Conditions | Yield |
---|---|
Stage #1: (S)-phenylephrine With sulfuric acid; acetic anhydride at 105℃; for 12h; Walden inversion; Stage #2: With water at 95℃; for 3h; Walden inversion; optical yield given as %ee; enantioselective reaction; | 99% |
With sulfuric acid; acetic anhydride und Erhitzen des Reaktionsprodukts mit wss.Salzsaeure und anschliessend mit wss.Ammoniak; |
(R)-phenylephrine-(R)-naproxen
Phenylephrin
Conditions | Yield |
---|---|
Stage #1: (R)-phenylephrine-(R)-naproxen With hydrogenchloride In water; toluene at 75 - 80℃; for 0.5h; pH=< 2; Stage #2: With ammonium hydroxide In water at 1 - 15℃; pH=~ 9; Product distribution / selectivity; | 90% |
Phenylephrin
Conditions | Yield |
---|---|
Stage #1: α-methylamino-m-hydroxy-acetophenone sulfate With hydrogen; (((R)-1-diphenylphosphino-2-[((S)-α-(N,N-dimethylamino)-o-diphenylphosphino-phenyl)methyl]ferrocene)-η5-2,4-dimethyl-pentadienyl)-ruthenium(II) iodide In methanol at 70℃; under 23272.3 Torr; for 48h; Stage #2: With ammonium hydroxide In water at 65℃; for 0.0833333h; pH=~ 4.8 - 9; | 88.7% |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Lg-tartaric acid 2: acetic acid anhydride; sulfuric acid / und Erhitzen des Reaktionsprodukts mit wss.Salzsaeure und anschliessend mit wss.Ammoniak View Scheme | |
Multi-step reaction with 2 steps 1.1: methanol / 2 h / 20 - 65 °C / Resolution of racemate 2.1: hydrogenchloride / toluene; water / 0.5 h / 75 - 80 °C / pH < 2 2.2: 1 - 15 °C / pH ~ 9 View Scheme |
3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride
A
(S)-phenylephrine
B
Phenylephrin
Conditions | Yield |
---|---|
With potassium hydroxide; hydrogen; [(R)-P-Phos RuCl2 (R)-DAIPEN] In water; isopropyl alcohol at 65℃; under 21002.1 Torr; for 1h; Product distribution / selectivity; | A n/a B n/a |
With hydrogen; [(S)-Cl-MeO-Biphep RuCl2](dmf)n In methanol at 75℃; under 22502.3 Torr; for 18h; Product distribution / selectivity; | A n/a B n/a |
With hydrogen; [RuCl-(S)-P-Phos(p-cymene)]Cl In methanol at 75℃; under 22502.3 Torr; for 18h; Product distribution / selectivity; | A n/a B n/a |
3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride
Phenylephrin
Conditions | Yield |
---|---|
With RuCl2[(S)-xylyl-2,2,6,6’-tetramethoxy-4,4’-bis(diphenylphosphino)-3,3-bipyridine][(R)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]; hydrogen; potassium hydroxide In water; isopropyl alcohol at 65℃; under 21752.2 - 24752.5 Torr; for 2.25h; Autoclave; optical yield given as %ee; enantioselective reaction; |
Phenylephrin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 5%-palladium/activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr 2: dichloromethane / 0 °C 3: boron tribromide / dichloromethane / 24 h / 0 °C View Scheme |
C10H15NO2
Phenylephrin
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at 0℃; for 24h; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 2,6-dimethylpyridine; copper(II) choride dihydrate; C50H54N2O6 / ethanol; dichloromethane / 30 h / 20 °C 2: 5%-palladium/activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr 3: dichloromethane / 0 °C 4: boron tribromide / dichloromethane / 24 h / 0 °C View Scheme |
Phenylephrin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: copper acetylacetonate; sodium tetrahydroborate / isopropyl alcohol; ethanol / 17 h / 30 °C / Inert atmosphere 2: hydrogenchloride; sodium nitrite / water / 0 - 120 °C View Scheme |
Phenylephrin
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In water at 0 - 120℃; | 51.7 mg |
Conditions | Yield |
---|---|
With hydrogenchloride In isopropyl alcohol at 55 - 65℃; for 0.5h; Product distribution / selectivity; | 84.5% |
With hydrogenchloride In water; isopropyl alcohol pH=7 - 8; enantioselective reaction; | 3.35 g |
Phenylephrin
calcium carbide
A
3-(2,2,3-trimethyl-oxazolidin-5-yl)-phenol
Conditions | Yield |
---|---|
In acetone | A 70% B n/a |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 4h; Reflux; | 63.2% |
Phenylephrin
ethyl isocyanate
(1R)-1-(3-hydroxyphenyl)-2-<(ethylcarbamoyl)amino>ethanol
Conditions | Yield |
---|---|
With triethylamine In diethyl ether Ambient temperature; | 21% |
Phenylephrin
ethyl isocyanate
(1R)-1-(3-Hydroxyphenyl)-2-(N-ethylcarbamoyl)amino ethanol
Conditions | Yield |
---|---|
With triethylamine In diethyl ether | 21% |
bis(trichloromethyl) carbonate
Phenylephrin
(R)-5-(3-hydroxyphenyl)-3-methyl-2-oxazolidone
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -78℃; for 0.5h; | 6% |
Phenylephrin
(-)-1-acetoxy-1-(3-acetoxy-phenyl)-2-methylamino-ethane
Phenylephrin
acetic anhydride
(R)-1-acetoxy-1-(3-acetoxy-phenyl)-2-(acetyl-methyl-amino)-ethane
Conditions | Yield |
---|---|
With sodium acetate In methanol |
Conditions | Yield |
---|---|
With triethylamine In diethyl ether Ambient temperature; |
Phenylephrin
ethyl isocyanate
ethylcarbamic acid (1R)-2<<(ethylamino)carbonyl>methylamino>ethyl ester
Conditions | Yield |
---|---|
With triethylamine In diethyl ether Ambient temperature; |
Phenylephrin
1-{(R)-2-Hydroxy-2-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl}-1,3-dimethyl-urea
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / diethyl ether / Ambient temperature 2: 69 percent / cesium carbonate / acetone / 48 h / Heating View Scheme |
Phenylephrin
3-Ethyl-1-{(R)-2-hydroxy-2-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl}-1-methyl-urea
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 21 percent / triethylamine / diethyl ether / Ambient temperature 2: 77 percent / cesium carbonate / acetone / 48 h / Heating View Scheme |
Phenylephrin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / diethyl ether / Ambient temperature 2: 38 percent / cesium carbonate / acetone / 48 h / Heating View Scheme |
Phenylephrin
Ethyl-carbamic acid (R)-2-(3,3-diethyl-1-methyl-ureido)-1-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / diethyl ether / Ambient temperature 2: 38 percent / cesium carbonate / acetone / 48 h / Heating View Scheme |
Phenylephrin
2-dimethylamino-4-phenylpyrimidine-5-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: Phenylephrin; 2-dimethylamino-4-phenylpyrimidine-5-carboxylic acid In tetrahydrofuran for 0.166667h; Stage #2: With 4-methyl-morpholine In tetrahydrofuran for 0.0333333h; Stage #3: With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran at 20℃; for 4h; Heating / reflux; |
Phenylephrine (59-42-7) is reported in EPA TSCA Inventory.
Phenylephrine with the CAS NO. 59-42-7 has the Synonyms of (-)-Phenylephrine;phenylephrine base; (-)-M-hydroxy-alpha-(methylaminomethyl)benzyl alcohol; (-)-M-hydroxy-alpha-(methylaminomethyl)benzylalcohol; (-)-M-oxedrine; (R)-3-hydroxy-alpha-[(methylamino)methyl]benzenemethanol hydrochloride; (R)-benzenemethano;(r)-phenylephrine. Phenylephrine is a selective α1-adrenergic receptor agonist used primarily as a decongestant, as an agent to dilate the pupil, and to increase blood pressure.
Physical properties about Phenylephrine are: (1)ACD/LogP: 0.117; (2)ACD/LogD (pH 5.5): -2.91; (3)ACD/LogD (pH 7.4): -1.78; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.572; (12)Molar Refractivity: 47.449 cm3; (13)Molar Volume: 144.258 cm3; (14)Polarizability: 18.81 10-24cm3; (15)Surface Tension: 49.1800003051758 dyne/cm; (16)Density: 1.159 g/cm3; (17)Flash Point: 163.4 °C; (18)Enthalpy of Vaporization: 61.709 kJ/mol; (19)Boiling Point: 341.068 °C at 760 mmHg
Uses of Phenylephrine: Phenylephrine is used as a decongestant sold as an oral medicine, as a nasal spray, or as eye drops. Phenylephrine is now the most common over-the-counter (OTC) decongestant in the United States. Phenylephrine is sometimes used as a vasopressor to increase the blood pressure in unstable patients with hypotension. It is used as an eye drop to dilate the pupil in order to facilitate visualization of the retina. It is often used in combination with tropicamide. Narrow-angle glaucoma is a contraindication to phenylephrine use.
When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
You can still convert the following datas into molecular structure:
(1)InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1;
(2)InChIKey=SONNWYBIRXJNDC-VIFPVBQESA-N;
(3)Smilesc1([C@H](CNC)O)cc(ccc1)O;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
infant | TDLo | ocular | 5500ug/kg (5.5mg/kg) | VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION | Anesthesiology. Vol. 36, Pg. 187, 1972. |
mouse | LD50 | intravenous | 38mg/kg (38mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP | Acta Pharmacologica et Toxicologica. Vol. 38, Pg. 474, 1976. |
mouse | LD50 | subcutaneous | 875mg/kg (875mg/kg) | Farmakologiya i Toksikologiya Vol. 28, Pg. 46, 1965. | |
mouse | LDLo | intraperitoneal | 60mg/kg (60mg/kg) | CARDIAC: OTHER CHANGES | Journal of Pharmacology and Experimental Therapeutics. Vol. 160, Pg. 22, 1968. |
rat | LD50 | intraduodenal | 65mg/kg (65mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969. | |
rat | LD50 | oral | 350mg/kg (350mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969. | |
rat | LD50 | subcutaneous | 28mg/kg (28mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 85, Pg. 119, 1945. | |
women | TDLo | ocular | 188ug/kg (.188mg/kg) | VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION | Anesthesiology. Vol. 36, Pg. 187, 1972. |
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