Clorprenaline CAS 3811-25-4

Introduction：Basic information about Clorprenaline CAS 3811-25-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Clorprenaline Basic information

• Product Name: Clorprenaline
• Synonyms: 1-(2-Chlorophenyl)-2-(isopropylamino)ethanol;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
• CAS: 3811-25-4
• MF: C11H16ClNO
• MW: 213.7
• EINECS: 223-291-8
• Mol File: 3811-25-4.mol

Clorprenaline Chemical Properties

• Melting point: 81-82 °C
• Boiling point: 329.7±27.0 °C(Predicted)
• density: 1.117±0.06 g/cm3(Predicted)
• form: Solid
• pka: 13.60±0.20(Predicted)
• color: White to off-white
• BRN: 2105716
• Major Application: forensics and toxicology pharmaceutical (small molecule) veterinary
• InChI: 1S/C11H16ClNO/c1-8(2)13-7-11(14)9-5-3-4-6-10(9)12/h3-6,8,11,13-14H,7H2,1-2H3
• InChIKey: SSMSBSWKLKKXGG-UHFFFAOYSA-N
• SMILES: CC(C)NCC(O)c1ccccc1Cl
• CAS DataBase Reference: 3811-25-4(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, 2-chloro-«alpha»-[[(1-methylethyl)amino]methyl]-(3811-25-4)

Safety Information

• Hazard Codes: Xn
• Risk Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• HS Code: 29221990
• Storage Class: 11 - Combustible Solids

Clorprenaline Usage And Synthesis

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 diethylether were added about 3 g of dibenzoyl peroxide. 5 g of bromine were addedto the resulting solution, and after 3 minutes, the color of bromine had beendischarged, indicating that the formation of ω-bromo-o-chloroacetophenonehad been initiated. A further amount of 288 g of bromine was added dropwiseto the reaction mixture over a 1.5 hour interval. After the addition of thebromine had been completed, the reaction mixture was stirred for one-halfhour and poured over about 1 kg of crushed ice.
After the ice had melted, the resulting aqueous and ethereal layers wereseparated. The ethereal layer containing ω-bromo-o-chloroacetophenone waswashed with successive 500 ml quantities of water, 5% sodium carbonatesolution and again with water to remove the hydrogen bromide formed as aby-product in the reaction. The ethereal layer was dehydrated by contactingwith anhydrous magnesium sulfate. The drying agent was removed
filtration and the ether was evaporated from the filtrate. The residueremaining 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 methanolwas cooled to about 25°C. A cold solution of 92.5 g of sodium borohydride inone liter of methanol was added as rapidly as possible to this cooled solutionwhile maintaining the temperature below about 25°C. After the addition hadbeen completed, the reaction mixture was allowed to stand for 4 hours atambient room temperature, to complete the reduction of the keto group of theω-bromo-o-chloroacetophenone. The reaction mixture containing a mixture ofo-chlorophenyl ethylene-β-bromohydrin and o-chlorophenyl ethylene oxidewas then evaporated in vacuo at room temperature to a syrup which waspoured into about one liter of 5% hydrochloric acid to decompose any boratealcohol complexes.The two compounds were dissolved in diethyl ether by extracting the acidiclayer three times with successive 500 ml portions of diethyl ether. Thecombined ether extracts were dried over anhydrous magnesium sulfate andfiltered, and the ether was removed by evaporation in vacuo. A residueconsisting of 400 g of a mixture of o-chlorophenyl ethylene-β-bromohydrinand 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 ofanhydrous ethanol. The reaction mixture was heated at refluxing temperaturefor about 16 hours, thus forming N-[β-(o-chlorophenyl)-β-hydroxyethyl]-isopropylamine. The solvent was removed in vacuo, and to the residue wasadded 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 whichwere discarded. The acidic layer was then made basic by the addition of 250ml of 5% (w/v) sodium hydroxide, thus liberating the free base of N-[β-(ochlorophenyl)-β-hydroxyethyl]-isopropylamine. The free base was extractedwith two successive one liter portions of diethyl ether. The combined etherextracts 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 Patent2,887,509.
The N-[β-(o-chlorophenyl)-β-hydroxyethyl]-isopropylamine obtained by theforegoing procedure was dissolved in about 3 liters of ether and dry hydrogenchloride gas was bubbled into the solution until it was saturated, whereuponthe hydrochloride salt of N-[β-(o-chlorophenyl)-β-(hydroxy)-ethyl]isopropylamine precipitated. The salt was separated from the ether byfiltration, and was dissolved in two liters of anhydrous ethanol. The alcoholicsolution was decolorized with charcoal and filtered.
Three liters of anhydrous ether were added thereto and the N-[β-(ochlorophenyl)-β-hydroxyethyl]-isopropylamine hydrochloride precipitated incrystalline form as the monohydrate. The mixture was maintained at about0°C for 40 hours and then filtered. The filter cake was washed with ether anddried. About 209 g of N-[β-(o-chlorophenyl)-β-(hydroxy)-ethyl]isopropylaminehydrochloride monohydrate, melting at about 163° to 164°C, were obtainedaccording to US Patent 2,816,059.

Therapeutic Function

Bronchodilator

Clorprenaline Preparation Products And Raw materials

• Raw materials: Potassium borohydride-->Isopropylamine-->2-Bromoethanol-->2-Bromo-2'-chloroacetophenone-->Benzeneacetaldehyde, 2-chloro-α-oxo--->2'-Chloroacetophenone