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Clorprenaline

Product Name
Clorprenaline
CAS No.
3811-25-4
Chemical Name
Clorprenaline
Synonyms
1-(2-chlorophenyl)-2-propan-2-ylamino-ethanol;E 241;CLORPRENALINE;Cloroprenaline;Chlorprenaline;Isoprofenamine;Clorprenalline;Isoprophenamine;(+-)-Chloroprenaline;Clorprenaline ISO17034
CBNumber
CB9291186
Molecular Formula
C11H16ClNO
Formula Weight
213.7
MOL File
3811-25-4.mol
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Clorprenaline Property

Melting point:
81-82 °C
Boiling point:
329.7±27.0 °C(Predicted)
Density 
1.117±0.06 g/cm3(Predicted)
pka
13.60±0.20(Predicted)
form 
Solid
color 
White to off-white
BRN 
2105716
CAS DataBase Reference
3811-25-4(CAS DataBase Reference)
NIST Chemistry Reference
Benzenemethanol, 2-chloro-«alpha»-[[(1-methylethyl)amino]methyl]-(3811-25-4)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36
Safety Statements 
26
WGK Germany 
3
HS Code 
29221990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
32571
Product name
Clorprenaline
Purity
VETRANAL
Packaging
10mg
Price
$223
Updated
2022/05/15
Biorbyt Ltd
Product number
orb593376
Product name
Clorprenaline
Packaging
50μg
Price
$425
Updated
2021/12/16
Biorbyt Ltd
Product number
orb593376
Product name
Clorprenaline
Packaging
100μg
Price
$635.8
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0007288
Product name
CLORPRENALINE
Purity
95.00%
Packaging
5G
Price
$909.56
Updated
2021/12/16
Biorbyt Ltd
Product number
orb593376
Product name
Clorprenaline
Packaging
500μg
Price
$957.1
Updated
2021/12/16
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Clorprenaline Chemical Properties,Usage,Production

Originator

Asthone,Eisai,Japan,1970

Uses

Bronchodilator.

Uses

Clorprenaline is a beta-2 adrenergic agonist with bronchodilatory activity.

Definition

ChEBI: 1-(2-chlorophenyl)-2-isopropylaminoethanol is a member of the class of monochlorobenzenes that is chlorobenzene which is substituted by a 1-hydroxy-2-[(propan-2-yl)amino]ethyl group at position 2. It is a member of monochlorobenzenes, a member of ethanolamines and a secondary amino compound.

Manufacturing Process

To a solution of 279 g of o-chloroacetophenone in 2 liters of anhydrous diethyl ether were added about 3 g of dibenzoyl peroxide. 5 g of bromine were added to the resulting solution, and after 3 minutes, the color of bromine had been discharged, indicating that the formation of ω-bromo-o-chloroacetophenone had been initiated. A further amount of 288 g of bromine was added dropwise to the reaction mixture over a 1.5 hour interval. After the addition of the bromine had been completed, the reaction mixture was stirred for one-half hour and poured over about 1 kg of crushed ice.
After the ice had melted, the resulting aqueous and ethereal layers were separated. The ethereal layer containing ω-bromo-o-chloroacetophenone was washed with successive 500 ml quantities of water, 5% sodium carbonate solution and again with water to remove the hydrogen bromide formed as a by-product in the reaction. The ethereal layer was dehydrated by contacting with anhydrous magnesium sulfate. The drying agent was removed
filtration and the ether was evaporated from the filtrate. The residue remaining after the evaporation consisted of about 400 g of ω-bromo-ochloroacetophenone. A solution of 400 g of ω-bromo-o-chloroacetophenone in one liter of methanol was cooled to about 25°C. A cold solution of 92.5 g of sodium borohydride in one liter of methanol was added as rapidly as possible to this cooled solution while maintaining the temperature below about 25°C. After the addition had been completed, the reaction mixture was allowed to stand for 4 hours at ambient room temperature, to complete the reduction of the keto group of the ω-bromo-o-chloroacetophenone. The reaction mixture containing a mixture of o-chlorophenyl ethylene-β-bromohydrin and o-chlorophenyl ethylene oxide was then evaporated in vacuo at room temperature to a syrup which was poured into about one liter of 5% hydrochloric acid to decompose any boratealcohol complexes. The two compounds were dissolved in diethyl ether by extracting the acidic layer three times with successive 500 ml portions of diethyl ether. The combined ether extracts were dried over anhydrous magnesium sulfate and filtered, and the ether was removed by evaporation in vacuo. A residue consisting of 400 g of a mixture of o-chlorophenyl ethylene-β-bromohydrin and o-chlorophenyl ethylene oxide was obtained.
400 g of a mixture of o-clilorophenyl ethylene-β-bromohydrin and ochlorophenyl ethylene oxide were dissolved in one liter of anhydrous ethanol.
To this solution was added a solution of 306 g of isopropylamine in one liter of anhydrous ethanol. The reaction mixture was heated at refluxing temperature for about 16 hours, thus forming N-[β-(o-chlorophenyl)-β-hydroxyethyl]- isopropylamine. The solvent was removed in vacuo, and to the residue was added a solution containing 200 ml of 12 N HCl in 2,500 ml of water.
The acidic solution was washed twice with 500 ml portions of ether which were discarded. The acidic layer was then made basic by the addition of 250 ml of 5% (w/v) sodium hydroxide, thus liberating the free base of N-[β-(ochlorophenyl)-β-hydroxyethyl]-isopropylamine. The free base was extracted with two successive one liter portions of diethyl ether. The combined ether extracts were dried over anhydrous magnesium sulfate, filtered and
concentrated in vacuo to remove all of the solvents. N-[β-(o-chlorophenyl)-β- hydroxyethyl]-isopropylamine was thus obtained, according to US Patent 2,887,509.
The N-[β-(o-chlorophenyl)-β-hydroxyethyl]-isopropylamine obtained by the foregoing procedure was dissolved in about 3 liters of ether and dry hydrogen chloride gas was bubbled into the solution until it was saturated, whereupon the hydrochloride salt of N-[β-(o-chlorophenyl)-β-(hydroxy)- ethyl]isopropylamine precipitated. The salt was separated from the ether by filtration, and was dissolved in two liters of anhydrous ethanol. The alcoholic solution was decolorized with charcoal and filtered.
Three liters of anhydrous ether were added thereto and the N-[β-(ochlorophenyl)-β-hydroxyethyl]-isopropylamine hydrochloride precipitated in crystalline form as the monohydrate. The mixture was maintained at about 0°C for 40 hours and then filtered. The filter cake was washed with ether and dried. About 209 g of N-[β-(o-chlorophenyl)-β-(hydroxy)-ethyl]isopropylamine hydrochloride monohydrate, melting at about 163° to 164°C, were obtained according to US Patent 2,816,059.

Therapeutic Function

Bronchodilator

Clorprenaline Preparation Products And Raw materials

Raw materials

Preparation Products

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Clorprenaline Suppliers

Service Chemical Inc.
Tel
--
Fax
--
Email
sales@chemos-group.com
Country
Germany
ProdList
6350
Advantage
71
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View Lastest Price from Clorprenaline manufacturers

Career Henan Chemical Co
Product
Clorprenaline 3811-25-4
Price
US $1.00/KG
Min. Order
1KG
Purity
95%-99%
Supply Ability
2000kg
Release date
2019-08-05

3811-25-4, ClorprenalineRelated Search:


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  • Benzenemethanol, 2-chloro-alpha-[[(1-methylethyl)amino]methyl]-
  • Isoprophenamineisoprofenamine
  • o-Chloro-alpha-[(isopropylamino)methyl]benzyl alcohol
  • CLORPRENALINE
  • 1-(2-chlorophenyl)-2-propan-2-ylamino-ethanol
  • Cloroprenaline
  • sodium 4-[[dimethylamino(sulfanylidene)methyl]disulfanyl]-1-butanesulfinate
  • Isoprophenamine
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  • (+-)-Chloroprenaline
  • 1-o-Chlorophenyl-2-isopropylaminoethanol
  • Benzenemethanol, 2-chloro-α-[[(1-methylethyl)amino]methyl]-
  • Benzyl alcohol, o-chloro-α-[(isopropylamino)methyl]- (6CI, 8CI)
  • E 241
  • Isoprofenamine
  • o-Chloro-α-(isopropylaminomethyl)benzyl alcohol
  • Clorprenalline
  • clorprenaline Solution, 100ppm
  • CLORPRENALINE HYDROCHLORIDE +98.5% CP2005
  • Clorprenaline USP/EP/BP
  • CLORPRENALINE HYDROCHLORIDE CAS 3811-25-4
  • Clorprenaline ISO17034
  • 3811-25-4
  • C11H16ClNO