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104-29-0 Usage

Chemical Properties

White to Off-White Solid

Uses

Different sources of media describe the Uses of 104-29-0 differently. You can refer to the following data:
1. Chlorphenesin is an antigen-associated immunosuppressant that inhibits IgE-mediated histamine release. Chlorphenesin is also used as an antimycotic agent.
2. chlorophenesin is a preservative with fungistatic and bactericidal properties.
3. It is used for relieving skeletal muscle pain.

Definition

ChEBI: Glycerol in which the hydrogen of one of the primary hydroxy groups is substituted by a 4-chlorophenyl group. It has antifungal and antibacterial properties, and is used for treatment of cutaneous and vaginal infections. Its 1-carbamate is used as a skelet l muscle relaxant for the treatment of painful muscle spasm.

Brand name

Maolate (Pharmacia & Upjohn).

Flammability and Explosibility

Notclassified

Check Digit Verification of cas no

The CAS Registry Mumber 104-29-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 104-29:
(5*1)+(4*0)+(3*4)+(2*2)+(1*9)=30
30 % 10 = 0
So 104-29-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H11ClO3/c10-7-1-3-9(4-2-7)13-6-8(12)5-11/h1-4,8,11-12H,5-6H2/t8-/m0/s1

104-29-0 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A17386)  3-(4-Chlorophenoxy)-1,2-propanediol, 99%   

  • 104-29-0

  • 25g

  • 350.0CNY

  • Detail
  • Alfa Aesar

  • (A17386)  3-(4-Chlorophenoxy)-1,2-propanediol, 99%   

  • 104-29-0

  • 100g

  • 1180.0CNY

  • Detail
  • Alfa Aesar

  • (A17386)  3-(4-Chlorophenoxy)-1,2-propanediol, 99%   

  • 104-29-0

  • 500g

  • 4862.0CNY

  • Detail

104-29-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name chlorphenesin

1.2 Other means of identification

Product number -
Other names Gecophen

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:104-29-0 SDS

104-29-0Synthetic route

4-chloro-phenol
106-48-9

4-chloro-phenol

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

3-monochloro-1,2-propanediol

chlorphenesin
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
4-chloro-phenol
106-48-9

4-chloro-phenol

glycerol
56-81-5

glycerol

chlorphenesin
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.
oxiranyl-methanol
556-52-5

oxiranyl-methanol

4-chloro-phenol
106-48-9

4-chloro-phenol

chlorphenesin
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
oxiranyl-methanol
556-52-5

oxiranyl-methanol

sodium 4-chlorophenolate
1193-00-6

sodium 4-chlorophenolate

chlorphenesin
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%
4-chlorophenyl 2,3-epoxypropyl ether
2212-05-7

4-chlorophenyl 2,3-epoxypropyl ether

chlorphenesin
104-29-0

chlorphenesin

Conditions
ConditionsYield
With β‐cyclodextrin In methanol; water at 40℃; for 10h;85%
With sulfuric acid for 1h; Ambient temperature;
4-chlorophenyl 2,3-epoxypropyl ether
2212-05-7

4-chlorophenyl 2,3-epoxypropyl ether

sodium phenoxide
139-02-6

sodium phenoxide

A

chlorphenesin
104-29-0

chlorphenesin

B

1-(4-chloro-phenoxy)-3-phenoxy-propan-2-ol
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%
2-Benzyloxy-3-(4-chloro-phenoxy)-propan-1-ol
62067-19-0

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

chlorphenesin
104-29-0

chlorphenesin

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

chlorphenesin carbamate

chlorphenesin
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;
chlorphenesin carbamate
886-74-8, 126632-50-6

chlorphenesin carbamate

A

chlorphenesin
104-29-0

chlorphenesin

B

3-(p-chlorophenoxy)-1,2-propanediol-2-carbamate
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;
3-(p-chlorophenoxy)-1,2-propanediol-2-carbamate
61514-96-3

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

A

chlorphenesin carbamate
886-74-8, 126632-50-6

chlorphenesin carbamate

B

chlorphenesin
104-29-0

chlorphenesin

Conditions
ConditionsYield
With sodium hydroxide In water at 0℃; Rate constant; degradation was studied;
3-(p-chlorophenoxy)-1,2-propanediol-2-carbamate
61514-96-3

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

chlorphenesin
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

chlorphenesin
104-29-0

chlorphenesin

Conditions
ConditionsYield
With potassium carbonate
4-chloro-phenol
106-48-9

4-chloro-phenol

chlorphenesin
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
potassium 4-chlorophenoxide
1121-74-0

potassium 4-chlorophenoxide

chlorphenesin
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

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

chlorphenesin
104-29-0

chlorphenesin

Conditions
ConditionsYield
With hydrogenchloride In methanol; water for 2h; Heating / reflux;
4-chlorophenyl 2,3-epoxypropyl ether
2212-05-7

4-chlorophenyl 2,3-epoxypropyl ether

A

chlorphenesin
104-29-0

chlorphenesin

B

(S)-1,2-epoxy-3-(4-chlorophenoxy) propane
129098-57-3

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

C

(R)-2-((4-chlorophenoxy)methyl)oxirane
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;
vinyl acetate
108-05-4

vinyl acetate

chlorphenesin
104-29-0

chlorphenesin

1-acetoxy-3-(4-chlorophenoxy)propan-2-ol
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%
chlorphenesin
104-29-0

chlorphenesin

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

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

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%
chlorphenesin
104-29-0

chlorphenesin

p-chlorophenoxyacetaldehyde
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;
chlorphenesin
104-29-0

chlorphenesin

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

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

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

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

chlorphenesin

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

3-(4-chlorophenoxy)-1,2-propanediol dimesylate
87481-87-6

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

Conditions
ConditionsYield
With pyridine89%
chlorphenesin
104-29-0

chlorphenesin

acetic anhydride
108-24-7

acetic anhydride

1-acetoxy-3-(4-chlorophenoxy)propan-2-ol
204584-11-2

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

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

divinyl butanedioate

chlorphenesin
104-29-0

chlorphenesin

1-O-vinylsuccinyl-chlorphenesin
935477-90-0

1-O-vinylsuccinyl-chlorphenesin

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

chlorphenesin

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

3-(4-chlorophenoxy)-1,2-propanediol ditosylate
87481-86-5

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

Conditions
ConditionsYield
With pyridine84%
carbon monoxide
201230-82-2

carbon monoxide

chlorphenesin
104-29-0

chlorphenesin

4-((4-chlorophenoxy)methyl)-1,3-dioxolan-2-one
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%
divinyl adipate
4074-90-2

divinyl adipate

chlorphenesin
104-29-0

chlorphenesin

1-O-vinyladipoyl-chlorphenesin

1-O-vinyladipoyl-chlorphenesin

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

chlorphenesin

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

4-((4-chlorophenoxy)methyl)-1,3-dioxolan-2-one
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%
azelaic acid divinyl ester
10355-49-4

azelaic acid divinyl ester

chlorphenesin
104-29-0

chlorphenesin

1-O-vinylazeloyl-chlorphenesin

1-O-vinylazeloyl-chlorphenesin

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

chlorphenesin

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

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%
divinyl sebacate
10355-50-7

divinyl sebacate

chlorphenesin
104-29-0

chlorphenesin

1-O-vinylsebacoyl-chlorphenesin

1-O-vinylsebacoyl-chlorphenesin

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

vinyl acetate

chlorphenesin
104-29-0

chlorphenesin

A

(R)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol
147220-31-3

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

B

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

(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%
vinyl acetate
108-05-4

vinyl acetate

chlorphenesin
104-29-0

chlorphenesin

Acetic acid (S)-1-acetoxymethyl-2-(4-chloro-phenoxy)-ethyl ester
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%
chlorphenesin
104-29-0

chlorphenesin

1-chloro-3-(4-chloro-phenoxy)-propan-2-ol
39735-79-0

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

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

chlorphenesin

chloroacetyl chloride
79-04-9

chloroacetyl chloride

Chloro-acetic acid 3-(4-chloro-phenoxy)-2-hydroxy-propyl ester
23958-75-0

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

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

chlorphenesin

chloroacetyl chloride
79-04-9

chloroacetyl chloride

Chloro-acetic acid 1-(2-chloro-acetoxymethyl)-2-(4-chloro-phenoxy)-ethyl ester
23958-86-3

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

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

chlorphenesin

urea
57-13-6

urea

5-(4-chloro-phenoxymethyl)-oxazolidin-2-one
14716-97-3

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

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

chlorphenesin

phenylboronic acid
98-80-6

phenylboronic acid

4-(4-chloro-phenoxymethyl)-2-phenyl-[1,3,2]dioxaborolane
2170-24-3

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

vinyl acetate
108-05-4

vinyl acetate

chlorphenesin
104-29-0

chlorphenesin

A

(S)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol
147220-31-3

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

B

(R)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol
147220-31-3

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

C

Acetic acid (S)-1-acetoxymethyl-2-(4-chloro-phenoxy)-ethyl ester
147220-41-5

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

D

Acetic acid (R)-1-acetoxymethyl-2-(4-chloro-phenoxy)-ethyl ester
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;
vinyl acetate
108-05-4

vinyl acetate

chlorphenesin
104-29-0

chlorphenesin

A

(S)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol
147220-31-3

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

B

(R)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol
147220-31-3

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

C

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

104-29-0Relevant articles and documents

A New and Efficient Heterogeneous System for the Oxidative Cleavage of 1,2-Diols and the Oxidation of Hydroquinones

Daumas, M.,Vo-Quang, Y.,Vo-Quang, L.,Goffic, F. Le

, p. 64 - 65 (1989)

Sodium periodate/wet silica gel in the presence of dichloromethane is an efficient reagent for the oxidative cleavage of 1,2-diols and the oxidation of hydroquinones.This easily prepared reagent provides a good alternative of classical metaperiodate oxidation, especially for the preparation of aldehydes, which easily form hydrates.

Kinetics and mechanism of degradation of chlorphenesin carbamate in strongly acidic aqueous solutions

Hara,Hayashi,Yoshida

, p. 3481 - 3484 (1986)

-

Exploration of the expeditious potential of Pseudomonas fluorescens lipase in the kinetic resolution of racemic intermediates and its validation through molecular docking

Soni, Surbhi,Dwivedee, Bharat P.,Sharma, Vishnu K.,Patel, Gopal,Banerjee, Uttam C.

, p. 85 - 94 (2017/12/26)

A profoundly time-efficient chemoenzymatic method for the synthesis of (S)-3-(4-chlorophenoxy)propan-1,2-diol and (S)-1-chloro-3-(2,5-dichlorophenoxy)propan-2-ol, two important pharmaceutical intermediates, was successfully developed using Pseudomonas fluorescens lipase (PFL). Kinetic resolution was successfully achieved using vinyl acetate as acylating agent, toluene/hexane as solvent, and reaction temperature of 30°C giving high enantioselectivity and conversion. Under optimized condition, PFL demonstrated 50.2% conversion, enantiomeric excess of 95.0%, enantioselectivity (E?=?153) in an optimum time of 1?hour and 50.3% conversion, enantiomeric excess of 95.2%, enantioselectivity (E?=?161) in an optimum time of 3?hours, for the two racemic alcohols, respectively. Docking of the R- and S-enantiomers of the intermediates demonstrated stronger H-bond interaction between the hydroxyl group of the R-enantiomer and the key binding residues of the catalytic site of the lipase, while the S-enantiomer demonstrated lesser interaction. Thus, docking study complemented the experimental outcome that PFL preferentially acylated the R form of the intermediates. The present study demonstrates a cost-effective and expeditious biocatalytic process that can be applied in the enantiopure synthesis of pharmaceutical intermediates and drugs.

A synthesis method of chlorphenesin

-

Paragraph 0082; 0083, (2017/09/01)

The invention relates to a synthetic method of chlorobenzene glyceryl ether. 3-chloro-1,2-propanediol and parachlorophenol are directly used as raw materials, high-corrosion chemical solvents are not introduced, a reaction is simple, the yield is high, and the yield can reach 95 percent or more under the optimal reaction condition. By adding a few phase transfer catalysts, the reaction can be promoted to be conducted quickly and effectively, and the reaction time can be shortened by at least two hours.

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