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Fenoterol

Product Name
Fenoterol
CAS No.
13392-18-2
Chemical Name
Fenoterol
Synonyms
lcohol;Th 1165;opropane;FENOTEROL;Phenoterol;AURORA KA-7877;Fenoterol USP/EP/BP;Fenoterol (Th-1165a;Fenoterol & Fenoterol Hydrobromide;1-(3,5-Dihydroxyphenyl)-2-[[1-(4-hydroxybenzyl)ethyl]amino]ethanol
CBNumber
CB6215967
Molecular Formula
C17H21NO4
Formula Weight
303.35
MOL File
13392-18-2.mol
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Fenoterol Property

Melting point:
181-183°C
Boiling point:
566.0±45.0 °C(Predicted)
Density 
1.289±0.06 g/cm3(Predicted)
storage temp. 
Store at -20°C
pka
pKa 8.5 (Uncertain);10.0 (Uncertain)
CAS DataBase Reference
13392-18-2(CAS DataBase Reference)
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Hazard and Precautionary Statements (GHS)

Signal word
Warning
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N-Bromosuccinimide Price

American Custom Chemicals Corporation
Product number
API0006491
Product name
FENOTEROL
Purity
95.00%
Packaging
500MG
Price
$494.55
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0006491
Product name
FENOTEROL
Purity
95.00%
Packaging
5G
Price
$1249.13
Updated
2021/12/16
Crysdot
Product number
CD31003831
Product name
Fenoterol
Purity
98+%
Packaging
100mg
Price
$49
Updated
2021/12/16
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Fenoterol Chemical Properties,Usage,Production

Originator

Berotec,Boehringer Ingelheim,W. Germany,1972

Uses

antiinflammatory

Definition

ChEBI: A member of the class resorcinols that is 5-(1-hydroxyethyl)benzene-1,3-diol in which one of the methyl hydrogens is replaced by a 1-(4-hydroxyphenyl)propan-2-amino group. A beta2-adrenergic agonist, it is used (as the ydrobromide salt) as a bronchodilator in the management of reversible airway obstruction.

Manufacturing Process

441 grams (1.4 mols) of 3,5-diacetoxy-α-bromo-acetophenone (MP 66°C), prepared by bromination of 3,5-diacetoxy-acetophenone, were added to a solution of 714 grams (2.8 mols) of 1-p-methoxyphenyl-2-benzylaminopropane in 1,000 cc of benzene, and the resulting solution mixture was refluxed for 1 hour. The molar excess of 1-p-methoxy-phenyl-2-benzylaminopropane precipitated out as its hydrobromide. After separation of the precipitated hydrobromide of the amino component, the hydrochloride of 1-pmethoxy- phenyl-2-(β-3',5'-diacetoxyphenyl-β-oxo)-ethyl-benzylamino-propane was precipitated from the reaction solution by addition of an ethanolic solution of hydrochloric acid. The precipitate was separated and, without further purification, was deacetylated by boiling it in a mixture of 2 liters of aqueous 10% hydrochloric acid and 1.5 liters of methanol.
The resulting solution was filtered through animal charcoal and, after addition of 2 liters of methanol, it was debenzylated by hydrogenation at 60°C over palladinized charcoal as a catalyst. After removal of the catalyst by filtration, the filtrate was concentrated by evaporation, whereupon the hydrochloride of 1-p-methoxyphenyl-2-(β-3',5'-dihydroxyphenyl-β-oxo)-ethylamino-propane (MP 244°C) crystallized out. For the purpose of demethylation, the 350 grams of the hydrochloride thus produced were refluxed for 2 hours with 3.5 liters of aqueous 48% hydrobromic acid. Upon cooling of the reaction solution, 320 grams of 1-p-hydroxyphenyl-2-(β-3',5'-dihydroxyphenyl-β-oxo)-ethylaminopropanehydrobromide (MP 220°C) crystallized out.
·220 grams of 1-p-hydroxyphenyl-2-(β-3',5'-dihydroxyphenyl-β-oxo)- ethylamino-propane hydrobromide were dissolved in 1 liter of methanol, the resulting solution was boiled with activated charcoal, the charcoal was filtered off and the filtrate was hydrogenated in the presence of Raney nickel at 60°C and 5 atmospheres gauge. Thereafter, the catalyst was filtered off, the methanolic solution was admixed with a small amount of concentrated hydrobromic acid, and the mixture was evaporated to dryness in vacuo. The residue was stirred with acetone, the mixture was vacuum filtered and the filter cake was recrystallized from a mixture of methanol and ether. The 1-phydroxyphenyl- 2-(β-3',5'-dihydroxyphenyl-β-hydroxy)-ethylamino-propane hydrobromide thus obtained had a melting point of 222° to 223°C.

brand name

Berotec [as hydrobromide](Boehringer Ingelheim);Dosberotec;Duovent;Fensol;Partusisten.

Therapeutic Function

Bronchodilator

World Health Organization (WHO)

Fenoterol, a beta 2-adrenoreceptor agonist with bronchodilator activity, was introduced in 1971 for the management of asthma. In the 1960's, the use of other sympathomimetics in pressurised aerosols had already been associated with an increase in mortality due to asthma. However, it was not clear whether patients died from the severity of the asthma attack or from its treatment.

Mechanism of action

Fenoterol is a selective stimulant of β2-adrenoreceptors. It dilates bronchi and blood vessels, has a pronounced tocolytic action, lowers contractile activity and reduces uterus tonicity. It is mainly used in premature births.

Clinical Use

Fenoterol is a selective β2-sympathomimetic agent that is in wide clinical use in Europe.

Synthesis

Fenoterol, 3,5-dihydroxy-|á[[(-p-hydroxy-|á-methylphenethyl)amino]methyl]- benzyl alcohol (23.3.16), is synthesized from 3,5-diacetoxyacetophenone, which is brominated to give 3,5-diacetoxybromacetophenone (23.3.12). This is reacted with 2-benzylamino-1-(4-methoxyphenyl)-propane, giving the corresponding tertiary amine 23.3.13. Hydrolysis of the acetyl group of this product and removal of the protective benzyl group by hydrogen reduction using a palladium on carbon catalyst gives a secondary amine 23.3.14. This is reacted with hydrobromic acid, which cleaves the ether bond in the benzene ring, producing phenol derivative 23.3.15. Finally, reduction of the carbonyl group with hydrogen gives the desired fenoterol (23.3.16).

Fenoterol Preparation Products And Raw materials

Raw materials

Preparation Products

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Fenoterol Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
zhangsn@titansci.com
Country
China
ProdList
14113
Advantage
59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2127
Advantage
70
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12338
Advantage
58
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4863
Advantage
58
Shanghai TaoSu Biochemical Technology Co., Ltd.
Tel
021-33632979
Fax
021-34692979
Email
info@tsbiochem.com
Country
China
ProdList
8073
Advantage
58
TianJin Alta Scientific Co., Ltd.
Tel
022-65378550-8551
Fax
+86-022-2532-9655
Email
contact@altascientific.com
Country
China
ProdList
2773
Advantage
58
ChemStrong Scientific Co.,Ltd
Tel
0755-66853366 15920483169
Fax
0755-28363542
Email
sales@chem-strong.com
Country
China
ProdList
17944
Advantage
56
Sichuan Wei Keqi Biological Technology Co., Ltd.
Tel
028-81700200 18116577057
Fax
028-81705658
Email
3003855609@qq.com
Country
China
ProdList
7893
Advantage
56
Chengdu HuaXia Chemical Reagent Co. Ltd
Tel
400-1166-196 13458535857
Fax
QQ:800101999
Email
cdhxsj@163.com
Country
China
ProdList
13358
Advantage
58
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View Lastest Price from Fenoterol manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Fenoterol 13392-18-2
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Fenoterol 13392-18-2
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-08
Career Henan Chemical Co
Product
Fenoterol 13392-18-2
Price
US $1.00/KG
Min. Order
1G
Purity
98%
Supply Ability
100KG
Release date
2018-08-20

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