403-33-8

Basic information

• Product Name: Methyl 4-fluorobenzoate
• Synonyms: RARECHEM AL BF 0076;Benzoic acid, 4-fluoro-, methyl ester;Benzoic acid, p-fluoro-, methyl ester;p-Fluorobenzoic acid, methyl ester;METHYL 4-FLUOROBENZOATE;METHYL 4-FLUOROBENZOIC ACID;METHYL P-FLUOROBENZOATE;ASISCHEM P32019
• CAS NO: 403-33-8
• Molecular Formula: C₈H₇FO₂
• Molecular Weight: 154.14
• EINECS: 206-956-7
• Product Categories: Aromatic Esters;Esters;Phenyls & Phenyl-Het;Acids & Esters;Fluorine Compounds;Phenyls & Phenyl-Het;C8 to C9;Carbonyl Compounds;Aryl Fluorinated Building Blocks;Building Blocks;C8 to C9;C8-C12;Carbonyl Compounds;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks
• Mol File: 403-33-8.mol
• Article Data: 169

Chemical Properties

• Melting Point: 4.5 °C
• Boiling Point: 90-92 °C20 mm Hg(lit.)
• Flash Point: 172 °F
• Appearance: /
• Density: 1.192 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.698mmHg at 25°C
• Refractive Index: n20/D 1.494(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 2085925
• CAS DataBase Reference: Methyl 4-fluorobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-fluorobenzoate(403-33-8)
• EPA Substance Registry System: Methyl 4-fluorobenzoate(403-33-8)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 22-37/38-41-36/38
• Safety Statements: 26-36/39-36
• WGK Germany: 2
• HazardClass: IRRITANT
• Hazardous Substances Data: 403-33-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 403-33-8 differently. You can refer to the following data:
1. 4-Fluorobenzoic Acid Methyl Ester, is an organic fluorinated building block used for the synthesis of various pharmaceutical compounds. It can be used for the preparation of Blonanserin (B595850).
2. Methyl 4-fluorobenzoate can be used in the synthesis of trisubstituted imidazole derivatives containing a 4-fluorophenyl group, a pyrimidine ring, and a CN- or CONH2-substituted benzyl moiety.

InChI:InChI=1/C8H10FN/c1-6(10)7-2-4-8(9)5-3-7/h2-6H,10H2,1H3

Upstream product

• 456-22-4 4-Fluorobenzoic acid 
• 67-56-1 methanol 
• 462-06-6 fluorobenzene 
• 201230-82-2 carbon monoxide 
• 122-01-0 4-chloro-benzoyl chloride 
• 619-45-4 4-methoxycarbonyl aniline 
• 459-57-4 4-fluorobenzaldehyde 
• 459-56-3 4-fluorobenzylic alcohol 
• 107-06-2 1,2-dichloro-ethane 
• 121629-15-0 1-chloro-1-fluoro-4-carbomethoxy-cyclohexane 
• 94-99-5 2,4-Dichlorobenzyl chloride 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 352-32-9 p-fluorotoluene 
• 705254-34-8 potassium trifluoro(4-(methoxycarbonyl)phenyl)borate 

Downstream Products

• 366-62-1 2-(4-fluoro-phenyl)-1-pyridin-2-yl-ethanone 
• 427-39-4 (4-fluorophenyl)diphenylmethanol 
• 101184-08-1 4-(1H-imidazol-1-yl)benzoic acid methyl ester 
• 1493-51-2 1,3-bis-(4-fluoro-phenyl)-1,3-propanedione 
• 38448-95-2 1-(4'-fluorophenyl)-3-phenylpropane-1,3-dione 
• 165901-26-8 2-(4-fluorophenyl)-4,5-dihydro-1H-imidazole 
• 459-56-3 4-fluorobenzylic alcohol 
• 256408-82-9 6-(4-fluorophenyl)-4-hydroxy-2H-pyran-2-one 
• 76481-34-0 3-(4'-fluorophenyl)pentan-3-ol 
• 861845-98-9 4-(3-amino-pyrrolidin-1-yl)-benzoic acid methyl ester 
• 868776-15-2 methyl 4-(4-methyl-1H-imidazol-1-yl)benzoate 
• 197172-67-1 N-(4-methoxycarbonylphenyl)-n-hexylamine 
• 354813-14-2 4-(4-methylpiperazin-1-yl)benzoic acid methyl ester 
• 220495-53-4 methyl 4-(1H-benzo[d]imidazol-1-yl)benzoate 

Relevant articles and documents

Absolute raman intensities of the carbonyl stretching band in para substituted methyl benzoates

The absolute Raman intensities of the vC=0 band of para-substituted methyl benzoates have been measured in CCl4 solution at different excitation frequencies. The intensities depend on a preresonance Raman effect (PRRE) and are correlated with theoretical expressions which describe the dispersion of the Raman intensity as a function of the excitation frequency and the experimental UV frequencies of the compounds, in particular the π→π* 1La band. The Raman intensities free from PRRE are deduced by extrapolating the experimental values to a zero excitation frequency. These extrapolated intensities depend on the electron-donating character of the substituents and on the extent of the conjugated system. The depolarization ratio of the vC=0 band in methyl benzoates increases with the excitation energies. This ratio is higher for the para-substituted derivatives.

Aerobic oxidative cleavage and esterification of C[dbnd]C bonds catalyzed by iron-based nanocatalyst

Functionalization of C[dbnd]C bonds by oxidative cleavage plays an important role in organic synthesis. However, the traditional functionalized products are mainly aldehydes, ketones and carboxylic acids, and the substrates are limited to examples of active aromatic olefins with very scarce inactive olefins. Herein we disclose an efficient protocol for the direct formation of esters by oxidative cleavage of C[dbnd]C bonds using heterogeneous iron nanocomposite catalyst supported on nitrogen-doped carbon materials with molecular oxygen and tert-butylhydroperoxide (TBHP) as the oxidants. The results show that molecular oxygen as the terminal oxidant is mainly responsible for the cleavage process, and that the auxiliary oxidant TBHP promotes the formation of the intermediate epoxide, thus increasing the selectivity of the product. The catalytic system has a wide range of substrate compatibility involving the challenging inactive aliphatic and long-chain alkyl aryl olefins. The catalyst was reused seven times with no loss in catalytic activity. Characterization and control experiments uncover that the core-shell Fe and Fe3C nanoparticles encapsulated by graphitic carbon play a predominant role in catalyzing the oxidative cleavage of olefins to esters. Preliminary mechanistic studies disclose that this process involves both free radical reactions and tandem sequential reactions.

Androgen receptor inhibitor and application thereof

The invention relates to the field of pharmacy, and particularly discloses an androgen receptor (AR) regulator combined with E3 ubiquitin ligase ligand or a salt thereof. Isomer and contains their pharmaceutical compositions.

Antibacterial and Antiviral Activities of 1,3,4-Oxadiazole Thioether 4H-Chromen-4-one Derivatives

Various 1,3,4-oxadiazole thioether 4H-chromen-4-one derivatives were conceived. The title compounds demonstrated striking inhibitory effects againstXac,Psa, andXoo. EC50data exhibited that A8 (19.7 μg/mL) had better antibacterial activity againstXoothan myricetin, BT, and TC. Simultaneously, the mechanism of action of A8 had been verified by SEM. The results of anti-tobacco mosaic virus indicated that A9 had the bestin vivoantiviral effect compared with ningnanmycin. From the data of MST, it could be seen that A9 (0.003 ± 0.001 μmol/L) exhibited a strong binding capacity, which was far superior to ningnanmycin (2.726 ± 1.301 μmol/L). This study shows that the 1,3,4-oxadiazole thioether 4H-chromen-4-one derivatives may become agricultural drugs with great potential.

GPR52 Antagonist Reduces Huntingtin Levels and Ameliorates Huntington's Disease-Related Phenotypes

GPR52 is an orphan G protein-coupled receptor (GPCR) that has been recently implicated as a potential drug target of Huntington's disease (HD), an incurable monogenic neurodegenerative disorder. In this research, we found that striatal knockdown of GPR52 reduces mHTT levels in adult HdhQ140 mice, validating GPR52 as an HD target. In addition, we discovered a highly potent and specific GPR52 antagonist Comp-43 with an IC50 value of 0.63 μM by a structure-activity relationship (SAR) study. Further studies showed that Comp-43 reduces mHTT levels by targeting GPR52 and promotes survival of mouse primary striatal neurons. Moreover, in vivo study showed that Comp-43 not only reduces mHTT levels but also rescues HD-related phenotypes in HdhQ140 mice. Taken together, our study confirms that inhibition of GPR52 is a promising strategy for HD therapy, and the GPR52 antagonist Comp-43 might serve as a lead compound for further investigation.

Ruthenium-Catalyzed Three-Component Alkylation: A Tandem Approach to the Synthesis of Nonsymmetric N,N-Dialkyl Acyl Hydrazides with Alcohols

The borrowing hydrogen strategy has been applied in the synthesis of nonsymmetric N,N-dialkylated acyl hydrazides via a tandem three-component reaction catalyzed by a phosphine free diaminocyclopentadienone ruthenium tricarbonyl complex. This strategy represents the first direct one-pot approach to nonsymmetric functionalized acyl hydrazides. Different aromatic acyl hydrazides underwent dialkylation with a variety of primary or secondary alcohols and methanol or ethanol as alkylating agents in mild reaction conditions and good yields. Deuterium labelling experiments suggested that the primary or secondary alcohol was the hydrogen source in this tandem process. DFT calculations show that the combination of the tandem mixed product cannot be perfectly explained neither structurally nor electronically, but might be dependent of the physical state of the aldehyde or ketone intermediate (gaz vs. liquid) at the reaction temperature. (Figure presented.).

Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids

The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.

Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst

The direct esterification of alcohols with non-noble metal-based catalytic systems faces great challenges. Here, we report a new chrome-based catalyst stabilized by a single pentaerythritol decorated Anderson-type polyoxometalate, [N(C4H9)4]3[CrMo6O18(OH)3C{(OCH2)3CH2OH}], which can realize the efficient transformation from alcohols to esters by H2O2oxidation in good yields and high selectivity without extra organic ligands. A variety of alcohols with different functionalities including some natural products and pharmaceutical intermediates are tolerated in this system. The chrome-based catalyst can be recycled several times and still keep the original configuration and catalytic activity. We also propose a reasonable catalytic mechanism and prove the potential for industrial applications.

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

Hydroxyl radical-mediated oxidative cleavage of CC bonds and further esterification reaction by heterogeneous semiconductor photocatalysis

A hydroxyl radical-mediated aerobic cleavage of alkenes and further sequence esterification reaction for the preparation of carbonyl compounds have been developed by using tubular carbon nitride (TCN) as a general heterogeneous photocatalyst under an oxygen atmosphere with visible light irradiation. This protocol has an excellent substrate scope and gives the desired aldehydes, ketones and esters in moderate to high yields. Importantly, this metal-free procedure employed photogenerated hydroxyl radicals in situ as green oxidation active species, avoiding the present additional initiators. The reaction could be carried out under solar light irradiation and was applicable to large-scale reactions. Furthermore, the recyclable TCN catalyst could be used several times without a significant loss of activities.