29182-97-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-N-methylacetanilide is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs and therapeutic agents. Its versatility in organic synthesis allows for the creation of a wide range of medicinal compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 2-Bromo-N-methylacetanilide is utilized as a building block, enabling the construction of complex organic molecules that can be further modified for specific applications.
Used as a Topical Analgesic:
2-Bromo-N-methylacetanilide has potential applications as a topical analgesic, providing pain relief when applied to the skin, due to its chemical properties that can interact with pain receptors.
Safety Considerations:
It is crucial to handle 2-Bromo-N-methylacetanilide with care and adhere to proper safety protocols to mitigate any health hazards associated with its use, given its potential to pose risks if not managed correctly.

InChI:InChI=1/C9H10BrNO/c1-11(9(12)7-10)8-5-3-2-4-6-8/h2-6H,7H2,1H3

Upstream product

• 13094-51-4 bromoacetic anhydride 
• 100-61-8 N-methylaniline 
• 6780-38-7 N-phthaloylglycine chloride 
• 95-51-2 o-chloroaniline 
• 139088-91-8 2-phthalimido-N-(2-chlorophenyl)acetamide 
• 579-10-2 N-acetyl-N-methylaniline 
• 22118-09-8 2-bromoacetyl chloride 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 212116-84-2 N-methyl-N-phenyl-2-{N-(3-benzyloxyphenyl)-N-[2-(N-tert-butoxycarbonylamino)acetyl]amino}acetamide 
• 205694-26-4 methyl 2-(3-{N-[2-(N-tert-butoxycarbonylamino)acetyl]-N-(N-methyl-N-phenylcarbamoylmethyl)amino}phenoxy)acetate 
• 183180-10-1 N-Methyl-N-phenyl-2-[N-(2-benzyloxyphenyl)-N-[2-(N-tertiarybutoxycarbonylamino)acetyl]amino]acetamide 
• 205694-28-6 ethyl 2-(3-{N-[2-(N-tert-butoxycarbonylamino)acetyl]-N-(N-methyl-N-phenylcarbamoylmethyl)amino}phenoxy)acetate 
• 205694-30-0 isopropyl 2-(3-{N-[2-(N-tert-butoxycarbonylamino)acetyl]-N-(N-methyl-N-phenylcarbamoylmethyl)amino}phenoxy)acetate 
• 205694-29-7 tert-butyl 2-(3-{N-[2-(N-tert-butoxycarbonylamino)acetyl]-N-(N-methyl-N-phenylcarbamoylmethyl)amino}phenoxy)acetate 
• 205694-31-1 cyclopentyl 2-(3-{N-[2-(N-tert-butoxycarbonylamino)acetyl]-N-(N-methyl-N-phenylcarbamoylmethyl)amino}phenoxy)acetate 
• 205694-32-2 cyclohexyl 2-(3-{N-[2-(N-tert-butoxycarbonylamino)acetyl]-N-(N-methyl-N-phenylcarbamoylmethyl)amino}phenoxy)acetate 
• 183180-12-3 N-methyl-N-phenyl-2-(2-{N-[2-(N-tert-butoxycarbonylamino)acetyl]-N-(N-methyl-N-phenylcarbamoylmethyl)amino}phenoxy)acetamide 
• 1196091-50-5 (R)-1-[(Methyl-phenyl-carbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane formate 
• 59852-31-2 4-chloro-benzylamine; hydrobromide 
• 59852-32-3 (4-methoxyphenyl)methanaminium bromide 
• 37488-40-7 benzylamine hydrobromide 

Relevant academic research and scientific papers

Modified benzoxazolone derivative as 18-kDa TSPO ligand

We have synthesized six new congeners of acetamidobenzoxazolone for Translocator Protein [18 kDa, TSPO] imaging. The best in vitro binding affinity (10.8?±?1.2?nm) for TSPO was found for N-methyl-2-(5-(naphthalen-1-yl)-2-oxobenzo[d]oxazol-3(2H)-yl)-N-phen

Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals

A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.

Discovery of Novel Acetamide-Based Heme Oxygenase-1 Inhibitors with PotentIn VitroAntiproliferative Activity

Heme oxygenase-1 (HO-1) promotes heme catabolism exercising cytoprotective roles in normal and cancer cells. Herein, we report the design, synthesis, molecular modeling, and biological evaluation of novel HO-1 inhibitors. Specifically, an amide linker in the central spacer and an imidazole were fixed, and the hydrophobic moiety required by the pharmacophore was largely modified. In many tumors, overexpression of HO-1 correlates with poor prognosis and chemoresistance, suggesting the inhibition of HO-1 as a possible antitumor strategy. Accordingly, compounds7iand7l-pemerged for their potency against HO-1 and were investigated for their anticancer activity against prostate (DU145), lung (A549), and glioblastoma (U87MG, A172) cancer cells. The selected compounds showed the best activity toward U87MG cells. Compound7lwas further investigated for its in-cell enzymatic HO-1 activity, expression levels, and effects on cell invasion and vascular endothelial growth factor (VEGF) extracellular release. The obtained data suggest that7lcan reduce cell invasivity acting through modulation of HO-1 expression.

Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst

This work presented the efficient intramolecular aromatic C–H insertion of diazoacetamide. The 1a–1o diazo compounds (except for 1k) were converted into their corresponding oxindoles via an intramolecular C–H insertion reaction in the presence of a Ru catalyst. The Ru-Pheox catalyst was shown to be highly efficient in this transformation in terms of the regioselectivity, producing the desired products in excellent yield (99%). The efficiency of the Ru catalyst reached 580 (TON) and 156 min?1 (TOF).

A copper(II)-mediated radical cross-dehydrogenative coupling/sulfinic acid elimination approach to 2-quinolones

A new cyclisation procedure to prepare 4-carboxy-quinolin-2-ones via a one-pot Cu(II)-mediated radical cross-dehydrogenative coupling/sulfinic acid elimination of linear anilides is described. Extensions to more complex substrates are also reported as are

Electrochemical dehydrogenative cyclization of 1,3-dicarbonyl compounds

The intramolecular C(sp3)-H/C(sp2)-H cross-coupling of 1,3-dicarbonyl compounds has been achieved through Cp2Fe-catalyzed electrochemical oxidation. The key to the success of these dehydrogenative cyclization reactions is

Site-Selective Conversion of Azido Groups at Carbonyl α-Positions to Diazo Groups in Diazido and Triazido Compounds

This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl moieties were transformed into α-diazo carbonyl groups in one step. As these reaction conditions do not involve aryl or general alkyl azides, site-selective conversions of di- and triazides were achieved. Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated.

Transfer Hydro-dehalogenation of Organic Halides Catalyzed by Ruthenium(II) Complex

A simple and efficient Ru(II)-catalyzed transfer hydro-dehalogenation of organic halides using 2-propanol solvent as the hydride source was reported. This methodology is applicable for hydro-dehalogenation of a variety of aromatic halides and α-haloesters and amides without additional ligand, and quantitative yields were achieved in many cases. The potential synthetic application of this method was demonstrated by efficient gram-scale transformation with catalyst loading as low as 0.5 mol %.

Transition-Metal-Free Fluoroarylation of Diazoacetamides: A Complementary Approach to 3-Fluorooxindoles

An efficient transition-metal-free fluoroarylation reaction of N-aryl diazoacetamides with NFSI (N-fluorobenzenesulfonimide) is described. This reaction directly provides 3-fluorooxindole derivatives in yields of 67-93% with high selectivity via a carbene

AUTOTAXIN INHIBITOR COMPOUNDS

Described herein are compounds that are autotaxin inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with autotaxin activity.