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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)
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)

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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.

Chemical Synthesis

Fenoterol, 3,5-dihydroxy-α[[(-p-hydroxy-α-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

Chengdu Saint - Kay Biotechnology Co., Ltd.
Email
676046971@qq.com
Country
China
ProdList
4508
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
1938
Advantage
70
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725;010-86181995
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12341
Advantage
58
MedChemexpress LLC
Tel
609-228-6898
Fax
609-228-5909
Email
sales@medchemexpress.com
Country
United States
ProdList
4788
Advantage
58
Shanghai TaoShu Biochemical Technology Co., Ltd.
Tel
021-33632979-
Fax
021-33632979
Email
service1@targetmol.com
Country
China
ProdList
7962
Advantage
58
Shanghai TaoSu Biochemical Technology Co., Ltd.
Tel
021-33632979
Fax
021-34692979
Email
info@tsbiochem.com
Country
China
ProdList
8074
Advantage
58
TianJin Alta Scientific Co., Ltd.
Tel
+86-022-6537-8550
Fax
+86-022-2532-9655
Email
contact@altascientific.com
Country
China
ProdList
2775
Advantage
58
Sichuan Wei Keqi Biological Technology Co., Ltd.
Tel
028-81700200-
Fax
028-81705658
Email
2851167785@qq.com
Country
China
ProdList
4725
Advantage
56
Chengdu HuaXia Chemical Reagent Co. Ltd
Tel
400-1166-196;028-84555506- ;028-84555506-
Fax
QQ:800101999
Email
cdhxsj@163.com;cdhxsj@163.com;cdhxsj@163.com
Country
China
ProdList
13363
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
Dideu Industries Group Limited
Product
Fenoterol USP/EP/BP 13392-18-2
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-05-28

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