25244-30-8

Basic information

• Product Name: 4-(allyloxy)-1-bromobenzene
• Synonyms: 4-(allyloxy)-1-bromobenzene;(4-Bromophenyl)allyl ether;1-Bromo-4-(allyloxy)benzene;4-Bromophenylallyl ether;Allyl(4-bromophenyl) ether;(4-Bromophenyl) (2-propenyl) ether;Allyl p-bromophenyl ether;Benzene, 1-bromo-4-(2-propenyloxy)-
• CAS NO: 25244-30-8
• Molecular Formula: C₉H₉BrO
• Molecular Weight: 213.07116
• EINECS: 246-754-6
• Mol File: 25244-30-8.mol

Chemical Properties

• Boiling Point: 247.9°Cat760mmHg
• Flash Point: 109.5°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 0.0286mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: 4-(allyloxy)-1-bromobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(allyloxy)-1-bromobenzene(25244-30-8)
• EPA Substance Registry System: 4-(allyloxy)-1-bromobenzene(25244-30-8)

Safety Data

• Hazardous Substances Data: 25244-30-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-(allyloxy)-1-bromobenzene is used as a key intermediate in organic synthesis for introducing the allyloxy group into different molecules. Its reactivity and functional groups make it a valuable component in creating a wide range of organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(allyloxy)-1-bromobenzene is utilized as a reagent in the production of various organic compounds. Its unique structure allows for the development of new drugs and pharmaceutical agents, contributing to the advancement of medicinal chemistry.
Used in Chemical Industry:
4-(allyloxy)-1-bromobenzene is employed as a building block in the synthesis of functional materials and other organic compounds in the chemical industry. Its potential applications include the creation of specialty chemicals, polymers, and other materials with specific properties for various industrial uses.
Overall, 4-(allyloxy)-1-bromobenzene's diverse applications across different industries highlight its importance as a versatile chemical compound with significant potential in the fields of organic synthesis, pharmaceutical development, and chemical material production.

InChI:InChI=1/C9H9BrO/c1-2-7-11-9-5-3-8(10)4-6-9/h2-6H,1,7H2

Upstream product

• 106-41-2 4-bromo-phenol 
• 106-95-6 allyl bromide 
• 7003-65-8 sodium 4-bromophenoxide 
• 107-05-1 3-chloroprop-1-ene 
• 1746-13-0 allyl phenyl ether 
• 1927-95-3 4-bromophenyl acetate 
• 67963-68-2 t-butyldimethylsilyl-4-bromophenol 
• 110-00-9 furan 
• 556-56-9 allyl iodid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 205981-40-4 (Z)-1-bromo-4-(prop-1-en-1-yloxy)benzene 

Downstream Products

• 13997-74-5 2-allyl-4-bromophenol 
• 108244-33-3 (4-bromo-phenyl)-(2,3-dibromo-propyl)-ether 
• 112996-29-9 8-(4'-allyloxyphenyl)-8-hydroxy-1-oxaspiro<4.5>deca-6,9-diene-2-one 
• 98704-58-6 2-(4-(allyloxy)phenyl)ethanol 
• 205981-40-4 (Z)-1-bromo-4-(prop-1-en-1-yloxy)benzene 
• 63834-59-3 1-bromo-4-(2,3-dihydroxypropoxy)benzene 
• 319911-32-5 5-[(4-bromophenoxy)methyl]-3-methyl-4,5-dihydroisoxazole 
• 323575-92-4 9-(4-hydroxyphenyl)-9H-fluoren-9-ol 
• 360775-65-1 C₁₈H₁₈O₅ 
• 134671-56-0 2-(4-bromophenoxy)acetaldehyde 

Relevant articles and documents

Synthesis and characterization of N-phenyl pyrrole anchored to Fischer carbene complex through ring closing metathesis oxidative aromatization and various aryl substituted Fischer carbene complexes

Ring closing metathesis of pentacarbonyl[(ethoxy)(N,N-diallyl anilyl)carbene]tungsten(0) complex, [(CO)5W=C(OCH2CH 3)C6H4N(CH2CHCH2) 2], 1 leads to the formation of pentacarbonyl[(ethoxy)(N-phenyl 2,5-dihydro pyrrolyl)carbene]tungsten(0) complex, [(CO)5W=C(OCH 2CH3)C6H4N (CH2CHCH 2)2], 2 in good yield. Further, complex 2 undergoes oxidative aromatization to afford N-phenyl pyrrole anchored to alkoxy carbene, 3. In addition, a number of aryl substituted carbene complexes [(CO) 5W=C(OCH2CH3)C6H4R], 4-7 (4: R = OCH2CH3; 5: R = OCH2CH=CH2; 6: R = OCH=CHCH2CH2CH2CH2CH 3; 7: OC6H5Br) have been synthesized from the reaction of 1-(allyloxy)-4-bromobenzene with W(CO)6 in presence of various concentration of n-BuLi and Meerwein's salt. All the complexes have been isolated in moderate to good yields and have been characterized by 1H NMR, 13C NMR, IR, UV-vis spectroscopic techniques and the solid state structures of 1, 2 and 4 have been unequivocally established by X-ray diffraction analysis.

Design of new synthetic strategies to cyclophanes via ring-closing metathesis

A simple synthetic methodology to cyclophanes containing hydroxyl groups has been reported. The key steps involved here are: Grignard reaction, double Claisen rearrangement, and ring-closing metathesis. The strategy reported here is protecting group-free synthesis.

Preparation method 3 - phenoxybromopropane or analogue thereof

The invention discloses a preparation method of 3 -phenoxybromopropane or an analogue thereof, wherein 3 - phenoxybromopropane and an allyl compound thereof are obtained through substitution reaction and addition reaction so as to avoid the inconvenience of using gaseous hydrogen bromide, 2nd-step addition reaction is realized by using the brominated salt and the acid in situ, and the process is simple in operation. The condition is easy to control, the atom economy is good, the aspect of environmental impact is low pollution, zero emission accords with the current green chemical synthesis direction, and the cost is economic.

Aluminium chloride-potassium iodide-acetonitrile system: A mild reagent system for aromatic claisen rearrangement at ambient temperature

Claisen rearrangement is used as the standard methods for the generation of complex organic substance. It is one of the well-known methods for the introduction of carbon-carbon bond. We have developed a protocol using allyl aryl ether as a substrate and AlCl3-KI as a mild reagent system and acetonitrile (CH3CN) is taken as solvent at ambient temperature. The reagent system presented in this current work is found to be appropriate for Claisen rearrangement of several aromatic alcohols with excellent yields.

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.

Discovery and SAR of Natural-Product-Inspired RXR Agonists with Heterodimer Selectivity to PPARδ-RXR

A known natural product, magnaldehyde B, was identified as an agonist of retinoid X receptor (RXR) α. Magnaldehyde B was isolated from Magnolia obovata (Magnoliaceae) and synthesized along with more potent analogs for screening of their RXRα agonistic activities. Structural optimization of magnaldehyde B resulted in the development of a candidate molecule that displayed a 440-fold increase in potency. Receptor-ligand docking simulations indicated that this molecule has the highest affinity with the ligand binding domain of RXRα among the analogs synthesized in this study. Furthermore, the selective activation of the peroxisome proliferator-activated receptor (PPAR) δ-RXR heterodimer with a stronger efficacy compared to those of PPARα-RXR and PPARγ-RXR was achieved in luciferase reporter assays using the PPAR response element driven reporter (PPRE-Luc). The PPARδactivity of the molecule was significantly inhibited by the antagonists of both RXR and PPARδ, whereas the activity of GW501516 was not affected by the RXR antagonist. Furthermore, the molecule exhibited a particularly weak PPARδagonistic activity in reporter gene assays using the Gal4 hybrid system. The obtained data therefore suggest that the weak PPARδagonistic activity of the optimized molecule is synergistically enhanced by its own RXR agonistic activity, indicating the potent agonistic activity of the PPARδ-RXR heterodimer.

Concise and practical approach for the synthesis of honokiol, a neurotrophic agent

An improved method has been developed for the synthesis of honokiol using a readily available p-bromophenol as a precursor. The key step involved in this method is ortho-lithiation facilitated by methoxymethyl ether (MOM). Other important steps are ortho-allyl phenyl ether Claisen rearrangement and a Suzuki coupling for the construction of biaryls. This method does not require pre-functionalization of aromatic ring with bromide for the generation of arylboronic acid.

Highly regioselective O-allylation of phenol derivatives using MMZCu(I)Y catalyst

A clean and effective method has been developed for the regioselective of O-allylation of phenol derivatives using a recyclable Cu(I)-exchanged multi-size porous material. Ease of preparation of catalyst through simple solid-state exchange and its compatibility in producing excellent amount of O-allylated products and a plausible mechanistic pathway for the regioselectivity are highlighted. This reported procedure is not requiring any external stabilizing ligand for Cu(I) species and further purification of products.

Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis

The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.

Chemoselective Epoxidation of Allyloxybenzene by Hydrogen Peroxide Over MFI-Type Titanosilicate

The chemoselective synthesis of 2-(phenoxymethyl)oxirane from allyloxybenzene is achieved with over 90 % yield in a sustainable reaction system using titanium-substituted silicalite-1 (TS-1) as a catalyst, hydrogen peroxide (H2O2) as an oxidant, and a mixture of MeOH/MeCN as a solvent at 40 °C. No acid-catalyzed side reactions prompted by the Lewis acidity of the Ti active site in TS-1 are observed. The TS-1 catalyst can also promote the formation of oxiranes from various p-substituted allyloxybenzenes in good yields. The reaction mechanism is investigated through the reaction with other allyloxy compounds. The results, which are supported by DFT calculations, indicate that an active species of Ti peroxides formed from the reaction of TS-1 with H2O2 selectively oxidizes the allyloxybenzene to 2-(phenoxymethyl)oxirane.