B 44 %Spectr.
2-chloro-1,3-bis(4′-methoxy-phenyl)-1,3-propanedione
710949-40-9

2-chloro-1,3-bis(4′-methoxy-phenyl)-1,3-propanedione

A

1,3-bis(4'-methoxyphenyl)propane-1,3-dione
18362-51-1

1,3-bis(4'-methoxyphenyl)propane-1,3-dione

B

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: 2-chloro-1,3-bis(4′-methoxy-phenyl)-1,3-propanedione With [Cu(tris(2-pyridylmethyl)amine)(CH3CN)](ClO4)2; lithium hexamethyldisilazane In diethyl ether; acetonitrile for 48h; Inert atmosphere; Glovebox;
Stage #2: With water In diethyl ether; acetonitrile
A n/a
B 28%
p-hydroxyphenacyl chloride
6305-04-0

p-hydroxyphenacyl chloride

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With methanol; diethyl ether
4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With diethyl ether
methoxybenzene
100-66-3

methoxybenzene

chloroacetyl chloride
79-04-9

chloroacetyl chloride

A

2-chloro-1,1-bis-(4-methoxy-phenyl)-ethene
2132-66-3

2-chloro-1,1-bis-(4-methoxy-phenyl)-ethene

B

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With aluminium trichloride at 20℃;
methoxybenzene
100-66-3

methoxybenzene

chloroacetyl chloride
79-04-9

chloroacetyl chloride

A

2-chloro-1-(2-methoxy-phenyl)-ethanone
53688-19-0

2-chloro-1-(2-methoxy-phenyl)-ethanone

B

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With carbon disulfide; aluminium trichloride in der Kaelte;
With iron(III) oxide at 20℃; for 0.25h; Friedel Crafts acylation; regioselective reaction;
triphenylacetic acid
595-91-5

triphenylacetic acid

methoxybenzene
100-66-3

methoxybenzene

Chloroacetic anhydride
541-88-8

Chloroacetic anhydride

A

(4-methoxyphenyl)triphenylmethane
7402-89-3

(4-methoxyphenyl)triphenylmethane

B

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
at 150 - 155℃;
4-Methoxystyrene
637-69-4

4-Methoxystyrene

A

Z-1-(2-chloroethenyl)phenyl methyl ether
18684-79-2

Z-1-(2-chloroethenyl)phenyl methyl ether

B

1-[(E)-2-chlorovinyl]-4-methoxybenzene
18684-94-1

1-[(E)-2-chlorovinyl]-4-methoxybenzene

C

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

D

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With chlorine dioxide In tetrachloromethane at 52 - 54℃; for 1.16667h; Further byproducts given. Title compound not separated from byproducts;A 4.2 % Chromat.
B 14.1 % Chromat.
C 1.5 % Chromat.
D 33.7 % Chromat.
With chlorine dioxide In tetrachloromethane at 52 - 54℃; for 1.16667h; Further byproducts given;A 4.2 % Chromat.
B 14.1 % Chromat.
C 1.5 % Chromat.
D 33.7 % Chromat.
4-Methoxystyrene
637-69-4

4-Methoxystyrene

A

Z-1-(2-chloroethenyl)phenyl methyl ether
18684-79-2

Z-1-(2-chloroethenyl)phenyl methyl ether

B

1-[(E)-2-chlorovinyl]-4-methoxybenzene
18684-94-1

1-[(E)-2-chlorovinyl]-4-methoxybenzene

C

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

D

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With chlorine dioxide In tetrachloromethane at 52 - 54℃; for 1.16667h; Further byproducts given;A 4.2 % Chromat.
B 14.1 % Chromat.
C 1.2 % Chromat.
D 33.7 % Chromat.
1-((E)-2-Chloro-1-methoxy-vinyl)-4-methoxy-benzene

1-((E)-2-Chloro-1-methoxy-vinyl)-4-methoxy-benzene

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane; water for 3h; Ambient temperature; Yield given;
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

trans-(4-methoxyphenyl)(3-(2-nitrophenyl)oxiran-2-yl)methanone
73936-40-0

trans-(4-methoxyphenyl)(3-(2-nitrophenyl)oxiran-2-yl)methanone

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 20℃; for 0.5h; Darzens Condensation; stereoselective reaction;100%
With methanol; sodium at 20℃; for 0.25h; Darzens Condensation;
2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

(S)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane

(S)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; f-amphox; hydrogen; potassium carbonate In ethanol; hexane at 25 - 30℃; under 60804.1 Torr; for 48h; Pressure; Inert atmosphere; Glovebox; Autoclave; enantioselective reaction;99%
With potassium tert-butylate; isopropyl alcohol; chloro[(1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine] (pentamethylcyclopentadienyl) rhodium at 25℃;96%
With borane-THF; potassium hydroxide; (S)-Corey-Bakshi-Shibata oxazaborolidine In diethyl ether; water at -30℃;
With (R)-alcohol dehydrogenase from Lactobacillus kefir DSM 20587 In aq. buffer at 30℃; for 12h; pH=7; Enzymatic reaction; stereoselective reaction;n/a
With nicotinamide adenine dinucleotide phosphate; isopropyl alcohol In dimethyl sulfoxide at 30℃; for 24h; pH=7.5; Enzymatic reaction; enantioselective reaction;n/a
5-(4-methylphenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
93378-56-4

5-(4-methylphenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

1-(4-methoxyphenyl)-2-{[5-(4-methylphenyl)-4-phenyl-4H-1,2,4-triazol-3-yl]thio}ethanone
743477-46-5

1-(4-methoxyphenyl)-2-{[5-(4-methylphenyl)-4-phenyl-4H-1,2,4-triazol-3-yl]thio}ethanone

Conditions
ConditionsYield
With potassium carbonate In acetone for 2h; Heating / reflux;99%
2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

(R)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane

(R)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane

Conditions
ConditionsYield
With formic acid; C31H33N2O3RuS; potassium formate In water; ethyl acetate at 60℃; for 4h; Inert atmosphere; enantioselective reaction;98%
With sodium perchlorate; hydrogen; chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II) In methanol at 30℃; under 76005.1 Torr; for 24h; Product distribution / selectivity;93%
With nicotinamide adenine dinucleotide phosphate; isopropyl alcohol In dimethyl sulfoxide at 30℃; for 24h; pH=7.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;90%
With glucose; glucose dehydrogenase from Bacillus subtilis CGMCC 1.1398; medium-chain dehydrogenase from Kuraishia capsulate CBS1993; NAD In aq. phosphate buffer for 16h; pH=7.0; Enzymatic reaction; enantioselective reaction;n/a
2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

(4-methoxyphenyl)(4-(4-methoxyphenyl)-1H-imidazol-2-yl)methanone
1097-25-2

(4-methoxyphenyl)(4-(4-methoxyphenyl)-1H-imidazol-2-yl)methanone

Conditions
ConditionsYield
With sodium azide; choline chloride; glycerol at 80℃; for 4h; Green chemistry;98%
3-methoxybenzenethiol
15570-12-4

3-methoxybenzenethiol

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

α-(3-methoxyphenyl-thio)-4-methoxyacetophenone
63675-73-0

α-(3-methoxyphenyl-thio)-4-methoxyacetophenone

Conditions
ConditionsYield
Stage #1: 3-methoxybenzenethiol With sodium methylate In methanol at 35℃;
Stage #2: 2-chloro-1-(4-methoxyphenyl)ethanone In methanol at 0 - 35℃; for 1.16667h;
97.4%
4-phenyl-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
16629-40-6

4-phenyl-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

1-(4-methoxyphenyl)-2-[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]ethanone
325694-22-2

1-(4-methoxyphenyl)-2-[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]ethanone

Conditions
ConditionsYield
With potassium carbonate In acetone for 3h; Heating / reflux;97%
2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

(+/-)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane
4973-18-6

(+/-)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 2℃;96.2%
95.9%
With formic acid; 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; sodium formate In water at 80℃; for 18h; pH=4.5; Inert atmosphere; chemoselective reaction;92%
potassium acetate
127-08-2

potassium acetate

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

p-methoxyphenacyl acetate
58518-78-8

p-methoxyphenacyl acetate

Conditions
ConditionsYield
With [bmim]Br at 20℃; for 0.666667h;96%
5-chloro-2-nitrobenzaldehyde
6628-86-0

5-chloro-2-nitrobenzaldehyde

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

C16H12ClNO5

C16H12ClNO5

Conditions
ConditionsYield
With sodium methylate In methanol at 15℃; for 0.25h; Darzens Condensation;96%
salicylaldehyde
90-02-8

salicylaldehyde

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

(1-benzofuran-2-yl)(4-methoxyphenyl)methanone
63157-19-7

(1-benzofuran-2-yl)(4-methoxyphenyl)methanone

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 20℃; for 0.0666667h; Rap-Stoermer reaction;95%
With potassium carbonate at 100℃; for 0.416667h; Rapp-Stoermer Benzofuran Synthesis; Inert atmosphere;86%
2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

A

(S)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane

(S)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane

B

(R)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane

(R)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane

Conditions
ConditionsYield
With formic acid*triethylamine; Ru/(S,S)-DPEN/MCF In dichloromethane at 20℃; for 12h;A 94%
B n/a
With Geotrichum sp. 38 in 5percent glucose In dimethyl sulfoxide at 30℃; for 17h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With dimethylsulfide borane complex; (S)-chiral pyrrolidine-based ionic liquid In toluene Heating; Title compound not separated from byproducts;
4-methoxybenzoic acid hydrazide
3290-99-1

4-methoxybenzoic acid hydrazide

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

3,6-bis(4-methoxyphenyl)-1,2,4-triazine
64327-01-1

3,6-bis(4-methoxyphenyl)-1,2,4-triazine

Conditions
ConditionsYield
With ammonium propionate; propionic acid In 1-methyl-pyrrolidin-2-one at 190℃; for 36h;94%
2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With bismuth(III) chloride; sodium tetrahydroborate; sodium iodide In acetone Ambient temperature;93.3%
With triphenyl phosphite; sodium hydrogencarbonate; (BrBu2Te)2O In water; N,N-dimethyl-formamide at 80℃; for 5h;89%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; acetic acid for 1.5h; Irradiation; Inert atmosphere;88%
With tris(2,2'-bipyridyl)ruthenium dichloride; 1,5-dimethoxynaphthalene; ascorbic acid In methanol; water for 15h; Inert atmosphere; Irradiation;81%
5-acetyl-2,4-dimethylthiazole
38205-60-6

5-acetyl-2,4-dimethylthiazole

thiosemicarbazide
79-19-6

thiosemicarbazide

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

2-(4-(4-methoxyphenyl)thiazol-2-yl)-1-(1-(2,4-dimethylthiazol-5-yl)ethylidene)hydrazine

2-(4-(4-methoxyphenyl)thiazol-2-yl)-1-(1-(2,4-dimethylthiazol-5-yl)ethylidene)hydrazine

Conditions
ConditionsYield
at 20℃; for 0.5h; Solvent;93%
5-acetyl-4-methyl-2-phenylthiazole
7520-94-7

5-acetyl-4-methyl-2-phenylthiazole

thiosemicarbazide
79-19-6

thiosemicarbazide

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

2-(4-(4-methoxyphenyl)thiazol-2-yl)-1-(1-(4-methyl-2-phenyl thiazol-5-yl)ethylidene)hydrazine

2-(4-(4-methoxyphenyl)thiazol-2-yl)-1-(1-(4-methyl-2-phenyl thiazol-5-yl)ethylidene)hydrazine

Conditions
ConditionsYield
at 20℃; for 0.5h; Solvent;93%
2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
72824-04-5

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

(S)-1-chloro-2-(4-methoxyphenyl)pent-4-en-2-ol

(S)-1-chloro-2-(4-methoxyphenyl)pent-4-en-2-ol

Conditions
ConditionsYield
With methanol; (S)-2-((2-hydroxy-3-(triphenylsilyl)benzyl)amino)-3-methyl-1-(pyrrolidin-1-yl)butan-1-one; zinc dimethoxide In toluene at 22℃; for 4h; Inert atmosphere; enantioselective reaction;93%
1-(2-hydroxy-5-nitrophenyl)ethanone
1450-76-6

1-(2-hydroxy-5-nitrophenyl)ethanone

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

2-(4-methoxy benzoyl) 3-methyl 5-nitro benzofuran
141645-11-6

2-(4-methoxy benzoyl) 3-methyl 5-nitro benzofuran

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 4h; Solvent; Molecular sieve; Inert atmosphere;92.15%
cyclohexene
110-83-8

cyclohexene

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

A

6-Methoxy-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one
101869-96-9

6-Methoxy-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In benzene for 4h; Irradiation;A 92%
B n/a
methyl magnesium iodide
917-64-6

methyl magnesium iodide

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

1-chloro-2-(4-methoxyphenyl)propan-2-ol
98815-47-5

1-chloro-2-(4-methoxyphenyl)propan-2-ol

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 1.5h;92%
1-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one
5334-56-5

1-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

5-[2-(4-methoxyphenyl)-2-oxoethyl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
1234320-82-1

5-[2-(4-methoxyphenyl)-2-oxoethyl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 7h; Reflux;92%
2-amino-phenol
95-55-6

2-amino-phenol

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

3-(4-methoxyphenyl)-2H-benzo[b][1,4]oxazine
112030-48-5

3-(4-methoxyphenyl)-2H-benzo[b][1,4]oxazine

Conditions
ConditionsYield
With iodine; potassium carbonate In tetrahydrofuran; water at 20℃; for 7.5h; Inert atmosphere; Green chemistry;92%
2-(phenylamino)pyridine
6631-37-4

2-(phenylamino)pyridine

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

2-(4-methoxyphenyl)-1-(pyridin-2-yl)-1H-indole
1310709-07-9

2-(4-methoxyphenyl)-1-(pyridin-2-yl)-1H-indole

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium fluoride In methanol at 90℃; for 24h;92%
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

1-chloro-2-(4-methoxyphenyl)but-3-en-2-ol

1-chloro-2-(4-methoxyphenyl)but-3-en-2-ol

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 2.5h; Inert atmosphere;91%
1-ethyl-4-ethynylbenzene
40307-11-7

1-ethyl-4-ethynylbenzene

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

C19H19N3O2

C19H19N3O2

Conditions
ConditionsYield
With sodium azide In water at 20℃; for 2h; Green chemistry;91%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

2-chloro-1-(4-methoxyphenyl)ethanone
2196-99-8

2-chloro-1-(4-methoxyphenyl)ethanone

(4-methoxyphenyl)-(3-methylbenzofuran-2-yl)methanone
32730-15-7

(4-methoxyphenyl)-(3-methylbenzofuran-2-yl)methanone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2.5h; Solvent; Molecular sieve; Inert atmosphere;90.2%

2196-99-8Relevant articles and documents

A new exploration towards aminothiazolquinolone oximes as potentially multi-targeting antibacterial agents: Design, synthesis and evaluation acting on microbes, DNA, HSA and topoisomerase IV

Wang, Liang-Liang,Battini, Narsaiah,Bheemanaboina, Rammohan R. Yadav,Ansari, Mohammad Fawad,Chen, Jin-Ping,Xie, Yun-Peng,Cai, Gui-Xin,Zhang, Shao-Lin,Zhou, Cheng-He

, p. 166 - 181 (2019)

This work did a new exploration towards aminothiazolquinolone oximes as potentially multi-targeting antimicrobial agents. A class of novel hybrids of quinolone, aminothiazole, piperazine and oxime fragments were designed for the first time, conveniently synthesized as well as characterized by 1H NMR, 13C NMR and HRMS spectra. Biological activity showed that some of the synthesized compounds exhibited good antimicrobial activities in comparison with the reference drugs. Especially, O-methyl oxime derivative 10b displayed excellent inhibitory efficacy against MRSA and S. aureus 25923 with MIC values of 0.009 and 0.017 mM, respectively. Further studies indicated that the highly active compound 10b showed low toxicity toward BEAS-2B and A549 cell lines and no obvious propensity to trigger the development of bacterial resistance. Quantum chemical studies have also been conducted and rationally explained the structural features essential for activity. The preliminarily mechanism exploration revealed that compound 10b could not only exert efficient membrane permeability by interfering with the integrity of cells, bind with topoisomerase IV–DNA complex through hydrogen bonds and π-π stacking, but also form a steady biosupramolecular complex by intercalating into DNA to exert the efficient antibacterial activity. The supramolecular interaction between compound 10b and human serum albumin (HSA) was a static quenching, and the binding process was spontaneous, where hydrogen bonds and van der Waals force played vital roles in the supramolecular transportation of the active compound 10b by HSA.

Straightforward Synthesis of α-Chloromethylketimines Catalyzed by Gold(I). A Clean Way to Building Blocks

Asensio, Gregorio,Cárcel, María,Olmos, Andrea,Ramírez De Arellano, Carmen,Sarmiento, Jeymy T.,Varea, Teresa

, p. 3114 - 3122 (2022/03/14)

α-Chloromethylketimines have been obtained through a gold-catalyzed hydroamination of aromatic and aliphatic 1-chloroalkynes with aromatic amines by using equimolar amounts of both reagents. This procedure has allowed the preparation and spectroscopic characterization of α-chloromethylketimines for the first time with a high degree of purity, complete conversion, and atom economy. The synthetic usefulness of the methodology has been demonstrated with the preparation of β-chloroamines and indoles.

Facile Synthesis of α-Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source

Luo, Zhibin,Meng, Yunge,Gong, Xinchi,Wu, Jie,Zhang, Yulan,Ye, Long-Wu,Zhu, Chunyin

supporting information, p. 173 - 177 (2020/01/02)

An operationally simple and safe synthesis of α-haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron-catalysed reaction of alkenes with KBr/KCl using O2 as terminal oxidant under the irradiation of visible-light. This strategy avoids the risks associated with handling halo-contained electrophiles (Cl2, Br2, NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.

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