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25054-53-9 Usage

Chemical Properties

off-white to blue-grey crystalline powder

Uses

Piperonyloyl chloride is suitable for use in a kinetic study to evaluate the solvolysis rate constants of piperonyloyl chloride in 27 different solvents. It may be used in the synthesis of the following compounds:2-phenylbenzimidazoles(Z)-3-hydroxy-1-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-phenylprop-2-en-1-onepongapinone A2-((1-(2-(N-(4-chlorophenyl)benzo[d][1,3]dioxole-5-carboxamido)ethyl)piperidin-4-yl)oxy)acetic acid phosphoric acid salt, inhibitor of platelet aggregationjusticidin B, the piscicidal components of Justicia Hayatai var. decumbenspiperazine derivatives

General Description

Piperonyloyl chloride is an acyl halide. It participates in the preparation of starting reagent (N-acyl indole), required for the synthesis of pyrrolophenanthridone alkaloids. Kinetic study of the solvolysis of piperonyloyl chloride in various pure and binary solvent mixtures has been proposed. Solvolysis reaction has been reported to proceed via electron-rich acyl transfer mechanism.

Check Digit Verification of cas no

The CAS Registry Mumber 25054-53-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,0,5 and 4 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 25054-53:
(7*2)+(6*5)+(5*0)+(4*5)+(3*4)+(2*5)+(1*3)=89
89 % 10 = 9
So 25054-53-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H5ClO3/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2

25054-53-9 Well-known Company Product Price

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  • Aldrich

  • (378895)  Piperonyloylchloride  99%

  • 25054-53-9

  • 378895-1G

  • 521.82CNY

  • Detail
  • Aldrich

  • (378895)  Piperonyloylchloride  99%

  • 25054-53-9

  • 378895-10G

  • 3,111.03CNY

  • Detail

25054-53-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-benzodioxole-5-carbonyl chloride

1.2 Other means of identification

Product number -
Other names piperonylic acid 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:25054-53-9 SDS

25054-53-9Synthetic route

Piperonylic acid
94-53-1

Piperonylic acid

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide In chloroform Reflux;98%
With thionyl chloride In ethanol Heating;91%
With thionyl chloride Heating;80%
4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

5-iodo-1,3-benzodioxole
5876-51-7

5-iodo-1,3-benzodioxole

A

p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

B

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

Conditions
ConditionsYield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;A n/a
B 92%
Piperonylic acid
94-53-1

Piperonylic acid

A

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

B

benzo[d][1,3]dioxole-5-carboxylic anhydride
6938-53-0

benzo[d][1,3]dioxole-5-carboxylic anhydride

Conditions
ConditionsYield
With thionyl chloride; benzene
thionyl chloride
7719-09-7

thionyl chloride

Piperonylic acid
94-53-1

Piperonylic acid

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

Piperonylic acid
94-53-1

Piperonylic acid

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

piperonal
120-57-0

piperonal

alkali

alkali

A

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

B

(+-)-2-cyclohexa-1,4-dienyl-1-methyl-ethylamine

(+-)-2-cyclohexa-1,4-dienyl-1-methyl-ethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) NaH / 1) DMF, 2) 25 deg C, 12 h
2: SOCl2 / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 1) C3H7SH, NaH / 1) DMF, 2) 25 deg C, 12 h
2: SOCl2 / 1 h / Heating
View Scheme
methyl 3,4-methylenedioxybenzoate
326-56-7

methyl 3,4-methylenedioxybenzoate

A

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

B

(+-)-2-cyclohexa-1,4-dienyl-1-methyl-ethylamine

(+-)-2-cyclohexa-1,4-dienyl-1-methyl-ethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) NaH / 1) DMF, 2) 25 deg C, 12 h
2: SOCl2 / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 1) C3H7SH, NaH / 1) DMF, 2) 25 deg C, 12 h
2: SOCl2 / 1 h / Heating
View Scheme
4-[2-(1-pyrrolidinyl)ethoxy]benzyl amine
122893-33-8

4-[2-(1-pyrrolidinyl)ethoxy]benzyl amine

A

3,4-Methylenedioxy-N-[4-[2-(1-pyrrolidinyl) ethoxy]benzyl] benzamide

3,4-Methylenedioxy-N-[4-[2-(1-pyrrolidinyl) ethoxy]benzyl] benzamide

B

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

Conditions
ConditionsYield
In chloroform
In chloroform
5-iodo-1,3-benzodioxole
5876-51-7

5-iodo-1,3-benzodioxole

terephthaloyl chloride
100-20-9

terephthaloyl chloride

A

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

B

4-iodobenzoic acid chloride
1711-02-0

4-iodobenzoic acid chloride

Conditions
ConditionsYield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 110℃; for 20h; Sealed tube; Inert atmosphere;A 96 %Spectr.
B n/a
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

butyryl chloride
141-75-3

butyryl chloride

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; for 16h; Sealed tube; Inert atmosphere;
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

5-acetamido-2-hydroxyacetophenone
7298-67-1

5-acetamido-2-hydroxyacetophenone

2-O-([1,3]dioxol-5-benzoate)-5-acetamido-acetophenone
1187016-32-5

2-O-([1,3]dioxol-5-benzoate)-5-acetamido-acetophenone

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 20℃; for 24h;100%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N-(3,4-dimethoxyphenethyl)-3,4-methylenedioxybenzamide
18780-56-8

N-(3,4-dimethoxyphenethyl)-3,4-methylenedioxybenzamide

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 0℃; for 1.5h; Sealed tube;99%
Stage #1: 2-(3,4-dimethoxyphenyl)-ethylamine With triethylamine In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: 3,4-(methylenedioxy)benzoyl chloride In dichloromethane Inert atmosphere;
2-methoxy-6-methyl-4(3H)-pyrimidinone
55996-28-6

2-methoxy-6-methyl-4(3H)-pyrimidinone

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

6-methyl-2-methoxy-4-O-piperonylpyrimidine
117034-25-0

6-methyl-2-methoxy-4-O-piperonylpyrimidine

Conditions
ConditionsYield
In pyridine; acetonitrile for 3h; Ambient temperature;98%
With pyridine In acetonitrile at 25℃; for 24h;98%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

benzo[1,3]dioxole-5-carboxylic acid methoxymethylamide
147030-72-6

benzo[1,3]dioxole-5-carboxylic acid methoxymethylamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;98%
With sodium hydroxide In water; acetonitrile at 20℃; for 0.5h;88%
With triethylamine In dichloromethane Substitution;
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: 3,4-(methylenedioxy)benzoyl chloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;
With dmap In toluene at 75℃; for 16h;68.2 mg
5-(4-methoxyphenyl)-4-methyl-6-piperidin-4-ylpyrimidin-2-amine
198554-74-4

5-(4-methoxyphenyl)-4-methyl-6-piperidin-4-ylpyrimidin-2-amine

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-5-(4-methoxyphenyl)-6-methylpyrimidin-2-amine
240496-93-9

4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-5-(4-methoxyphenyl)-6-methylpyrimidin-2-amine

Conditions
ConditionsYield
With triethylamine In chloroform for 1h; Cooling with ice;97%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

4-(4-methoxybenzyl)-6-piperidin-4-ylpyrimidin-2-amine
198554-72-2

4-(4-methoxybenzyl)-6-piperidin-4-ylpyrimidin-2-amine

4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidin-2-amine
198553-25-2

4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidin-2-amine

Conditions
ConditionsYield
With triethylamine In chloroform Cooling with ice;96%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

5-(iso-propyl)-1-aza-5-stannabicyclo[3.3.3]undecane

5-(iso-propyl)-1-aza-5-stannabicyclo[3.3.3]undecane

(±)-1-(benzo[d][1,3]dioxol-5-yl)-2-methylpropan-1-one
67292-69-7

(±)-1-(benzo[d][1,3]dioxol-5-yl)-2-methylpropan-1-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride In acetonitrile at 60℃; for 12h; Sealed tube;96%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

methylamine
74-89-5

methylamine

N-methylbenzo[d][1,3]dioxole-5-carboxamide
15777-84-1

N-methylbenzo[d][1,3]dioxole-5-carboxamide

Conditions
ConditionsYield
In dichloromethane95%
In water at 0℃;
With triethylamine In tetrahydrofuran Cooling with ice;
7-bromo-6-methylamino-2,2-dimethyl-2-silatetralin
880550-62-9

7-bromo-6-methylamino-2,2-dimethyl-2-silatetralin

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

N-(7-bromo-2,2-dimethyl-2-silatetralin-6-yl)-N-methylpiperonamide
880550-72-1

N-(7-bromo-2,2-dimethyl-2-silatetralin-6-yl)-N-methylpiperonamide

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃;95%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

berberrubine chloride
15401-69-1

berberrubine chloride

9-O-(piperonyl)berberrubine chloride
1297302-72-7

9-O-(piperonyl)berberrubine chloride

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.5h;95%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

4-heptylamine
16751-59-0

4-heptylamine

N-(heptan-4-yl)benzo[d][1,3]dioxole-5-carboxamide

N-(heptan-4-yl)benzo[d][1,3]dioxole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 10℃; for 1h; Inert atmosphere;94.4%
With triethylamine In dichloromethane at 0℃; for 1h;48.3%
In dichloromethane; ethyl acetate; triethylamine48.3%
pyrrolidine
123-75-1

pyrrolidine

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

benzo[d][1,3]dioxol-5-yl(pyrrolidin-1-yl)methanone
64654-10-0

benzo[d][1,3]dioxol-5-yl(pyrrolidin-1-yl)methanone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;94%
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;81%
In tetrahydrofuran; water for 0.5h; Ambient temperature; Yield given;
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

C17H19N3O3S

C17H19N3O3S

N-(3-((3-cyanobenzyl)oxy)-4-(N-methylethylsulfonamido)phenyl)benzo[d][1,3]dioxole-5-carboxamide

N-(3-((3-cyanobenzyl)oxy)-4-(N-methylethylsulfonamido)phenyl)benzo[d][1,3]dioxole-5-carboxamide

Conditions
ConditionsYield
With potassium carbonate In 1,4-dioxane for 2h; Inert atmosphere;94%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

3-(methanesulfonamido)-4-methoxyaniline
123343-92-0

3-(methanesulfonamido)-4-methoxyaniline

N-(3-methanesulfonylamino-4-methoxyphenyl)-3,4-methylenedioxybenzamide

N-(3-methanesulfonylamino-4-methoxyphenyl)-3,4-methylenedioxybenzamide

Conditions
ConditionsYield
With pyridine at 20℃; for 24h;93%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

4-amino-2-methoxy-N-methanesulphonyl aniline
57164-99-5

4-amino-2-methoxy-N-methanesulphonyl aniline

N-(3-methoxy-4-methanesulfonylaminophenyl)-3,4-methylenedioxybenzamide
870090-58-7

N-(3-methoxy-4-methanesulfonylaminophenyl)-3,4-methylenedioxybenzamide

Conditions
ConditionsYield
With pyridine at 20℃; for 24h;93%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

1-[(1R,2R)-2-{[4-(1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl]methanamine dihydrochloride

1-[(1R,2R)-2-{[4-(1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl]methanamine dihydrochloride

N-{[(1R,2R)-2-{[4-(1,2-benzisothiazol-3-yl)piperazin-1-yl]-methyl}cyclohexyl]methyl}-1,3-benzodioxole-5-carboxamide
1260022-09-0

N-{[(1R,2R)-2-{[4-(1,2-benzisothiazol-3-yl)piperazin-1-yl]-methyl}cyclohexyl]methyl}-1,3-benzodioxole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 7h;93%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

2-fluoro-4-(methoxy)aniline
458-52-6

2-fluoro-4-(methoxy)aniline

6-methoxy-2-(3,4-methylenedioxyphenyl)-1,3-benzothiazole

6-methoxy-2-(3,4-methylenedioxyphenyl)-1,3-benzothiazole

Conditions
ConditionsYield
With Lawessons reagent In diphenylether Microwave irradiation; Sealed tube; Heating; regioselective reaction;92%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

1-[(1S,2S)-2-{[4-(1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclopropyl]methanamine
1260025-97-5

1-[(1S,2S)-2-{[4-(1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclopropyl]methanamine

N-{[(1S,2S)-2-{[4-(1,2-benzisothiazol-3-yl)piperazin-1-yl]-methyl}cyclopropyl]methyl}-1,3-benzodioxole-5-carboxamide
1260022-16-9

N-{[(1S,2S)-2-{[4-(1,2-benzisothiazol-3-yl)piperazin-1-yl]-methyl}cyclopropyl]methyl}-1,3-benzodioxole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 7h;91%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

2-(3-aminophenyl)-5,6,7-trimethoxy-4H-chromen-4-one
1467668-53-6

2-(3-aminophenyl)-5,6,7-trimethoxy-4H-chromen-4-one

N-(3-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzo[d][1,3]dioxole-5-carboxamide

N-(3-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzo[d][1,3]dioxole-5-carboxamide

Conditions
ConditionsYield
With potassium carbonate In acetone91%
With iodine; triethylamine; phosphorous acid trimethyl ester In acetone at 20℃; for 0.0833333h;91%
With potassium carbonate In acetone at 20℃;
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

1-amino-5,6,7,8-tetrahydronaphthalene
2217-41-6

1-amino-5,6,7,8-tetrahydronaphthalene

N-[1-(5,6,7,8-tetrahydronaphthyl)]-3,4-methylenedioxybenzamide

N-[1-(5,6,7,8-tetrahydronaphthyl)]-3,4-methylenedioxybenzamide

Conditions
ConditionsYield
With pyridine In dichloromethane90%
isonipecotic acid
498-94-2

isonipecotic acid

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

1-(1,3-benzodioxol-5-ylcarbonyl)piperidine-4-carboxylic acid
198554-82-4

1-(1,3-benzodioxol-5-ylcarbonyl)piperidine-4-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 10℃; for 2.5h; Cooling with ice;90%
With potassium carbonate In tetrahydrofuran; water
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-6-yl)ethanone
18780-97-7

1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-6-yl)ethanone

pongapinone A

pongapinone A

Conditions
ConditionsYield
With magnesium dibromide etherate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.333333h;90%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

2-(3-aminophenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one

2-(3-aminophenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one

N-(3-(5-hydroxy-6,7-dimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzo[d][1,3]dioxol-5-carboxamide

N-(3-(5-hydroxy-6,7-dimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzo[d][1,3]dioxol-5-carboxamide

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃;90%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

O-pivaloylhydroxylamine trifluoromethanesulfonate salt
1293990-73-4

O-pivaloylhydroxylamine trifluoromethanesulfonate salt

N-(pivaloyloxy) benzo[d][1,3]dioxole-5-carboxamide

N-(pivaloyloxy) benzo[d][1,3]dioxole-5-carboxamide

Conditions
ConditionsYield
With sodium carbonate In water; ethyl acetate at 0 - 20℃; for 5h;90%
morpholine
110-91-8

morpholine

3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

benzo[d][1,3]dioxol-5-yl(morpholino)methanone
63916-59-6

benzo[d][1,3]dioxol-5-yl(morpholino)methanone

Conditions
ConditionsYield
In pyridine at 0℃; for 2h;89.7%
In dichloromethane at 0℃; for 2h;
In toluene Ambient temperature; Yield given;
With dmap In toluene at 75℃; for 16h;86.1 mg
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Benzo[1,3]dioxole-5-carboxylic acid 2-oxo-1,2-diphenyl-ethyl ester

Benzo[1,3]dioxole-5-carboxylic acid 2-oxo-1,2-diphenyl-ethyl ester

Conditions
ConditionsYield
With Piperonylic acid; sulfuric acid for 0.5h; Heating;89%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

phenylzinc chloride
28557-00-8

phenylzinc chloride

(3,4-methylenedioxyphenyl) phenyl methanone
54225-86-4

(3,4-methylenedioxyphenyl) phenyl methanone

Conditions
ConditionsYield
((t-Bu)2POH)2PdCl2 In 1-methyl-pyrrolidin-2-one at 25℃; for 0.5h;89%
3,4-(methylenedioxy)benzoyl chloride
25054-53-9

3,4-(methylenedioxy)benzoyl chloride

3-amino-naphthalene-1,8-dicarboxylic acid-anhydride
23204-38-8

3-amino-naphthalene-1,8-dicarboxylic acid-anhydride

C20H11NO6
1420467-54-4

C20H11NO6

Conditions
ConditionsYield
With pyridine In diethyl ether at 60 - 80℃;89%

25054-53-9Relevant articles and documents

Novel synthesis of graveoline and graveolinine

Bandatmakuru, Sreenivasula Reddy,Arava, Veera Reddy

, p. 2635 - 2641 (2018)

Cyclization of 2-aryl amides with base lead to quinolone derivatives. Both graveoline and graveolinine were synthesized.GRAPHICAL ABSTRACT (Figure presented.).

Synthesis and biological evaluation of novel piperidine-benzodioxole derivatives designed as potential leishmanicidal drug candidates

Fernandes, ítalo A.,De Almeida, Letícia,Ferreira, Patrícia Espuri,Marques, Marcos J.,Rocha, Raíssa P.,Coelho, Luiz F.L.,Carvalho, Diogo T.,Viegas, Claudio

, p. 3346 - 3349 (2015)

Abstract A novel series of ester and carbamate derivatives was synthesized and evaluated its activities against Leishmania amazonensis. All compounds exhibited weaker leishmanicidal activity than amphotericin B. However, results indicated that substituents on the aryl-acyl subunit are important for modulation of the leishmanicidal effect. The nitro derivative showed the highest activity of the series with an IC50 = 17.24 μM, and comparable potency to the 3,4-benzodioxole ester and n-hexyl carbamate derivatives. All compounds showed low toxicity against human cells. These results revealed interesting novel piperine-like molecular pattern for exploitation in search and development of effective and low toxic antileishmanial drug candidates.

Pd(II)-catalyzed annulation reactions of epoxides with benzamides to synthesize isoquinolones

Wang, Huihong,Cao, Fei,Gao, Weiwei,Wang, Xiaodong,Yang, Yuhang,Shi, Tao,Wang, Zhen

supporting information, p. 863 - 868 (2021/02/06)

Epoxides as alkylating reagents are unprecedentedly applied in Pd(II)-catalyzed C?H alkylation and oxidative annulation of substituted benzamides to synthesize isoquinolones rather than isochromans, which is accomplished through alerting the previously reported reaction mechanism by the addition of oxidant and TEA. Under these conditions, various isoquinolones have been prepared with yields up to 92%. In addition, this methodology has been successfully employed in the total syntheses of rupreschstyril, siamine, and cassiarin A in an expedient fashion.

Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**

Brauer, Jan,Quraishi, Elisabeth,Kammer, Lisa Marie,Opatz, Till

supporting information, p. 18168 - 18174 (2021/11/30)

A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1°,2°, benzylic, α-oxy & α-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.

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