21388-92-1

Basic information

• Product Name: Benzenemethanol, 4-bromo-, acetate
• Synonyms: Benzenemethanol, 4-bromo-, acetate (9CI);Benzyl alcohol, p-bromo-, acetate (6CI,8CI);4-(Acetoxymethyl)bromobenzene
• CAS NO: 21388-92-1
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229.073
• Mol File: 21388-92-1.mol

Chemical Properties

• Boiling Point: 265.397 °C at 760 mmHg
• Flash Point: 114.309 °C
• Density: 1.446 g/cm³
• CAS DataBase Reference: Benzenemethanol, 4-bromo-, acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, 4-bromo-, acetate(21388-92-1)
• EPA Substance Registry System: Benzenemethanol, 4-bromo-, acetate(21388-92-1)

Safety Data

• Hazardous Substances Data: 21388-92-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Benzenemethanol, 4-bromo-, acetate is employed as a reagent in pharmaceutical research for the preparation of various organic compounds. Its unique structure and properties make it a valuable component in the synthesis of new pharmaceutical agents.
Used in Agrochemical Production:
Benzenemethanol, 4-bromo-, acetate is also used as a precursor in the production of agrochemicals, contributing to the development of new pesticides and other agricultural products that can enhance crop protection and yield.
Used in Organic Synthesis:
Benzenemethanol, 4-bromo-, acetate plays a crucial role in organic synthesis, where it serves as a building block for the creation of a wide range of organic compounds, including those with potential applications in various industries.

Upstream product

• 64-19-7 acetic acid 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 127-09-3 sodium acetate 
• 106-38-7 para-bromotoluene 
• 873-75-6 4-bromobenzenemethanol 
• 141-78-6 ethyl acetate 
• 86605-93-8 (4-bromobenzyloxy)trimethylsilane 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 216443-67-3 4-bromo-1-[(ethoxymethoxy)methyl]benzene 
• 130534-91-7 1-bromo-4-[(methoxymethyloxy)methyl]benzene 
• 108-05-4 vinyl acetate 
• 57477-93-7 hydrazone of p-bromobenzaldehyde 
• 4393-06-0 1-Phenyl-2-propen-1-ol 

Downstream Products

• 873-75-6 4-bromobenzenemethanol 
• 183994-38-9 4-(diethylphosphono)phenylmethyl acetate 
• 1301606-98-3 {2'-{1-(p-methoxybenzyl)-1H-tetrazol-5-yl}biphenyl-4-yl}methyl acetate 
• 145040-37-5 candesartan cilexetil 
• 114798-36-6 2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde 
• 676129-93-4 (S)-3-methyl-2-((2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl)-amino)-butyric acid benzyl ester 
• 1215298-35-3 methyl 2-ethoxy-1-({2′-[1-(phenylmethyl)-1H-tetrazol-5-yl][1,1′-biphenyl]-4-yl}methyl)-1H-benzimidazole-7-carboxylate 
• 1307853-85-5 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 1-({4-[2-(1-benzyl-1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-2-ethoxy-1H-1,3-benzodiazole-7-carboxylate 
• 114798-26-4 lorsartan 
• 1301606-95-0 {2'-[1-(o-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}-methanol 
• 1307853-55-9 benzyl N-({2'-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)-L-valinate 
• 1307853-40-2 5-[4'-(bromomethyl)biphenyl-2-yl]-1-(p-methoxybenzyl)-1H-tetrazole 
• 1307853-69-5 methyl 2-(N-tert-butoxycarbonyl-N-{(2'-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate 
• 1307853-71-9 methyl 2-[({2'-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate 

Relevant articles and documents

Fe3O4@PEG core/shell nanoparticles as magnetic nanocatalyst for acetylation of amines and alcohols using ultrasound irradiations under solvent-free conditions

Abstract: Ultrasound irradiation was used to prepare one-pot Fe3O4@PEG core/shell nanostructure for the first time. The morphology, structure, and physicochemical properties were specified by different analytical techniques including field emission scanning electron microscopy, Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy, X-ray powder diffraction, and vibrating sample magnetometer. For acetylation of phenols, alcohols, and amines, the synthesized Fe3O4@PEG core/shell nanoparticles were used as an efficient heterogeneous and green catalyst with acetic anhydride under sonication applying mild reaction conditions. Different electron-withdrawing and electron-donating substrates indicate a prominent yield of desired products with the merit of reusability of Fe3O4@PEG nanocatalyst and magnetic separation. Graphical Abstract: [Figure not available: see fulltext.].

Acylation of Phenols, Alcohols, Thiols, Amines and Aldehydes Using Sulfonic Acid Functionalized Hyper-Cross-Linked Poly(2-naphthol) as a Solid Acid Catalyst

Abstract: The hyper-cross-linked porous poly(2-naphthol) fabricated by the Friedel–Crafts alkylation of 2-naphthol has been functionalized with sulfonic acid to obtain a solid acid catalyst. The catalyst is applied for the protection of phenol, alcohols, thiols, amines and aldehydes with acetic anhydride at room temperature. The catalytic protection using the new solid acid is featured by achieving high yield at neat condition, needing no aqueous work-up and/or chromatographic separation, and showing excellent recycling efficiency, suggesting the potential of this sulfonated porous polymers as a new protection protocol in a wide range of sustainable chemical reactions. Graphical Abstract: [Figure not available: see fulltext.].

Enantioselective Synthesis of cis- A nd trans-Borocyclopropylmethanol: Simple Building Blocks to Access Heterocycle-Substituted Cyclopropylmethanols

An enantioselective and non-oxidative methodology was developed to obtain enantioenriched cyclopropyl boronates using a diethanolamine-promoted selective decomplexation of dioxaborolane. The non-oxidative decomplexation of the dioxaborolane ligand from the cyclopropylmethoxide species formed in the dioxaborolane-mediated Simmons-Smith cyclopropanation reaction provided the enantio?-enriched CIDA-based (CIDA = N-cyclohexyliminodiacetic acid) boro?-cyclopropane in 92% yield and 95.6:4.4 er. A robustness screen has shown diethanolamine to be compatible with esters, carbamates and N-heterocycles, providing a tool to access enantioenriched cyclopropanes carrying not only base-sensitive but oxidizable functional groups as well. Diethanolamine was found to be compatible with the modified zinco-cyclopropanation reaction of allyl alcohol to remove residual dioxaborolane from the corresponding cis-N-heterocycle cyclopropylmethanol, thereby leading to improved yields.

Bu 4 NI-Catalyzed C-C Bond Cleavage and Oxidative Esteri??cation of Allyl Alcohols with Toluene Derivatives

A novel oxidative esterification of 1-arylprop-2-en-1-ols with toluene derivatives catalyzed by tetrabutylammonium iodide (TBAI) is reported. The optimization of the reaction conditions illustrates that each of experiment parameters including the catalyst, solvent, and oxidant is significant for present oxidative functionalization. This metal-free protocol has a broad substrate scope including the halogen groups for further functionalization and enriches the reactivity profile of allyl alcohol and toluene derivatives. In addition, this protocol represents a new transformation of allyl alcohol involving C-C bond cleavage and C-O bond forming.

Preparation of Polydopamine Sulfamic Acid-Functionalized Silica Gel as Heterogeneous and Recyclable Nanocatalyst for Acetylation of Alcohols and Amines Under Solvent-Free Conditions

To fabricate SiO2/PDA–SO3H nanocatalyst, a suitable method is designed for the loading of sulfonic acid groups on the surface of polydopamine (PDA)-encapsulated SiO2 nanoparticles. To bridge the gap between heterogeneous and homogeneous catalysis, surface functionalization of silica gel is an elegant procedure. The morphology, structure, and physicochemical features were specified using different analytical techniques including field emission scanning electron microscopy (FESEM), Fourier transformed infrared spectroscopy (FT-IR), high resolution-transmission electron microscopy (HR-TEM), energy dispersive X-ray spectroscopy (EDS), wavelength-dispersive X-ray spectroscopy (WDX), X-ray photoelectron spectroscopy (XPS), and back titration. The SiO2/PDA–SO3H nanoparticles are efficient nanocatalysts for the acetylation of many alcohols, phenols, and amines with acetic anhydride under solvent-free conditions in good to excellent yields. Moreover, the reuse and recovery of the catalyst was shown seven times without detectible loss in activity. Graphical Abstract: [Figure not available: see fulltext.]

Crown ether functionalized magnetic hydroxyapatite as eco-friendly microvessel inorganic-organic hybrid nanocatalyst in nucleophilic substitution reactions: an approach to benzyl thiocyanate, cyanide, azide and acetate derivatives

In this paper, high catalytic activity of 4′,4″-diformyl dibenzo-18-crown-6 anchored onto the functionalized magnetite hydroxyapatite (γ-Fe2O3@HAp–Crown) as a new, versatile and magnetically recoverable catalyst, was prepared. It evaluated as phase-transfer catalyst and molecular host system for nucleophilic substitution reactions of benzyl halides with thiocyanate, cyanide, azide and acetate anions in water. No evidence for the formation of by-products was observed and the products obtained in pure form without further purification. The nanocomposite was easily removed from solution via application of a magnetic field, allowing straightforward recovery and reuse. The synthesized nanocomposite was characterized by several techniques such as FT-IR, TGA-DTG, EDX, XRD, BET, FE-SEM, TEM and VSM.

Reusable and efficient polyvinylpolypyrrolidone-supported triflic acid catalyst for acylation of alcohols, phenols, amines, and thiols under solvent-free conditions

Abstract: A triflic acid-functionalized polyvinylpolypyrrolidone was prepared and fully characterized by FT-IR, TGA, and SEM. This super acidic solid catalyst shows high catalytic activity for selective acylation of alcohols, phenols, amines, and thiols with anhydrides under solvent-free conditions at room temperature. In addition, this method features an easy to handle solid super acid catalyst and an operationally simple procedure, affording the desired acylated products in excellent yields. Graphical abstract: [Figure not available: see fulltext.].

Doping of copper (I) oxide onto a solid support as a recyclable catalyst for acetylation of amines/alcohols/phenols and synthesis of trisubstituted imidazole

A study of copper-mediated C-heteroatom especially C-N and C-O bond formations using simpler methodologies has been carried out. In the present work, acetylation of various substrates such as amines, phenols and alcohols; synthesis of 2,4,5-trisubstituted imidazole is done using simple and easily available starting materials. Copper (I) oxide was synthesized in situ by the reduction of Fehling's solution with glucose followed by its anchoring onto different supports like silica, HAP, basic alumina and cellulose. Comparison and contrasts between the reactivity of copper (I) oxide supported onto different supports for these reactions are made. The reactivity of copper (I) oxide seems to be largely dependent on the nature of support and the most active catalyst for a particular reaction was further characterized by different spectroscopic techniques such as FTIR, XRD, TGA, XPS, SEM, TEM and AAS. The catalysts were found to be stable, easily recyclable without any significant loss in activity. Graphical abstract: Applications of solid supported copper (I) oxides (where solid support is silica, HAP, cellulose and basic alumina) are studied for various organic transformations with special emphasis on C-N and C-O bond formation reactions.[Figure not available: see fulltext.]

Transesterification Reactions Catalyzed by a Recyclable Heterogeneous Zinc/Imidazole Catalyst

We report the development of a universal and recyclable heterogeneous zinc/imidazole catalyst. The catalyst is recoverable through simple filtration and can be reused at least five times, retaining its catalytic activity. Leached zinc species were not responsible for the observed catalysis based on the hot filtration test and ICP-MS analysis. The heterogeneous zinc catalyst also promotes chemoselective transesterification over amidation. (Figure presented.).

Synthesis and characterization of ionic liquid immobilized on magnetic nanoparticles: A recyclable heterogeneous organocatalyst for the acetylation of alcohols

Herein, we describe a simple and efficient procedure for the preparation of 3-((3-(trisilyloxy)propyl)propionamide)-1-methylimidazolium chloride ionic liquid supported on magnetic nanoparticle (TPPA-IL-Fe3O4). The structure of this magnetic ionic liquid is fully characterized by FT-IR, TGA, XRD, VSM, SEM, EDX and DLS techniques. TPPA-IL-Fe3O4 is employed as a catalyst for the acetylation of alcohols with acetic anhydride under mild and heterogeneous conditions at room temperature with good to excellent yields. The magnetic catalyst could be readily separate from the reaction media by simple magnetic decantation, and reused several times without significant loss of its catalytic activity.