351-52-0

Basic information

• Product Name: 3-Fluoro-4-methoxybenzyl chloride
• Synonyms: 3-FLUORO-4-METHOXYBENZYL CHLORIDE;4-Chloromethyl-2-fluoro-1-methoxy-benzene;4-(Chloromethyl)-2-fluoroanisole, 4-(Chloromethyl)-2-fluorophenyl methyl ether, 4-(Chloromethyl)-2-fluoro-1-methoxybenzene;Benzene,4-(chloromethyl)-2-fluoro-1-methoxy-
• CAS NO: 351-52-0
• Molecular Formula: C₈H₈ClFO
• Molecular Weight: 174.6
• Product Categories: Fluorobenzene
• Mol File: 351-52-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 35-39℃
• Boiling Point: 62°C/0.2mmHg(lit.)
• Flash Point: 94.2 °C
• Appearance: /
• Density: 1.201 g/cm³
• Vapor Pressure: 0.091mmHg at 25°C
• Refractive Index: 1.499
• CAS DataBase Reference: 3-Fluoro-4-methoxybenzyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluoro-4-methoxybenzyl chloride(351-52-0)
• EPA Substance Registry System: 3-Fluoro-4-methoxybenzyl chloride(351-52-0)

Safety Data

• Hazard Codes: C
• RIDADR: UN 3261 8/PG II
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 351-52-0(Hazardous Substances Data)

Usage

General Description

3-Fluoro-4-methoxybenzyl chloride is a chemical compound with the molecular formula C8H8ClFO. It is a benzyl chloride derivative and contains a benzene ring substituted with a methoxy group at the 4 position and a fluorine atom at the 3 position. 3-Fluoro-4-methoxybenzyl chloride is primarily used in organic synthesis as a reagent for the introduction of the 4-methoxybenzyl group onto other molecules. It is also used in medicinal chemistry for the synthesis of pharmaceutical compounds. 3-Fluoro-4-methoxybenzyl chloride is a colorless to pale yellow liquid with a strong, pungent odor and is considered to be a hazardous substance, requiring proper handling and storage.

InChI:InChI=1/C8H8ClFO/c1-11-8-3-2-6(5-9)4-7(8)10/h2-4H,5H2,1H3

Upstream product

• 1427-34-5 1-chloro-1-(4-methoxyphenyl)-2,2,2-trifluoroethane 
• 109418-70-4 C₈H₈FO⁽¹⁺⁾ 
• 96047-32-4 3-fluoro-4-methoxybenzyl alcohol 
• 351-54-2 3-fluoro-p-anisaldehyde 
• 369-30-2 methyl 3-fluoro-4-methoxybenzoate 
• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 60-29-7 diethyl ether 
• 321-28-8 1-fluoro-2-methoxybenzene 

Downstream Products

• 587-43-9 diethyl-(3-fluoro-4-methoxy-benzyl)-amine 
• 1308881-82-4 1-(3'-fluoro-4'-methoxybenzyl)-5,6,7-trimethoxy-1H-indole 
• 421592-65-6 1,2-dihydro-4-[(3-fluoro-4-methoxyphenyl)-methyl]-5-methyl-3H-pyrazole-3-one 
• 1416250-69-5 tert-butyl 4-[6-bromo-1-(3-fluoro-4-methoxybenzyl)-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate 
• 1416250-70-8 tert-butyl 4-[1-(3-fluoro-4-methoxybenzyl)-2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate 
• 1005200-29-2 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[(3-fluoro-4-methoxybenzyl)sulfanyl]-1,3,4-oxadiazole 
• 369-97-1 3-fluoro-5-iodo-tyrosine 
• 392-27-8 3-bromo-5-fluoro-4-methoxy-phenethylamine 
• 500-59-4 4-(2-amino-ethyl)-2-bromo-6-fluoro-phenol 
• 458-40-2 2-(3-fluoro-4-methoxyphenyl)ethan-1-amine 
• 330-40-5 N-acetyl-3-fluoro-O-methyl-tyrosine ethyl ester 
• 350-29-8 3-fluoro-4-hydroxybenzoic acid 
• 403-90-7 3-fluoro-DL-tyrosine 
• 403-20-3 3-fluoro-p-anisic acid 

Relevant articles and documents

Design, synthesis, and in vitro/vivo anticancer activity of 4-substituted 7-(3-fluoro-4-methoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidines

In this paper, we report the design and synthesis of 4-substituted 7-(3-fluoro-4-methoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidines of scaffold 6 as anticancer agents. A total of 19 derivatives of scaffold 6 bearing a C-4 alkoxy, dialkylamino, alkyl, vinyl, or phenyl substituent were synthesized and evaluated. Among them, compound 6q having a C-4 ethyl group and a benzylic methyl group showed the most potent in vitro anticancer activity, inhibiting the proliferation of Hela, MDA-MB-231, and MDA-MB-426 cancer cells at submicromolar concentrations (GI50: 0.11–0.58 μM). Compound 6q arrested the cell cycle of MDA-MB-231 at G2/M phase, and showed in vivo activity on nude mice bearing MDA-MB-231 xenografts. Compound 6q has served as an anticancer lead for further optimization.

Gas-phase substituent effects in highly electron-deficient systems. II. stabilities of 1-aryl-2,2,2-trifluoroethyl cations based on chloride-transfer equilibria

The relative stabilities of 1-aryl-2,2,2-trifluoroethyl cations were determined based on the chloride ion-transfer equilibria in the gas phase. An application of the Yukawa-Tsuno equation to this substituent effect on the equilibrium constants gave a remarkably larger r+ of 1.53 and a ρ of-10.6, supporting our previous conclusion that the highly electron-deficient benzylic carbocation systems are characterized by extremely high resonance demands. This r+ value, furthermore, conformed a linear relationship between the r+ value and the relative stability of the unsubstituted member of the respective benzylic carbocations, clearly demonstrating a continuous spectrum of varying resonance demands characteristic of the stabilities of carbocations. The π-delocalization of the positive charge into the aryl π-system increases with the destabilization of a carbocation by the α-substituent(s) linked to the central carbon. In addition, the r + value of 1.53 for 1-aryl-2,2,2-trifluoroethyl cations was found to be in complete agreement with that for the solvolysis of 1-aryl-2,2,2- trifluoroethyl tosylates in 80% aq acetone. This reveals that the r+ value observed for this solvolysis must be the intrinsic resonance demand of a highly electron-deficient cationic transition state in the SN 1 ionizing process. The identity of the r+ value was consistent with our previous observation for other benzylic carbocation systems, indicating that the degree of the π-delocalization of the positive charge is identical between the cationic transition state and an intermediate cation for all benzylic systems, which cover a wide range of reactivity and stability of the carbocation. This leads us to the conclusion that the geometry of the transition state in the ionizing process of the SN1 solvolysis, which is a highly endothermic reaction, closely resembles the high-energy product, an intermediate cation.

USE OF QSAR IN DESIGN OF ANTIINFLAMMATORY FLUORINATED ARYLALKANOIC ACIDS

A series of 3-fluoro-4-alkoxyphenylalkanoic acids III was synthetized and their antiinflammatory activity and fibrinolytic capacity was evaluated.The suitable fluorinated derivative with better pharmacological profile than 3-chloro-4-benzyloxyphenylacetic acid (benzofenac) was selected.Experimental, biological activities of acids III were compared with those calculated by introducing the physico-chemical parameters into the formerly derived regression equations.Good coincidence was found out, as well as similarity of the regression equations derived for the originalseries of acids extended by the acids III.Lipophilicity of the acids under study was evaluated by partition thin-layer chromatography; the values of log P of benzyloxy derivatives IIIc-IIIf were lower than tabulated values - probably due to the intramolecular hydrophobic interactions of aromatic nuclei.