121-28-8

Basic information

• Product Name: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino]ethan-1-one
• Synonyms: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino]ethan-1-one;1-(3,4-Dihydroxyphenyl)-2-((1-methylethyl)amino)ethanone;(3,4-Dihydroxyphenyl)[(isopropylamino)methyl]ketone;1-(3,4-dihydroxyphenyl)-2-((1-methylethyl)amino)-ethanon;3',4'-dihydroxy-2-(isopropylamino)-acetophenon;3',4'-dihydroxy-2-(isopropylamino)acetophenone;3',4'-Dihydroxy-α-(isopropylamino)acetophenone;1-(3,4-dihydroxyphenyl)-2-(propan-2-ylamino)ethanone
• CAS NO: 121-28-8
• Molecular Formula: C₁₁H₁₅NO₃
• Molecular Weight: 209.2417
• EINECS: 204-461-0
• Mol File: 121-28-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 96℃
• Boiling Point: 409.7°Cat760mmHg
• Flash Point: 201.6°C
• Appearance: /
• Density: 1.185±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 2.69E-07mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino]ethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino]ethan-1-one(121-28-8)
• EPA Substance Registry System: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino]ethan-1-one(121-28-8)

Safety Data

• Hazardous Substances Data: 121-28-8(Hazardous Substances Data)

Usage

Preparation

Obtained by reductive condensation of 3,4-dihydroxy-phenylglyoxal with isopropylamine in ethanol under hydrogen atmosphere in the presence of 14% Pd/C.

InChI:InChI=1/C11H15NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,12-14H,6H2,1-2H3

Synthetic route

(S)-isoproterenol (2964-04-7) → Isoproterenone (121-28-8)

Conditions	Yield
With (R)-epinephrine dehydrogenase; NADH In aq. phosphate buffer at 45℃; pH=6; Enzymatic reaction;

2-chloro-3′,4′-dihydroxyacetophenone (56961-48-9) + isopropylamine (75-31-0) → Isoproterenone (121-28-8)

Conditions	Yield
With isopropyl alcohol
With ethanol

1-<3,4-dimethoxy-phenyl>-2-isopropylamino-ethanone → Isoproterenone (121-28-8)

Conditions	Yield
With hydrogenchloride at 160℃;

1-(4-hydroxy-3-methoxy-phenyl)-2-isopropylamino-ethanone → Isoproterenone (121-28-8)

Conditions	Yield
With hydrogenchloride at 140℃;

3-methoxy-4-hydroxyphenylglyoxal (32025-66-4) → Isoproterenone (121-28-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel; aqueous ethanol / Hydrogenation 2: concentrated aqueous HCl / 140 °C View Scheme

3,4-dihydroxyphenylglyoxal (29477-55-2) + isopropylamine (75-31-0) → Isoproterenone (121-28-8)

Conditions	Yield
With ethanol; palladium Hydrogenation;

Isoproterenone (121-28-8) → isoproterenol hydrochloride (51-30-9, 949-36-0)

Conditions	Yield
With sodium tetrahydroborate In methanol at 25℃; for 4h; Time;	85.7%

Isoproterenone (121-28-8) + propionyl chloride (79-03-8) → 1-(3,4-bis-propionyloxy-phenyl)-2-isopropylamino-ethanone

Conditions	Yield
With hydrogenchloride; propionic acid

Isoproterenone (121-28-8) + acetyl chloride (75-36-5) → 3,4-Diacetyloxy-α-isopropylaminoacetophenon

Conditions	Yield
With hydrogenchloride; acetic acid

Upstream product

• 2964-04-7 (S)-isoproterenol 
• 32025-66-4 3-methoxy-4-hydroxyphenylglyoxal 
• 56961-48-9 2-chloro-3′,4′-dihydroxyacetophenone 
• 75-31-0 isopropylamine 
• 29477-55-2 3,4-dihydroxyphenylglyoxal 

Downstream Products

• 51-30-9 isoproterenol hydrochloride 
• 47733-27-7 di-p-toluoylisoproterenol