2,3-dibromo-1,1-diethoxypropane
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
With potassium hydroxide; tetraoctyl ammonium bromide In Petroleum ether at 80℃; for 6h; | 79% |
With ammonia; sodium amide In diethyl ether at -34℃; for 0.25h; | 75% |
With ammonia; sodium amide at -30℃; | 75% |
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane Ambient temperature; | 70% |
ethanol
1-bromo-2,2-dichlorocyclopropane
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane Ambient temperature; | 57% |
Conditions | Yield |
---|---|
With sulfur dioxide; calcium chloride |
2,2-dibromo-propionaldehyde diethylacetal
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
With potassium tert-butylate; tert-butyl alcohol at 100℃; |
6,6-diethoxy-3-methyl-hex-4-yn-3-ol
sodium methylate
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
at 150℃; under 20 Torr; |
orthoformic acid triethyl ester
acetylene
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
(i) EtMgBr, (ii) /BRN= 605384/; Multistep reaction; | |
beim Behandeln von Acetylen-monomagnesiumbromid; |
2,2-dibromo-propionaldehyde diethylacetal
potassium tert-butylate
tert-butyl alcohol
Propiolaldehyde diethyl acetal
3-(1-ethoxy-prop-2-ynyloxy)-propenal
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
(heating); |
orthoformic acid triethyl ester
acrolein
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
(i) (bromination), (ii) /BRN= 605384/, (iii) NaNH2, liq. NH3; Multistep reaction; |
bromoethyne
diethyl phenyl orthoformate
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
With magnesium 1.) THF, 2.) THF, RT; Yield given. Multistep reaction; |
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
With sodium hydroxide at 160℃; |
orthoformic acid triethyl ester
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
With diethyl ether |
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
With potassium hydroxide | |
With potassium hydroxide |
2,3-dibromo-1,1-diethoxypropane
A
2-bromo-3,3-diethoxypropene
B
Propiolaldehyde diethyl acetal
propargyl alcohol
orthoformic acid triethyl ester
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
With manganese(IV) oxide; In(OSO2CF3)3 In chloroform for 42h; Heating; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 19.0 g / ZnCl2 / aq. ethanol / 1 h / 15 °C 2: 75 percent / NaNH2; NH3 / diethyl ether / 0.25 h / -34 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / HCl gas, TsOH / ethanol / 70 Torr 2: 1.) Mg / 1.) THF, 2.) THF, RT View Scheme |
orthoformic acid triethyl ester
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: NaNH2, liq. NH3 View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide at 82℃; for 10h; Time; Large scale; | 60 kg |
5-methyl-dihydro-furan-2-one
A
1-butylene
B
Propiolaldehyde diethyl acetal
C
3-Methylbutenoic acid
D
1-(2-methyl-cyclopropyl)-ethanone
Conditions | Yield |
---|---|
With niobium(v) loaded on MFI-type zeolite at 320℃; under 760.051 Torr; Reagent/catalyst; |
Propiolaldehyde diethyl acetal
isobutyraldehyde
6,6-Diethoxy-2-methyl-hex-4-yn-3-ol
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: isobutyraldehyde In tetrahydrofuran; cyclohexane at -78℃; for 3h; Stage #3: With hydrogenchloride In tetrahydrofuran; cyclohexane; water | 100% |
With n-butyllithium In diethyl ether; hexane for 2h; Ambient temperature; | 55% |
2-chloro-3-quinoline carboxaldehyde
Propiolaldehyde diethyl acetal
2-(3,3-diethoxy-prop-1-ynyl)-quinoline-3-carbaldehyde
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; Sonogashira reaction; | 100% |
Propiolaldehyde diethyl acetal
3-iodochlorobenzene
1-chloro-3-(3,3-diethoxyprop-1-ynyl)benzene
Conditions | Yield |
---|---|
With triethylamine; copper(l) iodide; [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride at 20℃; for 4h; Sonogashira Coupling; | 100% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 4h; | 100% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 25℃; for 4h; Sonogashira Cross-Coupling; Inert atmosphere; |
Propiolaldehyde diethyl acetal
(S)-Propylene oxide
(+)-6,6-diethoxy-4-hexyn-2-ol
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -30 - 20℃; for 4h; | 99% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane for 0.5h; Ambient temperature; | 90.6% |
ethyl-2-azidoacetate
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
Amberlyst A-21*CuI In dichloromethane at 20℃; for 12h; Huisgen cycloaddition; | 99% |
With copper(II) loaded mesoporous SBA-15 In dichloromethane at 20℃; Huisgen Cycloaddition; regioselective reaction; | 66% |
With copper(I) iodide adsorbed on Wyoming montmorillonite at 20℃; for 18h; Huisgen's cycloaddition; Neat (no solvent); |
Propiolaldehyde diethyl acetal
3-azidopropan-1-ol
Conditions | Yield |
---|---|
Amberlyst A-21*CuI In dichloromethane at 20℃; for 12h; Huisgen cycloaddition; | 99% |
Propiolaldehyde diethyl acetal
benzyl azide
1-benzyl-4-(diethoxymethyl)-1H-1,2,3-triazole
Conditions | Yield |
---|---|
Amberlyst A-21*CuI In dichloromethane at 20℃; for 12h; Huisgen cycloaddition; | 99% |
With Amberlyst A-21*copper(I) iodide In dichloromethane at 20℃; for 12h; Huisgen reaction; Automated synthesizer; Combinatorial reaction / High throughput screening (HTS); regioselective reaction; | 99% |
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In dichloromethane; water at 20℃; for 12h; | 98% |
6-bromoquinoline
Propiolaldehyde diethyl acetal
6-(3,3-diethoxyprop-1-ynyl)quinoline
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide at 90℃; Inert atmosphere; | 99% |
Propiolaldehyde diethyl acetal
4-diethoxymethyl-1-(3-trifluoroacetamidopropyl)-1,2,3-triazole
Conditions | Yield |
---|---|
With Amberlyst A-21*copper(I) iodide In dichloromethane at 20℃; for 12h; Huisgen reaction; Automated synthesizer; Combinatorial reaction / High throughput screening (HTS); regioselective reaction; | 99% |
Propiolaldehyde diethyl acetal
(S)-2-(tert-butyldiphenylsilyloxy)tetradecanal
(S)-5-(tert-butyldiphenylsilyloxy)-1,1-diethoxyheptadec-2-yn-4-ol
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -28 - 0℃; for 1h; Stage #2: (S)-2-(tert-butyldiphenylsilyloxy)tetradecanal In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; | 99% |
4-Trifluoromethylbenzaldehyde
Propiolaldehyde diethyl acetal
4,4-diethoxy-1-(4-(trifluoromethyl)phenyl)but-2-yn-1-ol
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-Trifluoromethylbenzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 99% |
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 4-Trifluoromethylbenzaldehyde In tetrahydrofuran; hexane at 25℃; for 16h; | 79% |
Propiolaldehyde diethyl acetal
p-chlorophenyldiazomethane
1-chloro-4-(4,4-diethoxybuta-1,2-dien-1-yl)benzene
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With copper(l) iodide; triethylamine In 1,4-dioxane for 0.166667h; Flow reactor; Stage #2: p-chlorophenyldiazomethane In 1,4-dioxane; dichloromethane at 20℃; for 0.166667h; Flow reactor; | 99% |
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: C19H29FN3OP In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; diastereoselective reaction; | 98% |
Propiolaldehyde diethyl acetal
N,N′-bis[6-(3,3-dimethylbutyrylamino)pyridin-2-yl]-5-iodoisophthalamide
5-(3,3-diethoxyprop-1-ynyl)-N1,N3-bis(6-(3,3-dimethylbutyrylamino)pyridin-2-yl)isophthalamide
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 20℃; for 20h; Sonogashira coupling; | 98% |
Propiolaldehyde diethyl acetal
C23H48O5Si2
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78 - 0℃; | 98% |
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: C19H30N3OP In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; diastereoselective reaction; | 97% |
Propiolaldehyde diethyl acetal
(4S)-4-tert-butoxy-3,4-dihydro-2H-pyrrole 1-oxide
C15H27NO4
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; triethylamine In acetonitrile at 0 - 20℃; for 24h; Kinugasa reaction; Inert atmosphere; | 97% |
Propiolaldehyde diethyl acetal
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); caesium carbonate; XPhos In tetrahydrofuran at 60℃; for 5.5h; Sonogashira coupling; Inert atmosphere; Sealed tube; stereoselective reaction; | 97% |
Propiolaldehyde diethyl acetal
2,6-dimethylbenzaldehyde
1-(2,6-dimethylphenyl)-4,4-diethoxybut-2-yn-1-ol
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2,6-dimethylbenzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 97% |
Propiolaldehyde diethyl acetal
p-methylazidobenzene
1-(4-methylphenyl)-1H-1,2,3-triazole-4-carboxaldehyde
Conditions | Yield |
---|---|
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 70℃; for 24h; Solvent; | 97% |
ethyl 2-bromoisobutyrate
Propiolaldehyde diethyl acetal
non-1-en-3-yn-2-ylbenzene
Conditions | Yield |
---|---|
With copper(I) thiophene-2-carboxylate; C45H50N3O2P; caesium carbonate In diethyl ether at 20℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction; | 97% |
Propiolaldehyde diethyl acetal
4-Methyl-N-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-benzenesulfonamide
(E)-N-(4,4'-diethoxy-1-styrylbut-2-ynyl)-4-toluenesulfonamide
Conditions | Yield |
---|---|
With n-butyllithium; zinc(II) chloride In tetrahydrofuran; hexane 1.) -78 deg C, 30 min; 2.) Et2O, -78 deg C, 30 min then 0 deg C, 5 h; | 96% |
With n-butyllithium; zinc(II) chloride In diethyl ether at -78℃; Yield given; |
Propiolaldehyde diethyl acetal
o-iodo-methyl-benzoic acid
1-(2-methoxycarbonylphenyl)-3,3-diethoxyprop-1-yne
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal; o-iodo-methyl-benzoic acid With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.166667h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 4h; Sonogashira Cross-Coupling; Inert atmosphere; | 96% |
With copper(l) iodide; bis(acetato)bis(triphenylphosphine)palladium(0); diethylamine In N,N-dimethyl-formamide for 2h; Ambient temperature; | 82% |
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: C19H29BrN3OP In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; diastereoselective reaction; | 96% |
Propiolaldehyde diethyl acetal
4-dimethylamino-benzaldehyde
C16H23NO3
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at 0℃; Inert atmosphere; Stage #2: 4-dimethylamino-benzaldehyde In tetrahydrofuran; hexane at 0℃; Inert atmosphere; | 96% |
Propiolaldehyde diethyl acetal
4-methoxy-benzaldehyde
4,4-diethoxy-1-(4-methoxyphenyl)but-2-yn-1-ol
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 96% |
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran; hexane at 25℃; for 16h; | 96% |
Conditions | Yield |
---|---|
With copper(I) thiophene-2-carboxylate; C55H70N3O2P; caesium carbonate In diethyl ether at 20℃; for 36h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 96% |
Propiolaldehyde diethyl acetal
benzaldehyde
(+/-)-4-hydroxy-4-phenylbut-2-ynal diethyl acetal
Conditions | Yield |
---|---|
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 95% |
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at 25℃; for 16h; | 95% |
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - -40℃; for 3h; | 94% |
Propiolaldehyde diethyl acetal
4-methyl-6-phenyl-3-trifluoromethanesulfonylpyridazine
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran for 3h; Ambient temperature; | 95% |
Propiolaldehyde diethyl acetal
{2-[(R)-1-(3,4-Dimethoxy-phenyl)-3-iodo-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester
{2-[(R)-3-(3,3-Diethoxy-prop-1-ynyl)-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester
Conditions | Yield |
---|---|
With diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 0℃; for 0.666667h; | 95% |
The 1-Propyne,3,3-diethoxy-, with the CAS registry number 10160-87-9, is also known as 3,3-diethoxypropyne. Its EINECS number is 233-430-4. It belongs to the product categories of Acetylenes; Functionalized Acetylenes. This chemical's molecular formula is C7H12O2 and molecular weight is 128.17. What's more, its systematic name is 3,3-Diethoxyprop-1-yne. Its storage temperature is 2-8 °C.
Physical properties of 1-Propyne,3,3-diethoxy- are: (1)ACD/LogP: 1.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.67; (4)ACD/LogD (pH 7.4): 1.67; (5)ACD/BCF (pH 5.5): 10.88; (6)ACD/BCF (pH 7.4): 10.88; (7)ACD/KOC (pH 5.5): 192.1; (8)ACD/KOC (pH 7.4): 192.1; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 18.46 Å2; (13)Index of Refraction: 1.421; (14)Molar Refractivity: 35.75 cm3; (15)Molar Volume: 140.9 cm3; (16)Polarizability: 14.17×10-24 cm3; (17)Surface Tension: 28.7 dyne/cm; (18)Density: 0.909 g/cm3; (19)Flash Point: 32.2 °C; (20)Enthalpy of Vaporization: 36.07 kJ/mol; (21)Boiling Point: 139 °C at 760 mmHg; (22)Vapour Pressure: 8.16 mmHg at 25 °C.
Preparation: this chemical can be prepared by 2,3-dibromo-1,1-diethoxy-propane at the temperature of 80 °C. This reaction will need reagent solid potassium hydroxyde and solvent petroleum ether with the reaction time of 6 hours. This reaction will also need catalyst tetraoctylammonium bromide. The yield is about 79%.
Uses of 1-Propyne,3,3-diethoxy-: it can be used to produce 5,5-diethoxy-pent-3-yn-2-ol at the ambient temperature. It will need reagents acetaldehyde, BuLi and solvents diethyl ether, hexane with the reaction time of 2 hours. The yield is about 70%.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. It is flammable, so you should keep it away from sources of ignition - No smoking. It is in case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)SMILES: C#CC(OCC)OCC
(2)InChI: InChI=1/C7H12O2/c1-4-7(8-5-2)9-6-3/h1,7H,5-6H2,2-3H3
(3)InChIKey: RGUXEWWHSQGVRZ-UHFFFAOYAB
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