Product Name

  • Name

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

  • EINECS 220-123-5
  • CAS No. 2635-13-4
  • Article Data44
  • CAS DataBase
  • Density 1.721 g/cm3
  • Solubility
  • Melting Point
  • Formula C7H5BrO2
  • Boiling Point 268.6 °C at 760 mmHg
  • Molecular Weight 201.019
  • Flash Point 107.5 °C
  • Transport Information
  • Appearance clear yellow-orange liquid
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 2635-13-4 (4-Bromo-1,2-(methylenedioxy)benzene)
  • Hazard Symbols IrritantXi
  • Synonyms Benzene,4-bromo-1,2-(methylenedioxy)- (6CI,7CI,8CI);1-Bromo-3,4-(methylenedioxy)benzene;3,4-Methylenedioxybromobenzene;3,4-Methylenedioxyphenyl bromide;5-Bromo-1,3-benzodioxolane;5-Bromo-1,3-benzodioxole;Benzodioxol-5-yl bromide;
  • PSA 18.46000
  • LogP 2.17780

Synthetic route

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

1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate

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

1,2-(methylenedioxy)-4-bromobenzene

Conditions
ConditionsYield
With [Cp*Ru(CH3CN)3]OTf; lithium bromide at 100℃; for 12h; Inert atmosphere;94%
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; potassium bromide In 1,4-dioxane at 130℃; for 16h; Inert atmosphere;83%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

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

1,2-(methylenedioxy)-4-bromobenzene

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.25h; Flow reactor; UV-irradiation;79%
potassium (3,4-(methylenedioxy)phenyl)trifluoroborate

potassium (3,4-(methylenedioxy)phenyl)trifluoroborate

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

1,2-(methylenedioxy)-4-bromobenzene

Conditions
ConditionsYield
With acetic acid; lithium bromide In dimethyl sulfoxide at 100℃; for 8h; Schlenk technique;75%
7-bromo-1-oxaspiro<2.5>octa-5,7-dien-4-one
202001-83-0

7-bromo-1-oxaspiro<2.5>octa-5,7-dien-4-one

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

1,2-(methylenedioxy)-4-bromobenzene

Conditions
ConditionsYield
With tert-butyldimethylsilyl chloride In tetrachloromethane at 70℃; for 4.5h;70%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

chloroform
67-66-3

chloroform

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

1,2-(methylenedioxy)-4-bromobenzene

7-bromo-1-oxaspiro<2.5>octa-5,7-dien-4-one
202001-83-0

7-bromo-1-oxaspiro<2.5>octa-5,7-dien-4-one

A

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

1,2-(methylenedioxy)-4-bromobenzene

B

4-Bromo-2-chloromethoxy-phenol

4-Bromo-2-chloromethoxy-phenol

Conditions
ConditionsYield
With chloro-trimethyl-silane In toluene Ambient temperature;
<4-amino-pyrocatechol>-methylene ether-sulfate

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

A

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

B

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

1,2-(methylenedioxy)-4-bromobenzene

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite at 0℃; Diazotization.Zersetzen des Diazoniumsalzes mit einer waessr. Loesung von Kaliumbromid, Natriumhypophosphit und Kupfersulfat;
5-bromo-2-hydroxybenzyl alcohol
2316-64-5

5-bromo-2-hydroxybenzyl alcohol

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

1,2-(methylenedioxy)-4-bromobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / NaIO4
2: 70 percent / TBDMSCl / CCl4 / 4.5 h / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: 60 percent / NaIO4
2: TMSCl / toluene / Ambient temperature
View Scheme
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

A

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

1,2-(methylenedioxy)-4-bromobenzene

B

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

5,6-dibromo-1,3-benzodioxole

Conditions
ConditionsYield
With N-Bromosuccinimide; chloro-trimethyl-silane In acetonitrile at 20℃; for 1h; Overall yield = 181 mg; regioselective reaction;
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

5-chloro-2-methyl-benzenamine
95-79-4

5-chloro-2-methyl-benzenamine

N-(3,4-methylenedioxy)benzo-5-chloro-o-toluidine
1203581-77-4

N-(3,4-methylenedioxy)benzo-5-chloro-o-toluidine

Conditions
ConditionsYield
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate In water at 20℃; for 4h; Inert atmosphere; Micellar solution;100%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

phenylboronic acid
98-80-6

phenylboronic acid

3,4-methylenedioxybiphenyl
24382-05-6

3,4-methylenedioxybiphenyl

Conditions
ConditionsYield
With palladium diacetate; N,N-diisopropyl-1,1-diphenylphosphanamine; potassium carbonate In tetrahydrofuran for 12h; Suzuki-Miyamura cross-coupling reaction; Heating;99%
With potassium phosphate In ethanol; water at 20℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry;98%
With sodium carbonate In ethanol; water at 80℃; for 8h; Suzuki-Miyaura coupling;97%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4'-methoxy-3,4-(methylenedioxy-)biphenyl
89346-90-7

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

Conditions
ConditionsYield
With sodium carbonate; tris[(perfluoroalkyl)phenyl]phosphane palladium In methanol at 75℃; for 2h; Suzuki coupling;99%
With sodium carbonate In ethanol; water at 20℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;93%
With sodium carbonate In ethanol; water at 80℃; for 8h; Suzuki-Miyaura coupling;91%
With tetraamminepalladium(II) chloride; tetra(n-butyl)ammonium hydroxide In water at 45℃; for 2h; Suzuki-Miyaura Coupling; Green chemistry;66%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2-methyl-3',4'-methylenedioxy-1,1'-biphenyl

2-methyl-3',4'-methylenedioxy-1,1'-biphenyl

Conditions
ConditionsYield
With potassium fluoride; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 3h; Suzuki coupling;99%
With KF; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene99%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

copper(I) iodide
7681-65-4

copper(I) iodide

acetonitrile
75-05-8

acetonitrile

Methyl 6-benzyloxy-4-oxo-4H-chromen-3-carboxylate
203919-27-1

Methyl 6-benzyloxy-4-oxo-4H-chromen-3-carboxylate

methyl 2-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-oxo-chroman-3-carboxylate

methyl 2-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-oxo-chroman-3-carboxylate

Conditions
ConditionsYield
With magnesium In tetrahydrofuran; toluene99%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

diisopropyl benzo[d][1,3]dioxol-5-ylphosphonate
1073561-79-1

diisopropyl benzo[d][1,3]dioxol-5-ylphosphonate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; N-ethyl-N,N-diisopropylamine In acetonitrile for 24h; modified Hirao coupling reaction; Heating;99%
Diethyl disulfide
110-81-6

Diethyl disulfide

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

1,2-(methylenedioxy)-4-bromobenzene

5-(ethylthio)-1,3-benzodioxole
5279-34-5

5-(ethylthio)-1,3-benzodioxole

Conditions
ConditionsYield
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.5h;
Stage #2: Diethyl disulfide In tetrahydrofuran; hexanes for 0.5h;
99%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

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

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

Conditions
ConditionsYield
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
99%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

1-ethyl-2,3-bis(4-methoxyphenyl)-1-(2-methylallyl)guanidine hydrochloride

1-ethyl-2,3-bis(4-methoxyphenyl)-1-(2-methylallyl)guanidine hydrochloride

4-(benzo[d][1,3]dioxol-5-ylmethyl)-1-ethyl-N,3-bis(4-methoxyphenyl)-4-methylimidazolidin-2-imine hydrochloride

4-(benzo[d][1,3]dioxol-5-ylmethyl)-1-ethyl-N,3-bis(4-methoxyphenyl)-4-methylimidazolidin-2-imine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-ethyl-2,3-bis(4-methoxyphenyl)-1-(2-methylallyl)guanidine hydrochloride With tris-(dibenzylideneacetone)dipalladium(0); nixantphos In toluene at 20℃; for 0.0333333h; Inert atmosphere;
Stage #2: 1,2-(methylenedioxy)-4-bromobenzene In toluene at 20 - 107℃; for 16h;
99%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

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

1,2-(methylenedioxy)-4-bromobenzene

piperonylonitrile
4421-09-4

piperonylonitrile

Conditions
ConditionsYield
With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate In tetrahydrofuran; water at 40℃; for 18h; Inert atmosphere;99%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

Sesamol
533-31-3

Sesamol

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 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 120℃; for 24h; Glovebox; Irradiation; Inert atmosphere;72%
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With magnesium In tetrahydrofuran Inert atmosphere;
Stage #2: With oxaziridine In tetrahydrofuran at 0 - 25℃; for 2h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;
63%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

3-trifluoromethylaniline
98-16-8

3-trifluoromethylaniline

5-(3-trifluoromethylaniline)benzodioxole

5-(3-trifluoromethylaniline)benzodioxole

Conditions
ConditionsYield
With [(π-cinnamyl)Pd(tBuXPhos)]OTf In water at 45℃; for 16h;99%
methanol
67-56-1

methanol

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

1,2-(methylenedioxy)-4-bromobenzene

5-methoxybenzo[d]1,3-dioxole
7228-35-5

5-methoxybenzo[d]1,3-dioxole

Conditions
ConditionsYield
With triethylamine at 20℃; for 48h; Irradiation; Schlenk technique;99%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

piperonal
120-57-0

piperonal

(1,3-benzodioxol-5-yl)-1,3-benzodioxole-5-methanol
109534-14-7

(1,3-benzodioxol-5-yl)-1,3-benzodioxole-5-methanol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h;98%
With n-butyllithium In hexane; ethyl acetate83%
With n-butyllithium In tetrahydrofuran at -78 - 20℃;79%
With n-butyllithium In tetrahydrofuran at 20℃;64%
With n-butyllithium 1.) hexane, THF, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to RT; Yield given. Multistep reaction;
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

aniline
62-53-3

aniline

N-(1,3-benzodioxol-5-yl)-N-phenylamine

N-(1,3-benzodioxol-5-yl)-N-phenylamine

Conditions
ConditionsYield
With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In toluene at 110℃; for 16h;98%
With potassium phosphate; copper(l) iodide; N′,N′-diphenyl-1H-pyrrole-2-carbohydrazide In diethylene glycol at 60℃; for 3h; Sealed tube; Molecular sieve;83%
With copper(l) iodide; N′-phenyl-1H-pyrrole-2-carbohydrazide; tetrabutylammomium bromide; potassium hydroxide In water at 20 - 130℃; Ullmann-Goldberg reaction; Microwave irradiation;80%
With N-methoxy-1H-pyrrole-2-carboxamide; potassium phosphate; copper(II) acetate monohydrate at 90℃; for 12h; Sealed tube;72%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

4-Vinylphenylboronic acid
2156-04-9

4-Vinylphenylboronic acid

4-styryl-1,2-(methylenedioxy)benzene
1135448-56-4

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

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 75℃; for 48h; Suzuki coupling; Inert atmosphere;98%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

sodium methylate
124-41-4

sodium methylate

5-methoxybenzo[d]1,3-dioxole
7228-35-5

5-methoxybenzo[d]1,3-dioxole

Conditions
ConditionsYield
With Methyl formate; copper(l) chloride In methanol at 110℃; for 2h; Autoclave;98%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

bis(p-methoxyphenyl)methanone
90-96-0

bis(p-methoxyphenyl)methanone

benzo[d][1,3]dioxol-5-ylbis(4-methoxyphenyl)methanol

benzo[d][1,3]dioxol-5-ylbis(4-methoxyphenyl)methanol

Conditions
ConditionsYield
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With magnesium In tetrahydrofuran; ethylene dibromide at 60℃; for 1h; Inert atmosphere;
Stage #2: bis(p-methoxyphenyl)methanone In tetrahydrofuran at 60℃; for 2h; Inert atmosphere;
98%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

5-bromopentan-1-nitrile
5414-21-1

5-bromopentan-1-nitrile

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

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

Conditions
ConditionsYield
With potassium hexafluorophosphate; bis(1,3-bis((4-methyl-2-pyridyl)imino)isoindolinato)nickel(II); C22H19N5NiO2 In N,N-dimethyl acetamide at 20℃; Inert atmosphere; Electrolysis; Sealed tube;98%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

5‐bromo‐6‐(6‐bromo‐2H‐1,3‐benzodioxol‐5‐yl)‐2H‐1,3‐benzodioxole
4791-90-6

5‐bromo‐6‐(6‐bromo‐2H‐1,3‐benzodioxol‐5‐yl)‐2H‐1,3‐benzodioxole

Conditions
ConditionsYield
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With 2,2,6,6‐tetrakis(trifluoromethyl)‐4λ3‐broma‐3,5‐dioxatricyclo[5.3.1.04,11]undeca‐1(11),7,9‐triene In dichloromethane at -30℃; Inert atmosphere;
Stage #2: With trimethylsilyl trifluoromethanesulfonate at -30℃; for 3h; Inert atmosphere;
98%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

1-bromo-2-iodo-4,5-(methylenedioxy)benzene
94670-76-5

1-bromo-2-iodo-4,5-(methylenedioxy)benzene

Conditions
ConditionsYield
With iodine; silver trifluoroacetate In dichloromethane for 10h;97%
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃; for 24h;91%
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃; for 24h;91%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N-mesityl-3,4-(methylenedioxy)aniline
137445-01-3

N-mesityl-3,4-(methylenedioxy)aniline

Conditions
ConditionsYield
With johnphos; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 80℃; for 2h; Arylation;97%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

diphenylamine
122-39-4

diphenylamine

N-(3,4-methylenedioxyphenyl)diphenylamine
1111667-16-3

N-(3,4-methylenedioxyphenyl)diphenylamine

Conditions
ConditionsYield
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); sodium t-butanolate In toluene at 100℃; for 3h; Inert atmosphere;97%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

1,3-dibenzyl-1-(but-3-en-1-yl)-2-cyanoguanidine

1,3-dibenzyl-1-(but-3-en-1-yl)-2-cyanoguanidine

N-[4-benzo[d][1,3]dioxol-5-ylmethyl]-1,3-dibenzyltetrahydropyrimidin-2[1H]ylidenecyanamide

N-[4-benzo[d][1,3]dioxol-5-ylmethyl]-1,3-dibenzyltetrahydropyrimidin-2[1H]ylidenecyanamide

Conditions
ConditionsYield
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With tris-(dibenzylideneacetone)dipalladium(0); 2′-(dicyclohexylphophanyl)-N2,N2,N6,N6-tetramethyl[1,1′-biphenyl]-2,6-diamine; sodium t-butanolate In toluene at 20℃; for 0.0166667h; Inert atmosphere; Schlenk technique;
Stage #2: 1,3-dibenzyl-1-(but-3-en-1-yl)-2-cyanoguanidine In toluene at 90℃; for 1h; Schlenk technique; Inert atmosphere;
97%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

(2-Amino-phenyl)-benzo[1,3]dioxol-5-yl-methanone
178210-71-4

(2-Amino-phenyl)-benzo[1,3]dioxol-5-yl-methanone

Conditions
ConditionsYield
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With magnesium In tetrahydrofuran for 1h; Inert atmosphere; Reflux;
Stage #2: anthranilic acid nitrile In tetrahydrofuran Inert atmosphere; Reflux;
Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; Inert atmosphere;
97%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

carbon dioxide
124-38-9

carbon dioxide

Piperonylic acid
94-53-1

Piperonylic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique;
Stage #2: 1,2-(methylenedioxy)-4-bromobenzene With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 3h; Schlenk technique; Sealed tube;
96%
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 60℃; for 0.416667h; Schlenk technique;
Stage #2: 1,2-(methylenedioxy)-4-bromobenzene With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 3h; Schlenk technique;
96%
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 2-(diphenylphosphino)-2’(3-(dimethylamino)-3-oxopropyl)-6’-(3-(icosyloxy)-3-oxopropyl)biphenyl; water; palladium diacetate; N-ethyl-N,N-diisopropylamine In toluene under 760.051 Torr; for 16h; Inert atmosphere; Schlenk technique; Irradiation;89%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

2,3,4-trimethoxyphenylboronic acid
118062-05-8

2,3,4-trimethoxyphenylboronic acid

1,2-(methylenedioxy)-4-(2',3',4'-trimethoxyphenyl)benzene
145343-47-1

1,2-(methylenedioxy)-4-(2',3',4'-trimethoxyphenyl)benzene

Conditions
ConditionsYield
With barium dihydroxide; palladium diacetate In ethanol for 2h; Product distribution; Ambient temperature; only in the absence of O2, var. of catalyst, base;96%
With barium dihydroxide; palladium diacetate In ethanol for 2h; Ambient temperature;96%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; benzene for 60h; Heating;73%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

tri(allyl)phenylsilane
2633-57-0

tri(allyl)phenylsilane

3,4-methylenedioxybiphenyl
24382-05-6

3,4-methylenedioxybiphenyl

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; palladium dichloride; tricyclohexylphosphine In water; dimethyl sulfoxide at 80℃; for 2h;96%
Stage #1: triallyl(phenyl)silane With tetrabutyl ammonium fluoride In water; dimethyl sulfoxide at 20℃; for 1h;
Stage #2: 1,2-(methylenedioxy)-4-bromobenzene With tricyclohexylphosphine; palladium dichloride In water; dimethyl sulfoxide at 80℃; for 2h;
96%
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.

4-Bromo-1,2-(methylenedioxy)benzene Chemical Properties

The Molecular Structure of 1,3-Benzodioxole, 5-bromo- (CAS NO.2635-13-4):

Empirical Formula: C7H5BrO2
Molecular Weight: 201.0174 
IUPAC Name: 5-bromo-1,3-benzodioxole 
Appearance: clear yellow-orange liquid
Nominal Mass: 200 Da
Average Mass: 201.0174 Da
Monoisotopic Mass: 199.947284 Da 
Index of Refraction: 1.602
Molar Refractivity: 40.1 cm3
Molar Volume: 116.7 cm3
Surface Tension: 51.6 dyne/cm
Density: 1.721 g/cm3
Flash Point: 107.5 °C
Enthalpy of Vaporization: 48.63 kJ/mol
Boiling Point: 268.6 °C at 760 mmHg
Vapour Pressure: 0.0126 mmHg at 25°C 
InChI
InChI=1/C7H5BrO2/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3H,4H2
Smiles
c12cc(Br)ccc1OCO2
Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives; Miscellaneous; Bromine Compounds; Miscellaneous Compounds

4-Bromo-1,2-(methylenedioxy)benzene Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
S37/39: Wear suitable gloves and eye/face protection
WGK Germany: 3
Hazard Note: Irritant

4-Bromo-1,2-(methylenedioxy)benzene Specification

 1,3-Benzodioxole, 5-bromo- (CAS NO.2635-13-4) is also called as 4-Bromomethylenedioxybenzene ; 1,2-Methylenedioxy-4-bromobenzene ; 1-Bromo-3,4-(methylenedioxy)benzene ; 3,4-Methylenedioxybromobenzene ; 3,4-Methylendioxybromobenzene ; 4-Bromo-1,2-methylenedioxybenzene . 1,3-Benzodioxole, 5-bromo- (CAS NO.2635-13-4) is used as intermediates of daily chemical products.

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