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Name	Glyceryl-o-tolyl ether	EINECS	N/A
CAS No.	59-47-2	Density	1.152g/cm³
PSA	49.69000	LogP	0.72700
Solubility	N/A	Melting Point	69-71 °C(lit.)
Formula	C10H14 O3	Boiling Point	153-154 °C4 mm Hg(lit.)
Molecular Weight	182.219	Flash Point	161.5°C
Transport Information	N/A	Appearance	N/A
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.	Risk Codes	22-36
Molecular Structure		Hazard Symbols	Xn
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	Article Data	40

Glyceryl-o-tolyl ether Synthetic route

: 95-48-7
ortho-cresol

: 96-24-2
3-monochloro-1,2-propanediol

: 59-47-2
mephenesin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With water
With ethanol

: 2210-79-9
o-Cresyl glycidyl ether

: 59-47-2
mephenesin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With water Erhitzen des Reaktionsprodukts mit wss. Na2CO3;

: 25772-91-2
1-chloro-3-(2-methylphenoxy)propan-2-ol

: 59-47-2
mephenesin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Glyceryl-o-tolyl ether Chemical Properties

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 cm³
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:

Glyceryl-o-tolyl ether 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.

Glyceryl-o-tolyl ether Safety Profile

Hazard Codes of Glyceryl-o-tolyl ether (CAS NO.59-47-2): Harmful Xn
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

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