2,3-dihydro-benzofuran-5-carbaldehyde
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 80℃; for 1h; | 83% |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 20 - 80℃; for 1h; Inert atmosphere; | 75% |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 80℃; for 1h; | 60% |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 80℃; for 4h; Cooling with ice; | 55% |
benzo[b]furan-5-carbonitrile
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: benzo[b]furan-5-carbonitrile With diisobutylaluminium hydride In n-heptane; dichloromethane at -20 - -15℃; for 0.166667h; Stage #2: With hydrogenchloride; water In n-heptane; dichloromethane | 78% |
Stage #1: benzo[b]furan-5-carbonitrile With diisobutylaluminium hydride In n-heptane; dichloromethane at -20 - -15℃; for 0.166667h; Stage #2: With hydrogenchloride; water In n-heptane; dichloromethane at 20℃; | 78% |
With diisobutylaluminium hydride In dichloromethane at -15℃; for 0.166667h; |
5-bromobenzofuran
N,N-dimethyl-formamide
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 5-bromobenzofuran With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2h; Stage #2: N,N-dimethyl-formamide In diethyl ether; pentane for 1h; | 75% |
With tert.-butyl lithium In diethyl ether; pentane at -78 - 8℃; for 0.833333h; | 70% |
Stage #1: 5-bromobenzofuran With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.333333h; Stage #2: N,N-dimethyl-formamide In diethyl ether; pentane at -78 - 20℃; for 0.5h; Product distribution / selectivity; | 70% |
N,N-dimethyl-formamide
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 5-bromobenzofuran With tert.-butyl lithium In diethyl ether at -78℃; for 0.333333h; Stage #2: N,N-dimethyl-formamide In diethyl ether at -25 - 20℃; for 3h; | 67% |
Stage #1: 5-bromobenzofuran With tert.-butyl lithium In diethyl ether at -78℃; for 0.333333h; Stage #2: N,N-dimethyl-formamide In diethyl ether at -25 - 20℃; | 67% |
3-ethynyl-4-methoxybenzaldehyde
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium chloride at 130℃; for 1.5h; | 58% |
3-(prop-1-enyl)-4-(prop-1-enyloxy)benzaldehyde
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 90℃; for 3h; | 50% |
4-hydroxy-3-(2-propen-1-yl)benzaldehyde
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 89 percent / K2CO3 / acetone / 2 h / 60 °C 2: 82 percent / [RuClH(CO)(PPh3)3] / CH2Cl2 / 14 h / 65 °C 3: 50 percent / ((Mes)2C3H5N2)Cl2Ru=CHPh / toluene / 3 h / 90 °C View Scheme |
4-(2-propenyloxy)benzaldehyde
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 41 percent / 0.17 h / 250 °C / microwave irradiation 2: 89 percent / K2CO3 / acetone / 2 h / 60 °C 3: 82 percent / [RuClH(CO)(PPh3)3] / CH2Cl2 / 14 h / 65 °C 4: 50 percent / ((Mes)2C3H5N2)Cl2Ru=CHPh / toluene / 3 h / 90 °C View Scheme |
3-allyl-4-allyloxybenzaldehyde
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 82 percent / [RuClH(CO)(PPh3)3] / CH2Cl2 / 14 h / 65 °C 2: 50 percent / ((Mes)2C3H5N2)Cl2Ru=CHPh / toluene / 3 h / 90 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: K2CO3 / acetone 2: 41 percent / 0.17 h / 250 °C / microwave irradiation 3: 89 percent / K2CO3 / acetone / 2 h / 60 °C 4: 82 percent / [RuClH(CO)(PPh3)3] / CH2Cl2 / 14 h / 65 °C 5: 50 percent / ((Mes)2C3H5N2)Cl2Ru=CHPh / toluene / 3 h / 90 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF 2: polyphosphoric acid / benzene / Heating 3: 1.) t-BuLi / 1.) Et2O, -78 deg C, 2.) Et2O View Scheme |
1-bromo-4-(2,2-diethoxyethoxy)benzene
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: polyphosphoric acid / benzene / Heating 2: 1.) t-BuLi / 1.) Et2O, -78 deg C, 2.) Et2O View Scheme |
isovanillin
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 85 percent / ethyldiisopropylamine / CH2Cl2 / 0.67 h / -78 - 20 °C 2: 88 percent / Pd(PPh3)2Cl2, Et3N / dimethylformamide / 1.5 h / 90 °C 3: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature 4: 58 percent / LiCl, HMPA / 1.5 h / 130 °C View Scheme |
4-methoxy-3-[2-(trimethylsilyl)ethynyl]benzaldehyde
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature 2: 58 percent / LiCl, HMPA / 1.5 h / 130 °C View Scheme |
4-methoxy-3-trifluoromethanesulfonyloxybenzaldehyde
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 88 percent / Pd(PPh3)2Cl2, Et3N / dimethylformamide / 1.5 h / 90 °C 2: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature 3: 58 percent / LiCl, HMPA / 1.5 h / 130 °C View Scheme |
5-bromobenzofuran
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride; iodine; magnesium In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide |
5-bromobenzofuran
4-bromo-phenol
Bromoacetaldehyde diethyl acetal
benzofuran-5-carbaldehyde
benzofuran-5-carbaldehyde
5-hydroxymethylbenzo[b]furan
Conditions | Yield |
---|---|
Stage #1: benzofuran-5-carbaldehyde With sodium tetrahydroborate In methanol Cooling with ice; Stage #2: With ammonium chloride In methanol Saturated solution; | 100% |
With sodium tetrahydroborate In methanol at 0℃; for 0.166667h; | 96% |
With 2,2'-bi(1,3,6,2-dioxazaborocane); water at 20℃; for 18h; Inert atmosphere; Sealed tube; | 86% |
benzofuran-5-carbaldehyde
benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanol
Conditions | Yield |
---|---|
Stage #1: 1-Bromo-3-ethoxy-4-methoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: benzofuran-5-carbaldehyde In tetrahydrofuran at -78℃; for 1h; Stage #3: With water In isopropyl alcohol | 100% |
benzofuran-5-carbaldehyde
ethyl 2-(bis(2-isopropylphenoxy)phosphoryl)acetate
(Z)-ethyl 3-(benzofuran-5-yl)acrylate
Conditions | Yield |
---|---|
Stage #1: ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran; methanol at -78℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Stage #2: benzofuran-5-carbaldehyde In tetrahydrofuran; methanol at -78℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; diastereoselective reaction; | 96% |
Conditions | Yield |
---|---|
In dichloromethane at 40℃; for 20h; | 96% |
benzofuran-5-carbaldehyde
benzo[b]furan-5-carbonitrile
Conditions | Yield |
---|---|
With ammonium sulfate; sodium carbonate; sulfur In dimethyl sulfoxide at 120℃; for 10h; Sealed tube; | 96% |
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 120℃; for 1h; Inert atmosphere; | 93% |
benzofuran-5-carbaldehyde
methylamine
benzofuran-5-yl-N-methylmethanamine
Conditions | Yield |
---|---|
Stage #1: benzofuran-5-carbaldehyde; methylamine In methanol; ethanol for 3h; Stage #2: With sodium tetrahydroborate In methanol at 20℃; Stage #3: With water In methanol | 91% |
Stage #1: benzofuran-5-carbaldehyde; methylamine In methanol; water at 0℃; for 0.916667h; Stage #2: With sodium tetrahydroborate In methanol; water for 0.75h; |
benzofuran-5-carbaldehyde
benzofuran-5-carbaldehyde oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 3h; | 91% |
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; | |
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 3h; | 4.6 g |
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 16h; |
BARBITURIC ACID
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
In 2-methyl-propan-1-ol for 0.75h; Reflux; Green chemistry; | 91% |
In 2-methyl-propan-1-ol for 0.75h; Reflux; | 91% |
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With bromine In chloroform at 20℃; for 1h; | 90% |
benzofuran-5-carbaldehyde
(1,3-benzothiazol-2-ylsulfonyl)fluoromethyl n-propyl ketone
(Z)-2-fluoro-1-(1-benzofuran-5-yl)-1-hexen-3-one
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; dichloromethane at 0 - 5℃; for 8h; Julia Olefin synthesis; stereoselective reaction; | 90% |
benzofuran-5-carbaldehyde
dimethyl 1-(1-diazo-2-oxopropyl)phosphonate
5-ethynylbenzo[b]furane
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; for 12h; | 90% |
benzofuran-5-carbaldehyde
Methyltriphenylphosphonium bromide
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Wittig Olefination; Inert atmosphere; Stage #2: benzofuran-5-carbaldehyde In tetrahydrofuran at 20℃; for 3h; Wittig Olefination; Inert atmosphere; | 86% |
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: benzofuran-5-carbaldehyde; 5-(difluoromethyl)-7-(3-piperidyl)-[1,2,4]triazolo[1,5-a]pyrimidine hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride In diphenylether Inert atmosphere; | 86% |
benzofuran-5-carbaldehyde
4-(trifluoromethyl)phenylmagnesium bromide
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Schlenk technique; | 85% |
tryptamine
benzofuran-5-carbaldehyde
1-benzofuran-5-yl-2,3,4,9-tetrahydro-1H-β-carboline
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane for 48h; | 83% |
benzofuran-5-carbaldehyde
2′-hydroxy-6′-methoxymethoxyacetophenone
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 20℃; | 82% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran; toluene at 20℃; for 6h; Sealed tube; Inert atmosphere; diastereoselective reaction; | 82% |
2-thioxo-4-thiazolidinone
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid In acetonitrile for 2h; Inert atmosphere; Reflux; | 81.2% |
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid In methanol; 1,2-dichloro-ethane | 81% |
Stage #1: benzofuran-5-carbaldehyde; (2S,4R,5R)-5-amino-2-(bis(4-fluorophenyl)methyl)tetrahydro-2H-pyran-4-ol With acetic acid In 1,2-dichloro-ethane for 0.5h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In MeOH; 1,2-dichloro-ethane Inert atmosphere; | 81% |
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water at 20℃; for 24h; Claisen-Schmidt Condensation; | 79% |
benzofuran-5-carbaldehyde
(5-methylpyrazine-2-yl)methylamine
C15H15N3O
Conditions | Yield |
---|---|
Stage #1: benzofuran-5-carbaldehyde; (5-methylpyrazine-2-yl)methylamine With sodium acetate; acetic acid In methanol at 20℃; for 0.5h; Stage #2: With sodium tetrahydroborate In methanol for 0.5h; Stage #3: With water; sodium hydrogencarbonate In methanol | 75% |
benzofuran-5-carbaldehyde
(8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine
N-benzofuran-5-ylmethylene-N'-(8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine
Conditions | Yield |
---|---|
In ethanol at 20℃; | 71% |
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With bromine; acetic acid at 100℃; for 0.5h; | 70% |
With bromine In chloroform at 20℃; Cooling; | 50% |
(2S,4R,5R)-5-amino-2-benzhydryltetrahydro-2H-pyran-4-ol
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: (2S,4R,5R)-5-amino-2-benzhydryl-tetrahydropyran-4-ol; benzofuran-5-carbaldehyde With acetic acid In 1,2-dichloro-ethane for 0.5h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In MeOH; 1,2-dichloro-ethane Inert atmosphere; | 69% |
cis-(3S,6S)-(6-benzhydryl-tetrahydropyran-3-yl)-amine
benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: cis-(3S,6S)-(6-benzhydryl-tetrahydropyran-3-yl)-amine; benzofuran-5-carbaldehyde With acetic acid In 1,2-dichloro-ethane for 0.5h; Stage #2: With sodium cyanoborohydride In methanol; 1,2-dichloro-ethane | 67% |
Stage #1: cis-(3S,6S)-(6-benzhydryl-tetrahydropyran-3-yl)-amine; benzofuran-5-carbaldehyde With acetic acid In acetic acid; 1,2-dichloro-ethane for 0.5h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In MeOH; 1,2-dichloro-ethane Inert atmosphere; | 67% |
The 5-Benzofurancarboxaldehyde, with CAS registry number 10035-16-2, belongs to the following product categories: (1)Furan & Benzofuran; (2)API intermediates. It has the systematic name of 1-benzofuran-5-carbaldehyde. This chemical is a kind of colorless to light yellow liquid. And the chemical formula of this chemical is C9H6O2.
Physical properties of 5-Benzofurancarboxaldehyde: (1)ACD/LogP: 2.09; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.09; (4)ACD/LogD (pH 7.4): 2.09; (5)ACD/BCF (pH 5.5): 22.89; (6)ACD/BCF (pH 7.4): 22.89; (7)ACD/KOC (pH 5.5): 327.24; (8)ACD/KOC (pH 7.4): 327.24; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 30.21 Å2; (13)Index of Refraction: 1.651; (14)Molar Refractivity: 43.14 cm3; (15)Molar Volume: 118 cm3; (16)Polarizability: 17.1×10-24cm3; (17)Surface Tension: 47.7 dyne/cm; (18)Enthalpy of Vaporization: 48.89 kJ/mol; (19)Vapour Pressure: 0.0203 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
The 5-Benzofurancarboxaldehyde irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=Cc2cc1c(occ1)cc2
(2)InChI: InChI=1/C9H6O2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-6H
(3)InChIKey: LLLBDLDNTMMZHL-UHFFFAOYAJ
(4)Std. InChI: InChI=1S/C9H6O2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-6H
(5)Std. InChIKey: LLLBDLDNTMMZHL-UHFFFAOYSA-N
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