824-53-3

Basic information

• Product Name: (2-bromo-4-methylphenyl)methanol
• Synonyms: (2-bromo-4-methylphenyl)methanol;2-Bromo-4-methylbenzyl alcohol;Benzenemethanol, 2-bromo-4-methyl-
• CAS NO: 824-53-3
• Molecular Formula: C₈H₉BrO
• Molecular Weight: 201.06046
• Mol File: 824-53-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2-bromo-4-methylphenyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2-bromo-4-methylphenyl)methanol(824-53-3)
• EPA Substance Registry System: (2-bromo-4-methylphenyl)methanol(824-53-3)

Safety Data

• Hazardous Substances Data: 824-53-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2-bromo-4-methylphenyl)methanol is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Industry:
(2-bromo-4-methylphenyl)methanol is used as a chemical intermediate in the preparation of 6,7-Dihydro-5H-diphenyl[a,c]cyclohepten-5-one compounds. These compounds are important in the synthesis of various organic molecules and can be used as precursors for the development of new chemical products.

Upstream product

• 824-54-4 2-bromo-4-methylbenzaldehyde 
• 88174-23-6 2,6-dibromo-4-methylbenzaldehyde 
• 7697-27-0 2-bromo-4-methylbenzoic acid 

Downstream Products

• 75366-14-2 1-(bromomethyl)-2-bromo-4-methylbenzene 
• 909034-71-5 tert-butyl 4-hydroxy-4-[2-(hydroxymethyl)-5-methylphenyl]piperidine-1-carboxylate 
• 1300038-68-9 2-(2-bromo-4-methylbenzyl)-2-nitrocyclohexanone 
• 1300038-74-7 2-(2-bromo-4-methylbenzyl)-2-nitrocycloheptanone 
• 1300038-81-6 2-(2-bromo-4-methylbenzyl)-2-nitrocyclooctanone 
• 1300038-61-2 2-bromo-1-iodomethyl-4-methylbenzene 
• 824-54-4 2-bromo-4-methylbenzaldehyde 
• 147542-02-7 2-bromo-1-(chloromethyl)-4-methylbenzene 

Relevant articles and documents

PYRIDO-PYRIMIDINONE AND PTERIDINONE COMPOUNDS AS INHIBITORS OF ENDORIBONUCLEASE INOSITOL REQUIRING ENZYME I (IRE I ALPHA) FOR THE TREATMENT OF CANCER DISEASES.

Described herein are pyrido-pyrimidinone and pteridinone compounds or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, and with the substituents and structural features described herein. Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods treating cancer, alone and in combination with other therapeutic agents.

Solvent-free mechanochemical oxidation and reduction of biomass-derived 5-hydroxymethyl furfural

The simultaneous synthesis of 5-hydroxymethyl-2-furoic acid and 2,5-hydroxymethylfuran from biomass-derived 5-hydroxymethyl furan was developed using a solvent-free mechanochemical approach. The results obtained for the Cannizzaro disproportionation reaction show quantitative conversions of the starting materials with reaction times of only 5 min. Employing solvent-free conditions allows for a more sustainable synthetic approach that is reflected in an Efactor 7 times smaller than that in previous reports. Additionally, initial results of the use of a sacrificial reagent, with the same solvent-free mechanochemical approach, for the selective reduction and oxidation of HMF are presented.

Morita-Baylis-Hillman Reaction of β,β-Disubstituted Enones: An Enantioselective Organocatalytic Approach for the Synthesis of Cyclopenta[b]annulated Arenes and Heteroarenes

The first enantioselective organocatalytic intramolecular Morita-Baylis-Hillman (MBH) reaction of sterically highly demanding β,β-disubstituted enones is presented. The MBH reaction of β,β-disubstituted-α,β-unsaturated electron-withdrawing systems was previously considered to be unfeasible. Towards this end, designer substrates, which under simple and practical reaction conditions generate a variety of cyclopenta[b]annulated arenes and heteroarenes in excellent enantiopurities and near-quantitative yields in remarkably short reaction times, are described. The reason for the unusually facile nature of this reaction is attributed to the synergy guided and entropically favored intramolecular reaction. Further, this strategy provides easy access to a substantial number of bioactive natural products and pharmaceutically significant compounds.

Bismuth-catalyzed synthesis of anthracenes via cycloisomerization of o-alkynyldiarylmethane

In this study, anthracenes were efficiently synthesized from o-alkynyldiarylmethane using a novel method that exploits the synergistic effect between Bi(OTf)3 as the catalyst, and trifluoroacetic acid (TFA). Through this reaction, we achieved the rapid and efficient synthesis of anthracenes bearing various functional groups under mild conditions.

Hydrazone-palladium catalyzed annulation of 1-allyl-2-bromobenzene derivatives with internal alkynes

Annulation of 1-allyl-2-bromobenzene derivatives with internal alkynes using a hydrazone-palladium catalyst system proceeded smoothly and gave the corresponding polysubstituted naphthalene derivatives in good to high yields.

N-protected 1,2-oxazetidines as a source of electrophilic oxygen: Straightforward access to benzomorpholines and related heterocycles by using a reactive tether

A hitherto unknown reactivity of a strained four-membered heterocycle, 1,2-oxazetidine, is reported. When reacted with organometallic compounds, this reagent provides electrophilic oxygen with a nitrogen-terminated two-carbon-atom tether. The synthetic versatility of the products obtained was demonstrated in various transformations, leading to efficient synthesis of six-, seven-, and eight-membered heterocyclic systems of pharmaceutical importance. Open and then close: The O-selective ring-opening reaction of 1,2-oxazetidines with organometallic compounds provides tethered phenol derivatives that can be used to access six-, seven-, and eight-membered heterocyclic systems in only a few steps (see scheme; Ts=tosyl).

Diastereo- and enantioselective intramolecular C(sp3)-H arylation for the synthesis of fused cyclopentanes

All C-H bonds are not equal: The intramolecular arylation of unactivated C(sp3)-H bonds in the presence of a chiral Pd/binepine catalyst allows the synthesis of fused cyclopentanes efficiently and in an diastereo- and enantioselective manner (see scheme).

Synthesis of benzo- and naphtho-fused bicyclo[n.3.1]alkane frameworks with a bridgehead nitrogen function by palladium-catalyzed intramolecular α′-arylation of α-nitroketones

The C-alkylation of cyclic α-nitroketones with α-halobenzyl halides in the presence of DBU followed by a Pd-catalyzed intramolecular C-arylation afforded benzo-and naphtho-fused bicyclo[n.3.1]alkane derivatives (n = 3, 4, 5) in excellent overall yields for the two-step sequence. In some of the reactions starting from α-nitrocyclooctanone, the major products were fused indane derivatives arising from an intramolecular attack of an intermediate Pd species onto the carbonyl group, followed by elimination.

Synthesis of 2-naphthols via carbonylative stille coupling reaction of 2-bromobenzyl bromides with tributylallylstannane followed by the heck reaction

A method for the synthesis of 2-naphthols 4 is described. The carbonylative Stille coupling reactions of 2-bromobenzyl bromides with tributylallylstannane to produce 2-bromobenzyl β,γ-unsaturated ketones 2 in satisfactory to excellent yields has been achieved. The isomerization of 2-bromobenzyl β,γ-unsaturated ketones 2 can readily occur under basic conditions to generate 2-bromobenzyl α,β-unsaturated ketones 3. The 2-bromobenzyl α,β-unsaturated ketones 3 can be transformed into 2-naphthols 4 via intramolecular Heck reaction in satisfactory to good yields (Figure presented).

Synthesis of benzocyclobutenes by palladium-catalyzed C-H activation of methyl groups: Method and mechanistic study

An efficient catalytic system has been developed for the synthesis of benzocyclobutenes by C-H activation of methyl groups. The optimal conditions employed a combination of Pd(OAc)2 and PtBu3 as catalyst, K2CO3 as the base, and DMF as solvent. A variety of substituted BCB were obtained under these conditions with yields in the 44-92% range, including molecules that are hardly accessible by other methods. The reaction was found limited to substrates bearing a quaternary benzylic carbon, but benzocyclobutenes bearing a tertiary benzylic carbon could be obtained indirectly from diesters by decarboxylation. Reaction substrates bearing a small substituent para to bromine gave an unexpected regioisomer that likely arose from a 1,4-palladium migration process. The formation of this "abnormal" regioisomer could be suppressed by introducing a larger subsituent para to bromine. DFT(B3PW91) calculations on the reaction of 2-bromo-tert-butylbenzene with Pd(PtBu3) with different bases (acetate, bicarbonate, carbonate) showed the critical influence of the coordination mode of the base to induce both an easy C-H activation and to allow for a pathway for 1,4-palladium migration. Carbonate is shown to be more efficient than the two other bases because it can abstract the proton easily and at the same time maintain κ1-coordination without extensive electronic reorganization.