94749-73-2

Basic information

• Product Name: 1-[4-[(6-Bromohexyl)oxy]butyl]benzene
• Synonyms: 1-[4-[(6-Bromohexyl)oxy]butyl]benzene;4-[(6-BROMOHEXYL)OXY]BUTYL]BENZENESALMETEROL;Benzene, [4-[(6-broMohexyl)oxy]butyl]-;6-(4-Phenylbutoxy)hexyl bromide;7-Oxa-11-phenylundecyl bromide
• CAS NO: 94749-73-2
• Molecular Formula: C₁₆H₂₅BrO
• Molecular Weight: 313.2731
• Mol File: 94749-73-2.mol

Chemical Properties

• Appearance: /
• Density: 1.143±0.06 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: 1-[4-[(6-Bromohexyl)oxy]butyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-[(6-Bromohexyl)oxy]butyl]benzene(94749-73-2)
• EPA Substance Registry System: 1-[4-[(6-Bromohexyl)oxy]butyl]benzene(94749-73-2)

Safety Data

• Hazardous Substances Data: 94749-73-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
1-[4-[(6-Bromohexyl)oxy]butyl]benzene is used as a key component in the production of industrial chemicals, such as surfactants and emulsifiers. Its surfactant properties allow it to reduce the surface tension of liquids, which is crucial for various industrial processes.
Used in Organic Synthesis:
1-[4-[(6-Bromohexyl)oxy]butyl]benzene serves as a building block in the synthesis of various organic compounds. Its unique structure and functional groups make it a versatile starting material for creating a wide range of chemical products.
Environmental and Health Considerations:
While 1-[4-[(6-Bromohexyl)oxy]butyl]benzene has significant industrial applications, it may pose environmental and health risks due to its potential toxicity and bioaccumulation. Therefore, it is essential to follow proper handling and disposal procedures when working with this chemical to minimize any adverse effects on the environment and human health.

Upstream product

• 629-03-8 1 ,6-dibromohexane 
• 3360-41-6 4-phenyl-butan-1-ol 
• 135235-81-3 6-(4-phenylbutyloxy)hexyl methanesulfonate 

Downstream Products

• 437603-43-5 2-(ethoxymethyl)-1-(2-{[6-(4-phenylbutoxy)hexyl]oxy}ethyl)-1H-imidazo[4,5-c]quinoline 
• 928118-32-5 C₄₇H₅₂N₄O₂ 
• 97664-54-5 6-(4-phenylbutoxy)hexanal 
• 384340-08-3 (1S)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[6-(4-phenylbutoxy)hexyl]amino}ethanol 
• 97664-55-6 N-[6-(4-phenylbutoxy)hexyl]benzenemethanamine 
• 168412-89-3 1-azido-6-(4-phenylbutoxy)hexane 
• 934842-69-0 4-hydroxy-1-[[[6-(4-phenylbutoxy)hexyl](phenylmethyl)amino]methyl]-1,3-benzenedimethanol 
• 163923-19-1 2-hydroxy-5-<<<6,6-(4-phenylbutoxy)hexylbenzyl>amino>acetyl>benzaldehyde 
• 89365-50-4 salmeterol 
• 497063-93-1 C₃₂H₄₀⁽²⁾H₃NO₄ 
• 497063-91-9 5-(2-{Benzyl-[6-(4-phenyl-butoxy)-hexyl]-amino}-acetyl)-2-hydroxy-benzoic acid methyl ester 
• 1025930-27-1 C₃₁⁽¹³⁾CH₄₀⁽²⁾H₃NO₄ 
• 261381-23-1 C₃₂⁽¹³⁾CH₄₁NO₅ 
• 590410-68-7 (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(4-phenylbutoxy)hexyl]-1,3-oxazolidin-2-one 

Relevant articles and documents

Salmeterol intermediate ionic liquid catalytic bromination technology

The invention discloses a salmeterol intermediate ionic liquid catalytic bromination technology. The salmeterol intermediate is (4-(6-bromohexaoxy)butylbenzene and is prepared from 6-(4-phenylbutyl-oxo)hexyl methanesulfonate and potassium bromide as raw materials under the conditions of ionic liquid [bmim]BF4 and acetonitrile. The technology has the advantages of short bromination reaction time, mild conditions and high total yield. The bromination reagent used by the technology is cheap and easily available and has low toxicity. The ionic liquid [bmim]BF4 is a medium having high halogenation activity, can realize strong nucleophilicity of halogen ions and can be widely used in many halogenation reactions.

Novel Bivalent Ligands Based on the Sumanirole Pharmacophore Reveal Dopamine D2 Receptor (D2R) Biased Agonism

The development of bivalent ligands has attracted interest as a way to potentially improve the selectivity and/or affinity for a specific receptor subtype. The ability to bind two distinct receptor binding sites simultaneously can allow the selective activation of specific G-protein dependent or β-arrestin-mediated cascade pathways. Herein, we developed an extended SAR study using sumanirole (1) as the primary pharmacophore. We found that substitutions in the N-1- and/or N-5-positions, physiochemical properties of those substituents, and secondary aromatic pharmacophores can enhance agonist efficacy for the cAMP inhibition mediated by Gi/o-proteins, while reducing or suppressing potency and efficacy toward β-arrestin recruitment. Compound 19 was identified as a new lead for its selective D2 G-protein biased agonism with an EC50 in the subnanomolar range. Structure-activity correlations were observed between substitutions in positions N-1 and/or N-5 of 1 and the capacity of the new bivalent compounds to selectively activate G-proteins versus β-arrestin recruitment in D2R-BRET functional assays.

PROCESS FOR THE PREPARATION OF SALMETEROL AND ITS INTERMEDIATES

The present invention discloses a process for the preparation of methyl 2-(benzyloxy)- 5-(2-bromoacetyl)benzoate (V), comprising: (d) benzylating methyl-5-acetyl-2-hydroxybenzoate (VIII) with benzyl chloride in the presence of a base and a catalyst in a suitable polar solvent to obtain 5-acetyl-2- benzyloxy benzoate (VII); (e) brominating methyl 5-acetyl-2-(benzyloxy)benzoate (VII) with a suitable brominating agent in one or more suitable' solvents in the presence of an acid catalyst to obtain methyl 2-(benzyloxy)-5-(2-bromoacetyl)benzoate V; (c) optionally, purifying the methyl 2-(benzyloxy)-5-(2-bromoacetyl)benzoate (V) in a suitable solvent; and (f) isolating the methyl 2-(benzyloxy)-5-(2-bromoacetyl)benzoate (V).

SUBSTITUTED ETHANOLAMINES

The present invention relates to new substituted ethanolamine adrenergic receptor modulators, pharmaceutical compositions thereof, and methods of use thereof.

A convenient synthesis of (R)-salmeterol via Rh-catalyzed asymmetric transfer hydrogenation

(R)-Salmeterol was synthesized in eight steps with salicaldehyde as the starting material. The key chiral intermediate, alcohol 5, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEG-BsDPEN or (S,S)-TsDPEN ligand and sodium formate as the hydrogen donor under mild conditions.

Alpha2C adrenoreceptor agonists

In its many embodiments, the present invention relates to a novel class of phenylmorpholine and phenylthiomorpholine compounds useful as α2C adrenergic receptor agonists, pharmaceutical compositions containing the compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the α2C adrenergic receptor agonists using such compounds or pharmaceutical compositions.

NOVEL PROCESS

The present invention relates to processes for the preparation of 4- hydroxy-α'' -[[[6-(4-phenylbutoxy)hexyl]amino]methyl]- 1,3-benzenedimethanol 1-hydroxy-2-naphthoate (salmeterol xinafoate) (Formula (12a)), the preparation of 4-hydroxy-α''-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-1,3-benzenedimethanol (salmeterol) (Formula (11)), the preparation of protected N-[6-(4-phenylbutoxy)hexyl]amine intermediates (Formula (7)), and the preparation of 6-substituted (4-phenylbutoxy)hexane intermediates (Formula (5)), shown below, wherein X is a leaving group and Pg is a protecting group.

SUBSTITUTED PHENYLPHOSPHATES AS MUTUAL PRODRUGS OF STEROIDS AND β -AGONISTS FOR THE TREATMENT OF PULMONARY INFLAMMATION AND BRONCHOCONSTRICTION

A mutual prodrug of a corticosteroid and a substituted phenylphosphate (β-agonist derivative) for formulation for delivery by aerosolization to inhibit pulmonary inflammation and bronchoconstriction is described. The mutual prodrug is preferably formulate

BENZYLPHOSPHATE AND SUBSTITUTED BENZYLPHOSPHATE PRODRUGS FOR TRE TREATMENT OF PULMONARY INFLAMMATION

A prodrug of a corticosteroid, lidocaine or related local anesthetic composition for formulation for delivery by aerosolization to inhibit inflammation in asthmatic lungs is described. The prodrug is preferably formulated in a 5 ml solution of a quarter normal saline having pH between 5.0 and 7.0 for the treatment of respiratory tract inflammation by an aerosol having mass medium average diameter predominantly between 1 to 5 μ produced by nebulization or dry powder inhaler.