193761-53-4

Basic information

• Product Name: (S)-1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANOL
• Synonyms: (S)-1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANOL;(aS)-a-(Bromomethyl)-3-nitro-4-(phenylmethoxy)benzenemethanol;(αS)-α-(BroMoMethyl)-3-nitro-4-(phenylMethoxy)benzeneMethanol
• CAS NO: 193761-53-4
• Molecular Formula: C₁₅H₁₄BrNO₄
• Molecular Weight: 352.17996
• Product Categories: Aromartics;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 193761-53-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 493.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.529±0.06 g/cm3(Predicted)
• Refractive Index: 1.638
• Storage Temp.: 2-8°C
• PKA: 12.21±0.20(Predicted)
• CAS DataBase Reference: (S)-1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANOL(193761-53-4)
• EPA Substance Registry System: (S)-1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANOL(193761-53-4)

Safety Data

• Hazardous Substances Data: 193761-53-4(Hazardous Substances Data)

Usage

Uses

An intermediate in synthesis of (R,R)-Formoterol.

InChI:InChI=1/C15H14BrNO4/c16-9-14(18)12-6-7-15(13(8-12)17(19)20)21-10-11-4-2-1-3-5-11/h1-8,14,18H,9-10H2/t14-/m1/s1

Upstream product

• 100-44-7 benzyl chloride 
• 14347-05-8 4-benzyloxy-3-nitroacetophenone 
• 6322-56-1 4'-hydroxy-3'-nitroacetophenone 
• 43229-01-2 4-benzyloxy-3-nitrophenacyl bromide 

Downstream Products

• 1361398-83-5 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)butyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 
• 306966-56-3 N-(2-(benzyloxy)-5-((S)-2-bromo-1-hydroxyethyl)phenyl)formamide 
• 1122063-33-5 (1S)-1-(3-amino-4-benzyloxyphenyl)-2-bromoethan-1-ol 
• 289657-25-6 (S)-1-(3-Amino-4-benzyloxy-phenyl)-2-{benzyl-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethyl]-amino}-ethanol 
• 67346-49-0 (S,S)-formoterol 
• 67346-50-3 (S,R)-Formoterol 
• 188730-96-3 (S)-4-benzyloxy-3-nitrostyrene oxide 

Relevant articles and documents

Dual β2-adrenoceptor agonists-PDE4 inhibitors for the treatment of asthma and COPD

We designed and synthesized a novel class of dual pharmacology bronchodilators targeting both b2-adrenoceptor and PDE4 by applying a multivalent approach. The most potent dual pharmacology molecule, compound 29, possessed good inhibitory activity on PDE4B2 (IC50 = 0.278 μM, which was more potent than phthalazinone, IC50 = 0.520 lM) and possessed excellent relaxant effects on tracheal rings precontracted by histamine (pEC50 = 9.3).

The asymmetric synthesis of (R,R)-formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG2000 and water

(R,R)-formoterol was synthesized in seven steps with 4-hydroxyl-3-nitro- acetophenone as the starting material. The key intermediate, the chiral secondary alcohol 4, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEGBsDPEN as the ligand and sodium formate as the hydrogen donor under mild conditions. With a mixture of PEG 2000 and water as the reaction media, the catalyst system could be recycled four times.

Carbamate Stereoisomer

The compound of formula (I) is a water-stable, long acting β2-selective adrenoceptor agonist useful as a bronchodilator in the treatment of bronchoconstriction associated with reversible obstructive airways diseases and the like.