446-48-0

Basic information

• Product Name: 2-Fluorobenzyl bromide
• Synonyms: α-Bromo-2-fluorotoluene ;2-fluoro(bromomethyl)benzene;2-FLUOROBENZYL BROMIDE 98%;2-Fluorobenzylbromide,98%;à-bromo-2-fluorotoluene;1-Fluoro-2-(bromomethyl)benzene;2-Fluorobenzyl bromi;2-Fluorobenzyl broMide, 98% 25GR
• CAS NO: 446-48-0
• Molecular Formula: C₇H₆BrF
• Molecular Weight: 189.02
• EINECS: 207-169-1
• Product Categories: Fluoro-contained benzyl bromide series;Benzyl
• Mol File: 446-48-0.mol

Chemical Properties

• Boiling Point: 84-85 °C15 mm Hg(lit.)
• Flash Point: 181 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.567 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.252mmHg at 25°C
• Refractive Index: n20/D 1.552(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: Lachrymatory
• BRN: 1099894
• CAS DataBase Reference: 2-Fluorobenzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluorobenzyl bromide(446-48-0)
• EPA Substance Registry System: 2-Fluorobenzyl bromide(446-48-0)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 23-26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 446-48-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluorobenzyl bromide is used as an alkylating agent for the synthesis of various pharmaceutical compounds. Its application in the pharmaceutical industry is due to its ability to introduce an alkyl group into a molecule, which can significantly alter the biological activity and properties of the target compound.
2-Fluorobenzyl bromide is used as a reagent in the synthesis of 2-pyrrolo[2,3-d]pyrimidines for their potential therapeutic applications. The introduction of the fluorine atom in the benzyl group can enhance the pharmacokinetic and pharmacodynamic properties of these compounds.
In the synthesis of 8-alkylated imidazolo[1,2-a]pyrimid-5-ones, 2-Fluorobenzyl bromide is used as an alkylating agent to introduce the desired alkyl group at the 8th position of the imidazolo[1,2-a]pyrimid-5-one scaffold. This modification can lead to the development of novel compounds with improved biological activities.
Furthermore, 2-Fluorobenzyl bromide is used in the synthesis of prasugrel, an antiplatelet drug used to prevent blood clots. The fluorine atom in the benzyl group of 2-Fluorobenzyl bromide plays a crucial role in the formation of the final product, contributing to its therapeutic efficacy.

InChI:InChI=1/C7H7FO/c8-7-4-2-1-3-6(7)5-9/h1-4,9H,5H2

Upstream product

• 95-52-3 2-Fluorotoluene 
• 446-51-5 2-fluorobenzyl alcohol 
• 7726-95-6 bromine 
• 10035-10-6 hydrogen bromide 
• 71-43-2 benzene 
• 506-68-3 bromocyane 
• 401-35-4 benzyl-(2-fluoro-benzyl)-methyl-amine 
• 368-06-9 (2-fluoro-benzyl)-(4-fluoro-benzyl)-methyl-amine 
• 446-52-6 2-Fluorobenzaldehyde 

Downstream Products

• 328-19-8 1-(2-fluoro-benzyl)-pyridinium; bromide 
• 2994-19-6 1-(2-fluoro-benzyl)-hexahydro-azepine 
• 368-06-9 (2-fluoro-benzyl)-(4-fluoro-benzyl)-methyl-amine 
• 326-62-5 2-fluorophenyl acetonitrile 
• 446-51-5 2-fluorobenzyl alcohol 
• 446-50-4 1-fluoro-2-(iodomethyl)benzene 
• 445-25-0 1-(bromo-chloro-methyl)-2-fluoro-benzene 
• 454-15-9 2-fluoro-5-nitrobenzyl bromide 
• 401-35-4 benzyl-(2-fluoro-benzyl)-methyl-amine 
• 399-30-4 1-(2-fluorophenyl)-N-methylmethanamine 
• 64977-47-5 7-Fluor-5-methylchrysen 
• 62640-65-7 cis-2-Fluor-2'-chlorstilben 

Relevant articles and documents

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ERα controls the breast tissue development and progression of breast cancer. In our search for novel compounds to target Estrogen Receptor Alpha Ligand-Binding Domain, we identified “N-(3-((1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide” derivatives as lead compounds. The Docking studies indicated good docking score for Metacetamol derivatives when docked into the 1XP6. A series of metacetamol derivatives have been synthesized, characterized and evaluated for cytotoxicity, anti bacterial and anti oxidant activities. Among the tested twelve hybrid compounds, “7a, 7g, 7h and 7i” derivatives showed promising cytotoxicity with IC50 value of 50 value of 30 μM, whereas Compounds “7a, 7b, 7c, 7d, 7g, 7j, 7k and 7l” showed moderate anti bacterial activity with the MIC value of 300 μM.

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An efficient palladium-catalyzed nucleophilic substitution/C–H activation/aromatization cascade reaction between readily available 2-halo-N-Ms-arylamines (Ms = methanesulfonyl) and benzyl halides/sulfonates has been described. A wide variety of phenanthridines were synthesized in a one-pot fashion in moderate to high yields (37–86 %). Notably, this method provides a straightforward, facile approach for the synthesis of phenanthridines. The practicality was further substantiated by successfully carrying out a gram-scale preparation.

Structure-Guided Design of EED Binders Allosterically Inhibiting the Epigenetic Polycomb Repressive Complex 2 (PRC2) Methyltransferase

PRC2 is a multisubunit methyltransferase involved in epigenetic regulation of early embryonic development and cell growth. The catalytic subunit EZH2 methylates primarily lysine 27 of histone H3, leading to chromatin compaction and repression of tumor suppressor genes. Inhibiting this activity by small molecules targeting EZH2 was shown to result in antitumor efficacy. Here, we describe the optimization of a chemical series representing a new class of PRC2 inhibitors which acts allosterically via the trimethyllysine pocket of the noncatalytic EED subunit. Deconstruction of a larger and complex screening hit to a simple fragment-sized molecule followed by structure-guided regrowth and careful property modulation were employed to yield compounds which achieve submicromolar inhibition in functional assays and cellular activity. The resulting molecules can serve as a simplified entry point for lead optimization and can be utilized to study this new mechanism of PRC2 inhibition and the associated biology in detail.

One-Step Synthesis of Substituted Benzofurans from ortho- Alkenylphenols via Palladium-Catalyzed C=H Functionalization

A dehydrogenative oxygenation of C(sp2)=H bonds with intramolecular phenolic hydroxy groups has been developed, which provides a straightforward and concise access to structurally diversely benzofurans from ortho-alkenylphenols. The reaction is catalyzed by palladium on carbon (Pd/C) without any oxidants and sacrificing hydrogen acceptors.

Synthetic scope, computational chemistry and mechanism of a base induced 5-endo cyclization of benzyl alkynyl sulfides

We present an experimental and computational study of the reaction of aryl substituted benzyl 1-alkynyl sulfides with potassium alkoxide in acetonitrile, which produces 2-aryl 2,3-dihydrothiophenes in poor to good yields. The cyclization is most efficient with electron withdrawing groups on the aromatic ring. Evidence indicates there is rapid exchange of protons and tautomerism of the alkynyl unit prior to cyclization. Theoretical calculations were also conducted to help rationalize the base induced 5-endo cyclization of benzyl 1-propynyl sulfide (1a). The potential energy surface was calculated for the formation of 2,3-dihydrothiophene in a reaction of benzyl 1-propynyl sulfide (1a) with potassium methoxide. Geometries were optimized with CAM-B3LYP/6-311+G(d,p) in acetonitrile with the CPCM solvent model. It is significant that the benzyl propa-1,2-dien-1-yl sulfane (6) possessed a lower benzylic proton affinity than the benzyl prop-2-yn-1-yl sulfane (8) thus favoring the base induced reaction of the former. From benzyl(propa-1,2-dien-1- yl sulfane (6), 2,3-dihydrothiophene can be formed via a conjugate base that undergoes 5-endo-trig cyclization followed by a protonation step.

Reductive bromination of aromatic aldehydes using alkylboron dibromides

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Acridine orange derivatives and their use in the quantitation of reticulocytes in whole blood

Quaternized derivatives of acridine orange and reagents incorporating such derivatives and their use in quantitatively determining reticulocyte levels in whole blood specimen by fluorescence flow cytometry techniques are disclosed. The quaternized derivatives of acridine orange are of the general formula: STR1 wherein Y is bromide (Br-) or iodide (I-), and X may be R1 and/or R2 substituted benzyl group STR2 R1 is hydrogen or fluorine, and R2 is fluorine, trifluoromethyl or hydrogen, or X may be hydroxyl ethylene.

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The preparation, physical and spectroscopic properties of 1-amino-2-arylethylphosphonic, and -phosphinic acids as well as -phosphine oxides, the phosphorus analogues of phenylalanine are described, and the reactions of 1-amino-2-(4-fluorophenyl)ethylphosphonates with acetals, isocyanides, esters, acid anhydrides, activated aromatic nitro- and halogen compounds, and with N-protected alanine are reported.It is shown that several of the 1-amino-2-arylethylphosphonic acids are strong inhibitors of PAL and anthocyanin synthesis and also are quite active botryticides.Among the active compounds were 1-amino-2-(4-fluorophenyl)ethylphosphonic acid, 3f, and the methyl-substituted compounds 3k, 3l, and 3m.The fluoroderivative 3f was also effective as a seed-dressing agent in barley showing a 100percent protection against the fungus Fusarium nivale at 600 ppm.