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104-29-0

Basic Information
CAS No.: 104-29-0
Name: 1,2-Propanediol,3-(4-chlorophenoxy)-
Molecular Structure:
Molecular Structure of 104-29-0 (1,2-Propanediol,3-(4-chlorophenoxy)-)
Formula: C9H11ClO3
Molecular Weight: 202.64
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;
EINECS: 203-192-6
Density: 1.318 g/cm3
Melting Point: 77-79 °C
Boiling Point: 369.45 °C at 760 mmHg
Flash Point: 177.237 °C
Solubility: Slightly soluble in water.
Appearance: white to off-white crystalline powder
Hazard Symbols:
Risk Codes: 20/21/22
Safety: 26-36
Transport Information:
PSA: 49.69000
LogP: 1.07200
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;
61514-96-3

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

104-29-0

chlorphenesin

Conditions
ConditionsYield
With hydrogenchloride In water at 40 - 60℃; for 192h; Kinetics; Thermodynamic data; various acid concentrations; apparent activation energies and entropies;
(+-)-1-chloro-3-<4-chloro-phenoxy>-propan-2-ol

(+-)-1-chloro-3-<4-chloro-phenoxy>-propan-2-ol

104-29-0

chlorphenesin

Conditions
ConditionsYield
With potassium carbonate
106-48-9

4-chloro-phenol

104-29-0

chlorphenesin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3 / acetone / Heating
2: 1N sulfuric acid / 1 h / Ambient temperature
View Scheme
1121-74-0

potassium 4-chlorophenoxide

104-29-0

chlorphenesin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) Me2SO3, (ii) /BRN= 4161425/, DMSO
2: H2, HCl / Pd-C / benzene; propan-2-ol
View Scheme

4-((4-chlorophenoxy)methyl)-2,2-dimethyl-1,3-dioxolane

104-29-0

chlorphenesin

Conditions
ConditionsYield
With hydrogenchloride In methanol; water for 2h; Heating / reflux;
2212-05-7

4-chlorophenyl 2,3-epoxypropyl ether

A

104-29-0

chlorphenesin

B

129098-57-3

(S)-1,2-epoxy-3-(4-chlorophenoxy) propane

C

129098-58-4

(R)-2-((4-chlorophenoxy)methyl)oxirane

Conditions
ConditionsYield
With Bacillus megaterium ECU1001 epoxide hydrolase In potassium phosphate buffer; dimethyl sulfoxide at 30℃; for 0.5h; pH=7; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
108-05-4

vinyl acetate

104-29-0

chlorphenesin

204584-11-2

1-acetoxy-3-(4-chlorophenoxy)propan-2-ol

Conditions
ConditionsYield
With porcine pancreatic lipase In di-isopropyl ether at 20℃; for 3h; Enzymatic reaction; regioselective reaction;98%
104-29-0

chlorphenesin

18162-48-6

tert-butyldimethylsilyl chloride

3-(4-chlorophenoxy)-1,2-bis(tert-butyldimethylsiloxy)propane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;93%
104-29-0

chlorphenesin

43018-72-0

p-chlorophenoxyacetaldehyde

Conditions
ConditionsYield
With sodium periodate; silica gel In dichloromethane for 0.25h;90%
With polymer-supported phenyliodine(III) diacetate In dichloromethane at 20℃; for 6h;90%
With lead(IV) acetate; benzene
With sodium periodate; silica gel In dichloromethane
With sodium periodate In water for 1h; Ambient temperature;
104-29-0

chlorphenesin

18162-48-6

tert-butyldimethylsilyl chloride

1-((tert-butyldimethylsilyl)oxy)-3-(4-chlorophenoxy)propan-2-ol

Conditions
ConditionsYield
With 1H-imidazole In tetrahydrofuran at 20℃; for 24h;90%
104-29-0

chlorphenesin

124-63-0

methanesulfonyl chloride

87481-87-6

3-(4-chlorophenoxy)-1,2-propanediol dimesylate

Conditions
ConditionsYield
With pyridine89%
104-29-0

chlorphenesin

108-24-7

acetic anhydride

204584-11-2

1-acetoxy-3-(4-chlorophenoxy)propan-2-ol

Conditions
ConditionsYield
With pyridine at 4℃;85%
With pyridine; dmap In dichloromethane62%
13416-90-5

divinyl butanedioate

104-29-0

chlorphenesin

935477-90-0

1-O-vinylsuccinyl-chlorphenesin

Conditions
ConditionsYield
With Lipozyme(R) In acetone at 50℃; for 1h;84.7%
104-29-0

chlorphenesin

98-59-9

p-toluenesulfonyl chloride

87481-86-5

3-(4-chlorophenoxy)-1,2-propanediol ditosylate

Conditions
ConditionsYield
With pyridine84%
201230-82-2

carbon monoxide

104-29-0

chlorphenesin

40492-32-8

4-((4-chlorophenoxy)methyl)-1,3-dioxolan-2-one

Conditions
ConditionsYield
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;83%
4074-90-2

divinyl adipate

104-29-0

chlorphenesin

1-O-vinyladipoyl-chlorphenesin

Conditions
ConditionsYield
With Lipozyme(R) In acetone at 50℃; for 2h;72.5%
104-29-0

chlorphenesin

530-62-1

1,1'-carbonyldiimidazole

40492-32-8

4-((4-chlorophenoxy)methyl)-1,3-dioxolan-2-one

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 23℃; for 18h; Inert atmosphere;67%
10355-49-4

azelaic acid divinyl ester

104-29-0

chlorphenesin

1-O-vinylazeloyl-chlorphenesin

Conditions
ConditionsYield
With Lipozyme(R) In acetone at 50℃; for 2h;56.8%
104-29-0

chlorphenesin

3-(4-chloro-2-hydroxyphenoxy)propane-1,2-diol

Conditions
ConditionsYield
Stage #1: chlorphenesin With 4,5-dichlorophthalic anhydride; 6,7-dichlorobenzo[d][1,2]dioxine-1,4-dione In chloroform at 50℃; for 24h;
Stage #2: With water; sodium hydrogencarbonate In methanol at 50℃; for 1h; Inert atmosphere; regioselective reaction;
52%
10355-50-7

divinyl sebacate

104-29-0

chlorphenesin

1-O-vinylsebacoyl-chlorphenesin

Conditions
ConditionsYield
With Lipozyme(R) In acetone at 50℃; for 2h;51.9%
108-05-4

vinyl acetate

104-29-0

chlorphenesin

A

147220-31-3

(R)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol

B

(S)-3-(4-chlorophenoxy)propane-1,2-diol

Conditions
ConditionsYield
With pseudomonas fluorescens lipase In toluene at 30℃; for 1h; Catalytic behavior; Concentration; Solvent; Temperature; Time; Resolution of racemate; Enzymatic reaction; enantioselective reaction;A 48%
B 49%
108-05-4

vinyl acetate

104-29-0

chlorphenesin

147220-41-5

Acetic acid (S)-1-acetoxymethyl-2-(4-chloro-phenoxy)-ethyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 72h; Ambient temperature; lipase Amano PS;38%
104-29-0

chlorphenesin

39735-79-0

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

Conditions
ConditionsYield
With hydrogenchloride; acetic acid at 100 - 110℃;
104-29-0

chlorphenesin

79-04-9

chloroacetyl chloride

23958-75-0

Chloro-acetic acid 3-(4-chloro-phenoxy)-2-hydroxy-propyl ester

Conditions
ConditionsYield
With N,N-dimethyl-aniline
104-29-0

chlorphenesin

79-04-9

chloroacetyl chloride

23958-86-3

Chloro-acetic acid 1-(2-chloro-acetoxymethyl)-2-(4-chloro-phenoxy)-ethyl ester

Conditions
ConditionsYield
With N,N-dimethyl-aniline
104-29-0

chlorphenesin

14716-97-3

5-(4-chloro-phenoxymethyl)-oxazolidin-2-one

Conditions
ConditionsYield
at 180 - 200℃; for 5h;
104-29-0

chlorphenesin

98-80-6

phenylboronic acid

2170-24-3

4-(4-chloro-phenoxymethyl)-2-phenyl-[1,3,2]dioxaborolane

108-05-4

vinyl acetate

104-29-0

chlorphenesin

A

147220-31-3

(S)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol

B

147220-31-3

(R)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol

C

147220-41-5

Acetic acid (S)-1-acetoxymethyl-2-(4-chloro-phenoxy)-ethyl ester

D

147220-41-5

Acetic acid (R)-1-acetoxymethyl-2-(4-chloro-phenoxy)-ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran lipase PS; Title compound not separated from byproducts;
108-05-4

vinyl acetate

104-29-0

chlorphenesin

A

147220-31-3

(S)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol

B

147220-31-3

(R)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol

C

911835-63-7

Acetic acid 1-acetoxymethyl-2-(4-chloro-phenoxy)-ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 25h; lipase amano PS; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
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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.