203314-29-8

Usage

Uses

Used in Pharmaceutical Industry:
2-bromo-5-methylphenylacetic acid is used as a key intermediate for the synthesis of various pharmaceuticals, leveraging its bromine substituent to facilitate chemical reactions that are crucial in the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 2-bromo-5-methylphenylacetic acid is utilized as a building block for creating a range of organic compounds. Its reactivity allows for versatile transformations, making it a valuable component in the synthesis of complex organic molecules.
Used in Chemical Research:
2-bromo-5-methylphenylacetic acid is employed as a research compound in chemical studies, where its unique properties and reactivity are explored for new reaction pathways and mechanisms, contributing to the advancement of synthetic chemistry.

Upstream product

• 50-00-0 formaldehyd 
• 106-38-7 para-bromotoluene 
• 792917-15-8 2-(2-bromo-5-methylphenyl)acetamide 
• 621-36-3 m-methylphenylacetic acid 
• 27561-50-8 1-bromo-2-(bromomethyl)-4-methylbenzene 
• 1085539-03-2 (2-bromo-5-methylphenyl)acetonitrile 
• 77344-70-8 1-(2-bromo-5-methylphenyl)ethanone 

Downstream Products

• 6939-93-1 4-bromo-isophthalic acid 
• 951155-03-6 ((R)-8-bromo-5-methyl-1,2,3,4-tetrahydronaphthalen-2-yl)-(S)-1-(phenylethyl)amine 
• 1381802-56-7 ((S)-8-bromo-5-methyl-1,2,3,4-tetrahydronaphthalen-2-yl)-(S)-1-(phenylethyl)amine 
• 633312-83-1 C₁₈H₂₀BrN 
• 1394290-38-0 ((R)-8-bromo-5-methyl-1,2,3,4-tetrahydronaphthalen-2-yl)-(S)-1-(phenylethyl)amine hydrochloride 
• 1160714-18-0 (R)-5-methyl-8-(N⁴-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-ylamine benzoate 
• 1160714-39-5 (2R)-5-methyl-8-(4-methylpiperazin-1-yl)-N-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydro-naphthalen-2-amine 
• 1195212-99-7 C₉H₁₁BrO 

Relevant academic research and scientific papers

Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp3)-H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process

Described herein is a chiral magnesium bisphosphate-catalyzed asymmetric double C(sp3)-H bond functionalization triggered by a sequential hydride shift/cyclization process. This reaction consists of stereoselective domino C(sp3)-H bond functionalization: (1) a highly enantio- and diastereoselective C(sp3)-H bond functionalization by chiral magnesium bisphosphate (first [1,5]-hydride shift), and (2) a highly diastereoselective C(sp3)-H bond functionalization by an achiral catalyst (Yb(OTf)3, second [1,5]-hydride shift).

Regioisomerism in the synthesis of a chiral aminotetralin drug compound: Unraveling mechanistic details and diastereomer-specific in-depth NMR investigations

During chemical process development of a novel 2-aminotetralin derivative intended for use as an antidepressant, scrutiny of the byproduct present in the drug molecule revealed a set of regioisomers. Detailed studies showed that this impurity issue origin

Optimization and scale-up of a Pd-catalyzed aromatic C-N bond formation: A key step in the synthesis of a novel 5-HT1B receptor antagonist

Searching for the best synthetic route for a given target molecule is a complex task and, by the same token, a key deliverable from a process R&D department. In this vein the challenge for our group was to identify a sustainable manufacturing process for a chiral compound, AR-A2, to be developed for the treatment of certain neurological disorders. Besides designing a method for assembling the core (R)-2-aminotetralin nucleus, a key feature in the overall synthesis was to provide a robust procedure for creating a new C-N bond between an aromatic ring and a heterocyclic moiety. The methodology employed a Buchwald-Hartwig coupling, and a highly efficient catalytic process was developed using Pd(OAc)2 as precatalyst, with loadings as low as 0.47 mol % (in laboratory trials one order of magnitude lower) together with (R)-BINAP as ligand. Optimizing the reaction conditions allowed a virtually quantitative conversion of the brominated aromatic substrate after heating to 110-115 °C in toluene for 4 h. Telescoping this step with a succeeding catalytic hydrogenation to effect an N-debenzylation, followed by precipitation of the benzoate salt offered an overall yield for the two consecutive steps of 88% at 125-kg batch size, combined with excellent stereochemical product purity of 98% ee.

2- and 2,5-substituted phenylketoenols

The invention relates to novel phenyl-substituted cyclic ketoenols of the formula (I) in which Het represents one of the groups ?in which A, B, D, G, X and Z are each as defined in the description, to a plurality of processes and intermediates for their preparation, and to their use as pesticides.