1451-83-8

Basic information

• Product Name: 2-bromo-3-methylpropiophenone
• Synonyms: 2-bromo-3-methylpropiophenone;2-bromo-1-(3-methylphenyl)propan-1-one;2-Bromo-1-m-tolyl-propan-1-one
• CAS NO: 1451-83-8
• Molecular Formula: C₁₀H₁₁BrO
• Molecular Weight: 227.09774
• EINECS: 208-460-6
• Mol File: 1451-83-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 134-135 °C(Press: 8 Torr)
• Appearance: /
• Density: 1.357±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-bromo-3-methylpropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-3-methylpropiophenone(1451-83-8)
• EPA Substance Registry System: 2-bromo-3-methylpropiophenone(1451-83-8)

Safety Data

• Hazardous Substances Data: 1451-83-8(Hazardous Substances Data)

Usage

Application

2-bromo-3-methylpropiophenone employed as an important intermediate for raw material for organic synthesis, agrochemical, pharmaceutical and dyestuff field. Also used as intermediate for 4-methylmethcathinone.

Agricultural Uses

2-bromo-3-methylpropiophenone is a useful compound in the research.

Synthetic route

3'-Methylpropiophenone (51772-30-6) → 2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8)

Conditions	Yield
With bromine In dichloromethane at 20℃; for 0.5h;	100%
With bromine In dichloromethane for 10h; Inert atmosphere;	59%
Stage #1: 3'-Methylpropiophenone With bromine In dichloromethane for 10h; Inert atmosphere; Stage #2: In dichloromethane	59%

toluene (108-88-3) → 2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane 2: bromine / dichloromethane View Scheme

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) + tert-butylamine (75-64-9) → 2-(N-tert-butylamino)-3'-methylpropiophenone (1193779-18-8)

Conditions	Yield
at 70℃; for 2h;	98%
at 70℃; for 2h;	98%

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) + phenylacetylene (536-74-3) → 2,7-dimethyl-2-(1-oxo-1-(m-tolyl)propan-2-yl)-4-phenylnaphthalen-1(2H)-one

Conditions	Yield
With 1,10-Phenanthroline; tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium carbonate In toluene at 120℃; for 16h; Schlenk technique; Inert atmosphere;	63%
With 1,10-Phenanthroline; tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium carbonate In toluene at 120℃; for 16h; Schlenk technique; Sealed tube; Inert atmosphere;	63%

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) + Cyclopropylamine (765-30-0) → 2-(cyclopropylamino)-1-(3’-tolyl)-1-oxopropane

Conditions	Yield
In tetrahydrofuran at 50℃; for 18h; Sealed tube;	45%

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) + ethanolamine (141-43-5) → PAL-589 (1350768-23-8)

Conditions	Yield
In acetonitrile at 20 - 40℃; Inert atmosphere;	20%

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) + isopropylamine (75-31-0) → (+/-)-1-Isopropylamino-1-<3-methyl-benzoyl>-aethan

Conditions	Yield
In acetonitrile at 20℃; for 7h;

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) → (+/-)-threo-1-(3'-methylphenyl)-1-oxy-brompropan

Conditions	Yield
With sodium tetrahydroborate In methanol

pyrrolidine (123-75-1) + 2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) → 2-(N-pyrrolidinyl)-3'-methylpropiophenone (1214940-01-8)

Conditions	Yield
In water; acetonitrile at 20℃; for 4h;

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) + Cyclopentamine (1003-03-8) → 2-(N-cyclopentylamino)-3'-methylpropiophenone (1214939-96-4)

Conditions	Yield
In acetonitrile at 40℃; for 6h;	226 mg

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) → 2-(methylamino)-1-(3-methylphenyl)propan-1-one hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / Reflux 2.1: carbonochloridic acid 1-chloro-ethyl ester / dichloromethane / 2 h / Reflux 2.2: 1 h / Reflux 2.3: 18 h / 20 °C View Scheme

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) + benzyl-methyl-amine (103-67-3) → C18H21NO

Conditions	Yield
In tetrahydrofuran Reflux;

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) + methylamine (74-89-5) → 3‐methylmethcathinone

Conditions	Yield
In dichloromethane for 12h;

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) → phenyl methyl(1-oxo-1-(m-tolyl)propan-2-yl)carbamate

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 12 h 2: triethylamine / dichloromethane View Scheme

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) → benzyl methyl(1-oxo-1-(m-tolyl)propan-2-yl)carbamate

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 12 h 2: triethylamine / dichloromethane View Scheme

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) → methyl methyl(1-oxo-1-(m-tolyl)propan-2-yl)carbamate

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 12 h 2: triethylamine / dichloromethane View Scheme

2-bromo-1-(3-methylphenyl)propan-1-one (1451-83-8) + N-phenylglycine methyl ester (23284-84-6) → methyl (2R,3S)-3-methyl-4-oxo-2-(phenylamino)-4-(m-tolyl)butanoate + methyl 3-methyl-4-oxo-2-(phenylamino)-4-(m-tolyl)butanoate + methyl 3-methyl-4-oxo-2-(phenylamino)-4-(m-tolyl)butanoate

Conditions

Yield

With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; sodium hydrogencarbonate In 1,4-dioxane; acetonitrile at 15℃; for 24h; Schlenk technique; Molecular sieve; Irradiation; Overall yield = 50 percent; stereoselective reaction;

A n/a B n/a C n/a

Upstream product

• 108-88-3 toluene 
• 51772-30-6 3'-Methylpropiophenone 

Downstream Products

• 1193779-18-8 2-(N-tert-butylamino)-3'-methylpropiophenone 
• 1246816-62-5 2-(methylamino)-1-(3-methylphenyl)propan-1-one hydrochloride 
• 1350768-23-8 PAL-589 
• 1214939-96-4 2-(N-cyclopentylamino)-3'-methylpropiophenone 
• 1214940-01-8 2-(N-pyrrolidinyl)-3'-methylpropiophenone 

Relevant articles and documents

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