oxiranyl-methanol
2-methoxy-phenol
A
2-(2-methoxyphenoxy)-1,3-propanediol
B
guaifenesin
Conditions | Yield |
---|---|
With calcined hydrotalcite In tetrahydrofuran at 120℃; for 4h; Kinetics; Reagent/catalyst; Temperature; Autoclave; | A 5% B 95% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 65 - 70℃; for 12h; | 90% |
With sodium hydroxide at 90 - 95℃; | 56% |
With tetrabutylammomium bromide; potassium carbonate; palladium dichloride In water at 60℃; for 5h; | 55% |
Stage #1: 2-methoxy-phenol With potassium hydroxide at 64.84℃; Inert atmosphere; Stage #2: oxiranyl-methanol With hydrogenchloride Inert atmosphere; |
Conditions | Yield |
---|---|
With perchloric acid | 81% |
With perchloric acid In water at 80℃; | 80% |
With sulfuric acid; water at 70℃; for 2h; | 59.1% |
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide at 210℃; for 0.25h; Microwave irradiation; | 75% |
Stage #1: 2-methoxy-phenol With sodium hydroxide In ethanol; water for 0.5h; Heating; Stage #2: 3-monochloro-1,2-propanediol In ethanol; water for 8h; Heating; | 61% |
With sodium hydroxide |
Conditions | Yield |
---|---|
Stage #1: 2-methoxy-phenol With potassium chloride; sodium sulfite at 50℃; for 3h; Reflux; Stage #2: 3-Amino-1,2-propanediol at 90℃; for 5h; Temperature; Concentration; | 72% |
4-hydroxymethyl-1,3-dioxolan-2-one
2-methoxy-phenol
A
1,3-bis(2-methoxyphenoxy)propan-2-ol
B
guaifenesin
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 160℃; for 9.5h; Inert atmosphere; Schlenk technique; | A 9% B 64% |
Conditions | Yield |
---|---|
With ethanol |
methocarbamol
A
3-(2-methoxyphenoxy)propanediol 2-carbamate
B
guaifenesin
Conditions | Yield |
---|---|
With water at 70℃; Product distribution; Rate constant; further temperatures, pH 8.0-10.0; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 43 percent / NaOH / 16 h / 80 °C 2: 81 percent / perchloric acid View Scheme | |
Multi-step reaction with 2 steps 1: 2.) 50percent aq. NaOH / 1.) 80 deg C, 2.) 4 h 2: 80 percent / 72percent HClO4 / H2O / 80 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOEt / ethanol 2: K2CO3 / acetone View Scheme |
2-methoxy-phenol
epichlorohydrin
A
1-chloro-3-(2-methoxyphenoxy)-2-propyl alcohol
B
1,3-bis(2-methoxyphenoxy)propan-2-ol
C
guaifenesin
D
2-(2-methoxy-phenoxymethyl)-oxirane
Conditions | Yield |
---|---|
With sodium hydroxide In toluene at 25 - 30℃; Solvent; Concentration; |
Conditions | Yield |
---|---|
With potassium carbonate; Diethyl carbonate at 105 - 110℃; for 8h; | 78 %Spectr. |
Conditions | Yield |
---|---|
With ethanol In water at 80℃; |
guaifenesin
Conditions | Yield |
---|---|
With hydrogenchloride In water at 37℃; pH=0.2; Kinetics; pH-value; |
guaifenesin
Conditions | Yield |
---|---|
With hydrogenchloride In water at 37℃; pH=0.2; Kinetics; pH-value; |
guaifenesin
Conditions | Yield |
---|---|
With hydrogenchloride In water at 37℃; pH=0.2; Kinetics; pH-value; |
guaifenesin
Conditions | Yield |
---|---|
With hydrogenchloride In water at 37℃; pH=0.2; Kinetics; pH-value; |
guaifenesin
Conditions | Yield |
---|---|
With hydrogenchloride In water at 37℃; pH=0.2; Kinetics; pH-value; |
guaifenesin
Conditions | Yield |
---|---|
With hydrogenchloride In water at 37℃; pH=0.2; Kinetics; pH-value; |
Conditions | Yield |
---|---|
In water at 35 - 50℃; for 1h; Product distribution / selectivity; | 96.15% |
guaifenesin
2(2-methoxyphenoxy)ethanale
Conditions | Yield |
---|---|
With sodium periodate In water at 10℃; for 1h; | 95% |
guaifenesin
Conditions | Yield |
---|---|
In ethanol for 3h; Reflux; | 94% |
guaifenesin
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 94% |
guaifenesin
acetic anhydride
(RS)-3-(2-methoxyphenoxy)-propane-1,2-diyl diacetate
Conditions | Yield |
---|---|
With pyridine at 4℃; for 4h; | 90% |
Conditions | Yield |
---|---|
Stage #1: guaifenesin With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Stage #2: 2,2-dimethylsuccinic anhydride In tetrahydrofuran; mineral oil at 20℃; | 90% |
Conditions | Yield |
---|---|
With phosphorus pentoxide; silica gel In acetonitrile at 20℃; | 88% |
carbon monoxide
guaifenesin
rac-4-(2-methoxyphenoxymethyl)-[1,3]dioxolan-2-one
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; oxygen; sodium acetate; potassium iodide In 1,2-dimethoxyethane at 100℃; under 10343.2 Torr; for 3h; Autoclave; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With phosphorus pentoxide; silica gel In acetonitrile at 20℃; | 85% |
Conditions | Yield |
---|---|
In ethanol for 3h; Reflux; | 83% |
N-methylsulfamoyl chloride
guaifenesin
1-[(2-Methoxyphenoxy)methyl]-1,2-ethanediol bis(methylsulfamate) (ester)
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Ambient temperature; | 82% |
guaifenesin
1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose
3-(2-methoxyphenoxy)-1-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)propane-1,2-diol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 4h; | 82% |
guaifenesin
Conditions | Yield |
---|---|
In ethanol for 3h; Reflux; | 82% |
guaifenesin
1-O-acetyl-2,3,5-tri-O-benzoyl-D-xylofuranose
3-(2-methoxyphenoxy)-1-O-(2,3,5-tri-O-benzoyl-β-D-xylofuranosyl)propane-1,2-diol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 5h; | 80% |
guaifenesin
Conditions | Yield |
---|---|
In ethanol for 3h; Reflux; | 80% |
guaifenesin
Conditions | Yield |
---|---|
In ethanol for 3h; Reflux; | 80% |
Conditions | Yield |
---|---|
In ethanol; N,N-dimethyl-formamide at 70℃; for 1.5h; Reflux; | 80% |
Conditions | Yield |
---|---|
Stage #1: guaifenesin With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Stage #2: maleic anhydride In tetrahydrofuran; mineral oil at 20℃; | 80% |
guaifenesin
acetic anhydride
A
(RS)-3-(2-methoxyphenoxy)-propane-1,2-diyl diacetate
B
1-O-acetyl-3-(2-methoxyphenoxy)propane-1,2-diol
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 3h; | A 10% B 78% |
Conditions | Yield |
---|---|
In ethanol for 3h; Reflux; | 75% |
1-benzoylimidazole
guaifenesin
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 8h; regioselective reaction; | A 75% B 15% |
Conditions | Yield |
---|---|
With ammonium hydroxide In methanol at 70℃; pH=8 - 9; | 74% |
guaifenesin
CVT-4786
Conditions | Yield |
---|---|
Stage #1: guaifenesin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; toluene at 25℃; for 0.0833333h; pH=6.8; Stage #2: With sodium hypochlorite; sodium chlorite In aq. phosphate buffer; water; toluene at 50℃; for 24h; pH=6.8; | 73% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite In water; acetonitrile at 35℃; aq. phosphate buffer; chemoselective reaction; | 37.4% |
Conditions | Yield |
---|---|
Stage #1: guaifenesin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; toluene at 25℃; pH=6.8; Stage #2: With sodium hypochlorite; sodium chlorite In aq. phosphate buffer; toluene at 50℃; for 24h; chemoselective reaction; | A 10 %Spectr. B 73% |
Conditions | Yield |
---|---|
With ammonium hydroxide In methanol at 70℃; pH=8 - 9; | 73% |
Conditions | Yield |
---|---|
Stage #1: guaifenesin With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Stage #2: 2,3-Dimethylmaleic anhydride In tetrahydrofuran; mineral oil at 20℃; | 73% |
IUPAC Name: 3-(2-Methoxyphenoxy)propane-1,2-diol
Synonyms of Guaifenesin (CAS NO.93-14-1): (+-)-3-(o-Methoxyphenoxy)-1,2-propanediol ; 1,2,3-Propanetriol, ether with 2-methoxyphenol ;1,2-Propanediol, 3-(2-methoxyphenoxy)- ; 3-(2-Methoxyphenoxy)-1,2-propanediol ; Aether glycerinoguaiacolicus
CAS NO: 93-14-1
Molecular Formula: C10H14O4
Molecular Weight: 198.22
Molecular Structure:
EINECS: 202-222-5
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 7
Polar Surface Area: 36.92 Å2
Index of Refraction: 1.538
Molar Refractivity: 51.9 cm3
Molar Volume: 165.8 cm3
Surface Tension: 45.6 dyne/cm
Density: 1.195 g/cm3
Flash Point: 169.6 °C
Enthalpy of Vaporization: 63.53 kJ/mol
Boiling Point: 356.8 °C at 760 mmHg
Vapour Pressure: 1.04E-05 mmHg at 25°C
Melting Point: 77-81 °C
Water Solubility: 5 g/100 mL (25 °C)
Appearance: White Solid
Product Categories og Guaifenesin (CAS NO.93-14-1): Benzhydrols, Benzyl & Special Alcohols;Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;API's
There are similar medicines derived from the guaiac tree were in use as a generic remedy by Native Americans when explorers reached North America in the 1500s. Guaifenesin was first approved by the Food and Drug Administration in 1952.Guaifenesin is sold as pills or syrups under many brand names. It is also included in many other over-the-counter cough and cold remedy combinations
Guaifenesin (CAS NO.93-14-1) is mainly used in the treatment of coughing, but the drug has numerous other uses, including medical, veterinary, and personal.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | 335mg/kg (335mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 54, Pg. 688, 1958. | |
mouse | LD50 | intramuscular | 2210mg/kg (2210mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 429, 1974. | |
mouse | LD50 | intraperitoneal | 495mg/kg (495mg/kg) | "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 398, 1972. | |
mouse | LD50 | intravenous | 400mg/kg (400mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 429, 1974. | |
mouse | LD50 | oral | 690mg/kg (690mg/kg) | "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 398, 1972. | |
mouse | LD50 | subcutaneous | 800mg/kg (800mg/kg) | AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" | Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 1355, 1965. |
rabbit | LD50 | oral | 2553mg/kg (2553mg/kg) | Applied Therapeutics. Vol. 9, Pg. 55, 1967. | |
rat | LD50 | intramuscular | 4gm/kg (4000mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 429, 1974. |
rat | LD50 | intraperitoneal | 1gm/kg (1000mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 191, Pg. 147, 1971. |
rat | LD50 | intravenous | 360mg/kg (360mg/kg) | BEHAVIORAL: ATAXIA KIDNEY, URETER, AND BLADDER: HEMATURIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Proceedings of the Society for Experimental Biology and Medicine. Vol. 85, Pg. 323, 1954. |
rat | LD50 | oral | 1510mg/kg (1510mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Pharmacological Research Communications. Vol. 1, Pg. 413, 1969. |
rat | LD50 | subcutaneous | 2550mg/kg (2550mg/kg) | Drugs in Japan Vol. 6, Pg. 210, 1982. |
Safety Information about Guaifenesin (CAS NO.93-14-1):
Hazard Codes: Xn
Risk Statements: 22-36/37/38
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany: 1
RTECS: TY8400000
Hazard Note: Harmful
Guaifenesin has side effect if consumption in above-normal quantities.May be cause nausea, vomiting, and the formation of kidney stones of URIC ACID.
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam .
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Use only in a chemical fume hood.
Storage: Store in a cool, dry place. Store in a tightly closed container.
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