115548-15-7

Basic information

• Product Name: (R)-4-(3-AMINO-BUTYL)-PHENOL
• Synonyms: (R)-4-(3-AMINO-BUTYL)-PHENOL;(R)-1-METHYL-3-(P-HYDROXY-PHENYL)-PROPYLAMINE;(R)-2-AMINO-4-(4-HYDROXYPHENYL)BUTANE
• CAS NO: 115548-15-7
• Molecular Formula: C10H15NO
• Molecular Weight: 165.23
• Product Categories: pharmacetical
• Mol File: 115548-15-7.mol

Chemical Properties

• Boiling Point: 295.3 °C at 760 mmHg
• Flash Point: 132.4 °C
• Appearance: /
• Density: 1.047 g/cm³
• Vapor Pressure: 0.000874mmHg at 25°C
• Refractive Index: 1.552
• PKA: 10.02±0.15(Predicted)
• CAS DataBase Reference: (R)-4-(3-AMINO-BUTYL)-PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-(3-AMINO-BUTYL)-PHENOL(115548-15-7)
• EPA Substance Registry System: (R)-4-(3-AMINO-BUTYL)-PHENOL(115548-15-7)

Safety Data

• Hazardous Substances Data: 115548-15-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-4-(3-Amino-butyl)-phenol is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its unique structure and reactivity. Its presence of both phenolic and amine functional groups allows for versatile chemical modifications, making it a valuable building block for the development of new drugs.
Used in Industrial Products:
(R)-4-(3-Amino-butyl)-phenol is utilized as a raw material or additive in the production of various industrial products, such as polymers, coatings, and adhesives. Its chemical properties, including its reactivity and compatibility with other materials, contribute to the performance and functionality of these products.
Used in Research and Development:
(R)-4-(3-Amino-butyl)-phenol serves as a promising molecule for research and development in various scientific fields. Its unique structure and properties make it an interesting subject for studies related to chemical synthesis, material science, and medicinal chemistry, potentially leading to the discovery of new applications and uses.

InChI:InChI=1/C10H15NO/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-8,12H,2-3,11H2,1H3/t8-/m1/s1

Upstream product

• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 
• 123-08-0 4-hydroxy-benzaldehyde 
• 22214-30-8 4-(4'-hydroxyphenyl)but-3-en-2-one 
• 1222558-29-3 [((E)-4-(4-methoxyphenyl)but-3-en-2-ylidene)amino]hydroxide 
• 51062-15-8 (+)-(R)-1-Methyl-3-(4-methoxyphenyl)-1-propylamine 

Relevant articles and documents

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study

β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.

General and selective synthesis of primary amines using Ni-based homogeneous catalysts

The development of base metal catalysts for industrially relevant amination and hydrogenation reactions by applying abundant and atom economical reagents continues to be important for the cost-effective and sustainable synthesis of amines which represent highly essential chemicals. In particular, the synthesis of primary amines is of central importance because these compounds serve as key precursors and central intermediates to produce value-added fine and bulk chemicals as well as pharmaceuticals, agrochemicals and materials. Here we report a Ni-triphos complex as the first Ni-based homogeneous catalyst for both reductive amination of carbonyl compounds with ammonia and hydrogenation of nitroarenes to prepare all kinds of primary amines. Remarkably, this Ni-complex enabled the synthesis of functionalized and structurally diverse benzylic, heterocyclic and aliphatic linear and branched primary amines as well as aromatic primary amines starting from inexpensive and easily accessible carbonyl compounds (aldehydes and ketones) and nitroarenes using ammonia and molecular hydrogen. This Ni-catalyzed reductive amination methodology has been applied for the amination of more complex pharmaceuticals and steroid derivatives. Detailed DFT computations have been performed for the Ni-triphos based reductive amination reaction, and they revealed that the overall reaction has an inner-sphere mechanism with H2metathesis as the rate-determining step.

MOF-derived cobalt nanoparticles catalyze a general synthesis of amines

The development of base metal catalysts for the synthesis of pharmaceutically relevant compounds remains an important goal of chemical research. Here, we report that cobalt nanoparticles encapsulated by a graphitic shell are broadly effective reductive amination catalysts. Their convenient and practical preparation entailed template assembly of cobaltdiamine- dicarboxylic acid metal organic frameworks on carbon and subsequent pyrolysis under inert atmosphere.The resulting stable and reusable catalysts were active for synthesis of primary, secondary, tertiary, and N-methylamines (more than 140 examples).The reaction couples easily accessible carbonyl compounds (aldehydes and ketones) with ammonia, amines, or nitro compounds, and molecular hydrogen under industrially viable and scalable conditions, offering cost-effective access to numerous amines, amino acid derivatives, and more complex drug targets.

Enzymatic asymmetric synthesis of enantiomerically pure aliphatic, aromatic and arylaliphatic amines with (R)-selective amine transaminases

Seven (R)-selective amine transaminases (R-ATAs) recently discovered by an in silico-based approach in sequence databases were produced recombinantly in Escherichia coli and subjected to partial purification by ammonium sulfate precipitation. A range of additives and various buffers were investigated to identify best conditions to ensure good storage stability and stable activity during biocatalysis. All enzymes show pH optima between pH 7.5-9. These R-ATAs were then applied in the asymmetric synthesis of twelve aliphatic, aromatic and arylaliphatic (R)-amines starting from the corresponding prochiral ketones using a lactate dehydrogenase/glucose dehydrogenase system to shift the equilibrium. For all ketones, at least one enzyme was found that allows complete conversion to the corresponding chiral amine having excellent optical purities >99% ee. Variations in substrate profiles are also discussed based on the phylogenetic relationships between the seven R-ATAs. Thus, we have identified a versatile toolbox of (R)-amine transaminases showing remarkable properties for application in biocatalysis. Copyright

Derivatives related to betaxolol with α- and β-adrenergic activities

The paper describes the synthesis and the pharmacological evaluation of some derivatives of betaxolol, all with an N-aralkylamine instead of the tertiobutylamine. These compounds have been tested for β1-adrenergic receptor antagonism on guinea pig atria, β2-adrenergic receptor antagonism on guinea pig trachea and α-adrenergic blocking activity on rat aorta. Compound U12 with a marked α-blocking activity and compound R8 with a β1/α ratio = 1 were selected for a haemodynamic study in the dog. The decrease in cardiac work and the diminution of total peripheral resistance exhibited by U12 are consistent with a dual α/β-blocking agent. Finally, structure-activity relationships are discussed.

Phenethanolamines, compositions containing the same, and method for effecting weight control

Optically active N-3-(4-substituted phenyl)propyl-β-phenethanolamines are provided as well as pharmaceutical compositions containing such compounds. A method for effecting weight control in obese animals utilizing optically active phenethanolamines is disclosed. Novel intermediates useful in the preparation of optically active β-phenethanolamines are provided.