cyclopropylcarbinyl bromide
4-difluoromethoxy-3-hydroxybenzaldehyde
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-difluoromethoxy-3-hydroxybenzaldehyde With potassium carbonate; potassium iodide In dimethyl sulfoxide at 70℃; for 1h; Stage #2: cyclopropylcarbinyl bromide In dimethyl sulfoxide at 70℃; for 4h; | 99% |
With trimethylbenzylammonium bromide; potassium carbonate; potassium iodide In tetrahydrofuran at 0℃; Concentration; Reflux; | 98.5% |
With potassium carbonate In tetrahydrofuran at 0℃; for 14h; Heating / reflux; | 97% |
Cyclopropylmethanol
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
With potassium tert-butylate In 1,4-dioxane at 70 - 75℃; for 4h; Reagent/catalyst; Solvent; Temperature; | 96.6% |
3-(cyclopropylmethoxy)-4-hydroxybenzaldehyde
sodium chlorodifluoroacetate
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide at 120℃; for 2h; | 84% |
3,4-dihydroxybenzaldehyde
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / N,N-dimethyl-formamide; water / 2 h / 120 °C 2: potassium carbonate / tetrahydrofuran / 14 h / 0 °C / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 20 - 85 °C 1.2: 8 - 10 h / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 6 h / 75 - 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium hydroxide / N,N-dimethyl-formamide; water / 2 h / 120 °C 2: caesium carbonate / N,N-dimethyl-formamide / 1 h / 65 °C View Scheme |
4-benzyloxy-3-hydroxy-benzaldehyde
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 65 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C 3: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 120 °C View Scheme |
4-(benzyloxy)-3-(cyclopropylmethoxy)benzaldehyde
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C 2: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 120 °C View Scheme |
vanillin
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 90 °C 2: lithium chloride / N,N-dimethyl-formamide / Reflux 3: potassium carbonate / tetrahydrofuran / 1 h / 20 °C View Scheme |
4-(difluoromethoxy)-3-methoxybenzaldehyde
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: lithium chloride / N,N-dimethyl-formamide / Reflux 2: potassium carbonate / tetrahydrofuran / 1 h / 20 °C View Scheme |
3-fluoro-4-hydroxybenzaldehyde
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / N,N-dimethyl-formamide; water / 2 h / 95 - 100 °C 2: potassium tert-butylate / 1,4-dioxane / 4 h / 70 - 75 °C View Scheme |
(R)-2-methylpropane-2-sulfinamide
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
(R)-2-methyl-2-propanesulfinic acid 3-cyclopropylmethoxy-4-(difluoromethoxy)benzylideneamide
Conditions | Yield |
---|---|
With titanium(IV) tetraethanolate In tetrahydrofuran at 20℃; for 12h; | 99.8% |
(S)-2-methylpropane-2-sulfinamide
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
(S)-2-methyl-2-propanesulfinic acid 3-cyclopropylmethoxy-4-(difluoromethoxy)benzylideneamide
Conditions | Yield |
---|---|
With titanium(IV) tetraethanolate In tetrahydrofuran at 20℃; for 12h; | 98.8% |
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid
Conditions | Yield |
---|---|
With sodium chlorite; aminosulfonic acid In water; acetic acid at 20℃; for 1h; | 97% |
With dihydrogen peroxide; potassium hydroxide In methanol at 65℃; for 1h; | 97% |
With sodium chlorite; aminosulfonic acid In water; acetic acid at 20℃; for 1h; Concentration; | 97.3% |
ethyl (triphenylphosphoranylidene)acetate
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
In dichloromethane at 20℃; Wittig Olefination; Inert atmosphere; | 97% |
(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfinate
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfinate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde In tetrahydrofuran at 0 - 20℃; for 12h; | 95.8% |
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
3-cyclopropylmethoxy-4-difluoromethoxy-benzaldehyde oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; triethylamine In acetonitrile at 20℃; for 20h; Heating / reflux; | 95% |
With hydroxylamine hydrochloride; sodium carbonate In dimethyl sulfoxide at 20℃; |
methylmagnesium bromide
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: methylmagnesium bromide; 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde In tetrahydrofuran at -78℃; Stage #2: With water; ammonium chloride In tetrahydrofuran | 94% |
dimedone
para-bromophenacyl bromide
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: dimedone; para-bromophenacyl bromide; 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With pyridine In acetonitrile for 3h; Reflux; Stage #2: With triethylamine In acetonitrile Reflux; | 89% |
dimedone
para-bromophenacyl bromide
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: dimedone; para-bromophenacyl bromide; 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With pyridine In acetonitrile at 70℃; for 3h; Stage #2: With triethylamine In acetonitrile at 70℃; for 16h; Temperature; stereospecific reaction; | 89% |
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-methanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 0.166667h; | 87% |
Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃; for 24h; Stage #2: With sodium hydroxide; water | 81% |
With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; |
4-Nitrophenacyl bromide
dimedone
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-Nitrophenacyl bromide; dimedone; 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With pyridine In acetonitrile for 3h; Reflux; Stage #2: With triethylamine In acetonitrile Reflux; | 86% |
4-Nitrophenacyl bromide
dimedone
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-Nitrophenacyl bromide; dimedone; 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With pyridine In acetonitrile at 70℃; for 3h; Stage #2: With triethylamine In acetonitrile at 70℃; for 14h; Temperature; stereospecific reaction; | 86% |
dimedone
2-bromo-1-(3,4-dichlorophenyl)ethanone
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: dimedone; 2-bromo-1-(3,4-dichlorophenyl)ethanone; 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With pyridine In acetonitrile for 3h; Reflux; Stage #2: With triethylamine In acetonitrile Reflux; | 85% |
dimedone
2-Bromo-4'-methoxyacetophenone
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: dimedone; 2-Bromo-4'-methoxyacetophenone; 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With pyridine In acetonitrile for 3h; Reflux; Stage #2: With triethylamine In acetonitrile Reflux; | 84% |
dimedone
2-Bromo-4'-methoxyacetophenone
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: dimedone; 2-Bromo-4'-methoxyacetophenone; 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With pyridine In acetonitrile at 70℃; for 3h; Stage #2: With triethylamine In acetonitrile at 70℃; for 15h; Temperature; stereospecific reaction; | 84% |
acetic anhydride
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate at 140 - 150℃; for 3.5h; Perkin Carboxylic Acid Synthesis; | 84% |
3,5-dichloro-4-picoline
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
1-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3,5-dichloro-1-pyridin-4-yl)ethanone
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -30 - -20℃; for 1h; | 75% |
Stage #1: 3,5-dichloro-4-picoline; 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With potassium tert-butylate In tetrahydrofuran at -30 - -20℃; Stage #2: With water; ammonium chloride In tetrahydrofuran at -10 - -5℃; |
pyridin-4-yl-acetic acid ethyl ester
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
3-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-2-(pyridin-4-yl)acrylic acid ethyl ester
Conditions | Yield |
---|---|
With ammonium acetate In acetic acid for 18h; Reflux; | 75% |
1-propynylmagnesium bromide
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; | 74% |
3,5-dichloro-4-aminopyridine
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
3,5-dichloro-N-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzylidene)pyridin-4-amine
Conditions | Yield |
---|---|
Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With trifluoroacetic acid; trimethyl orthoformate In toluene at 20 - 30℃; Inert atmosphere; Reflux; Stage #2: 3,5-dichloro-4-aminopyridine With trifluoroacetic acid In toluene at 40 - 110℃; | 73% |
Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With toluene-4-sulfonic acid; trimethyl orthoformate In toluene for 3h; Reflux; Stage #2: 3,5-dichloro-4-aminopyridine With toluene-4-sulfonic acid In toluene at 70 - 80℃; for 30h; Reflux; | 23% |
With N,O-Bis(trimethylsilyl)trifluoroacetamide; toluene-4-sulfonic acid In acetonitrile for 48h; Reagent/catalyst; Reflux; | 70 %Chromat. |
Nitroethane
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid at 90℃; for 9h; Inert atmosphere; | 54% |
methanol
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
With Oxone at 55 - 60℃; for 3h; | 52% |
With Oxone at 55 - 60℃; for 3h; | 52% |
3,5-dichloro-4-methylpyridin-1-ium-1-olate
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
(R/S)-1-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3,5-dichloro-1-oxypyridin-4-yl)ethanol
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -35℃; for 0.666667h; Inert atmosphere; | 42% |
With potassium tert-butylate In tetrahydrofuran at -35℃; for 1.16667h; |
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
3-cyclopropylmethoxy-4-difluoromethoxybenzyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaBH4 / methanol; tetrahydrofuran / 20 °C 2: SOCl2; DMF / toluene View Scheme |
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)acetonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaBH4 / methanol; tetrahydrofuran / 20 °C 2: SOCl2; DMF / toluene 3: ethanol; H2O; dimethylformamide / 2 h / 60 °C View Scheme |
(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfinate
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 12 h / 0 - 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C 2.2: -78 °C View Scheme |
The 4-(Difluoromethoxy)-3-(cyclopropylmethoxy)benzaldehyde, its cas register number is 151103-09-2. It also can be called as Benzaldehyde,3-(cyclopropylmethoxy)-4-(difluoromethoxy)- and the Systematic name about this chemical is 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde.
Physical properties about 4-(Difluoromethoxy)-3-(cyclopropylmethoxy)benzaldehyde are: (1)ACD/LogP: 2.69; (2)ACD/LogD (pH 7.4): 2.69; (3)ACD/BCF (pH 5.5): 65.2; (4)ACD/BCF (pH 7.4): 65.2; (5)ACD/KOC (pH 5.5): 692.21; (6)ACD/KOC (pH 7.4): 692.21; (7)#H bond acceptors: 3; (8)#H bond donors: 0; (9)#Freely Rotating Bonds: 6; (10)Polar Surface Area: 35.53Å2; (11)Index of Refraction: 1.529; (12)Molar Refractivity: 58.49 cm3; (13)Molar Volume: 189.6 cm3; (14)Polarizability: 23.18x10-24cm3; (15)Surface Tension: 39.2 dyne/cm; (16)Enthalpy of Vaporization: 57.39 kJ/mol; (17)Vapour Pressure: 0.000157 mmHg at 25°C
You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(c(cc1C=O)OCC2CC2)OC(F)F
(2)InChI: InChI=1/C12H12F2O3/c13-12(14)17-10-4-3-9(6-15)5-11(10)16-7-8-1-2-8/h3-6,8,12H,1-2,7H2
(3)InChIKey: AHVVCELVGCPYGI-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C12H12F2O3/c13-12(14)17-10-4-3-9(6-15)5-11(10)16-7-8-1-2-8/h3-6,8,12H,1-2,7H2
(5)Std. InChIKey: AHVVCELVGCPYGI-UHFFFAOYSA-N
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