methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 20℃; for 0.5h; | 92% |
With sodium hydroxide In ethanol; water at 20℃; for 0.5h; pH=3 - 4; Solvent; Large scale; | 91% |
ethyl 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropionate
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water at 20℃; for 0.5h; | 90% |
(-)-4-(2,2-dichlorocyclopropyl)phenol
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In chloroform; acetone | |
With sodium hydroxide |
4-Vinylphenol
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 48 h / 20 °C 2: trimethyldodecylammonium chloride; sodium hydroxide / 24 h / 20 °C 3: sodium hydroxide / methanol; water / 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: caesium carbonate / acetonitrile / 24 h / 20 °C 2: sodium hydroxide; tetrabutylammomium bromide / 12 h / 0 - 20 °C 3: sodium hydroxide / ethanol / 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: caesium carbonate / acetonitrile / 12 h / 20 °C 2: sodium hydroxide; tetrabutylammomium bromide / chloroform / 12 h / 0 - 20 °C / Autoclave; Large scale 3: sodium hydroxide / ethanol; water / 0.5 h / 20 °C / pH 3 - 4 / Large scale View Scheme |
p-Coumaric Acid
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium acetate / N,N-dimethyl-formamide / 150 °C 2: caesium carbonate / acetonitrile / 24 h / 20 °C 3: sodium hydroxide; tetrabutylammomium bromide / 12 h / 0 - 20 °C 4: sodium hydroxide / ethanol / 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: potassium acetate / N,N-dimethyl-formamide / 150 °C 2: potassium carbonate / acetonitrile / 48 h / 20 °C 3: trimethyldodecylammonium chloride; sodium hydroxide / 24 h / 20 °C 4: sodium hydroxide / methanol; water / 0.5 h / 20 °C View Scheme |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide; tetrabutylammomium bromide / 12 h / 0 - 20 °C 2: sodium hydroxide / ethanol / 0.5 h / 20 °C View Scheme |
4-hydroxy-benzaldehyde
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ethylenediamine / N,N-dimethyl-formamide / 6 h / 150 °C / Large scale 2: caesium carbonate / acetonitrile / 12 h / 20 °C 3: sodium hydroxide; tetrabutylammomium bromide / chloroform / 12 h / 0 - 20 °C / Autoclave; Large scale 4: sodium hydroxide / ethanol; water / 0.5 h / 20 °C / pH 3 - 4 / Large scale View Scheme | |
Multi-step reaction with 3 steps 1: diethylamine / toluene / 2 h / 150 °C / Green chemistry 2: sodium hydroxide; tetrabutylammomium bromide / 40 °C / Green chemistry 3: magnesium; titanium tetrachloride / dichloromethane; tetrahydrofuran / 2 h / 0 - 120 °C / Green chemistry View Scheme |
tetrachloromethane
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With titanium tetrachloride; magnesium In tetrahydrofuran; dichloromethane at 0 - 120℃; for 2h; Green chemistry; | 98.6 %Chromat. |
bromoethyl isobutyrate
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
Stage #1: 4-(2,2-dichlorocyclopropyl)phenyl acetate With potassium carbonate In methanol at 20℃; for 10h; Stage #2: bromoethyl isobutyrate In methanol for 24h; Reflux; Stage #3: With water Temperature; Alkaline conditions; | 240 g |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
dicyclohexyl-carbodiimide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 20h; | A 95% B n/a |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With 9-mesityl-2,7-dimethyl-10-phenylacridin-10-ium tetrafluoroborate; potassium carbonate at 20℃; Inert atmosphere; Irradiation; diastereoselective reaction; | 91% |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
glycine ethyl ester hydrochloride
dicyclohexyl-carbodiimide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 20h; | A 87.5% B n/a |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
methyl 3-aminopropanoate hydrochloride
dicyclohexyl-carbodiimide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 20h; | A 84.2% B n/a |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
methyl γ-aminobutyrate hydrochloride
dicyclohexyl-carbodiimide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 20h; | A 83.4% B n/a |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
L-glutamic dimethyl ester hydrochloride
dicyclohexyl-carbodiimide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 20h; | A 80% B n/a |
methanol
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate
Conditions | Yield |
---|---|
With tert.-butylnitrite at 40℃; for 48h; | 79% |
With tert.-butylnitrite at 40℃; for 48h; Green chemistry; | 79% |
Benzophenone oxime
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Schlenk technique; Inert atmosphere; | 78% |
4-methylphenyl methylsulfide
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In methanol; acetonitrile at 20℃; for 6h; Inert atmosphere; Electrochemical reaction; | 66% |
4-nitro-phenol
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 20h; | 59.9% |
Hexafluorobenzene
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With Ir(dFFppy)2(dtbbpy)PF6; lithium carbonate In dimethyl sulfoxide at 35℃; for 48h; Inert atmosphere; Irradiation; Sealed tube; | 54% |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
A
2-(p-acetylphenoxy)-2-methylpropionic acid
Conditions | Yield |
---|---|
With sodium hydroxide for 56h; Heating; Further byproducts given; | A n/a B 7% C 42% D 4% |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
A
4-(1-carboxy-1-methyl-ethoxy)-benzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide for 56h; Heating; Further byproducts given; | A n/a B 7% C 42% D 4% |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
B
2-(4-formylphenoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide for 56h; Heating; Further byproducts given; | A 7% B n/a C 42% D 4% |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
A
2-(p-acetylphenoxy)-2-methylpropionic acid
B
4-(1-carboxy-1-methyl-ethoxy)-benzoic acid
D
2-(4-formylphenoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide for 56h; Mechanism; Heating; | A n/a B n/a C 7% D n/a E 42% F 4% G n/a |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide for 96h; Heating; pH 7; |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
N-{2-[4-(2,2-Dichlorcyclopropyl)phenoxy]-2-methylpropanoyl}glycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 87.5 percent / Et3N; DMAP / CH2Cl2 / 20 h / 20 °C 2: 94.9 percent / NaOH / methanol; H2O / 4 h / 20 °C View Scheme |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 84.2 percent / Et3N; DMAP / CH2Cl2 / 20 h / 20 °C 2: 95 percent / NaOH / methanol; H2O / 4 h / 20 °C View Scheme |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 59.9 percent / DCC; DMAP / CH2Cl2 / 20 h / 20 °C 2: 27.9 percent / pyridine / H2O / 24 h / 20 °C View Scheme |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
sulfuric acid
methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate
Conditions | Yield |
---|---|
In methanol; diethyl ether |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
2-amino-1-(4-hydroxyphenyl)ethyl ketone
2-(4-(2,2-dichlorocyclopropyl)phenoxy)-N-(2-(4-hydroxyphenyl)-2-oxoethyl)-2-methylpropanamide
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; | 760 mg |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
2-amino-1-(4-hydroxyphenyl)ethyl ketone
C34H33Cl4NO6
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; | 1.15 g |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
2-(4-hydroxyphenyl)acetamide
2-(4-(2,2-dichlorocyclopropyl)phenoxy)-N-(2-(4-hydroxyphenyl)-2-oxoethyl)-2-methylpropanamide
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; | 760 mg |
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
2-(4-hydroxyphenyl)acetamide
C34H33Cl4NO6
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; | 1.15 g |
The molecular structure of Ciprofibrate (CAS NO.52214-84-3):
IUPAC Name: 2-[4-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Molecular Weight: 289.15446 g/mol
Molecular Formula: C13H14Cl2O3
Density: 1.37 g/cm3
Boiling Point: 424.9 °C at 760 mmHg
Flash Point: 210.7 °C
Index of Refraction: 1.579
Molar Refractivity: 70.16 cm3
Molar Volume: 211 cm3
Surface Tension: 50.8 dyne/cm
Enthalpy of Vaporization: 71.62 kJ/mol
Vapour Pressure: 5.63E-08 mmHg at 25 °C
Storage Temp.: 2-8 °C
XLogP3-AA: 3.4
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 4
Exact Mass: 288.032
MonoIsotopic Mass: 288.032
Topological Polar Surface Area: 46.5
Heavy Atom Count: 18
Canonical SMILES: CC(C)(C(=O)O)OC1=CC=C(C=C1)C2CC2(Cl)Cl
InChI: InChI=1S/C13H14Cl2O3/c1-12(2,11(16)17)18-9-5-3-8(4-6-9)10-7-13(10,14)15/h3-6,10H,7H2,1-2H3,(H,16,17)
InChIKey: KPSRODZRAIWAKH-UHFFFAOYSA-N
EINECS: 257-744-6
Product Categories: Intracellular receptor
Ciprofibrate (CAS NO.52214-84-3) is a kind of lipid-lowering drugs. It has anti-platelet aggregation and the role of soluble fibrin.
1. | otr-rat-orl 3650 mg/kg/1Y C | CNREA8 Cancer Research. 46 (1986),4601. |
Hazard Codes: T
Risk Statements: 45
R45:May cause cancer.
Safety Statements: 53-22-36/37/39-45
S53:Avoid exposure - obtain special instructions before use.
S22:Do not breathe dust.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS: UF0880000
Questionable carcinogen with experimental tumorigenic data. Experimental reproductive data. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl−.
Ciprofibrate (CAS NO.52214-84-3) is also named as 2-(p-(2,2-Dichlorocyclopropyl)phenoxy)-2-methylpropionic acid ; BRN 1984981 ; CCRIS 173 ; Ciprofibrato ; Ciprofibrato [INN-Spanish] ; Ciprofibratum ; Ciprofibratum [INN-Latin] ; UNII-F8252JGO9S ; WIN 35833 . Ciprofibrate (CAS NO.52214-84-3) is white or almost white crystalline powder.
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