55667-12-4

Basic information

• Product Name: 2-(BENZYLOXY)-4-(BROMOMETHYL)-1-METHOXYBENZENE
• Synonyms: 2-(BENZYLOXY)-4-(BROMOMETHYL)-1-METHOXYBENZENE;Benzene,4-(bromomethyl)-1-methoxy-2-(phenylmethoxy)-
• CAS NO: 55667-12-4
• Molecular Formula: C₁₅H₁₅BrO₂
• Molecular Weight: 307.19
• Mol File: 55667-12-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 94.5 °C
• Boiling Point: 390.68°C at 760 mmHg
• Flash Point: 167.644°C
• Appearance: /
• Density: 1.349g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 2-(BENZYLOXY)-4-(BROMOMETHYL)-1-METHOXYBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(BENZYLOXY)-4-(BROMOMETHYL)-1-METHOXYBENZENE(55667-12-4)
• EPA Substance Registry System: 2-(BENZYLOXY)-4-(BROMOMETHYL)-1-METHOXYBENZENE(55667-12-4)

Safety Data

• Hazardous Substances Data: 55667-12-4(Hazardous Substances Data)

Usage

Description

2-(Benzyloxy)-4-(bromomethyl)-1-methoxybenzene, also known as 4-(Bromomethyl)-2-methoxyphenyl benzyl ether, is a chemical compound with the molecular formula C15H15BrO2. It is a benzyl ether derivative with a bromomethyl group attached to a 1-methoxy-4-benzyloxybenzene. 2-(BENZYLOXY)-4-(BROMOMETHYL)-1-METHOXYBENZENE is characterized by its unique structure and reactivity, making it a valuable reagent for the modification and functionalization of organic molecules.

Uses

Used in Organic Synthesis:
2-(Benzyloxy)-4-(bromomethyl)-1-methoxybenzene is used as a versatile building block in organic synthesis for the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable reagent for the modification and functionalization of organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-(Benzyloxy)-4-(bromomethyl)-1-methoxybenzene is used as a key intermediate in the development of drugs. Its potential applications include the synthesis of new drug candidates and the modification of existing drugs to improve their efficacy and safety.
Used in Agrochemicals:
2-(Benzyloxy)-4-(bromomethyl)-1-methoxybenzene is also used in the development of agrochemicals, where it serves as a building block for the synthesis of various agrochemical compounds. Its unique properties make it suitable for the development of new pesticides, herbicides, and other agricultural chemicals.
Used in Materials Science:
In the field of materials science, 2-(Benzyloxy)-4-(bromomethyl)-1-methoxybenzene is used for the synthesis of new materials with specific properties. Its unique structure and reactivity make it a valuable component in the development of advanced materials for various applications, such as polymers, coatings, and adhesives.

InChI:InChI=1/C15H15BrO2/c1-17-14-8-7-13(10-16)9-15(14)18-11-12-5-3-2-4-6-12/h2-9H,10-11H2,1H3

Upstream product

• 1860-60-2 3-benzyloxy-4-methoxy-benzyl alcohol 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 621-59-0 isovanillin 
• 100-39-0 benzyl bromide 
• 4383-06-6 3-hydroxy-4-methoxybenzyl alcohol 
• 148235-40-9 3-benzyloxy-4-methoxybenzoic acid benzyl ester 

Downstream Products

• 909203-44-7 arctigenin 
• 89018-71-3 2-(3-Benzyloxy-4-methoxy-benzyl)-2-(3,4,5-trimethoxy-phenyl)-[1,3]dithiane 
• 93376-04-6 (+/-)-Prestegane B 
• 111959-15-0 (3R^*,4R^*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 105485-74-3 2-[4-methoxy-3-(phenylmethoxy)phenyl]-1-(3,4,5-trimethoxyphenyl)-ethanone 
• 206112-90-5 2-[2-(3-Benzyloxy-4-methoxy-benzyl)-[1,3]dithian-2-yl]-furan 
• 206112-98-3 3-[2-(3-Benzyloxy-4-methoxy-benzyl)-[1,3]dithian-2-yl]-furan 
• 206113-08-8 2-[2-(3-Benzyloxy-4-methoxy-benzyl)-[1,3]dithian-2-yl]-5-methyl-furan 
• 696664-22-9 2-(3'-benzyloxy-4'-methoxyphenethyl)quinoline 
• 536974-74-0 4-((3-(benzyloxy)-4-methoxybenzyl)(4H-1,2,4-triazol-4-yl)amino)benzonitrile 
• 537674-82-1 4-((3-hydroxy-4-methoxybenzyl)(4H-1,2,4-triazol-4-yl)amino)benzonitrile 
• 932033-64-2 4-(3-benzyloxy-4-methoxy-phenyl)-5-(3,4,5-trimethoxy-phenyl)-isoxazole 
• 932033-71-1 2-(3-benzyloxy-4-methoxy-phenyl)-3-dimethylamino-1-(3,4,5-trimethoxy-phenyl)-propenone 
• 696664-24-1 (-)-(S)-2-(3'-benzyloxy-4'-methoxyphenethyl)-1,2,3,4-tetrahydro-1-methylquinoline 

Relevant articles and documents

A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction

The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields.

Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction

An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis.

Dual aromatase-steroid sulfatase inhibitors

By introducting the steroid sulfatase inhibitory pharmacophore into aromatase inhibitor 1 (YM511), two series of single agent dual aromatase-sulfatase inhibitors (DASIs) were generated. The best DASIs in'vitro (JEG-3 cells) are 5, (IC50(aromatase) = 0.82 nM; IC 50(sulfatase) = 39 nM), and 14, (IC50(aromatase) = 0.77 nM; IC50(sulfatase) = 590 nM). X-ray crystallography of 5, and docking studies of selected compounds into an aromatase homology model and the steroid sulfatase crystal structure are presented. Both 5 and 14 inhibit aromatase and sulfatase in PMSG pretreated adult female Wistar rats potently 3 h after a single oral 10 mg/kg dose. Almost complete dual inhibition is observed for 5 but the levels were reduced to 85% (aromatase) and 72% (sulfatase) after 24 h. DASI 5 did not inhibit aldosterone synthesis. The development of a potent and selective DASI should allow the therapeutic potential of dual aromatase-sulfatase inhibition in hormone-dependent breast cancer to be assessed.