2635-13-4

Basic information

• Product Name: 4-Bromo-1,2-(methylenedioxy)benzene
• Synonyms: 4-Bromo-1,2-(methylenedioxy)benzene-5;1-Bromo-3,4-(methylenedioxy)benzene 97%;5-Bromo-1,3-benzodioxolane;3,4-Methylenedioxy bromobenzene 1,3-Benzodioxol-5-bromo;4-BROMO-1,2-(METHYLENEDIOXY)ENZENE;4-Bromo-1,2-methylenedioxybenzene 99%;5-Bromo-1,3-benzodioxole 99%;BROMOBENZODIOXOLE
• CAS NO: 2635-13-4
• Molecular Formula: C₇H₅BrO₂
• Molecular Weight: 201.02
• EINECS: 220-123-5
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Miscellaneous;Bromine Compounds;Miscellaneous Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Protected Alcohols/Phenols
• Mol File: 2635-13-4.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 85-86 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow-orange/Liquid
• Density: 1.669 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.013mmHg at 25°C
• Refractive Index: n20/D 1.583(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol (Sparingly)
• Stability: Light Sensitive
• BRN: 127407
• CAS DataBase Reference: 4-Bromo-1,2-(methylenedioxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-1,2-(methylenedioxy)benzene(2635-13-4)
• EPA Substance Registry System: 4-Bromo-1,2-(methylenedioxy)benzene(2635-13-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 2635-13-4(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow-orange liquid

General Description

The coupling of 1-bromo-3,4-(methylenedioxy)benzene with β-methallyl alcohol was catalyzed by Pd(OAc)2 in combination with P(t-Bu)3.

InChI:InChI=1/C7H5BrO2/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3H,4H2

Synthetic route

Methylenedioxybenzene (274-09-9) → 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4)

Conditions	Yield
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) → 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4)

Conditions	Yield
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) + Methylenedioxybenzene (274-09-9) → 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4)

Conditions	Yield
In acetonitrile at 20℃; for 0.25h; Flow reactor; UV-irradiation;	79%

potassium (3,4-(methylenedioxy)phenyl)trifluoroborate → 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4)

Conditions	Yield
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) → 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4)

Conditions	Yield
With tert-butyldimethylsilyl chloride In tetrachloromethane at 70℃; for 4.5h;	70%

N-Bromosuccinimide (128-08-5) + Methylenedioxybenzene (274-09-9) + chloroform (67-66-3) → 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4)

7-bromo-1-oxaspiro<2.5>octa-5,7-dien-4-one (202001-83-0) → 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + 4-Bromo-2-chloromethoxy-phenol

Conditions	Yield
With chloro-trimethyl-silane In toluene Ambient temperature;

<4-amino-pyrocatechol>-methylene ether-sulfate → Methylenedioxybenzene (274-09-9) + 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4)

Conditions	Yield
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) → 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4)

Conditions	Yield
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) → 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + 5,6-dibromo-1,3-benzodioxole (5279-32-3)

Conditions	Yield
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) + 5-chloro-2-methyl-benzenamine (95-79-4) → N-(3,4-methylenedioxy)benzo-5-chloro-o-toluidine (1203581-77-4)

Conditions	Yield
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) + phenylboronic acid (98-80-6) → 3,4-methylenedioxybiphenyl (24382-05-6)

Conditions	Yield
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) + 4-methoxyphenylboronic acid (5720-07-0) → 4'-methoxy-3,4-(methylenedioxy-)biphenyl (89346-90-7)

Conditions	Yield
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) + 2-Methylphenylboronic acid (16419-60-6) → 2-methyl-3',4'-methylenedioxy-1,1'-biphenyl

Conditions	Yield
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 toluene	99%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + copper(I) iodide (7681-65-4) + acetonitrile (75-05-8) + Methyl 6-benzyloxy-4-oxo-4H-chromen-3-carboxylate (203919-27-1) → methyl 2-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-oxo-chroman-3-carboxylate

Conditions	Yield
With magnesium In tetrahydrofuran; toluene	99%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + diisopropyl hydrogenphosphonate (1809-20-7) → diisopropyl benzo[d][1,3]dioxol-5-ylphosphonate (1073561-79-1)

Conditions	Yield
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) + 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) → 5-(ethylthio)-1,3-benzodioxole (5279-34-5)

Conditions	Yield
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) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzodioxole (94838-82-1)

Conditions	Yield
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-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

Conditions	Yield
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) + 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) → piperonylonitrile (4421-09-4)

Conditions	Yield
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) → Sesamol (533-31-3)

Conditions	Yield
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) + 3-trifluoromethylaniline (98-16-8) → 5-(3-trifluoromethylaniline)benzodioxole

Conditions	Yield
With [(π-cinnamyl)Pd(tBuXPhos)]OTf In water at 45℃; for 16h;	99%

methanol (67-56-1) + 1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) → 5-methoxybenzo[d]1,3-dioxole (7228-35-5)

Conditions	Yield
With triethylamine at 20℃; for 48h; Irradiation; Schlenk technique;	99%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + piperonal (120-57-0) → (1,3-benzodioxol-5-yl)-1,3-benzodioxole-5-methanol (109534-14-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h;	98%
With n-butyllithium In hexane; ethyl acetate	83%
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) + aniline (62-53-3) → N-(1,3-benzodioxol-5-yl)-N-phenylamine

Conditions	Yield
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) + 4-Vinylphenylboronic acid (2156-04-9) → 4-styryl-1,2-(methylenedioxy)benzene (1135448-56-4)

Conditions	Yield
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) + sodium methylate (124-41-4) → 5-methoxybenzo[d]1,3-dioxole (7228-35-5)

Conditions	Yield
With Methyl formate; copper(l) chloride In methanol at 110℃; for 2h; Autoclave;	98%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + bis(p-methoxyphenyl)methanone (90-96-0) → benzo[d][1,3]dioxol-5-ylbis(4-methoxyphenyl)methanol

Conditions	Yield
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) + 5-bromopentan-1-nitrile (5414-21-1) → 5-(benzo[d][1,3]dioxol-5-yl)pentanenitrile

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

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

Conditions	Yield
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) + 2,4,6-trimethylaniline (88-05-1) → N-mesityl-3,4-(methylenedioxy)aniline (137445-01-3)

Conditions	Yield
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) + diphenylamine (122-39-4) → N-(3,4-methylenedioxyphenyl)diphenylamine (1111667-16-3)

Conditions	Yield
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) + 1,3-dibenzyl-1-(but-3-en-1-yl)-2-cyanoguanidine → N-[4-benzo[d][1,3]dioxol-5-ylmethyl]-1,3-dibenzyltetrahydropyrimidin-2[1H]ylidenecyanamide

Conditions	Yield
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) + anthranilic acid nitrile (1885-29-6) → (2-Amino-phenyl)-benzo[1,3]dioxol-5-yl-methanone (178210-71-4)

Conditions	Yield
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) + carbon dioxide (124-38-9) → Piperonylic acid (94-53-1)

Conditions	Yield
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) + 2,3,4-trimethoxyphenylboronic acid (118062-05-8) → 1,2-(methylenedioxy)-4-(2',3',4'-trimethoxyphenyl)benzene (145343-47-1)

Conditions	Yield
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) + tri(allyl)phenylsilane (2633-57-0) → 3,4-methylenedioxybiphenyl (24382-05-6)

Conditions	Yield
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) → Methylenedioxybenzene (274-09-9)

Conditions	Yield
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.

Upstream product

• 128-08-5 N-Bromosuccinimide 
• 274-09-9 Methylenedioxybenzene 
• 109586-40-5 1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate 
• 2316-64-5 5-bromo-2-hydroxybenzyl alcohol 
• 202001-83-0 7-bromo-1-oxaspiro<2.5>octa-5,7-dien-4-one 
• 67-66-3 chloroform 

Downstream Products

• 94-53-1 Piperonylic acid 
• 6269-83-6 α-<2-Morpholino-aethyl>-α-<3,4,5-trimethoxy-phenyl>-piperonylalkohol 
• 6269-84-7 α-<2-Morpholino-aethyl>-α-<4-methoxy-phenyl>-piperonylalkohol 
• 16929-05-8 4-n-butyl-1,2-methylenedioxybenzene 
• 77545-60-9 5-(2-Cyclohexen-1-on-3-yl)-benzo<1,2-d><1,3>dioxol 
• 144412-92-0 1-<3,4-(Methylenedioxy)phenyl>-2-cyclohexen-1-ol 
• 107770-11-6 1-benzyl-3-<3,4-(methylenedioxy)phenyl>-2-pyrrolidine 
• 127218-44-4 1-(1,3-Benzodioxol-5-yl)-4-methoxycyclohexene 
• 129920-39-4 4-(benzyloxy)-1-(1,3-benzodioxol-5-yl)cyclohex-1-ene 
• 128592-58-5 (S)-1-Benzo[1,3]dioxol-5-yl-2-[(S)-1-(2,6-dichloro-phenyl)-ethyl]-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline 
• 120040-58-6 Benzo[1,3]dioxol-5-yl-((S)-5-benzyloxy-2,5-dihydro-furan-3-yl)-methanol 
• 120040-58-6 Benzo[1,3]dioxol-5-yl-((R)-5-benzyloxy-2,5-dihydro-furan-3-yl)-methanol 
• 40918-96-5 methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate 
• 7605-45-0 methyl E-3-<3,4-(methylenedioxy)phenyl>-2-methylacrylate 

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Anti-inflammatory, ulcerogenic and platelet activation evaluation of novel 1,4-diaryl-1,2,3-triazole neolignan-celecoxib hybrids

This study reports the synthesis of novel neolignans-celecoxib hybrids and the evaluation of their biological activity. Analogs 8–13 (L13-L18) exhibited anti-inflammatory activity, inhibited glycoprotein expression (P-selectin) related to platelet activation, and were considered non– ulcerogenic in the animal model, even with the administration of 10 times higher than the dose used in reference therapy. In silico drug-likeness showed that the analogs are compliant with Lipinski's rule of five. A molecular docking study showed that the hybrids 8–13 (L13-L18) fitted similarly with celecoxib in the COX-2 active site. According to this data, it is possible to infer that extra hydrophobic interactions and the hydrogen interactions with the triazole core may improve the selectivity towards the COX-2 active site. Furthermore, the molecular docking study with P-selectin showed the binding affinity of the analogs in the active site, performing important interactions with amino acid residues such as Tyr 48. Whereas the P-selectin is a promising target to the design of new anti-inflammatory drugs with antithrombotic properties, a distinct butterfly-like structure of 1,4-diaryl-1,2,3-triazole neolignan-celecoxib hybrids synthesized in this work may be a safer alternative to the traditional COX-2 inhibitors.

Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons

A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).

Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis

Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in the activation of imine and carbonyl groups in various transformations with good yields and selectivity. Lewis acidity of the bis-selenonium salts was found to be stronger than that of the monoselenonium systems, attributed to the synergistic effect of the two cationic selenonium centers. In addition, the bis-selenonium catalysts are not inhibited by strong bases or moisture.