1451-82-7

Basic information

• Product Name: 2-bromo-4-methylpropiophenone
• Synonyms: 2-bromo-4-methylpropiophenone;2-bromo-1-(4-methylphenyl)propan-1-one;2-Bromo-1-(4-methylphenyl)-1-propanone;4-Methylphenyl 1-BroMoethyl Ketone;1-Propanone,2-broMo-1-(4-Methylphenyl)-;2-BROMO-4'-METHYLPROPIOPHENE;2-Bromo-1-(p-tolyl);Quality guarantee EG-2201 power
• CAS NO: 1451-82-7
• Molecular Formula: C₁₀H₁₁BrO
• Molecular Weight: 227.1
• EINECS: 1592732-453-0
• Product Categories: Aromatics;Intermediates;Miscellaneous Reagents;Medical research
• Mol File: 1451-82-7.mol

Chemical Properties

• Melting Point: 75-77℃
• Boiling Point: 273℃
• Flash Point: 59℃
• Appearance: /Solid
• Density: 1.357
• Storage Temp.: Refrigerator
• Solubility: Soluble in chloroform and methanol.
• CAS DataBase Reference: 2-bromo-4-methylpropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-4-methylpropiophenone(1451-82-7)
• EPA Substance Registry System: 2-bromo-4-methylpropiophenone(1451-82-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 1451-82-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1451-82-7 differently. You can refer to the following data:
1. 2-Bromo-4'-methylpropiophenone (cas# 1451-82-7) is a compound useful in organic synthesis.
2. It employed as an important intermediate for raw material for organic synthesis, agrochemical, pharmaceutical and dyestuff field. Also used as intermediate for 4-methylmethcathinone.

Reference

Philp, M.; Shimmon, R.; Stojanovska, N.; Tahtouh, M.; Fu, S. L., Development and validation of a presumptive colour spot test method for the detection of piperazine analogues in seized illicit materials. Anal. Methods 2013, 5, 5402-5410. Alexander Wick; Jonathan Frost; Bernard Gaudilliere; Jean Bertin; Regis Dupont; Rousseau, J., Therapeutically useful 1-phenyl-2-piperidinoalkanol derivatives. US Patent 4690931 1987. Masami Tsuda; Mitsushi Tanaka; Nakamura, A., Pyrrole derivatives and medicinal composition. US Patent 5998459 1999.

Chemical Properties

Off-White Solid

Upstream product

• 5337-93-9 4'-methylpropiophenone 
• 563-76-8 α-bromopropionyl bromide 
• 108-88-3 toluene 
• 7726-95-6 bromine 
• 71-43-2 benzene 
• 7148-74-5 2-Bromopropionyl chloride 
• 25574-04-3 1-p-tolyl-1-propanol 
• 106-38-7 para-bromotoluene 
• 1432028-75-5 3-(dimethylamino)-2-methyl-1-(p-tolyl)prop-2-en-1-one 

Downstream Products

• 15482-26-5 2-hydroxy-1-(4-methylphenyl)propan-1-one 
• 236117-38-7 2-iodo-1-(p-tolyl)propan-1-one 
• 1189805-46-6 1-(4-methylphenyl)-2-methylaminopropan-1-one 
• 64403-76-5 2-(5-amino-2-imino-[1,3,4]thiadiazol-3-yl)-1-p-tolyl-propan-1-one 
• 59849-34-2 2-benzoylimino-5-methyl-3-phenyl-4-p-tolyl-thiazolidin-4-ol 
• 1451-87-2 2-methoxy-1-p-tolylpropan-1-one 
• 79443-97-3 methyl 2-(4-methylphenyl)propanoate 
• 104484-32-4 (Z)-3-(4-Methoxy-phenyl)-2-(1-methyl-2-oxo-2-p-tolyl-ethylsulfanyl)-acrylic acid 
• 83363-04-6 Dimethyl-dithiocarbamic acid 1-methyl-2-oxo-2-p-tolyl-ethyl ester 
• 91306-36-4 2-(1-bromoethyl)-2-(p-tolyl)-1,3-dioxolane 
• 784076-40-0 (+/-)-1-Isopropylamino-1-<4-methyl-benzoyl>-aethan 
• 5337-93-9 4'-methylpropiophenone 
• 501892-27-9 2-(N-tert-butylamino)-4'-methylpropiophenone 
• 847453-67-2 ethyl 5,5-dimethyl-4-[1-(4-methylbenzoyl)ethyl]-2-oxotetrahydrofuran-3-carboxylate 

Relevant articles and documents

Design, synthesis and broad-spectrum Bcr-Abl inhibitory activity of novel thiazolamide-benzamide derivatives

Bcr-Abl plays an important role in the pathogenesis and development of chronic myeloid leukemia (CML). But Bcr-Abl is prone to mutation, so it increases the difficulty of clinical treatment. Therefore, it is crucial to design a new class of broad-spectrum Bcr-Abl inhibitors. Herein, forty novel thiazolamide-benzamide derivatives were synthesized and evaluated their broad-spectrum Bcr-Abl inhibitory activities. The newly synthesized compounds were characterized by using spectrum data (1H NMR, APCI-MS and IR) and elemental analysis. The protein kinase results indicated that eight compounds (3a, 3e, 3m, 3n, 3p, 4c, 4f, 4g) showed high activities to wild-type and T315I mutation. The most potent compound 3m exhibited an Abl IC50 value as low as 1.273 μM and showed inhibition to the T315I mutant with IC50 value 39.89 μM. 3m could prove to be a new promising lead compound for the further development of broad-spectrum Bcr-Abl inhibitors to overcome clinical acquired resistance.

α-PPP and its derivatives are selective partial releasers at the human norepinephrine transporter: A pharmacological characterization of interactions between pyrrolidinopropiophenones and uptake1 and uptake2 monoamine transporters

While classical cathinones, such as methcathinone, have been shown to be monoamine releasing agents at human monoamine transporters, the subgroup of α-pyrrolidinophenones has thus far solely been characterized as monoamine transporter reuptake inhibitors. Herein, we report data from previously undescribed α-pyrrolidinopropiophenone (α-PPP) derivatives and compare them with the pharmacologically well-researched α-PVP (α-pyrrolidinovalerophenone). Radiotracer-based in vitro uptake inhibition assays in HEK293 cells show that the investigated α-PPP derivatives inhibit the human high-affinity transporters of dopamine (hDAT) and norepinephrine (hNET) in the low micromolar range, with α-PVP being ten times more potent. Similar to α-PVP, no relevant pharmacological activity was found at the human serotonin transporter (hSERT). Unexpectedly, radiotracer-based in vitro release assays reveal α-PPP, MDPPP and 3Br-PPP, but not α-PVP, to be partial releasing agents at hNET (EC50 values in the low micromolar range). Furthermore, uptake inhibition assays at low-affinity monoamine transporters, i.e., the human organic cation transporters (hOCT) 1–3 and human plasma membrane monoamine transporter (hPMAT), bring to light that all compounds inhibit hOCT1 and 2 (IC50 values in the low micromolar range) while less potently interacting with hPMAT and hOCT3. In conclusion, this study describes (i) three new hybrid compounds that efficaciously block hDAT while being partial releasers at hNET, and (ii) highlights the interactions of α-PPP-derivatives with low-affinity monoamine transporters, giving impetus to further studies investigating the interaction of drugs of abuse with OCT1-3 and PMAT.

Reactivity of substrates with multiple competitive reactive sites toward NBS under neat reaction conditions promoted by visible light

Regioselectivity of visible-light-induced transformations of a range of (hetero)aryl alkyl-substituted ketones bearing several competitive reactive sites (α-carbonyl, benzyl and aromatic ring) with N-bromosuccinimide (NBS) was studied under solvent-free reaction conditions (SFRC) and in the absence of inert-gas atmosphere, radical initiators and catalysts. An 8-W energy-saving household lamp was used for irradiation. Heterogeneous reaction conditions were dealt with throughout the study. All substrates were mono- or dibrominated at the α-carbonyl position, and additionally, some benzylic or aromatic bromination was observed in substrates with benzylic carbon atoms or electron-donating methoxy groups, respectively. Surprisingly, ipso-substitution of the acyl group with a bromine atom took place with (4-methoxynaphthyl) alkyl ketones. While the addition of the radical scavenger TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxy) decreased the extent of α- and ring bromination, it completely suppressed the benzylic bromination and α,α-dibromination with NBS under SFRC.

Enantioselective Synthesis of Nitrogen-Nitrogen Biaryl Atropisomers via Copper-Catalyzed Friedel-Crafts Alkylation Reaction

Nitrogen-nitrogen bonds containing motifs are ubiquitous in natural products and bioactive compounds. However, the atropisomerism arising from a restricted rotation around an N-N bond is largely overlooked. Here, we describe a method to access the first enantioselective synthesis of N-N biaryl atropisomers via a Cu-bisoxazoline-catalyzed Friedel-Crafts alkylation reaction. A wide range of axially chiral N-N bisazaheterocycle compounds were efficiently prepared in high yields with excellent enantioselectivities via desymmetrization and kinetic resolution. Heating experiments showed that the axially chiral bisazaheterocycle products have high rotational barriers.

Access to α,α-dihaloacetophenones through anodic C[dbnd]C bond cleavage in enaminones

We have developed a method to synthesize α,α-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl2 or Br2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C[dbnd]C of the N,N-dimethyl enaminone to generate α,α-dihaloketones. The electrosynthesis reaction can be conveniently carried out in an undivided electrolytic cell at room temperature. In addition, various functional groups are compatible with this green protocol which can be applied simultaneously to the gram scale without significantly lower yield.

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.

Is the 3,4-methylendioxypyrovalerone/mephedrone combination responsible for enhanced stimulant effects? A rat study with investigation of the effect/concentration relationships

Rationale: The use of synthetic cathinones as recreational drugs frequently sold in combination has been increasing exponentially. However, the consequences of combining cathinones on the resulting stimulant effects and the pharmacokinetics have been poorly investigated. Objective and methods: To study 3,4-methylenedioxypyrovalerone (MDPV; 3?mg/kg) and mephedrone (4-MMC; 30?mg/kg)-induced effects on rat locomotor activity and pharmacokinetics, administered alone or in combination by the intragastric route. The pharmacokinetic parameters were determined using non-compartmental analysis and the relationships between the locomotor activity and drug concentrations using sigmoidal Emax modeling. Results: Locomotor activity significantly increased during the first hour post-administration with the MDPV/4-MMC combination in comparison to MDPV (p max (16.4 ± 5.5 versus 62.2 ± 14.2?μg/L, p 0 → ∞ (708 ± 91 versus 3316 ± 682?μg/L/min, p max model fitted the observed data well; MDPV being markedly more potent than 4-MMC (EC50, 0.043 versus 0.7?μmol/L). The enhancing factor representing the MDPV contribution to the alteration in the relationships between locomotor activity and 4-MMC concentrations was 0.3. Conclusion: An MDPV/4-MMC combination results in enhanced stimulant effects in the rat, despite significant reduction in MDPV bioavailability. Enhanced effects could be explained by increased MDPV distribution and/or possible complementation at the brain dopaminergic targets. However, the exact consequences of the MDPV/4-MMC combination in humans remain to be clarified.

Synthesis of α,β-dibromo ketones by photolysis of α-bromo ketones with N-bromosuccinimide: Photoinduced β-bromination of α-bromo ketones

Irradiation of α-bromopropiophenones in the presence of NBS results in the formation of α,β-dibromopropiophenones, which can be viewed as β-bromination of α-bromopropiophenones. The reaction is believed to go through a series of reactions; photoinduced C–Br bond cleavage, elimination of HBr to give α,β-unsaturated ketone intermediates, and addition of Br2, which are formed by the reaction between HBr and NBS. From mechanistic studies of the reaction, we have also found a very convenient method for α-debromination of the α,β-dibromopropiophenones which is by simple irradiation of the dibromo ketones in acetone or 2-propanol without the use of any additives. Our results demonstrate that bromine can be added into or eliminated from the alpha, beta, or both positions to the carbonyl group by photochemical methods, which make synthetic options of bromine containing carbonyl compounds versatile.

NBS-mediated synthesis of β-keto sulfones from benzyl alcohols and sodium arenesulfinates

An efficient synthetic route towards the synthesis of β-keto sulfones has been developed from secondary benzyl alcohols using N-bromosuccinimide (NBS). The present protocol utilizes NBS as oxidant as well as brominating agent, readily accessible benzyl alcohols and sodium arenesulfinates as the sulfonylating reagent under mild conditions. The control experiments revealed that the reaction proceeds via oxidation of alcohol to ketone, α-bromination of ketone and nucleophilic substitution by sodium arenesulfinate. Furthermore, the efficiency of the methodology was tested with a gram scale reaction and also shown the synthetic utility.

Formal Total Synthesis of Hybocarpone Enabled by Visible-Light-Promoted Benzannulation

The formal total synthesis of hybocarpone was achieved in eight steps from commercially available 1,2,4-trimethoxybenzene. Key transformations include a visible-light-promoted benzannulation to construct the key α-naphthol intermediate and a modified CAN-mediated dimerization/hydration cascade sequence to generate the vicinal all-carbon quaternary centers in a stereocontrolled manner. The total synthesis of boryquinone was also achieved in seven steps.