1‐cyclopropyl‐4,4,4‐trifluorobutane‐1,3‐dione
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation; | 98% |
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate
A
((3R,6S)-3-methyl-5-phenyl-6-propyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction; | A 97% B n/a |
Conditions | Yield |
---|---|
Stage #1: 2,3-dibromopropionic acid; acetyl chloride With copper(l) chloride; zinc In diethyl ether at 10 - 20℃; for 11h; Inert atmosphere; Stage #2: With Methylenetriphenylphosphorane In diethyl ether Temperature; Solvent; Concentration; | 96% |
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-6-methyl-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate
A
((3R,6S)-6-isobutyl-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction; | A 94% B n/a |
A
2-fluoro-1-tetralone
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With Selectfluor In water; acetonitrile at 20℃; | A 93% B n/a |
Conditions | Yield |
---|---|
With water; nitrile hydratase SP361 at 30℃; for 24h; in potassium phosphate buffer (pH = 7); | 92% |
With phosphoric acid; phosphorus pentoxide at 140℃; | |
With sodium hydroxide | |
With potassium hydroxide | |
In sodium hydroxide |
trans-Crotonaldehyde
Cyclopropanecarboxaldehyde
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
90% |
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-6-(methylsulfonyl)-1,3-diphenylhex-1-yn-3-yl cyclopropanecarboxylate
A
((3R,6S)-3-methyl-6-(2-(methylsulfonyl)ethyl)-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction; | A 87% B n/a |
Conditions | Yield |
---|---|
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃; | 80% |
With Iron(III) nitrate nonahydrate; oxygen In acetonitrile at 25℃; under 760.051 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Schlenk technique; | 80% |
With Oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate In water; acetone at 22℃; for 3h; Oxidation; | 71% |
With air at 21℃; for 2h; |
tert-butyl(cyclopropylmethoxy)dimethylsilane
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With ruthenium(IV) oxide; sodium periodate | 78% |
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-5-((tertbutyldimethylsilyl)oxy)-1,3-diphenylpent-1-yn-3-yl cyclopropanecarboxylate
A
((3R,6R)-6-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction; | A 52% B n/a |
Methyl 4-bromobutyrate
propargyl alcohol
A
methyl cyclopropylcarboxylate
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With lithium amide In diethyl ether for 4h; Heating; | A 20% B n/a |
Conditions | Yield |
---|---|
With potassium hydroxide at 100℃; Versetzen des Reaktionsgemisches mit Wasser; | |
With sodium hydroxide at 100℃; Versetzen des Reaktionsgemisches mit Wasser; |
Conditions | Yield |
---|---|
With potassium hypochlorite | |
With manganese(II) nitrate; oxygen; cobalt(II) nitrate In acetic acid at 100℃; for 6h; |
Conditions | Yield |
---|---|
With permanganate(VII) ion at 0 - 5℃; |
cyclopropanecarboxylic acid phenyl ester
A
phenol
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
at 360℃; |
Conditions | Yield |
---|---|
With carbon dioxide; n-pentylsodium |
cyclopropanecarboxylic anhydride
A
propene
B
1,2-propanediene
C
butadiene monoxide
D
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
at 666.9℃; |
2-Cyclopropyl-4,4-dimethyl-4,5-dihydro-oxazole
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide; sodium hypochlorite; tetra(n-butyl)ammonium hydrogensulfate 1.) ethyl acetate, water, room temp.; 2.) CH3OH, 5 h, room temp.; Yield given. Multistep reaction; |
cyclopropanecarboxylic acid chloride
A
1-chlorocyclopropane-1-carboxylic acid
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With N-chloro-succinimide; sodium hydrogencarbonate 1.) 135 deg C, 1.5 h, 2.) acetone, 0 deg C; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With potassium hydroxide; potassium permanganate; copper(II) sulfate In benzene Yield given; |
cyclopropylmethyl methyl ether
A
methyl cyclopropylcarboxylate
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With ruthenium tetroxide In water; acetone at 30℃; |
Conditions | Yield |
---|---|
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis; |
A
alprenolol
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis; |
Conditions | Yield |
---|---|
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis; |
Conditions | Yield |
---|---|
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis; |
Conditions | Yield |
---|---|
With thionyl chloride In toluene Heating; | 100% |
With thionyl chloride for 3h; Heating; | 95% |
With thionyl chloride for 4h; Heating; | 88% |
4-(hexyn-1-yl)anisole
cyclopropanecarboxylic acid
(E)-2-iodo-1-(4-methoxyphenyl)hex-1-en-1-yl cyclopropanecarboxylate
Conditions | Yield |
---|---|
With N-iodo-succinimide In 1,2-dichloro-ethane at 70℃; for 1h; stereoselective reaction; | 100% |
2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-amine 1',1'-dioxide
cyclopropanecarboxylic acid
N-{2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1',1'-dioxido-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-yl}cyclopropanecarboxamide
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 100% |
1,2,3-Benzotriazole
cyclopropanecarboxylic acid
(1H-benzo[d][1,2,3]triazol-1-yl)(cyclopropyl)methanone
Conditions | Yield |
---|---|
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 20℃; for 0.5h; Stage #2: cyclopropanecarboxylic acid In dichloromethane at 20℃; for 4h; | 100% |
With thionyl chloride at 0 - 20℃; Reagent/catalyst; | 70% |
With thionyl chloride In dichloromethane at 20℃; |
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 100% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 100% |
(piperidin-4-yl)carbamic acid tert-butyl ester
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
Stage #1: cyclopropanecarboxylic acid With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: (piperidin-4-yl)carbamic acid tert-butyl ester In dichloromethane at 20℃; Inert atmosphere; | 100% |
Stage #1: cyclopropanecarboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: (piperidin-4-yl)carbamic acid tert-butyl ester In dichloromethane at 20℃; Inert atmosphere; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 0 - 20℃; for 12h; |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 100% |
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 18h; | 100% |
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 tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve; | 99% |
5-bromoindoline
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With trimethylsilyl iodide for 96h; | 98% |
cyclopropanecarboxylic acid
cyclopropanecarboxylic acid benzyl ester
Conditions | Yield |
---|---|
With triethylamine In various solvent(s) at 83℃; for 24h; | 98% |
Conditions | Yield |
---|---|
With sulfuric acid In ethanol | 98% |
styrene
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With N-iodo-succinimide In dichloromethane at 20 - 22℃; for 0.25h; regioselective reaction; | 98% |
tert-butyl 1,4-diazepine-1-carboxylate
cyclopropanecarboxylic acid
tert-butyl 4-(cyclopropylaminocarbamoyl)-1,4-N-cycloheptane-1-carboxylate
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h; Inert atmosphere; | 98% |
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h; | 98% |
Cyclohexanethiol
cyclopropanecarboxylic acid
Cyclopropanecarbothioic acid S-cyclohexyl ester
Conditions | Yield |
---|---|
With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature; | 97% |
1,1'-carbonyldiimidazole
cyclopropanecarboxylic acid
1-cyclopropcarbonylimidazole
Conditions | Yield |
---|---|
at 20℃; for 20h; | 96% |
at 20℃; for 20h; | 96% |
In tetrahydrofuran Heating; |
ethyl 2-(2-hydroxyphenyl)acetate
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Steglich Esterification; Inert atmosphere; | 96% |
tri-p-fluorophenylstibine
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide In diethyl ether at 20℃; for 24h; | 96% |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate In isopropyl alcohol at 83℃; for 24h; Microwave irradiation; | 96% |
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; Inert atmosphere; | 96% |
levonorgestrel
cyclopropanecarboxylic acid
D-(-)-norgestrel 17β-cyclopropanecarboxylate
Conditions | Yield |
---|---|
With sodium carbonate; trifluoroacetic anhydride In benzene for 1h; Ambient temperature; | 95.9% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tert-butyl methyl ether at 0 - 50℃; for 24h; | 95% |
With lithium aluminium tetrahydride | 83% |
With lithium aluminium tetrahydride | 67% |
benzyl alcohol
cyclopropanecarboxylic acid
cyclopropanecarboxylic acid benzyl ester
Conditions | Yield |
---|---|
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 17h; Heating; | 95% |
With 2,5-dimethylpyridine; 4,5-dichloro-1,2,3-dithiazolium chloride In dichloromethane 1) -78 deg C, 2 h, 2) to room temperature, 12 h; | 76% |
With tributyl-amine; 2-chloro-1-ethylpyridinium tetrafluoroborate In dichloromethane Ambient temperature; |
6-methoxy-9-(propa-1,2-dien-1-yl)-9H-purine
cyclopropanecarboxylic acid
(E)-3-(6-methoxy-9H-purin-9-yl)allyl cyclopropanecarboxylate
Conditions | Yield |
---|---|
With silver carbonate In acetonitrile at 80℃; for 8h; chemoselective reaction; | 95% |
3-bromoaniline
cyclopropanecarboxylic acid
N-(3-bromophenyl)cyclopropanecarboxamide
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 95% |
The Cyclopropanecarboxylic acid, with its CAS registry number 1759-53-1, is a kind of clear colourless to light yellow liquid. This is insoluble in water while soluble in ethyl acetate and ether. As to its usage, it is usually applied as the intermediate of plant growth regulator trinexapac-ethyl and also as the pharmaceutic intermediates. Besides, its product categories are including Pharmaceutical Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Cyclopropanes; Simple 3-Membered Ring Compounds.
The characteristics of this chemical are as follows: (1)ACD/LogP: 0.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.72; (4)ACD/LogD (pH 7.4): -2.51; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 4.2; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.3; (13)Index of Refraction: 1.521; (14)Molar Refractivity: 19.94 cm3; (15)Molar Volume: 65.4 cm3; (16)Polarizability: 7.9×10-24 cm3; (17)Surface Tension: 57.9 dyne/cm; (18)Density: 1.314 g/cm3; (19)Flash Point: 71.7 °C; (20)Enthalpy of Vaporization: 46.22 kJ/mol; (21)Boiling Point: 183 °C at 760 mmHg; (22)Vapour Pressure: 0.362 mmHg at 25°C; (23)Exact Mass: 86.036779; (24)MonoIsotopic Mass: 86.036779; (25)Topological Polar Surface Area: 37.3; (26)Heavy Atom Count: 6; (27)Complexity: 73.6.
Production method of this chemical: Cyclopropanecarbonitrile could react to produce cyclopropanecarboxylic acid. This reaction could happen in the presence of the reagent of aq. NaOH solution.
Use of this chemical: Cyclopropanecarboxylic acid could react to produce cyclopropylmethanol. This reaction could happen in the presence of the reagent of lithium aluminum hydride.
When you are dealing with this chemical, you should be very cautious. For one thing, it is irritant which may cause inflammation to the skin or other mucous membranes. And it may causes burns and it will be dangerous if swallowed. For another thing, it is corrosive which may destroy living tissue on contact. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, and if in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). Besides, take off immediately all contaminated clothing when contact.
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1CC1C(=O)O
(2)InChI: InChI=1S/C4H6O2/c5-4(6)3-1-2-3/h3H,1-2H2,(H,5,6)
(3)InChIKey: YMGUBTXCNDTFJI-UHFFFAOYSA-N
Below are the toxicity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 172mg/kg (172mg/kg) | Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969. | |
mouse | LD50 | intravenous | 180mg/kg (180mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03926, | |
mouse | LD50 | subcutaneous | 172mg/kg (172mg/kg) | Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969. |
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