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274-09-9 Usage

Description

1,3-Benzodioxole, widely found in plant products, has shown potent antioxidant and antibacterial activities. It has recently been reported that 1,3-benzodioxole derivatives possess cytotoxic activity against several human tumor cell lines, including human colon carcinoma cells and multidrug-resistant nasopharyngeal carcinoma cells. No cytotoxic effects were noticed at a concentration of 10-4 M.

Chemical Properties

clear colourless to light yellow liquid. Insoluble in acids.

Uses

1,3-Benzodioxole is useful in gemological stimulant detection. It is also used as a precursor for perfumes, photo initiators, agrochemicals and pharmaceuticals. 1,3-benzodimine is an intermediate for the synthesis of the drugs oxolinic acid, cinoxacin and miloxacin.

Definition

ChEBI: 1,3-benzodioxole is a benzodioxole consisting of a benzene ring substituted by a the methylenedioxy group.

Application

1,3-Benzodioxole belong to methylenedioxyphenyl (MDP) compounds that regulate cytochrome P 450-dependent drug oxidation, which is important in the process of eliminating drugs from the body. a hydrogen abstraction process can take place from the methylene-bridgea carbon of the benzodioxole compound and form a methylenedioxybenzene radical. It is therefore highly likely that 1,3-benzodioxole could serve as hydrogen donor for a CQ-based system initiating the photopolymerization of dental composite resin. In addition, 1,3-benzodioxole is an important organic intermediate (building block) to synthetize substituted methylenedioxybenzene products.

General Description

Supersonic jet fluorescence spectra of 1,3-benzodioxole has been studied. The far-infrared spectrum of the vapour of 1,3-benzodioxole has been reported. The electronic absorption spectra and the laser-induced fluorescence spectra of supersonic-jet-cooled 1,3-benzodioxole molecules has been investigated.

Check Digit Verification of cas no

The CAS Registry Mumber 274-09-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,7 and 4 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 274-09:
(5*2)+(4*7)+(3*4)+(2*0)+(1*9)=59
59 % 10 = 9
So 274-09-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O2/c1-2-4-7-6(3-1)5-8-9-7/h1-4H,5H2

274-09-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A14192)  1,3-Benzodioxole, 99%   

  • 274-09-9

  • 50g

  • 384.0CNY

  • Detail
  • Alfa Aesar

  • (A14192)  1,3-Benzodioxole, 99%   

  • 274-09-9

  • 250g

  • 2549.0CNY

  • Detail
  • Alfa Aesar

  • (A14192)  1,3-Benzodioxole, 99%   

  • 274-09-9

  • 1000g

  • 6560.0CNY

  • Detail
  • Aldrich

  • (159166)  1,3-Benzodioxole  99%

  • 274-09-9

  • 159166-50G

  • 428.22CNY

  • Detail

274-09-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-Benzodioxole

1.2 Other means of identification

Product number -
Other names 1,3-Benzodioxole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:274-09-9 SDS

274-09-9Synthetic route

5-chloro-1,3-benzodioxole
7228-38-8

5-chloro-1,3-benzodioxole

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 5h;100%
Stage #1: 5-chloro-1,3-benzodioxole With ethidium Bromide; magnesium; iron(II) chloride; magnesium chloride In tetrahydrofuran at 22 - 52℃; for 23h;
Stage #2: With water In tetrahydrofuran
In isopropyl alcohol for 15h; Irradiation; Inert atmosphere;100 %Chromat.
3,4-(methylenedioxy)-benzeneboronic acid
94839-07-3

3,4-(methylenedioxy)-benzeneboronic acid

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; tetrahydroxydiboron; 1,3-bis(bis(4-methoxyphenyl)phosphino)propane In water; 1,2-dichloro-ethane at 70℃; for 0.25h;99%
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water In toluene at 90℃; for 1h; Microwave irradiation; Green chemistry;62%
Stage #1: 3,4-(methylenedioxy)-benzeneboronic acid With (HOCH2)2CMeCH2O-polymer In tetrahydrofuran Cyclization;
Stage #2: With Ag(NH3)NO3 In tetrahydrofuran for 8h; Protodeboronation; Heating; Further stages.;
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide; cyclohexanol at 110℃; for 12h;96%
With tris(dibenzylideneacetone)dipalladium (0); tris(2,4-di-tert-butylphenyl)phosphite; caesium carbonate In cyclohexanol at 120℃; for 10h;85 %Chromat.
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium tert-butylate; isopropyl alcohol at 100℃; Schlenk technique; Inert atmosphere;88%Chromat.
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; carbon dioxide; palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 12h; Reagent/catalyst; Solvent; Irradiation;100 %Spectr.
With triethylamine In acetonitrile at 20℃; for 15h; Irradiation; Inert atmosphere;94 %Spectr.
dichloromethane
75-09-2

dichloromethane

benzene-1,2-diol
120-80-9

benzene-1,2-diol

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 50 - 100℃; for 5.5h; Reagent/catalyst; Temperature; Microwave irradiation;95%
In 1-methyl-pyrrolidin-2-one Reagent/catalyst;94.69%
With sodium hydroxide In dimethyl sulfoxide at 90 - 120℃; for 0.5h; Temperature; Solvent; Reagent/catalyst;85.4%
chlorobromomethane
74-97-5

chlorobromomethane

benzene-1,2-diol
120-80-9

benzene-1,2-diol

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

dibenzo-tetroxecin
263-29-6

dibenzo-tetroxecin

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20 - 110℃;A 88%
B 11%
diiodomethane
75-11-6

diiodomethane

benzene-1,2-diol
120-80-9

benzene-1,2-diol

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 1h; Inert atmosphere;80%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 12h;62.1%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 12h;62.1%
With potassium hydroxide; hydrogen
With sodium hydride 1.) HMPT, room temp.; 2.) room temp., 20 min; Yield given. Multistep reaction;
carbon dioxide
124-38-9

carbon dioxide

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

5-iodo-1,3-benzodioxole

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

Piperonylic acid
94-53-1

Piperonylic acid

Conditions
ConditionsYield
With tetraethylammonium tosylate; triphenylphosphine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide Pt anode/Pt cathode; electrolysis with 2.5 mA/cm2;A 13%
B 76%
5-chloro-1,3-benzodioxole
7228-38-8

5-chloro-1,3-benzodioxole

1,2,4,5-tetramethylbenzene
95-93-2

1,2,4,5-tetramethylbenzene

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

3,4-methylenedioxy-2',3',5',6'-tetramethyl-biphenyl
954367-93-2

3,4-methylenedioxy-2',3',5',6'-tetramethyl-biphenyl

Conditions
ConditionsYield
With triethylamine In 2,2,2-trifluoroethanol for 7h; Photolysis;A n/a
B 76%
cyclohexenone
930-68-7

cyclohexenone

triethylsilyl chloride
994-30-9

triethylsilyl chloride

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

5-iodo-1,3-benzodioxole

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

((3-(benzo[d][1,3]dioxol-5-yl)cyclohex-1-en-1-yl)oxy)triethylsilane
1416985-76-6

((3-(benzo[d][1,3]dioxol-5-yl)cyclohex-1-en-1-yl)oxy)triethylsilane

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II); manganese; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl acetamide at 20℃; for 1h;A 5 mg
B 76%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

tert-butylmagnesium chloride
677-22-5

tert-butylmagnesium chloride

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

5-(tert-butyl)benzo[d][1,3]dioxole
7228-36-6

5-(tert-butyl)benzo[d][1,3]dioxole

Conditions
ConditionsYield
With 1.54H2O*Cl2Ni; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate In tetrahydrofuran at -10℃; for 1.5h; Kumada coupling reaction; Inert atmosphere;A 17 mg
B 73%
5-iodo-1,3-benzodioxole
5876-51-7

5-iodo-1,3-benzodioxole

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction;72%
1-(benzo[d][1,3]dioxole-5-carbonyl)piperidine-2,6-dione

1-(benzo[d][1,3]dioxole-5-carbonyl)piperidine-2,6-dione

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With nickel(II) acetate tetrahydrate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 170℃; for 48h;72%
With nickel(II) acetate tetrahydrate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 170℃; for 48h; Inert atmosphere; Glovebox; Sealed tube;72 %Chromat.
carbon dioxide
124-38-9

carbon dioxide

1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate
109586-40-5

1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

Piperonylic acid
94-53-1

Piperonylic acid

Conditions
ConditionsYield
With bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; tetrabutylammomium bromide; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine; tert-butyl XPhos In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Irradiation;A 16%
B 70%
Sesamol
533-31-3

Sesamol

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
Stage #1: Sesamol With fluorosulfonyl fluoride; triethylamine In dimethyl sulfoxide at 20℃; for 3h;
Stage #2: With formic acid; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In dimethyl sulfoxide at 20℃; for 2h;
65%
5-chloro-1,3-benzodioxole
7228-38-8

5-chloro-1,3-benzodioxole

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

1-allyl-3,4-methylenedioxybenzene
94-59-7

1-allyl-3,4-methylenedioxybenzene

Conditions
ConditionsYield
In water; acetonitrile for 6.25h; Irradiation; Flow reactor;A 10 %Chromat.
B 50%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

Triethoxysilane
998-30-1

Triethoxysilane

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

4-(triethoxysilyl)-1,2-(methylenedioxy)benzene
376353-50-3

4-(triethoxysilyl)-1,2-(methylenedioxy)benzene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; johnphos; bis(dibenzylideneacetone)-palladium(0) In 1-methyl-pyrrolidin-2-one at 60℃; for 12h;A n/a
B 44%
benzo[d][1,3]dioxol-5-yl tert-butyl carbonate

benzo[d][1,3]dioxol-5-yl tert-butyl carbonate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzodioxole
94838-82-1

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzodioxole

B

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With cesium fluoride; 2-mercaptopyridine sodium salt In acetonitrile at 30 - 35℃; for 36h; Irradiation; Inert atmosphere;A 44%
B 5 %Chromat.
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

benzene-1,2-diol
120-80-9

benzene-1,2-diol

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
TS-2 In 1,4-dioxane at 330℃; for 5h; Product distribution / selectivity; Gas phase;30%
tegafur In 1,4-dioxane at 330℃; for 5h; Product distribution / selectivity; Gas phase;28%
1,2-dibromomethane
74-95-3

1,2-dibromomethane

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
<p>-(CH2)3-<sup>+</sup>PBu3</p> In water at 110℃; for 2h;10%
5,6-dibromo-1,3-benzodioxole
5279-32-3

5,6-dibromo-1,3-benzodioxole

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With methanol; sodium amalgam
chlorobromomethane
74-97-5

chlorobromomethane

benzene-1,2-diol
120-80-9

benzene-1,2-diol

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With potassium hydroxide
[1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide
20757-83-9

[1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide

benzene-1,2-diol
120-80-9

benzene-1,2-diol

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

acetone
67-64-1

acetone

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
at 45℃; reagiert analog mit Protocatechualdehyd, aber nicht mit Protocatechusaeure;
benzene-1,2-diol
120-80-9

benzene-1,2-diol

1,2-dibromomethane
74-95-3

1,2-dibromomethane

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With potassium hydroxide; brass turnings at 110℃;
benzene-1,2-diol
120-80-9

benzene-1,2-diol

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

dibenzo-tetroxecin
263-29-6

dibenzo-tetroxecin

Conditions
ConditionsYield
With potassium hydroxide; chlorobromomethane
piperazine
110-85-0

piperazine

1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

1-(3,4-methylenedioxyphenyl)piperazine
55827-51-5

1-(3,4-methylenedioxyphenyl)piperazine

C

1,4-Bis-benzo[1,3]dioxol-5-yl-piperazine

1,4-Bis-benzo[1,3]dioxol-5-yl-piperazine

Conditions
ConditionsYield
With sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine In o-xylene at 120℃; Yield given;
polystyrene

polystyrene

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

phenylacetaldehyde
122-78-1

phenylacetaldehyde

C

phenylacetylene
536-74-3

phenylacetylene

D

isopropenylbenzene
98-83-9

isopropenylbenzene

Conditions
ConditionsYield
With air at 400 - 650℃; Oxidation; Formation of xenobiotics;
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

sodium t-butanolate
865-48-5

sodium t-butanolate

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

3,3',4,4'-bis(methylenedioxy)biphenyl
4791-89-3

3,3',4,4'-bis(methylenedioxy)biphenyl

C

piperonyl butoxide

piperonyl butoxide

Conditions
ConditionsYield
With palladium diacetate; tri-tert-butyl phosphine In xylene at 120℃; for 6h; Substitution; Suzuki coupling;
<4-amino-pyrocatechol>-methylene ether-hydrochloride

<4-amino-pyrocatechol>-methylene ether-hydrochloride

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With sodium hydroxide; tin(ll) chloride Diazotization;
methanol
67-56-1

methanol

5,6-dibromo-1,3-benzodioxole
5279-32-3

5,6-dibromo-1,3-benzodioxole

sodium-amalgam

sodium-amalgam

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Potassium; benzo[1,3]dioxole-5-sulfonate
143018-62-6

Potassium; benzo[1,3]dioxole-5-sulfonate

Conditions
ConditionsYield
Stage #1: Methylenedioxybenzene With sulfuric acid; potassium acetate; acetic anhydride In ethyl acetate at 3 - 20℃; for 20h; Cooling with ice;
Stage #2: With potassium acetate In ethanol; ethyl acetate at 3℃; for 0.75h;
100%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

5-nitro-1,3-benzodioxole
2620-44-2

5-nitro-1,3-benzodioxole

Conditions
ConditionsYield
With nitric acid at 50 - 60℃; for 0.5h; Temperature;99.8%
With nitric acid In acetic acid90.6%
With sulfuric acid; nitric acid In acetic acid at -5℃;90%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; lithium bromide In acetonitrile at 20℃; for 2h;99%
With N-Bromosuccinimide; methyl bis[4-(trifluoromethyl)phenyl]selenonium tetrafluoroborate In 1,2-dichloro-ethane at 23℃; for 48h; Inert atmosphere; Darkness;99%
With N-Bromosuccinimide; (Z)-N-[3,5-bis(trifluoromethyl)phenyl]-4-(dimethyliminio)pyridine-1(4H)-carbimidothioate In dichloromethane at 25℃; for 36h; Darkness; regioselective reaction;98%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

benzene-1,2-diol
120-80-9

benzene-1,2-diol

Conditions
ConditionsYield
With 1,3-dimethyl-2-imidazolidinone; sodium hexamethyldisilazane In tetrahydrofuran at 185℃; for 12h; further reagent: LDA;99%
With sodium di(ethyl)amine In N,N,N,N,N,N-hexamethylphosphoric triamide; benzene for 12h; Heating;85%
With aluminium(III) iodide In carbon disulfide for 7h; Heating; Var. solvent, time and substrate reagent ratio;80%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

benzo[1,3]dioxol-5-ylglyoxylic acid ethyl ester
86358-30-7

benzo[1,3]dioxol-5-ylglyoxylic acid ethyl ester

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 20℃; for 1h; Friedel-Crafts acylation;99%
With aluminum (III) chloride In dichloromethane at 0℃; Friedel Crafts acylation;92%
Stage #1: Methylenedioxybenzene; Ethyl oxalyl chloride In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: With aluminum (III) chloride In dichloromethane for 0.25h; Inert atmosphere;
46%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

6-chlorosulfonyl-1,4-benzodioxane
63758-12-3

6-chlorosulfonyl-1,4-benzodioxane

Conditions
ConditionsYield
With thionyl chloride In water99%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

acetic anhydride
108-24-7

acetic anhydride

1-(benzo[d][1,3]dioxol-6-yl)ethanone
3162-29-6

1-(benzo[d][1,3]dioxol-6-yl)ethanone

Conditions
ConditionsYield
With trifluoroacetic acid at 20℃; for 1.5h; Friedel-Crafts Acylation;98%
at 120℃; Friedel-Crafts Acylation;90%
With diatomite-solid acid catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Time; Friedel-Crafts Acylation;90.3%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

ethyl 3-chloro-3-(3,4-dichlorophenylthio)propanoate
161890-43-3

ethyl 3-chloro-3-(3,4-dichlorophenylthio)propanoate

ethyl 3-(1,3-benzodioxol-5-yl)-3-(3,4-dichlorophenylthio)propanoate
161890-23-9

ethyl 3-(1,3-benzodioxol-5-yl)-3-(3,4-dichlorophenylthio)propanoate

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -20℃;98%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

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

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

Conditions
ConditionsYield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water-d2 In tetrahydrofuran; toluene at 90℃; for 2h; Microwave irradiation;98%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

benzoic acid
65-85-0

benzoic acid

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

(3,4-methylenedioxyphenyl) phenyl methanone

Conditions
ConditionsYield
With trifluoroacetic acid; trifluoroacetic anhydride at 20℃; for 12h; Friedel-Crafts Acylation; Inert atmosphere;98%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

5-chloro-1,3-benzodioxole
7228-38-8

5-chloro-1,3-benzodioxole

Conditions
ConditionsYield
With chlorine In chloroform at 35℃; for 2h; Temperature;96.2%
With ammonium persulfate; N-chloro-succinimide; oxygen; methylene green In acetonitrile at 20℃; for 24h; Reagent/catalyst; Irradiation; regioselective reaction;93%
With N-chloro-succinimide In various solvent(s) at 27℃; for 1h;92%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

2,2-dichloro-1,3-benzodioxole
2032-75-9

2,2-dichloro-1,3-benzodioxole

Conditions
ConditionsYield
With phosphorus pentachloride for 0.833333h; Reflux;96%
With 2,2'-azobis(isobutyronitrile); chlorine In tetrachloromethane at 80 - 85℃; for 3.5h;95%
With 2,2'-azobis(isobutyronitrile); Pentafluorobenzene; chlorine at 85℃; for 1h; Reflux;90%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

A

4-nitro-(1,3-benzodioxolyl)
72744-45-7

4-nitro-(1,3-benzodioxolyl)

B

5-nitro-1,3-benzodioxole
2620-44-2

5-nitro-1,3-benzodioxole

Conditions
ConditionsYield
With nitric acid at 25℃; for 1h;A n/a
B 96%
With nitric acid at 20 - 30℃; for 1h; other educts and mononitroderivatives; influence of heterocyclic side ring-size on orientation during nitration;
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

(2-allyl-3-isopropoxy-4-methoxyphenyl)methanol
634616-23-2

(2-allyl-3-isopropoxy-4-methoxyphenyl)methanol

5-(2-allyl-3-isopropoxy-4-methoxybenzyl)benzo[d][1,3]dioxole

5-(2-allyl-3-isopropoxy-4-methoxybenzyl)benzo[d][1,3]dioxole

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 25℃; for 2h; Inert atmosphere;96%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

acetic acid
64-19-7

acetic acid

1-(benzo[d][1,3]dioxol-6-yl)ethanone
3162-29-6

1-(benzo[d][1,3]dioxol-6-yl)ethanone

Conditions
ConditionsYield
In nitrobenzene at 80℃; Friedel-Crafts Acylation;96%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

oxalyl dichloride
79-37-8

oxalyl dichloride

benzo[1,3]dioxol-5-sulfonyl chloride
115010-10-1

benzo[1,3]dioxol-5-sulfonyl chloride

Conditions
ConditionsYield
Stage #1: Methylenedioxybenzene With sulfur trioxide-N,N-dimethylformamide complex In 1,1-dichloroethane at 75℃; for 22.0833h;
Stage #2: oxalyl dichloride In 1,1-dichloroethane at 26 - 67℃; for 6.5h;
95.5%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

8-benzyloxy-3,7-dimethoxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline

8-benzyloxy-3,7-dimethoxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline

3-benzo[1,3]dioxol-5-yl-8-benzyloxy-7-methoxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline

3-benzo[1,3]dioxol-5-yl-8-benzyloxy-7-methoxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at -78 - -30℃; Substitution;95%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

C14H18O4

C14H18O4

(+)-galbacin

(+)-galbacin

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at -78 - 20℃; for 12h; Friedel-Crafts Alkylation;95%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

2-allyl-3,4-dimethoxybenzyl alcohol
408340-61-4

2-allyl-3,4-dimethoxybenzyl alcohol

5-(2-allyl-3,4-dimethoxybenzyl)benzo[d][1,3]dioxole

5-(2-allyl-3,4-dimethoxybenzyl)benzo[d][1,3]dioxole

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 25℃; for 2h; Inert atmosphere;95%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

acetyl chloride
75-36-5

acetyl chloride

1-(benzo[d][1,3]dioxol-6-yl)ethanone
3162-29-6

1-(benzo[d][1,3]dioxol-6-yl)ethanone

Conditions
ConditionsYield
With indium(III) tosylate In dodecane; nitromethane for 2.5h; Friedel-Crafts Acylation; Schlenk technique; Reflux;94%
With 10percent AlCl3 on polystyrene In dichloromethane at 45℃; Friedel-Crafts Acylation;94%
With diatomite-solid acid catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Friedel-Crafts Acylation;71.5%
With carbon disulfide; aluminium trichloride at -15℃;
With aluminum (III) chloride In dichloromethane at -50℃; for 2h; Friedel-Crafts Acylation; Sealed tube; Inert atmosphere;
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

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

5-iodo-1,3-benzodioxole

Conditions
ConditionsYield
With N-iodo-succinimide In various solvent(s) at 27℃; for 0.416667h;94%
With N-iodo-succinimide; acetic acid at 20℃; for 65h; Inert atmosphere;83%
With iodine; mercury(II) oxide In dichloromethane for 9h; Ambient temperature;50%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

chloranil
118-75-2

chloranil

2-(4-hydroxy-2,3,5,6-tetrachlorophenoxy)-1,3-benzodioxole

2-(4-hydroxy-2,3,5,6-tetrachlorophenoxy)-1,3-benzodioxole

Conditions
ConditionsYield
In acetonitrile for 5h; Irradiation;94%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

formaldehyd
50-00-0

formaldehyd

5-(chloromethyl)-1,3-benzodioxole
20850-43-5

5-(chloromethyl)-1,3-benzodioxole

Conditions
ConditionsYield
With hydrogenchloride; cetyltrimethylammonim bromide; phosphorus trichloride In water at 70℃; for 0.05h; Temperature; Reagent/catalyst;94%
With hydrogenchloride In water at 20℃;80%
With hydrogenchloride In water at 20 - 25℃; for 4.91667h; Concentration;69.8%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

2-(but-3-en-2-yl)-3,4-dimethoxyphenylmethanol
494798-08-2

2-(but-3-en-2-yl)-3,4-dimethoxyphenylmethanol

5-(2-(but-3-en-2-yl)-3,4-dimethoxybenzyl)benzo[d][1,3]dioxole

5-(2-(but-3-en-2-yl)-3,4-dimethoxybenzyl)benzo[d][1,3]dioxole

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 25℃; for 2h; Inert atmosphere;94%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

2-iodo-4,5-dimethoxybenzoic acid
61203-48-3

2-iodo-4,5-dimethoxybenzoic acid

benzo[d][1,3]dioxol-5-yl(2-iodo-4,5-dimethoxyphenyl)methanone

benzo[d][1,3]dioxol-5-yl(2-iodo-4,5-dimethoxyphenyl)methanone

Conditions
ConditionsYield
Friedel-Crafts Acylation;94%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

5-benzo[1,3]dioxol-5-yl-5,8-dihydro[1,3]dioxolo[4,5-g]-isochromen-7-one

5-benzo[1,3]dioxol-5-yl-5,8-dihydro[1,3]dioxolo[4,5-g]-isochromen-7-one

7,8,16,17-bis(methylenedioxy)-5,11-dihydro-10H-5,10-[1,2]benzenobenzo[4',5']cyclohepta[1',2':4,5]benzo[1,2-d][1,3]dioxol-10-ol

7,8,16,17-bis(methylenedioxy)-5,11-dihydro-10H-5,10-[1,2]benzenobenzo[4',5']cyclohepta[1',2':4,5]benzo[1,2-d][1,3]dioxol-10-ol

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In nitromethane at 101℃; for 10h;94%

274-09-9Relevant articles and documents

-

Dallacker,Binsack

, p. 492 (1961)

-

Transition metal catalyzed preparation of Grignard compounds

Bogdanovi, Borislav,Schwickardi, Manfred

, p. 4610 - 4612 (2000)

The "inorganic Grignard reagents", in particular those of 1, have surprisingly been shown to be efficient homogeneous catalysts for the conversion of inactive chloroarenes and heteroarenes (via the aryl-iron intermediate 2) into the corresponding Grignard

H2-Free Selective Dehydroxymethylation of Primary Alcohols over Palladium Nanoparticle Catalysts

Yamaguchi, Sho,Kondo, Hiroki,Uesugi, Kohei,Sakoda, Katsumasa,Jitsukawa, Koichiro,Mitsudome, Takato,Mizugaki, Tomoo

, p. 1135 - 1139 (2020/12/29)

The dehydroxymethylation of primary alcohols is a promising strategy to transform biomass-derived oxygenates into hydrocarbon fuels. In this study, a novel, highly efficient, and reusable heterogeneous catalyst system was established for the H2-free dehydroxymethylation of primary alcohol using cerium oxide-supported palladium nanoparticles (Pd/CeO2). A wide range of aliphatic and aromatic alcohols including biomass-derived alcohols were converted into the corresponding one-carbon shorter hydrocarbons in high yields in the absence of any additives, accompanied by the production of H2 and CO. Pd/CeO2 was easily recovered from the reaction mixture and reused, retaining its high activity, thus, providing a simple and sustainable methodology to produce hydrocarbon fuels from biomass-derived oxygenates.

Efficient base-free hydrodehalogenation of organic halides catalyzed by a well-defined diphosphine-ruthenium(II) complex

Gao, Pengxiang,Liu, Qingbin,Liu, Yahuan,Ma, Ning,Wang, Zheng,Zhao, Ziwei

, (2021/10/29)

A base-free, robust catalytic system based on the diphosphine-ruthenium(II) complex cation has been developed for the hydrodehalogenation of a wide range of aryl- and alkyl-chlorides/bromides (27 examples) with molecule hydrogen. Notably, the reaction proceeds at 120 °C with low catalyst loading (0.1 mol%) and exhibits a good tolerance toward functional groups, such as amido, carboxyl, sulfonyl, methoxyl, ester groups. All dehalogenation products are confirmed by GC, GC–MS and NMR spectroscopy. Moreover, a mechanism for the diphosphine-ruthenium(II) complex cation catalyzed dehalogenation process has been proposed. This hydrodehalogenation methodology shows a potential application for the organic transformation and degradation of organic halides.

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