ethylene dibromide
3,4-dihydroxybenzaldehyde
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 16h; | 97% |
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 70℃; for 16h; | 97% |
With sodium hydroxide; tetrabutylammomium bromide In water | 90% |
1,2-dichloro-ethane
3,4-dihydroxybenzaldehyde
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 105℃; for 4h; | 90% |
With potassium carbonate In acetone at 50 - 60℃; for 29h; |
9-methyl-9H-fluorene-9-carbonyl chloride
6-bromo-1,4-benzodioxane
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; potassium formate; tetra-(n-butyl)ammonium iodide; tricyclohexylphosphine tetrafluoroborate; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate at 100℃; for 18h; Reagent/catalyst; Solvent; Sealed tube; Glovebox; Inert atmosphere; | 81% |
benzo-1,4-dioxane
hexamethylenetetramine
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
In trifluoroacetic acid at 90 - 95℃; for 24h; | 72% |
benzo-1,4-dioxane
hydrogen cyanide
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride; aluminium trichloride Zersetzung des Reaktionsprodukts durch Erhitzen mit verd. Salzsaeure; |
benzo-1,4-dioxane
N,N-dimethyl-formamide
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With N-Bromosuccinimide; n-butyllithium 1) MeOH, 2) THF, -78 deg C; Multistep reaction; |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With zinc(II) cyanide; hydrogenchloride; aluminium trichloride anschliessendes Behandeln mit wss. Salzsaeure; |
ethylene dibromide
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With ethanol |
3,4-dihydroxybenzaldehyde
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide |
1-benzoyl-1-<2-(hydroxy)phenoxy>ethane
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1) AlCl3, 2) 10percent HCl / 1) benzene, temp ,40 deg C, 2) benzene, 1 h, 50 deg C 2: 48percent HBr / 15 h / Ambient temperature 3: 48 percent / NaOMe / methanol / 24 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 78 percent / NaOEt / dimethylformamide / 0.5 h / Ambient temperature 2: 1) AlCl3, 2) 10percent HCl / 1) benzene, temp ,40 deg C, 2) benzene, 1 h, 50 deg C 3: 48percent HBr / 15 h / Ambient temperature 4: 48 percent / NaOMe / methanol / 24 h / Heating View Scheme |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 48percent HBr / 15 h / Ambient temperature 2: 48 percent / NaOMe / methanol / 24 h / Heating View Scheme |
benzene-1,2-diol
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; water / 100 °C 2: hydrogen chloride; aluminium chloride / Zersetzung des Reaktionsprodukts durch Erhitzen mit verd. Salzsaeure View Scheme |
6-iodo-1,4-benzodioxane
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium formate; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane / dimethyl sulfoxide / Inert atmosphere; Sealed tube 2: water View Scheme |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With water |
3,4-dibromobenzaldehyde
ethylene glycol
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With potassium carbonate; triethylamine In N,N-dimethyl-formamide at 80℃; Inert atmosphere; |
vanillin
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminum (III) chloride; pyridine / dichloromethane / 24 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 100 - 110 °C View Scheme |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
ethyl acetoacetate
Conditions | Yield |
---|---|
With piperidine; acetic acid In benzene for 15h; Heating; | 100% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
1-phenyl-3-trimethylsilylmethyl-3,4-pentadien-1-ol
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In diethyl ether at -78℃; for 4h; | 100% |
trimethylsulphonium iodide
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
6-Oxiranyl-2,3-dihydro-benzo[1,4]dioxine
Conditions | Yield |
---|---|
With potassium hydroxide; water In acetonitrile at 60℃; for 1.5h; | 100% |
diethoxyphosphoryl-acetic acid ethyl ester
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
(E)-ethyl 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylate
Conditions | Yield |
---|---|
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With lithium chloride In tetrahydrofuran at 20℃; for 0.25h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Stage #2: 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Horner-Wadsworth-Emmons Olefination; Inert atmosphere; | 100% |
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde In tetrahydrofuran at 20℃; for 17h; Inert atmosphere; | 93% |
nitromethane
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
(E)-6-(2-nitrovinyl)-2,3-dihydro[1,4]benzodioxine
Conditions | Yield |
---|---|
With ammonium acetate at 100℃; Inert atmosphere; | 99% |
With ethanol; methylamine hydrochloride; sodium carbonate | |
With sodium hydroxide at 15℃; | |
Henry reaction; |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
2,3-dihydro-1,4-benzodioxin-6-carboxylic acid
Conditions | Yield |
---|---|
With sodium chlorite; sodium dihydrogen phosphate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 20℃; for 45h; | 99% |
With urea hydrogen peroxide adduct; sodium hydroxide In methanol; water for 1.5h; Reflux; | 81% |
With potassium permanganate at 70 - 80℃; for 0.666667h; | 76% |
1-(4-fluorophenyl)-1H-indazole-5-amine
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 48h; | 99% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With 1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-1H-imidazolium bromide; water-d2; potassium carbonate In toluene at 40℃; for 12h; | 99% |
With 1,3,5-triscyano-2,4,6-tris(N-carbazolyl)benzene; water-d2; sodium carbonate; triisopropylsilanethiol In ethyl acetate at 20℃; for 36h; Inert atmosphere; Sealed tube; Irradiation; | 91% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
malononitrile
Conditions | Yield |
---|---|
With nickel(II) ferrite In ethanol at 20℃; for 32h; Knoevenagel Condensation; Green chemistry; | 98.9% |
With triethylamine In methanol Reflux; | |
With piperidine In ethanol at 20℃; for 2h; |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
dihydrobenzo[1,4]dioxin-6-ol
Conditions | Yield |
---|---|
With potassium fluoride; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; Cooling with ice; | 98% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 50℃; for 16h; | 94% |
Stage #1: 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 50℃; for 16h; Stage #2: With sodium hydroxide In methanol; water for 2h; | 94% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
2,3-dihydrobenzo[b][1,4]dioxin-6-carbaldoxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium hydroxide In ethanol at 80℃; for 4h; Inert atmosphere; | 98% |
With hydroxylamine hydrochloride; sodium acetate In ethanol for 12h; | |
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 60℃; for 1h; |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
dimethyl 2-((tertbutyldiphenylsilyl)methyl)cyclopropane-1,1-dicarboxylate
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 30 - 32℃; for 6h; | 98% |
1-methyl-2-thioxoimidazolidin-4-one
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
(5Z)-5-(2,3-dihydro-1,4-benzodioxan-6-ylmethylene)-1-methyl-2-thioxoimidazolidin-4-one
Conditions | Yield |
---|---|
With propylamine at 80℃; for 1h; Knoevenagel condensation; Microwave irradiation; | 98% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
2,3-dihydrobenzo[b][1,4]dioxine-6-carbonitrile
Conditions | Yield |
---|---|
With HCl·DMPU; hydroxylamine hydrochloride In acetonitrile at 60℃; | 98% |
With oxygen; acetonitrile; copper(l) chloride In N,N-dimethyl acetamide at 130℃; for 24h; Schlenk technique; | 87% |
With ammonia; oxygen In tert-Amyl alcohol at 40℃; under 750.075 Torr; for 24h; Green chemistry; | 85% |
With hydroxylamine hydrochloride; sodium sulfate In N,N-dimethyl-formamide at 170℃; for 4h; | 81% |
Multi-step reaction with 2 steps 1.1: hydroxylamine hydrochloride / methanol; water / 0.5 h / 20 °C 1.2: 20 °C 2.1: acetic anhydride / Reflux View Scheme |
4-chloro-2-hydroxy acetophenone
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
(E)-1-(4-chloro-2-hydroxyphenyl)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)prop-2-en-1-one
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 40h; Ambient temperature; | 97% |
With potassium hydroxide In ethanol Ambient temperature; | 97% |
With sodium hydroxide In methanol at 20℃; | 37.89% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanol
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde With sodium tetrahydroborate In ethanol at 0 - 20℃; for 1h; Stage #2: With water In ethanol | 97% |
With methanol; sodium tetrahydroborate at 0℃; for 0.5h; | 95% |
With sodium tetrahydroborate In methanol at 25℃; for 2h; | 93% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
(trifluoromethyl)trimethylsilane
1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2,2-trifluoroethanol
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde; (trifluoromethyl)trimethylsilane With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: With water In N,N-dimethyl-formamide for 4h; Acidic conditions; | 97% |
5-Bromo-2-hydroxyacetophenone
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
(E)-1-(5-bromo-2-hydroxyphenyl)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)prop-2-en-1-one
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 40h; Ambient temperature; | 96% |
With potassium hydroxide In ethanol Ambient temperature; | 96% |
With sodium hydroxide In methanol at 20℃; | 58.33% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
1-(2-benzyloxy-5-fluorophenyl)-ethanone
1-(2-benzyloxy-5-fluorophenyl)-3-(6-benzodioxan-1,4-yl)propenone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 40h; Ambient temperature; | 96% |
With potassium hydroxide In ethanol Ambient temperature; | 96% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
1-(2-(benzyloxy)-5-bromophenyl)ethanone
1-(2-benzyloxy-5-bromophenyl)-3-(6-benzodioxan-1,4-yl)propenone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 40h; Ambient temperature; | 96% |
With potassium hydroxide In ethanol Ambient temperature; | 96% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
4-methoxy-aniline
Dimethyl phosphite
dimethyl (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(4-methoxyphenylamino)methylphosphonate
Conditions | Yield |
---|---|
With titanium(IV) oxide In neat (no solvent) at 50℃; for 0.166667h; Green chemistry; | 96% |
hydrogen cyanide
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Conditions | Yield |
---|---|
With Prunus communis hydroxynitrile lyase 5 L331A mutant In tert-butyl methyl ether at 10℃; for 12h; pH=3.5; Catalytic behavior; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | 96% |
With hydroxynitrile lyase isozyme 5 from Prunus communis In tert-butyl methyl ether at 25℃; for 7h; pH=5; Enzymatic reaction; | 84% |
With (R)-oxynitrilase In di-isopropyl ether Enzymatic reaction; |
1-<5-chloro-2-(phenylmethoxy)phenyl>ethanone
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
1-(2-benzyloxy-5-chlorophenyl)-3-(6-benzodioxan-1,4-yl)propenone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 40h; Ambient temperature; | 95% |
With potassium hydroxide In ethanol Ambient temperature; | 95% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
2-benzyloxy-4,5-dimethylacetophenone
1-(2-benzyloxy-4,5-dimethylphenyl)-3-(6-benzodioxan-1,4-yl)propenone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 40h; Ambient temperature; | 95% |
With potassium hydroxide In ethanol Ambient temperature; | 95% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
malonic acid dimethyl ester
C14H14O6
Conditions | Yield |
---|---|
With piperidine; acetic acid In benzene Knoevenagel condensation; | 95% |
With piperidine; acetic acid In benzene Dean-Stark; Reflux; |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
p-toluidine
Dimethyl phosphite
dimethyl (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(p-tolylamino)methylphosphonate
Conditions | Yield |
---|---|
With titanium(IV) oxide In neat (no solvent) at 50℃; for 0.2h; Green chemistry; | 95% |
2-aminofluorene
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
Dimethyl phosphite
dimethyl (((9H-fluoren-2-yl)amino)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)phosphonate
Conditions | Yield |
---|---|
With polystyrene-supported p-toluenesulfonic acid In neat (no solvent) at 70℃; for 0.0833333h; Kabachnik-Fields Reaction; Microwave irradiation; Green chemistry; | 95% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
4-amino-1-phenylpiperazine
Conditions | Yield |
---|---|
In toluene at 100℃; | 95% |
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
acrylic acid methyl ester
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane at 30 - 40℃; Morita-Baylis-Hillman Alkylation; Sonication; | 95% |
With 1,4-diaza-bicyclo[2.2.2]octane In methanol at 20℃; Morita-Baylis-Hillman Alkylation; |
The 1,4-Benzodioxin-6-carboxaldehyde,2,3-dihydro- is an organic compound with the formula C9H8O3. It belongs to the product categories of Aromatic Aldehydes & Derivatives (substituted); Aldehydes; Benzodioxanes Carbonyl Compounds; Building Blocks; C9; Heterocyclic Building Blocks. Its EINECS registry number is 249-763-3. With the CAS registry number 29668-44-8, its IUPAC name is 2,3-dihydro-1,4-benzodioxine-6-carbaldehyde. When you are using this chemical, please be cautious about it. This chemical may cause inflammation to the skin or other mucous membranes. It is yellowish-beige powder and chunks. The product should be sealed and stored in cool, dry and well-ventilated place. What's more, it should be protected from strong oxides.
Physical properties of 1,4-Benzodioxin-6-carboxaldehyde,2,3-dihydro-: (1)ACD/LogP: 1.54; (2)#H bond acceptors: 3; (3)#Freely Rotating Bonds: 1; (4)Index of Refraction: 1.588; (5)Molar Refractivity: 43.77 cm3; (6)Molar Volume: 130 cm3; (7)Surface Tension: 51.1 dyne/cm; (8)Density: 1.262 g/cm3; (9)Flash Point: 116 °C; (10)Enthalpy of Vaporization: 45.76 kJ/mol; (11)Boiling Point: 221.2 °C at 760 mmHg; (12)Vapour Pressure: 0.109 mmHg at 25°C.
Preparation of 1,4-Benzodioxin-6-carboxaldehyde,2,3-dihydro-: this chemical can be prepared by 3,4-dihydroxy-benzaldehyde and 1,2-dibromo-ethane. This reaction will need reagent sodium hydroxide and solvent H2O. The reaction time is 1 hour. The yield is about 50%.
Uses of 1,4-Benzodioxin-6-carboxaldehyde,2,3-dihydro-: it can be used to produce 5,10,15,20-tetrakis-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-porphyrine by heating. This reaction will need solvent propionic acid with reaction time of 1 hour. The yield is about 16.4%.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1COC2=C(O1)C=CC(=C2)C=O
(2)InChI: InChI=1S/C9H8O3/c10-6-7-1-2-8-9(5-7)12-4-3-11-8/h1-2,5-6H,3-4H2
(3)InChIKey: CWKXDPPQCVWXAG-UHFFFAOYSA-N
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