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

• 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 
• 1193779-18-8 2-(N-tert-butylamino)-3'-methylpropiophenone 

Relevant articles and documents

Novel benzene-based carbamates for ache/bche inhibition: Synthesis and ligand/structure-oriented sar study

A series of new benzene-based derivatives was designed, synthesized and comprehensively characterized. All of the tested compounds were evaluated for their in vitro ability to potentially inhibit the acetyl-and butyrylcholinesterase enzymes. The selectivity index of individual molecules to cholinesterases was also determined. Generally, the inhibitory potency was stronger against butyryl-compared to acetylcholinesterase; however, some of the compounds showed a promising inhibition of both enzymes. In fact, two compounds (23, benzyl ethyl(1-oxo-1-phenylpropan-2-yl)carbamate and 28, benzyl (1-(3-chlorophenyl)-1-oxopropan-2-yl) (methyl)carbamate) had a very high selectivity index, while the second one (28) reached the lowest inhibitory concentration IC50 value, which corresponds quite well with galanthamine. Moreover, comparative receptor-independent and receptor-dependent structure–activity studies were conducted to explain the observed variations in inhibiting the potential of the investigated carbamate series. The principal objective of the ligand-based study was to comparatively analyze the molecular surface to gain insight into the electronic and/or steric factors that govern the ability to inhibit enzyme activities. The spatial distribution of potentially important steric and electrostatic factors was determined using the probability-guided pharmacophore mapping procedure, which is based on the iterative variable elimination method. Additionally, planar and spatial maps of the host–target interactions were created for all of the active compounds and compared with the drug molecules using the docking methodology.

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

3,8-DIAZA-BICYCLO[4.2.0]OCT-3-YL AMIDES

The present invention relates to 3,8-diaza-bicyclo[4.2.0]oct-3-yl amide derivatives of formula (I), wherein the relative configuration of the diazabicyclooctane moiety is cis; and wherein Ar1, and Ar2 are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.