52846-75-0

Basic information

• Product Name: rac 4-(3-Aminobutyl)phenol
• Synonyms: rac 4-(3-Aminobutyl)phenol;3-AMino-1-(4-hydroxyphenyl)butane;4-(4'-Hydroxyphenyl)-2-aMinobutane;RaceMic 3-AMino-1-(4-hydroxyphenyl)butane
• CAS NO: 52846-75-0
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.2322
• Product Categories: Amines;Aromatics;Metabolites & Impurities
• Mol File: 52846-75-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: rac 4-(3-Aminobutyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: rac 4-(3-Aminobutyl)phenol(52846-75-0)
• EPA Substance Registry System: rac 4-(3-Aminobutyl)phenol(52846-75-0)

Safety Data

• Hazardous Substances Data: 52846-75-0(Hazardous Substances Data)

Usage

Uses

A metabolite of the antihypertensive agent, Labetalol (L096500).

Synthetic route

4-(4-hydroxyphenyl)-2-oxobutane (5471-51-2) → p-hydroxyhomoamphetamine (52846-75-0)

Conditions	Yield
With nickel(II) tetrafluoroborate hexahydrate; ammonia; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine In 2,2,2-trifluoroethanol at 120℃; for 24h; chemoselective reaction;	93%
With ammonia; hydrogen In tetrahydrofuran at 120℃; for 15h;	89%
With palladium 10% on activated carbon; ammonium formate In methanol for 5h;

(+)-(R)-1-Methyl-3-(4-methoxyphenyl)-1-propylamine (51062-15-8) → p-hydroxyhomoamphetamine (52846-75-0)

Conditions	Yield
With hydrogen bromide

4-oxy-benzylacetone oxime → p-hydroxyhomoamphetamine (52846-75-0)

Conditions	Yield
With sodium amalgam; acetic acid at 50 - 60℃;

[((E)-4-(4-methoxyphenyl)but-3-en-2-ylidene)amino]hydroxide (1222558-29-3) → p-hydroxyhomoamphetamine (52846-75-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / PtO2 / methanol / 6 h / 60 °C / 15200 Torr 2: HBr View Scheme

4-(4'-hydroxyphenyl)but-3-en-2-one (22214-30-8, 59417-71-9, 3160-35-8) → p-hydroxyhomoamphetamine (52846-75-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 1 h / 20 °C / 1520.1 Torr 2: palladium 10% on activated carbon; ammonium formate / methanol / 5 h View Scheme

4-hydroxy-benzaldehyde (123-08-0) → p-hydroxyhomoamphetamine (52846-75-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 2 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 1 h / 20 °C / 1520.1 Torr 3: palladium 10% on activated carbon; ammonium formate / methanol / 5 h View Scheme

C18H13NO4 + p-hydroxyhomoamphetamine (52846-75-0) → 8-hydroxy-5-(1-hydroxy-2-((4-(4-hydroxyphenyl)butan-2-yl)amino)ethyl)quinolin-2(1H)-one hydrochloride

Conditions	Yield
Stage #1: C18H13NO4; p-hydroxyhomoamphetamine With sodium tetrahydroborate In methanol; dimethyl sulfoxide for 1h; Stage #2: With 5%-palladium/activated carbon; hydrogen In methanol for 1h; Stage #3: With hydrogenchloride In ethyl acetate for 2h;	94%

p-hydroxyhomoamphetamine (52846-75-0) + acetic anhydride (108-24-7) → N-[3-(4-hydroxyphenyl)-1-methylpropyl]acetamide (1204483-45-3) + 4-(3-acetylaminobutyl)phenyl acetate (1204484-14-9)

Conditions	Yield
With triethylamine In ethyl acetate at 0℃; for 1h;	A 74% B 7%

3-methyl-5-(2-oxiranylmethoxy-styryl)-isoxazole (79798-34-8) + p-hydroxyhomoamphetamine (52846-75-0) → 4-[3-(2-Hydroxy-3-{2-[(E)-2-(3-methyl-isoxazol-5-yl)-vinyl]-phenoxy}-propylamino)-butyl]-phenol (78351-27-6)

Conditions	Yield
In ethanol 1.) reflux, 1 h, 2.) 25 deg C, overnight;	30%

p-hydroxyhomoamphetamine (52846-75-0) + 2,4,6-triphenylpyrylium tetrafluoroborate (448-61-3) → C33H30NO(1+)*BF4(1-)

Conditions	Yield
Stage #1: p-hydroxyhomoamphetamine With acetic acid In dichloromethane at 20℃; Stage #2: 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; for 6h;	22%
In ethanol at 80 - 85℃; for 4h;

p-hydroxyhomoamphetamine (52846-75-0) + 1-[2-(cyclopropyl-methoxy)-ethyl]-4-(2,3-epoxypropoxy)-benzene (63659-17-6) → 4-(3-{3-[4-(2-Cyclopropylmethoxy-ethyl)-phenoxy]-2-hydroxy-propylamino}-butyl)-phenol; hydrochloride

Conditions	Yield
With hydrogenchloride In ethanol for 12h; Heating;	19%

3,4-dimethoxyphenylacetone (776-99-8) + p-hydroxyhomoamphetamine (52846-75-0) → 4-{3-[2-(3,4-dimethoxy-phenyl)-1-methyl-ethylamino]-butyl}-phenol

Conditions	Yield
With formic acid

p-hydroxyhomoamphetamine (52846-75-0) → [3-(4-hydroxy-phenyl)-1-methyl-propyl]-urea

Conditions	Yield
With hydrogenchloride; potassium cyanate

p-hydroxyhomoamphetamine (52846-75-0) + benzoyl chloride (98-88-4) → 1-(3-benzoylamino-butyl)-4-benzoyloxy-benzene

Conditions	Yield
With sodium hydroxide

p-hydroxyhomoamphetamine (52846-75-0) + 2-cyclopenten-1-yl chloride (96-40-2) → optically inactive 4-(3-cyclopent-2-enylamino-butyl)-phenol

Conditions	Yield
With 1,4-dioxane

p-hydroxyhomoamphetamine (52846-75-0) + allyl bromide (106-95-6) → 4-(3-Allylamino-butyl)-phenol

Conditions	Yield
With benzene

p-hydroxyhomoamphetamine (52846-75-0) + cyclopentanone (120-92-3) → 4-(3-Cyclopentylamino-butyl)-phenol

Conditions	Yield
With methanol; platinum Hydrogenation;

p-hydroxyhomoamphetamine (52846-75-0) + 1-bromo-butene-(2t) → 4-[3-(buten-(2t)-ylamino)-butyl]-phenol

Conditions	Yield
With benzene

p-hydroxyhomoamphetamine (52846-75-0) + 2,4,6-triphenylpyrylium tetrafluoroborate (448-61-3) → 6-(4-hydroxyphenyl)-4-methyl-1,1-diphenylhex-1-en-3-one

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid / dichloromethane / 20 °C 1.2: 6 h / 20 °C 2.1: lithium methanolate; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 15 h / 80 °C / 37503.8 Torr / Autoclave; Sealed tube View Scheme

p-hydroxyhomoamphetamine (52846-75-0) → methyl 2-(di-(tert-butoxycarbonyl)amino)-6-(4-hydroxyphenyl)-4-methylhexanoate

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 4 h / 80 - 85 °C 2: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / dimethyl sulfoxide; water / 20 h / 20 °C / Schlenk technique; Sealed tube; Irradiation View Scheme

Upstream product

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

Downstream Products

• 1204483-45-3 N-[3-(4-hydroxyphenyl)-1-methylpropyl]acetamide 
• 1204484-14-9 4-(3-acetylaminobutyl)phenyl acetate 
• 78351-27-6 4-[3-(2-Hydroxy-3-{2-[(E)-2-(3-methyl-isoxazol-5-yl)-vinyl]-phenoxy}-propylamino)-butyl]-phenol 

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.

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.