312314-37-7

Basic information

• Product Name: 2-(benzyloxy)-5-fluorobenzaldehyde
• Synonyms: 2-(benzyloxy)-5-fluorobenzaldehyde;5-fluoro-2-phenylmethoxybenzaldehyde
• CAS NO: 312314-37-7
• Molecular Formula: C₁₄H₁₁FO₂
• Molecular Weight: 230.2343432
• Mol File: 312314-37-7.mol

Chemical Properties

• Boiling Point: 369.3±27.0 °C(Predicted)
• Appearance: /
• Density: 1.211±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-(benzyloxy)-5-fluorobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(benzyloxy)-5-fluorobenzaldehyde(312314-37-7)
• EPA Substance Registry System: 2-(benzyloxy)-5-fluorobenzaldehyde(312314-37-7)

Safety Data

• Hazardous Substances Data: 312314-37-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(benzyloxy)-5-fluorobenzaldehyde is utilized as an intermediate for the synthesis of bioactive compounds and new drug candidates. Its presence of a fluorine atom and benzyloxy group allows for the development of molecules with specific therapeutic properties, contributing to the advancement of novel pharmaceutical agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(benzyloxy)-5-fluorobenzaldehyde serves as a key intermediate in the production of active ingredients for pesticides and other agrochemicals. Its chemical structure facilitates the creation of compounds with targeted biological activity, enhancing crop protection and management strategies.
Used in Organic Synthesis:
2-(benzyloxy)-5-fluorobenzaldehyde is employed as a versatile building block in organic synthesis. Its functional groups enable a range of chemical reactions, allowing for the construction of complex organic molecules with potential applications in various fields, including materials science and specialty chemicals.

Upstream product

• 371-41-5 4-Fluorophenol 
• 347-54-6 5-fluoro-2-hydroxybenzaldehyde 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 312314-45-7 4-benzyloxy-7-fluoroindole 
• 312314-40-2 methyl 7-fluoro-4-phenylmethoxy-1H-indole-2-carboxylate 
• 312314-43-5 4-benzyloxy-7-fluoroindole-2-carboxylic acid 
• 312314-51-5 4-benzyloxy-7-fluoro-N,N-dimethyltryptamine 
• 312314-54-8 (4-benzyloxy-7-fluoro-1H-indol-3-yl)-oxo-acetyl chloride 
• 312314-48-0 N,N-diethyl-4-benzyloxy-7-fluoroindol-3-ylglyoxalylamide 

Relevant articles and documents

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Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines

A series of fluorinated analogues of the hallucinogenic tryptamines N,N-diethyltryptamine (DET), 4-hydroxy-N,N-dimethyltryptamine (4-OH-DMT, psilocin), and 5-methoxy-DMT was synthesized to investigate possible explanations for the inactivity of 6-fluoro-DET as a hallucinogen and to determine the effects of fluorination on the molecular recognition and activation of these compounds at serotonin receptor subtypes. The target compounds were evaluated using in vivo behavioral assays for hallucinogen-like and 5-HT(1A) agonist activity and in vitro radioligand competition assays for their affinity at 5-HT(2A), 5-HT(2C), and 5-HT(1A) receptor sites. Functional activity at the 5-HT(2A) receptor was determined for all compounds. In addition, for some compounds functional activity was determined at the 5-HT(1A) receptor. Hallucinogen-like activity, evaluated in the two-lever drug discrimination paradigm using LSD-trained rats, was attenuated or abolished for all of the fluorinated analogues. One of the tryptamines, 4-fluoro-5-methoxy-DMT (6), displayed high 5-HT(1A) agonist activity, with potency greater than that of the 5-HT(1A) agonist 8-OH-DPAT. The ED50 of 6 in the two-lever drug discrimination paradigm using rats trained to discriminate the 5-HT(1A) agonist LY293284 was 0.17μmol/kg, and the K(i) at [3H]8-OH-DPAT-labeled 5-HT(1A) receptors was 0.23 nM. The results indicate that fluorination of hallucinogenic tryptamines generally has little effect on 5-HT(2A/2C) receptor affinity or intrinsic activity. Affinity at the 5-HT(1A) receptor was reduced, however, in all but one example, and all of the compounds tested were full agonists but with reduced functional potency at this serotonin receptor subtype. The one notable exception was 4-fluoro-5-methoxy-DMT (6), which had markedly enhanced 5-HT(1A) receptor affinity and functional potency. Although it is generally considered that hallucinogenic activity results from 5-HT(2A) receptor activation, the present results suggest a possible role for involvement of the 5-HT(1A) receptor with tryptamines.