Glyceryl-o-tolyl ether supplier

Name
MEPHENESIN
EINECS
CAS No. 59-47-2
Article Data40
CAS DataBase
Density 1.152g/cm³
Solubility
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
Appearance
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
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

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

: 95-48-7
ortho-cresol

Fuller's earth: Fuller's earth

: 59-47-2
mephenesin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetone / Heating 2: 1N sulfuric acid / 1 h / Ambient temperature View Scheme

: 124-38-9
carbon dioxide

: 2210-79-9
o-Cresyl glycidyl ether

A: 59-47-2
mephenesin

B: 1878-24-6
4-[(2-methylphenoxy)methyl]-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With C44H22Cl8N4(2-)Mn(3+)IO3(1-); tetrabutylammomium bromide In neat (no solvent) under 750.075 Torr; for 120h; Catalytic behavior; Heating;

...Expand

: 108-05-4
vinyl acetate

: 59-47-2
mephenesin

: 138710-05-1, 105476-17-3
1-acetoxy-3-(2-methylphenoxy)propan-2-ol

Conditions

Conditions	Yield
With porcine pancreatic lipase In di-isopropyl ether at 20℃; for 3h; Enzymatic reaction; regioselective reaction;	97%

: 13416-90-5
divinyl butanedioate

: 59-47-2
mephenesin

: 929005-15-2
1-O-vinylsuccinylmephenesin

Conditions

Conditions	Yield
With Lipozyme(R) In acetone at 50℃; for 1h;	85.2%

: 4074-90-2
divinyl adipate

: 59-47-2
mephenesin

: 1-O-vinyladipoyl-mephenesin

Conditions

Conditions	Yield
With Lipozyme(R) In acetone at 50℃; for 2h;	78.5%

: 59-47-2
mephenesin

: 108-24-7
acetic anhydride

: 138710-05-1, 105476-17-3
1-acetoxy-3-(2-methylphenoxy)propan-2-ol

Conditions

Conditions	Yield
With pyridine; dmap In dichloromethane	66%

: 10355-49-4
azelaic acid divinyl ester

: 59-47-2
mephenesin

: 1-O-vinylazeloyl-mephenesin

Conditions

Conditions	Yield
With Lipozyme(R) In acetone at 50℃; for 2h;	64.1%

: 10355-50-7
divinyl sebacate

: 59-47-2
mephenesin

: 1-O-vinylsebacoyl-mephenesin

Conditions

Conditions	Yield
With Lipozyme(R) In acetone at 50℃; for 2h;	60%

: 108-05-4
vinyl acetate

: 59-47-2
mephenesin

: 138710-06-2
Acetic acid (S)-1-acetoxymethyl-2-o-tolyloxy-ethyl ester

Conditions

Conditions	Yield
In tetrahydrofuran for 240h; Ambient temperature; lipase Amano PS;	35%

: 22633-62-1
1-(2,2-dimethoxyethyl)piperidine

: 59-47-2
mephenesin

: 98654-32-1
1-(4-o-tolyloximethyl-[1,3]dioxolan-2-ylmethyl)-piperidine

Conditions

Conditions	Yield
at 120℃;

: 108-30-5
succinic acid anhydride

: 59-47-2
mephenesin

: succinic acid mono-(β-hydroxy-β'-o-tolyloxy-isopropyl ester)

Conditions

Conditions	Yield
With pyridine Erhitzen auf dem Dampfbad;

: 1445-45-0
Trimethyl orthoacetate

: 59-47-2
mephenesin

: 2-methoxy-2-methyl-4-o-tolyloximethyl-[1,3]dioxolane

: 75-44-5
phosgene

: 59-47-2
mephenesin

: 533-06-2
2-hydroxy-3-(o-tolyloxy)propyl carbamate

Conditions

Conditions	Yield
With N,N-dimethyl-aniline; benzene Behandeln einer Loesung des Reaktionsprodukts in Benzol mit wss. NH3;

: 75-44-5
phosgene

: 59-47-2
mephenesin

: 100254-95-3
1,2-bis-carbamoyloxy-3-o-tolyloxy-propane

Conditions

Conditions	Yield
With antipyrine; chloroform; toluene Behandeln der vom Antipyrin-hydrochlorid befreiten Reaktionsloesung mit NH3;

: 75-44-5
phosgene

: 59-47-2
mephenesin

: 1878-24-6
4-[(2-methylphenoxy)methyl]-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With antipyrine; chloroform; toluene

: 110-43-0
n-pentyl methyl ketone

: 59-47-2
mephenesin

: 6288-82-0
2-methyl-2-pentyl-4-o-tolyloximethyl-[1,3]dioxolane

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; toluene

: 97-97-2
chloroacetaldehyde dimethyl acetal

: 59-47-2
mephenesin

: 100388-92-9
2-chloromethyl-4-o-tolyloximethyl-[1,3]dioxolane

Conditions

Conditions	Yield
With sulfuric acid

: 13820-09-2
trimethyl orthovalerate

: 59-47-2
mephenesin

: 2-butyl-2-methoxy-4-o-tolyloximethyl-[1,3]dioxolane

Conditions

Conditions	Yield
With sulfuric acid

: 59-47-2
mephenesin

: 20260-53-1
pyridine-3-carbonyl chloride hydrochloride

: 533-07-3
nicotinic acid-(2-hydroxy-3-o-tolyloxy-propyl ester)

Conditions

Conditions	Yield
With pyridine

: 59-47-2
mephenesin

: 1505-68-6
5-o-tolyloxymethyl-oxazolidin-2-one

: 75-44-5
phosgene

: 59-47-2
mephenesin

: 75-04-7
ethylamine

: 6288-77-3
ethyl-carbamic acid-(2-hydroxy-3-o-tolyloxy-propyl ester)

...Expand

: 59-47-2
mephenesin

: 78-39-7
Triethyl orthoacetate

: 2-ethoxy-2-methyl-4-o-tolyloximethyl-[1,3]dioxolane

: 59-47-2
mephenesin

: 75-87-6
chloral

: 6055-48-7
1-o-tolyloxy-2,3-bis-(2,2,2-trichloro-1-hydroxy-ethoxy)-propane

Conditions

Conditions	Yield
With toluene

: 75-44-5
phosgene

: 59-47-2
mephenesin

: 107-15-3
ethylenediamine

: 106381-70-8
(2-amino-ethyl)-carbamic acid-(2-hydroxy-3-o-tolyloxy-propyl ester)

...Expand

: 59-47-2
mephenesin

: 122-51-0
orthoformic acid triethyl ester

: 131868-26-3
2-ethoxy-4-o-tolyloxymethyl-[1,3]dioxolane

: 59-47-2
mephenesin

: 115-80-0
Triethyl orthopropionate

: 2-ethoxy-2-ethyl-4-o-tolyloximethyl-[1,3]dioxolane

Conditions

Conditions	Yield
With sulfuric acid

: 59-47-2
mephenesin

: 105-58-8
Diethyl carbonate

: 1878-24-6
4-[(2-methylphenoxy)methyl]-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With sodium methylate Entfernen des entstehenden Aethanols;

: 623-50-7
ethyl 2-hydroxyacetate

: 59-47-2
mephenesin

: 100258-09-1
1-Glycoloyloxy-3-o-tolyloxypropan-2-ol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid

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

Product Name

MEPHENESIN

Synthetic route

Glyceryl-o-tolyl ether Chemical Properties

Glyceryl-o-tolyl ether Toxicity Data With Reference

Glyceryl-o-tolyl ether Safety Profile

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