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Chlorphenesin

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Name

Chlorphenesin

EINECS 203-192-6
CAS No. 104-29-0 Density 1.318 g/cm3
PSA 49.69000 LogP 1.07200
Solubility Slightly soluble in water. Melting Point 77-79 °C
Formula C9H11ClO3 Boiling Point 369.45 °C at 760 mmHg
Molecular Weight 202.638 Flash Point 177.237 °C
Transport Information N/A Appearance white to off-white crystalline powder
Safety 26-36 Risk Codes 20/21/22
Molecular Structure Molecular Structure of 104-29-0 (Chlorphenesin) Hazard Symbols N/A
Synonyms

1,2-Propanediol,3-(p-chlorophenoxy)- (6CI,7CI,8CI);3-(4-Chlorophenoxy)-1,2-propanediol;3-(p-Chlorophenoxy)propane-1,2-diol;Adermykon;Demykon;ElestabCPN;Gecophen;Glycerol a-p-chlorophenyl ether;p-Chlorophenyl glyceryl ether;p-Chlorophenyl-a-glycerylether;p-Chlorphenesin;

Article Data 26

Chlorphenesin Synthetic route

106-48-9

4-chloro-phenol

96-24-2

3-monochloro-1,2-propanediol

104-29-0

chlorphenesin

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide at 105℃; for 3h; Concentration; Reagent/catalyst;95.1%
With sodium hydroxide In ethanol for 2h; Heating;81%
With alkali
106-48-9

4-chloro-phenol

56-81-5

glycerol

104-29-0

chlorphenesin

Conditions
ConditionsYield
With potassium carbonate; Diethyl carbonate at 150℃; for 15h; Temperature; Reagent/catalyst; Green chemistry;95%
With potassium carbonate; Diethyl carbonate at 105 - 110℃; for 20h;77 %Spectr.
556-52-5

oxiranyl-methanol

106-48-9

4-chloro-phenol

104-29-0

chlorphenesin

Conditions
ConditionsYield
Stage #1: 4-chloro-phenol With potassium carbonate In acetonitrile at 70℃; for 0.5h;
Stage #2: oxiranyl-methanol In acetonitrile
90%
With tetrabutylammomium bromide; potassium carbonate; palladium dichloride In water at 60℃; for 4.5h;69%
With pyridine
With pyridine
556-52-5

oxiranyl-methanol

1193-00-6

sodium 4-chlorophenolate

104-29-0

chlorphenesin

Conditions
ConditionsYield
With cerium(IV) triflate; sodium dodecyl-sulfate at 20℃; for 4h;89%
Stage #1: sodium 4-chlorophenolate With Amberlite IRA-400 resin In water
Stage #2: oxiranyl-methanol In ethanol at 50℃; for 2h;
85%
2212-05-7

4-chlorophenyl 2,3-epoxypropyl ether

104-29-0

chlorphenesin

Conditions
ConditionsYield
With β‐cyclodextrin In methanol; water at 40℃; for 10h;85%
With sulfuric acid for 1h; Ambient temperature;
2212-05-7

4-chlorophenyl 2,3-epoxypropyl ether

139-02-6

sodium phenoxide

A

104-29-0

chlorphenesin

B

112718-82-8

1-(4-chloro-phenoxy)-3-phenoxy-propan-2-ol

Conditions
ConditionsYield
With β‐cyclodextrin In water at 60℃; for 8h;A 19%
B 75%
62067-19-0

2-Benzyloxy-3-(4-chloro-phenoxy)-propan-1-ol

104-29-0

chlorphenesin

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In isopropyl alcohol; benzene
886-74-8, 126632-50-6

chlorphenesin carbamate

104-29-0

chlorphenesin

Conditions
ConditionsYield
With hydrogenchloride In water at 40 - 60℃; for 192h; Kinetics; Mechanism; Thermodynamic data; various acid concentrations; apparent activation energies and entropies;
886-74-8, 126632-50-6

chlorphenesin carbamate

A

104-29-0

chlorphenesin

B

61514-96-3

3-(p-chlorophenoxy)-1,2-propanediol-2-carbamate

Conditions
ConditionsYield
With sodium hydroxide In water at 0℃; Kinetics; Mechanism; Thermodynamic data; other concentrations of reagent, other temperature; isomerization, degradation, rate-pH profile were studied; apparent activation energies, and entropies were calculated;
61514-96-3

3-(p-chlorophenoxy)-1,2-propanediol-2-carbamate

A

886-74-8, 126632-50-6

chlorphenesin carbamate

B

104-29-0

chlorphenesin

Conditions
ConditionsYield
With sodium hydroxide In water at 0℃; Rate constant; degradation was studied;

Chlorphenesin Specification

The 1,2-Propanediol,3-(4-chlorophenoxy)-, with the CAS registry number 104-29-0, is also known as Chlorphenesin. It belongs to the classification codes of Central Nervous System Agents; Drug / Therapeutic Agent; Muscle Relaxants, Central; Neuromuscular Agents; Peripheral Nervous System Agents. Its EINECS registry number is 203-192-6. This chemical's molecular formula is C9H11ClO3 and molecular weight is 202.63. What's more, both its IUPAC name and systematic name are the same which is called 3-(4-Chlorophenoxy)propane-1,2-diol. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 1,2-Propanediol,3-(4-chlorophenoxy)- are: (1)ACD/LogP: 1.713; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.71; (4)ACD/LogD (pH 7.4): 1.71; (5)ACD/BCF (pH 5.5): 11.80; (6)ACD/BCF (pH 7.4): 11.80; (7)ACD/KOC (pH 5.5): 203.59; (8)ACD/KOC (pH 7.4): 203.59; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 6 ; (12)Polar Surface Area: 49.69 Å2; (13)Index of Refraction: 1.565; (14)Molar Refractivity: 50.121 cm3; (15)Molar Volume: 153.788 cm3; (16)Polarizability: 19.869×10-24cm3; (17)Surface Tension: 50.629 dyne/cm; (18)Density: 1.318 g/cm3; (19)Flash Point: 177.237 °C; (20)Enthalpy of Vaporization: 65.013 kJ/mol; (21)Boiling Point: 369.45 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of 1,2-Propanediol,3-(4-chlorophenoxy)-: this chemical can be prepared by 4-chloro-phenol with 3-chloro-propane-1,2-diol. This reaction needs reagent NaOH and solvent ethanol heating for 2 hours. The yield is 81 %.

1,2-Propanediol,3-(4-chlorophenoxy)- can be prepared by 4-chloro-phenol with 3-chloro-propane-1,2-diol.

Uses of 1,2-Propanediol,3-(4-chlorophenoxy)-: it is used to produce other chemicals. For example, it can react with acetoxyethene to get acetic acid 1-acetoxymethyl-2-(4-chloro-phenoxy)-ethyl ester. The reaction occurs with reagent tetrahydrofuran at ambient temperature for 72 hours. The yield is 38 %.

1,2-Propanediol,3-(4-chlorophenoxy)- can react with acetoxyethene to get acetic acid 1-acetoxymethyl-2-(4-chloro-phenoxy)-ethyl ester.

When you are dealing with this chemical, you should be very careful. This chemical is harmful by inhalation, in contact with skin and if swallowed. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: Clc1ccc(OCC(O)CO)cc1
(2) InChI: InChI=1S/C9H11ClO3/c10-7-1-3-9(4-2-7)13-6-8(12)5-11/h1-4,8,11-12H,5-6H2
(3) InChIKey: MXOAEAUPQDYUQM-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 subcutaneous 911mg/kg (911mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: MUSCLE WEAKNESS
Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 470, 1948.

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