Conditions | Yield |
---|---|
With acetic acid; 1,1'-(phenyl-l3-iodanediyl)bis(pyridinium)trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; Inert atmosphere; Molecular sieve; chemoselective reaction; | 99% |
With trifluorormethanesulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In 1,4-dioxane at 20℃; for 0.25h; | 98% |
With manganese (VII)-oxide In tetrachloromethane; acetone at -70℃; | 92% |
Conditions | Yield |
---|---|
With sodium iodide at 192℃; under 4500.45 Torr; Reagent/catalyst; Temperature; Pressure; | 97.12% |
Stage #1: 3-acetyl-2-oxo-4,5-dihydrofuran With hydrogenchloride In water at 100℃; for 2h; Stage #2: With sodium hydroxide In water at 80 - 100℃; for 2h; | 90.2% |
With 1-methyl-pyrrolidin-2-one; sodium iodide at 170℃; for 3h; | 59% |
Conditions | Yield |
---|---|
With sodium iodide; nickel dibromide; zinc In tetrahydrofuran at 0℃; for 96h; | 97% |
2,5-dichloro-2-pentene
Cyclopropyl methyl ketone
Conditions | Yield |
---|---|
With sulfuric acid at 40 - 45℃; for 2h; | 95.2% |
3-diphenylphosphinoyl-5-hydroxypentan-2-one
Cyclopropyl methyl ketone
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 30℃; for 2h; | 95% |
With potassium tert-butylate In tert-butyl alcohol for 2h; | 81% |
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide at 90 - 100℃; for 1.5h; Reagent/catalyst; Temperature; | 88.04% |
With potassium hydroxide Versetzen mit Wasser und anschliessend Erhitzen; | |
With sodium hydroxide; water Versetzen mit Wasser und anschliessend Erhitzen; |
Conditions | Yield |
---|---|
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water In methanol at 110℃; for 6h; | 86% |
With 3,4,5-trihydroxybenzoic acid; water at 60℃; for 6h; Sealed tube; Green chemistry; | 75% |
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I) In methanol; water at 110℃; for 6h; Schlenk technique; regioselective reaction; | > 99 %Spectr. |
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water; silver trifluoromethanesulfonate In methanol at 120℃; for 6h; |
acetoacetic acid methyl ester
ethylene dibromide
Cyclopropyl methyl ketone
Conditions | Yield |
---|---|
Stage #1: acetoacetic acid methyl ester; ethylene dibromide With sodium hydride at 55℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 60℃; for 2h; pH=8 - 9; | 84% |
Conditions | Yield |
---|---|
With oxygen; copper(l) chloride; palladium dichloride In water; N,N-dimethyl-formamide at 40℃; for 6h; | 80% |
cyclopropylmethyl ketone 2,4-dinitrophenylhydrazone
A
Cyclopropyl methyl ketone
B
benzene-1,2,4-triamine
Conditions | Yield |
---|---|
With vanadium(II) chloride In tetrahydrofuran for 1h; Heating; | A 74% B n/a |
Conditions | Yield |
---|---|
With sulfonic acid resin at 50℃; for 2h; Reagent/catalyst; Temperature; | 68.8% |
at 430℃; for 0.005h; degree of conversion, other temperatures and reaction times; | |
at 710 - 760℃; Thermodynamic data; E(excit.), isomerization; |
Conditions | Yield |
---|---|
In diethyl ether 1.) 0 deg C; 2.) 2 h, reflux; | 63% |
cyclopropyl methyl ketone oxime
Cyclopropyl methyl ketone
Conditions | Yield |
---|---|
With triethylammonium chlorochromate(VI) In 1,2-dichloro-ethane for 2h; | 61% |
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane 0 deg C to reflux; | 60% |
3, 5-dichloro-2-pentanone
A
5-chloro-2-pentanone
B
Cyclopropyl methyl ketone
Conditions | Yield |
---|---|
With tetraethylammonium tosylate In dimethyl sulfoxide electrolysis; | A 36% B 51% |
(C4H9)3SnOCH(CH3)C3H5
Cyclopropyl methyl ketone
Conditions | Yield |
---|---|
With Bromotrichloromethane | 50% |
With CCl3Br | 50% |
With t-C4H9OOC4H9-t byproducts: C3H7COCH3; | |
With t-C4H9OOC4H9-t byproducts: C3H7COCH3; |
5-Hydroxy-2-pentanone
A
2-Methyl-4,5-dihydrofuran
B
pent-4-en-2-one
C
Cyclopropyl methyl ketone
D
acetaldehyde
E
2-Pentanone
F
acetone
Conditions | Yield |
---|---|
at 550℃; for 0.005h; Product distribution; 400 - 500 deg C; | A 6.7% B 43% C 15% D 2.41% E 9% F 10.8% |
Conditions | Yield |
---|---|
With oxygen In hexane at 68.84℃; under 750.075 Torr; for 24h; Molecular sieve; | 42% |
Conditions | Yield |
---|---|
Stage #1: cyclopropylmethyl-methyl-amine hydrochloride; sodium pyruvate With hydrogenchloride; sodium hydroxide; air; phosphoric acid In water at 28℃; for 46h; pH=8; aq. phosphate buffer; Microbiological reaction; Resolution of racemate; Stage #2: With sulfuric acid In water optical yield given as %ee; | A n/a B n/a C 34.2% |
Conditions | Yield |
---|---|
With piperidine; n-butyllithium; bromo(bromomethyl)triphenylphosphorane In diethyl ether; hexane for 12h; Heating; | A 31% B 9% |
oxirane
(Acetylmethylen)tri(n-butyl)phosphoran
Cyclopropyl methyl ketone
Conditions | Yield |
---|---|
at 150℃; for 15h; | 30% |
acetic acid
cyclopropanecarboxylic acid
A
4-butanolide
B
Cyclopropyl methyl ketone
C
acetone
Conditions | Yield |
---|---|
catalyst B at 360℃; for 2 - 30.17h; | A 1.05% B 2.39% C 2.46% |
catalyst A at 360℃; for 2 - 24h; | A 0.58% B 0.74% C 0.41% |
Conditions | Yield |
---|---|
at 525℃; Erhitzen; |
Conditions | Yield |
---|---|
With potassium carbonate | |
With potassium hydroxide | |
With potassium hydroxide | |
With diphenylmercury(II) In toluene Heating; |
Conditions | Yield |
---|---|
With potassium permanganate |
1-Acetylcyclopropane-1-carboxylic acid
Cyclopropyl methyl ketone
Conditions | Yield |
---|---|
at 200℃; |
methylmagnesium bromide
cyclopropropanecarbonitrile
Cyclopropyl methyl ketone
Conditions | Yield |
---|---|
Behandeln des Reaktionsprodukts mit Wasser; |
Conditions | Yield |
---|---|
analog verlaeuft die Reaktion mit β-Campholensaeurenitril, Zimtsaeurenitril und α.β-Diphenyl-n-valeronitril; |
1-chloro-1-cyclopropylethene
A
Cyclopropyl methyl ketone
B
Cyclopropylacetylene
Conditions | Yield |
---|---|
With silver perchlorate In acetic acid |
2,2-dimethyltetrahydrofuran
1-Cyclopropyl-ethylidene-oxonium
A
Cyclopropyl methyl ketone
B
2,2-Dimethyl-tetrahydro-furanium
Conditions | Yield |
---|---|
at 24.9℃; Thermodynamic data; ΔG0; |
Conditions | Yield |
---|---|
Stage #1: trimethylsilylacetylene With n-butyllithium In hexanes; diethyl ether at -78℃; for 1.16667h; Stage #2: Cyclopropyl methyl ketone In hexanes; diethyl ether at 20℃; for 48h; | 100% |
With methyllithium 1.) ether, room temperature, 2 h; Multistep reaction; |
4-Trifluoromethylbenzaldehyde
Cyclopropyl methyl ketone
(E)-1-cyclopropyl-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
Conditions | Yield |
---|---|
With sodium methylate In methanol at 23℃; for 16h; | 100% |
With sodium hydroxide In ethanol; water at 60℃; | 91% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; | 100% |
Cyclopropyl methyl ketone
ethyl 2-cyanoacetate
(E,Z)-ethyl 2-cyano-3-cyclopropyl-2-butenoate
Conditions | Yield |
---|---|
99.5% | |
29% | |
With ammonium acetate; acetic acid In benzene |
Conditions | Yield |
---|---|
With diiodosilane In dichloromethane at -42℃; for 0.0833333h; | 99.5% |
With diphosphorus tetraiodide In acetone at 20℃; for 1.5h; | 88% |
With trimethylsilyl iodide In tetrachloromethane 1.) -20 deg C, 0.5 h, 2.) 25 deg C, 2 h; | 85% |
With pyridine hydroiodide; tetra-(n-butyl)ammonium iodide In acetonitrile for 4h; Heating; | 5% |
With trimethylsilyl iodide In tetrachloromethane at -20℃; for 0.5h; Product distribution; var. cyclopropyl ketones; other temp., time; |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 8h; Heating; | 99% |
Cyclopropyl methyl ketone
2-bromo-1-cyclopropylethan-1-one
Conditions | Yield |
---|---|
With bromine In methanol at -5℃; for 2h; | 99% |
With bromine In methanol at 0 - 20℃; for 1.5h; | 99% |
With bromine In methanol at 25℃; for 16h; | 98% |
Cyclopropyl methyl ketone
A
(R)-1-cyclopropylethanol
B
(S)-1-methyl-1-cyclopropylmethanol
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (SC,SC,RFC)-1-(diphenylphosphino)-2-[1-N-((4S)-4-tert-butyl-2-oxazolinyl-2-ylmethyl)ethyl]ferrocene; hydrogen; potassium carbonate In isopropyl alcohol at 25℃; under 15201 Torr; for 2h; Glovebox; Autoclave; enantioselective reaction; | A 99% B n/a |
With sodium hydroxide; 3-pinanyl-9-borabicyclo[3.3.1]nonane; dihydrogen peroxide 1.) 6000 atm, 25 deg C, 5.5 days, 2.) THF, 60 deg C, 4 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; | |
With 3-pinanyl-9-borabicyclo[3.3.1]nonane under 4560000 Torr; for 132h; Yield given. Title compound not separated from byproducts; |
Cyclopropyl methyl ketone
N,N-dimethyl acetamide
2-cyclopropyl-2-oxoethyl acetate
Conditions | Yield |
---|---|
Stage #1: Cyclopropyl methyl ketone; N,N-dimethyl acetamide With trifluorormethanesulfonic acid; thallium(III) acetate at 60℃; for 0.333333h; Stage #2: With water for 0.166667h; Further stages.; | 99% |
Cyclopropyl methyl ketone
N,N-dimethyl-formamide
Formic acid 2-cyclopropyl-2-oxo-ethyl ester
Conditions | Yield |
---|---|
Stage #1: Cyclopropyl methyl ketone; N,N-dimethyl-formamide With trifluorormethanesulfonic acid; thallium(III) acetate at 60℃; for 0.333333h; Stage #2: With water for 0.166667h; Further stages.; | 99% |
Conditions | Yield |
---|---|
With copper(ll) bromide In water at 180℃; for 6h; | 99% |
Cyclopropyl methyl ketone
methyl cyclopropylcarboxylate
1,3-dicyclopropyl-1,3-propanedione
Conditions | Yield |
---|---|
Stage #1: Cyclopropyl methyl ketone; methyl cyclopropylcarboxylate With ethanol; sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With 18-crown-6 ether at 40℃; for 3h; | 99% |
With sodium methylate In dimethyl sulfoxide at 55℃; for 8h; | 78% |
With sodium methylate In dimethyl sulfoxide at 55℃; for 8h; | 78% |
Cyclopropyl methyl ketone
4-nitrobenzaldehdye
1-cyclopropyl-3-hydroxy-3-(4-nitrophenyl)propan-1-one
Conditions | Yield |
---|---|
With magnesium iodide diethyletherate; triethylamine In dichloromethane at 20℃; for 0.5h; Catalytic behavior; chemoselective reaction; | 99% |
Cyclopropyl methyl ketone
α,α-dichloroethylcyclopropane
Conditions | Yield |
---|---|
With phosphorus pentachloride; N-methyl-N-phenylformamide at -25℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere; | 98.9% |
Stage #1: Cyclopropyl methyl ketone With 1-octyl-3-methyl-imidazolium bromide Stage #2: With thionyl chloride at 30℃; for 4h; Temperature; Reagent/catalyst; | 98.9% |
With phosphorus pentachloride In 5,5-dimethyl-1,3-cyclohexadiene at -20 - 0℃; for 6h; | 84% |
Cyclopropyl methyl ketone
(methoxymethyl)triphenylphosphonium chloride
2-cyclopropylpropanal
Conditions | Yield |
---|---|
Stage #1: Cyclopropyl methyl ketone; (methoxymethyl)triphenylphosphonium chloride With potassium tert-butylate In tetrahydrofuran at -10 - 30℃; for 3h; Stage #2: With sulfuric acid In tetrahydrofuran at 60℃; for 1h; | 98.2% |
Conditions | Yield |
---|---|
With [Re(NH{CH2CH2P(iPr2)}2)(CO)3]Br; potassium tert-butylate; hydrogen In toluene at 110℃; under 22502.3 Torr; for 17h; Inert atmosphere; Glovebox; Autoclave; | 98% |
With phenylsilane; C14H15MnN5O3(1+)*BF4(1-) In acetonitrile at 80℃; for 5h; Reagent/catalyst; | 93% |
With lithium aluminium tetrahydride In diethyl ether Reflux; | 85% |
Cyclopropyl methyl ketone
ethyl 2-cyanoacetate
ethyl 2-cyano-3-cyclopropyl-2-butenoate
Conditions | Yield |
---|---|
With bis(acetylacetonate)oxovanadium at 20℃; for 4h; Reagent/catalyst; Knoevenagel Condensation; | 98% |
50% | |
With ammonium acetate; acetic acid; benzene |
Cyclopropyl methyl ketone
malononitrile
2-(1-cyclopropylethylidene)malononitrile
Conditions | Yield |
---|---|
With pyridine; molybdenum hexacarbonyl In 2-methyl-propan-1-ol at 20℃; for 1h; | 98% |
With ammonium acetate; acetic acid In toluene for 10h; Reflux; Dean-Stark; | 80% |
51% |
Cyclopropyl methyl ketone
triphenylphosphine
(4-Oxo-pentyl)-triphenyl-phosphonium; bromide
Conditions | Yield |
---|---|
With hydrogen bromide In chloroform at 120℃; for 24h; | 98% |
Cyclopropyl methyl ketone
N,N-dimethyl-formamide dimethyl acetal
1-cyclopropyl-3-(dimethylamino)-2-propen-1-one
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 110℃; for 24h; | 98% |
at 20 - 120℃; for 26h; | 85% |
at 110℃; neat (no solvent); | 66% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 1h; Friedlaender reaction; Heating; | 98% |
Conditions | Yield |
---|---|
With magnesium iodide diethyletherate; triethylamine In dichloromethane at 20℃; for 0.5h; Catalytic behavior; chemoselective reaction; | 98% |
Cyclopropyl methyl ketone
2,3,4,6-Tetra-O-benzyl-D-glucopyranose
(S,2E,4Z)-4,6-bis(benzyloxy)-1-cyclopropyl-7-hydroxyhepta-2,4-dien-1-one
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; lithium hydroxide In water at 60℃; for 0.25h; Aldol Condensation; | 98% |
Conditions | Yield |
---|---|
Stage #1: Cyclopropyl methyl ketone With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In toluene Reflux; Large scale; Stage #2: 2-methanesulfonyl-4-trifluoromethyl-benzonitrile In toluene at 60℃; for 5h; Reagent/catalyst; Concentration; Reflux; Large scale; | 97.1% |
Cyclopropyl methyl ketone
1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone
Conditions | Yield |
---|---|
With L-proline potassium salt In dimethyl sulfoxide at 20℃; for 18h; Friedlaender Quinoline Synthesis; regioselective reaction; | 97% |
With L-proline In dimethyl sulfoxide at 50℃; for 48h; Friedlaender synthesis; regioselective reaction; | 85% |
Cyclopropyl methyl ketone
phenylacetylene
2-cyclopropyl-4-phenylbut-3-yn-2-ol
Conditions | Yield |
---|---|
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: Cyclopropyl methyl ketone In tetrahydrofuran; hexane at -78 - 20℃; for 0.666667h; Inert atmosphere; | 96% |
Stage #1: phenylacetylene With potassium hydroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 0.0833333h; Stage #2: Cyclopropyl methyl ketone at 70℃; for 0.166667h; Further stages.; | 85% |
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane Stage #2: Cyclopropyl methyl ketone In tetrahydrofuran at 0℃; for 2h; | 63% |
Cyclopropyl methyl ketone
allylmagnesium bromide
2-cyclopropyl-pent-4-en-2-ol
Conditions | Yield |
---|---|
In diethyl ether for 1h; Heating; | 96% |
1.Introduction of Cyclopropyl methyl ketone
Cyclopropyl methyl ketone (CAS NO.765-43-5), its Synonyms are Ethanone, 1-cyclopropyl- ; Ethanone, 1-cyclopropyl- (9CI) ; Ketone, cyclopropyl methyl (8CI) ; Methyl cyclopropyl ketone ; Acetylcyclopropane .
2.Properties of Cyclopropyl methyl ketone
(1) Molecular Weight 84.11642 [g/mol] (2) Molecular Formula C5H8O (3) XLogP3 0.5
(4) H-Bond Acceptor 1 (5) Rotatable Bond Count 1 (6) Tautomer Count 3
(7) Exact Mass 84.057515 (8) MonoIsotopic Mass 84.057515 (9) Topological Polar Surface Area 17.1
(10) Heavy Atom Count 6 (11) Complexity 72 (12) Covalently-Bonded Unit Count 1 (13) Feature 3D Acceptor Count 1
(14) Effective Rotor Count 1.6 (15) Conformer Sampling RMSD 0.4 (16) CID Conformer Count 6
3.Structure descriptors of Cyclopropyl methyl ketone
IUPAC Name: 1-cyclopropylethanone
InChI: InChI=1S/C5H8O/c1-4(6)5-2-3-5/h5H,2-3H2,1H3
InChIKey: HVCFCNAITDHQFX-UHFFFAOYSA-N
Canonical SMILES : CC(=O)C1CC1
4.Safety information of Cyclopropyl methyl ketone
Hazard Codes:F
Risk Statements:11
11:Highly Flammable
Safety Statements:9-16-29-33
9:Keep container in a well-ventilated place
16:Keep away from sources of ignition-No smoking
29:Do not empty into drains
33:Take precautionary measures against static discharges
RIDADR:UN 1224 3/PG 2
WGK Germany:3
RTECS:KM5648000
HazardClass:3
PackingGroup:II
A dangerous fire hazard when exposed to heat or flame. When heated to decomposition it emits acrid smoke and fumes.
5. Toxity data of Cyclopropyl methyl ketone
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD | skin | > 2gm/kg (2000mg/kg) | National Technical Information Service. Vol. OTS0559687, |
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