Conditions | Yield |
---|---|
With sodium tris(tert-butoxo)aluminium hydride In tetrahydrofuran; diethylene glycol dimethyl ether at -78℃; for 3h; | 100% |
With diethylene glycol dimethyl ether; lithium tri-t-butoxyaluminum hydride | |
With sodium tetrahydroborate; cadmium(II) chloride In N,N,N,N,N,N-hexamethylphosphoric triamide; acetonitrile at -5℃; for 0.0833333h; Yield given; | |
With thexyl-s-butoxyborane In tetrahydrofuran at 25℃; for 96h; Yield given; | |
Stage #1: cyclopropanecarboxylic acid chloride With aluminium hydride In tetrahydrofuran at 20℃; for 1h; Metallation; Stage #2: With pyridinium chlorochromate In tetrahydrofuran; dichloromethane at 20℃; for 6h; Oxidation; | 98 % Chromat. |
Conditions | Yield |
---|---|
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h; | 99% |
With nonane; 9-borabicyclo; lithium 9-boratabicyclo In tetrahydrofuran for 1h; Ambient temperature; | 85% |
With 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium 1.) THF, room temp.; 2.) THF, pentane, -20 deg C, 10 min and room temp., 1 h; Yield given. Multistep reaction; | |
With ThxBHO-s-Bu In tetrahydrofuran at 25℃; for 96h; Yield given; |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; oxygen In acetonitrile at 20℃; | 96% |
With sodium dichromate at 20℃; for 0.5h; | 89% |
KMnO4 on aluminum silicate at 20℃; for 0.833333h; | 89% |
Conditions | Yield |
---|---|
91.2% | |
84% |
Conditions | Yield |
---|---|
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran for 1h; Ambient temperature; | 88% |
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran for 1h; Ambient temperature; | 84% |
1-Cyclopropylmethoxy-2-methyl-anthraquinone
A
1-hydroxy-2-methyl-anthraquinone
B
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
In methanol for 2h; Mechanism; Product distribution; Irradiation; | A 82.4% B 68% |
Conditions | Yield |
---|---|
With sodium iodide; nickel dibromide; zinc In tetrahydrofuran for 46h; Ambient temperature; | 81% |
N-Formylpiperidine
cyclopropylmagnesium bromide
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
In diethyl ether for 0.25h; Ambient temperature; | 80% |
Conditions | Yield |
---|---|
for 0.166667h; Ambient temperature; | 75% |
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; sodium carbonate In tetralin; water | 71% |
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In decane; water at 65 - 95℃; for 0.333333h; | 70% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride at -78℃; | 41% |
With hydrogenchloride; diethyl ether; tin(ll) chloride anschliessend Behandeln mit Wasser; | |
With lithium aluminium tetrahydride |
Conditions | Yield |
---|---|
With sodium tetrafluoroborate; [D3]acetonitrile; [Cu(salicylate)2(NCMe)]2; tetrabutyl-ammonium chloride; oxygen In acetonitrile at 40℃; for 24h; Schlenk technique; | A 30% B 25% |
triphenyl phosphite ozonide
1,1,2-tricyclopropylethene
A
dicyclopropyl ketone
B
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
In dichloromethane 1) -78 deg C, 2) -60 deg C, 24h; | A n/a B 21% |
Cyclopropylmethanol
A
1,2,4-Tribromobutane
B
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: Cyclopropylmethanol With N,N-dimethylthiourea In dichloromethane at 20℃; Stage #2: With N-Bromosuccinimide In dichloromethane at 20℃; for 3h; | A 5% B n/a |
methyl tetrahydrofuran-2-carboxylate
A
2,3-dihydro-2H-furan
B
2,5-dihydrofuran
C
methanol
D
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
at 500℃; Leiten ueber Aluminiumoxid auf Bimsstein; | |
at 400℃; Leiten ueber Silicagel; | |
at 500℃; Leiten ueber Natriumphosphat und Phosphorsaeure auf Bimsstein; |
methyl tetrahydrofuran-2-carboxylate
Cyclopropanecarboxaldehyde
ethyl tetrahydrofurancarboxylate
A
2,3-dihydro-2H-furan
B
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With monoaluminum phosphate at 350℃; | |
at 350℃; Leiten ueber Aluminiumphosphat/Bimsstein im Kohlendioxid-Strom; |
cyclopropyl(piperidin-1-yl)methanone
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether |
Conditions | Yield |
---|---|
With sulfuric acid; chromic acid |
Conditions | Yield |
---|---|
With sodium carbonate at 165℃; |
Conditions | Yield |
---|---|
With water; oxygen; copper | |
With osmium(VIII) oxide; water; oxygen |
2,3-dihydro-2H-furan
A
1-butylene
B
Ketene
C
trans-Crotonaldehyde
D
ethene
E
acrolein
F
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
at 626.9 - 1026.9℃; Kinetics; Product distribution; Heating; |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
2,2-dibromocyclopropane-1-methanol
methyllithium
A
2,3-butadien-1-ol
B
1-cyclopropylethanol
C
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
In diethyl ether at -78℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
In diethyl ether at -78℃; Product distribution; reactions of gem-dibromocyclopripanemethanol derivatives with methyllithium, formation and ring opening of intemediate of bicyclo<1.1.0>butan-2-olate; |
2,2-dibromocyclopropane-1-methanol
A
2,3-butadien-1-ol
B
1-cyclopropylethanol
C
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With methyllithium In diethyl ether at -78℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With triethylsilane; water 1) CH2Cl2, reflux, 2) heating; Yield given. Multistep reaction; |
cyclopropylmagnesium bromide
N,N-dimethyl-formamide
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride 1.) THF, 1 h, room temp.; Yield given. Multistep reaction; |
formylcyclopropyl anion
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With tert-butyl alcohol In gas at 24.9℃; under 0.3 - 0.4 Torr; Rate constant; Equilibrium constant; Thermodynamic data; ΔG, TΔS; |
1-(Cyclopropyl-methoxy-methoxy)-2-methyl-anthracene-9,10-diol
A
1-hydroxy-2-methyl-anthraquinone
B
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With air Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane Heating; | 100% |
benzylamine
Cyclopropanecarboxaldehyde
N-benzyl-1-cyclopropyl methanimine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 48h; | 100% |
With magnesium sulfate In dichloromethane at 20℃; for 48h; | 100% |
With magnesium sulfate In dichloromethane at 20℃; for 48h; | 100% |
Cyclopropanecarboxaldehyde
methyl 7-{4-[2-(butoxy)ethoxy]phenyl}-2,3-dihydro-1H-1-benzazepine-4-carboxylate
methyl 7-{4-[2-(butoxy)ethoxy]phenyl}-1-cyclopropylmethyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate
Conditions | Yield |
---|---|
With sodium triacetoxyborohydride In 1,2-dichloro-ethane at 20℃; | 100% |
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane Heating; | 100% |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane Heating; | 100% |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane Heating; | 100% |
benzylamine
Cyclopropanecarboxaldehyde
Benzyl-[1-cyclopropyl-meth-(E)-ylidene]-amine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane Heating; | 100% |
2-amino-4-methylpentane
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane Heating; | 100% |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane Heating; | 100% |
(R)-2-methoxy-1-phenylethylamine
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water | 100% |
(R)-2-methylpropane-2-sulfinamide
Cyclopropanecarboxaldehyde
[N(E),R(S)]-N-(cyclopropylmethylene)-2-methyl-2-propanesulfinamide
Conditions | Yield |
---|---|
With titanium(IV) tetraethanolate In tetrahydrofuran at 20℃; for 17h; | 100% |
With copper(II) sulfate In dichloromethane at 20℃; Inert atmosphere; | 100% |
With titanium(IV) tetraethanolate In tetrahydrofuran at 75℃; for 2h; | 90% |
BOC-glycine
tert-butylisonitrile
benzylamine
Cyclopropanecarboxaldehyde
([benzyl-(tert-butylcarbamoyl-cyclopropyl-methyl)-carbamoyl]-methyl)-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: BOC-glycine; benzylamine; Cyclopropanecarboxaldehyde In methanol at 20℃; for 0.5h; Ugi condensation; Stage #2: tert-butylisonitrile In methanol at 20℃; Ugi condensation; | 100% |
Cyclopropanecarboxaldehyde
C16H14O4
Conditions | Yield |
---|---|
With piperidine; acetic acid In benzene at 100℃; for 16h; Knoevenagel condensation; Inert atmosphere; optical yield given as %de; | 100% |
(1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate
Cyclopropanecarboxaldehyde
C18H29NO4
Conditions | Yield |
---|---|
Stage #1: (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate; Cyclopropanecarboxaldehyde With tris(ethoxy)monochloro titanium; triethylamine In dichloromethane at 0℃; for 5h; Aldol condensation; Stage #2: With water In dichloromethane Cooling; stereoselective reaction; | 100% |
2-((1R,4R)-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)isoindoline-1,3-dione
Cyclopropanecarboxaldehyde
2-((trans)-4-(cyclopropylmethoxy)cyclohexyl)isoindoline-1,3-dione
Conditions | Yield |
---|---|
With triethylsilane; bismuth(III) bromide In acetonitrile at 20℃; | 100% |
methyl 3-(3,5-dimethoxyphenyl)-3-oxopropanoate
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With piperidine; acetic acid In benzene at 100℃; for 16h; Knoevenagel Condensation; Inert atmosphere; | 100% |
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane for 6h; Inert atmosphere; | 100% |
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane for 6h; Inert atmosphere; | 100% |
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane for 6h; Inert atmosphere; | 100% |
7-(trifluoromethyl)-1,2,3,4-tetrahydro-5-nitroisoquinoline hydrochloride
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 7-(trifluoromethyl)-1,2,3,4-tetrahydro-5-nitroisoquinoline hydrochloride; Cyclopropanecarboxaldehyde With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h; | 100% |
4-<(Diphenylphosphinoyl)methyl>morpholine
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-<(Diphenylphosphinoyl)methyl>morpholine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Inert atmosphere; Stage #2: Cyclopropanecarboxaldehyde In tetrahydrofuran; hexane at 0 - 5℃; for 0.5h; | 100% |
N-desmethylthebaine hydrochloride
Cyclopropanecarboxaldehyde
N-(cyclopropylmethyl)northebaine
Conditions | Yield |
---|---|
With formic acid; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; triethylamine In acetonitrile at 60℃; for 2.5h; Inert atmosphere; | 100% |
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With zinc(II) chloride In chloroform at 20℃; for 24h; regioselective reaction; | 100% |
(R)-1-(4-bromophenyl)ethylamine
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: (R)-1-(4-bromophenyl)ethylamine; Cyclopropanecarboxaldehyde In methanol at 20℃; for 16h; Stage #2: With sodium tetrahydroborate at 0 - 20℃; for 4h; | 100% |
t-butylsulfonamide
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 18h; | 100% |
Cyclopropanecarboxaldehyde
N-(cyclopropylmethylidene)hydroxylamine
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium carbonate In ethanol for 2h; Ambient temperature; | 99% |
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 20℃; for 2h; | 99% |
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 20℃; for 2h; | 99% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 0 - 20℃; | 99% |
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at 0 - 20℃; Large scale; | 96% |
With sodium hydroxide In methanol; water at 0 - 20℃; | 86% |
Cyclopropanecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine With potassium carbonate In water; ethyl acetate at 20℃; for 8h; Stage #2: Cyclopropanecarboxaldehyde With sodium tris(acetoxy)borohydride In tetrahydrofuran; water; ethyl acetate for 0.166667h; | 99% |
4-{[(2,4-dimethyl-thiazol-5-yl)methyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester
Cyclopropanecarboxaldehyde
4-{[cyclopropylmethyl-(2,4-dimethyl-thiazol-5-ylmethyl)]-amino}-piperidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 25h; | 99% |
The Cyclopropanecarboxaldehyde with CAS registry number of 1489-69-6 is also known as 1-(Formyl)cyclopropane. The IUPAC name is Cyclopropanecarbaldehyde. It belongs to product categories of Pharmaceutical Intermediates; Cyclopropanes; Simple 3-Membered Ring Compounds; Aldehydes; C1 to C6; Carbonyl Compounds. In addition, the formula is C4H6O and the molecular weight is 70.09. This chemical is a clear colorless liquid that soluble in water. It may catch fire in contact with air and has a very low flash point or evolve highly flammable gases in contact with water. Besides, it may destroy living tissue on contact. What's more, this chemical should be sealed in cool, dry place.
Physical properties about Cyclopropanecarboxaldehyde are: (1)ACD/LogP: 0.21; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.21; (4)ACD/LogD (pH 7.4): 0.21; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 31; (8)ACD/KOC (pH 7.4): 31; (9)#H bond acceptors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.599; (12)Molar Refractivity: 20.44 cm3; (13)Molar Volume: 59.8 cm3; (14)Surface Tension: 45 dyne/cm; (15)Density: 1.171 g/cm3; (16)Flash Point: 7.2 °C; (17)Enthalpy of Vaporization: 33.88 kJ/mol; (18)Boiling Point: 99.5 °C at 760 mmHg; (19)Vapour Pressure: 38.2 mmHg at 25 °C.
Preparation of Cyclopropanecarboxaldehyde: it is prepared by reaction of cyclopropylmethanol. The reaction needs reagent pyridinium chlorochromate and solvent CH2Cl2 with other condition of ambient temperature for 3 hours. The yield is about 60%.
Uses of Cyclopropanecarboxaldehyde: it is used to produce cyclopropanecarbaldehyde-oxime. The reaction occurs with reagents NH2OH*HCl, Na2CO3 and solvent aq. ethanol with other condition of ambient temperature for 2 hours. The yield is about 99%.
When you are using this chemical, please be cautious about it. As a chemical, it is highly flammable and causes burns. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep away from sources of ignition. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1CC1C=O
2. InChI: InChI=1S/C4H6O/c5-3-4-1-2-4/h3-4H,1-2H2
3. InChIKey: JMYVMOUINOAAPA-UHFFFAOYSA-N
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