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59-47-2

Basic Information
CAS No.: 59-47-2
Name: MEPHENESIN
Article Data: 40
Molecular Structure:
Molecular Structure of 59-47-2 (MEPHENESIN)
Formula: C10H14 O3
Molecular Weight: 182.219
Synonyms: 1,2-Propanediol,3-(o-tolyloxy)- (8CI); (?à)-Mephenesin; 1,2-Dihydroxy-3-(2-methylphenoxy)propane;3-(2-Methylphenoxy)propane-1,2-diol; 3-(2-Tolyloxy)-1,2-propanediol;3-(o-Methylphenoxy)-1,2-propanediol; 3-(o-Tolyloxy)-1,2-propanediol;3-o-Toloxy-1,2-propanediol; Atensin; Avosyl; Avoxyl; BDH 312; Cresoxydiol;Cresoxypropanediol; Curythan; Daserd; Daserol; Decontractyl; Dioloxol; Glycerylo-tolyl ether; Glykresin; Glyotol; Kinavosyl; Lissephen; Memphenesin; Mephedan;Mephelor; Mephenesin; Mephenesine; Mephensin; Mepherol; Mephesin; Mephin;Mephson; Mervaldin; Myanesin; Myanol; Myasin; Mycocuran; Myodetensin;Myodetensine; Myolysin; Myopan; Myoserol; Myoten; Myoxane; NSC 25234; NSC36140; NSC 50788; NSC 8134; Oranixon; Prolax; RP 3602; Relaxar; Relaxil;Renarcol; Rhex; Sansdolor; Sinan; Spartoloxyn; Spasmolyn; Stilalgin; Thoxidil;Tolansin; Tolax; Tolcil; Tolhart; Tolosate; Toloxyn; Tolserol; Tolseron;Tolsin; Tolulexin; Tolulox; Tolyspaz; Walconesin; o-Cresyl glycerol ether;o-Cresyl a-glyceryl ether
Density: 1.152g/cm3
Melting Point: 69-71 °C(lit.)
Boiling Point: 153-154 °C4 mm Hg(lit.)
Flash Point: 161.5°C
Hazard Symbols: Xn
Risk Codes: 22-36
Safety: Poison by intraperitoneal, intravenous, and subcutaneous routes. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes. See also ETHERS.
PSA: 49.69000
LogP: 0.72700
Synthetic route
95-48-7

ortho-cresol

96-24-2

3-monochloro-1,2-propanediol

59-47-2

mephenesin

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 210℃; for 0.25h; Microwave irradiation;94%
With sodium hydroxide In ethanol for 2h; Heating;79%
With sodium hydroxide; water
With sodium ethanolate
With sodium ethanolate 1.) EtOH, RT, 30 min, 2.) EtOH, a) reflux, 4 h, b) RT, overnight; Yield given. Multistep reaction;
556-52-5

oxiranyl-methanol

95-48-7

ortho-cresol

59-47-2

mephenesin

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate; palladium dichloride In water at 60℃; for 5h;66%
With tetrabutylammomium bromide; sodium hydroxide at 20℃; for 5h;0.7 g
95-48-7

ortho-cresol

56-81-5

glycerol

59-47-2

mephenesin

Conditions
ConditionsYield
With carbon dioxide; calcium oxide at 200℃;
With sodium acetate at 200 - 210℃;
With potassium carbonate; Diethyl carbonate at 105 - 110℃; for 28h;76 %Spectr.
Etherification;
sodium hydroxide Etherification;
96-24-2

3-monochloro-1,2-propanediol

4549-72-8

sodium o-cresolate

59-47-2

mephenesin

Conditions
ConditionsYield
With water
With ethanol
2210-79-9

o-Cresyl glycidyl ether

59-47-2

mephenesin

Conditions
ConditionsYield
With sulfuric acid for 1h; Ambient temperature;
With water at 25℃; pH=7.2; Microbiological reaction; Enzymatic reaction; enantioselective reaction;
63991-86-6

Acetic acid 1-acetoxymethyl-2-o-tolyloxy-ethyl ester

59-47-2

mephenesin

Conditions
ConditionsYield
With sodium hydroxide In isopropyl alcohol at 85℃; Hydrolysis;20 mg
106-89-8

epichlorohydrin

potassium-<2-methyl-phenolate>

potassium-<2-methyl-phenolate>

59-47-2

mephenesin

Conditions
ConditionsYield
With water Erhitzen des Reaktionsprodukts mit wss. Na2CO3;
25772-91-2

1-chloro-3-(2-methylphenoxy)propan-2-ol

59-47-2

mephenesin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 231 mg / NaH / ethyl acetate; hexane / 0.08 h
2: 100 - 110 °C
3: 20 mg / aq. NaOH / propan-2-ol / 85 °C
View Scheme
2210-79-9

o-Cresyl glycidyl ether

(+-)-1-methyl-heptylamine

(+-)-1-methyl-heptylamine

59-47-2

mephenesin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 - 110 °C
2: 20 mg / aq. NaOH / propan-2-ol / 85 °C
View Scheme
95-48-7

ortho-cresol

C-chloro-formamidine hydrochloride

C-chloro-formamidine hydrochloride

59-47-2

mephenesin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aq. NaOH / propan-2-ol / 84 °C
2: 231 mg / NaH / ethyl acetate; hexane / 0.08 h
3: 100 - 110 °C
4: 20 mg / aq. NaOH / propan-2-ol / 85 °C
View Scheme
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Chemistry

IUPAC Name:  3-(2-Methylphenoxy)propane-1,2-diol
Synonyms of Glyceryl-o-tolyl ether (CAS NO.59-47-2): 1,2-Dihydroxy-3-(2-methylphenoxy)propane ; 1-Ortho-tolylglycerol ether ; 1-o-Tolylglycerol ether ; 3-(2-Methylphenoxy)-1,2-propanediol ; 3-(2-Tolyloxy)-1,2-propanediol ; 3-(o-Methylphenoxy)-1,2-propanediol ; 3-(o-Tolyloxy)propane-1,2-diol ; 3-o-Toloxy-1,2-propanediol  4-06-00-01952 (Beilstein Handbook Reference) ; alpha,beta-Dihydroxy-gamma-(2-methylphenoxy)propane ; alpha-(o-Tolyl)glyceryl ether ; o-Cresol glyceryl ether ; o-Cresyl alpha-glyceryl ether ; o-Cresyl glycerol ether ; o-Kresol-glycerinaether ; o-Kresol-glycerinaether [German] ;
CAS NO: 59-47-2
Molecular Formula of Glyceryl-o-tolyl ether (CAS NO.59-47-2): C10H14O3 
Molecular Weight: 182.2164  
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 6
Polar Surface Area: 27.69 Å2
Index of Refraction: 1.545
Molar Refractivity: 50.05 cm3
Molar Volume: 158.1 cm
Surface Tension: 46.1 dyne/cm
Density: 1.152 g/cm3
Flash Point: 161.5 °C
Enthalpy of Vaporization: 58.26 kJ/mol
Boiling Point: 310.9 °C at 760 mmHg
Vapour Pressure: 0.000249 mmHg at 25°C
Molecular Structure:

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
hamster LD50 intraperitoneal 322mg/kg (322mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
hamster LD50 oral 821mg/kg (821mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
mouse LD50 intraperitoneal 320mg/kg (320mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 55, Pg. 1272, 1959.
mouse LD50 intravenous 175mg/kg (175mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 248, Pg. 3642, 1959.
mouse LD50 oral 720mg/kg (720mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 242, 1967.
mouse LD50 subcutaneous 285mg/kg (285mg/kg) BEHAVIORAL: ANTICONVULSANT Acta Pharmacologica et Toxicologica. Vol. 19, Pg. 247, 1962.
rabbit LD50 intravenous 125mg/kg (125mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: REGIDITY

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
International Journal of Neuropharmacology. Vol. 5, Pg. 305, 1966.
rabbit LDLo oral 2300mg/kg (2300mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 89, Pg. 145, 1952.
rat LD50 intraperitoneal 283mg/kg (283mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
rat LD50 intravenous 133mg/kg (133mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

KIDNEY, URETER, AND BLADDER: HEMATURIA
Proceedings of the Society for Experimental Biology and Medicine. Vol. 85, Pg. 323, 1954.
rat LD50 oral 625mg/kg (625mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ANTIPSYCHOTIC

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 280, 1961.

Safety Profile

Hazard Codes of Glyceryl-o-tolyl ether (CAS NO.59-47-2): HarmfulXn
Risk Statements: 22-36 
R22: Harmful if swallowed. R36: Irritating to eyes.
Safety Statements: 26 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS: TZ1225000