3-Fluorotoluene

Base Information

• Chemical Name: 3-Fluorotoluene
• CAS No.: 352-70-5
• Molecular Formula: C7H7F
• Molecular Weight: 110.131
• Hs Code.: 29036990
• European Community (EC) Number: 206-524-8
• NSC Number: 8860
• UN Number: 2388
• UNII: F72W445DQ0
• DSSTox Substance ID: DTXSID2059855
• Nikkaji Number: J61.495E
• Wikidata: Q27277748
• Pharos Ligand ID: C7K1Z98NQLD6
• ChEMBL ID: CHEMBL345698
• Mol file: 352-70-5.mol

Synonyms:3-Fluorotoluene;1-Fluoro-3-methylbenzene;352-70-5;M-FLUOROTOLUENE;Benzene, 1-fluoro-3-methyl-;Toluene, m-fluoro-;1-Fluoro-3-methyl-benzene;1-Methyl-3-fluorobenzene;3-Fluorobenzyl radical;UNII-F72W445DQ0;CHEMBL345698;F72W445DQ0;NSC 8860;NSC-8860;EINECS 206-524-8;EC 206-524-8;2599-73-7;meta-Fluorotoluene;Benzyl, m-fluoro-;FTO (CHRIS Code);3-Fluorotoluene, 99%;Methyl, (3-fluorophenyl)-;SCHEMBL11881;M-FLUOROTOLUENE [MI];1-fluoranyl-3-methyl-benzene;DTXSID2059855;NSC8860;BDBM50008564;MFCD00000339;STL301893;AKOS000119943;AM86893;PS-11961;F0040;FT-0628938;EN300-19503;m-Fluorotoluene [UN2388] [Flammable liquid];A822704;J-504630;Q27277748;F0001-1021;Z104474044;3-(METHOXYCARBONYL)-1,2,2-TRIMETHYLCYCLOPENTANE-1-CARBOXYLICACID

Chemical Property of 3-Fluorotoluene

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 20.1mmHg at 25°C
• Melting Point: -87 °C
• Refractive Index: n20/D 1.469(lit.)
• Boiling Point: 118.2 °C at 760 mmHg
• Flash Point: 9.4 °C
• PSA: 0.00000
• Density: 1.001 g/cm³
• LogP: 2.13410
• Storage Temp.: Store below +30°C.
• Water Solubility.: immiscible
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 110.053178385
• Heavy Atom Count: 8
• Complexity: 70.8
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

3-Fluorotoluene >99.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: CC1=CC(=CC=C1)F
• General Description: 3-Fluorotoluene (m-fluorotoluene) is a key aromatic compound used as a model system to study substituent effects on methyl groups attached to benzene rings. It serves as a foundational molecule in investigations of electronic interactions between substituents (e.g., halogens, OMe, SCF3, CN) and the aromatic π-system, particularly through 19F NMR analysis. The study highlights its role in elucidating how substituents influence electron density distribution, with effects ranging from additive (e.g., CN) to saturation (e.g., halogens, SCF3) upon substitution. These insights advance the understanding of through-space and inductive effects in substituted toluenes.

Technology Process of 3-Fluorotoluene

There total 61 articles about 3-Fluorotoluene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

potassium trifluoro(3-methylphenyl)borate → m-Fluorotoluene (352-70-5)

Guidance literature:

With lithium hydroxide monohydrate; silver trifluoromethanesulfonate; Selectfluor; In ethyl acetate; at 55 ℃; Sealed tube;

DOI:10.1016/j.tet.2014.10.055

Reference yield: 43.0%

lead(IV) tetraacetate (546-67-8) + trifluoroborane diethyl ether (109-63-7) + toluene (108-88-3,15644-74-3,16713-13-6) → p-fluorotoluene (352-32-9) + 2-Fluorotoluene (95-52-3) + m-Fluorotoluene (352-70-5)

Guidance literature:

mercury(II) diacetate; Stirring of toluene in BF3*Et2O contg. Pb(OAc)4 and overnight at room temp.; GC anal. 13% recovery of toluene.;

DOI:10.1039/C39900001065

Reference yield: 13.9%

2-methylchlorobenzene (95-49-8) → p-fluorotoluene (352-32-9) + 2-Fluorotoluene (95-52-3) + m-Fluorotoluene (352-70-5)

Guidance literature:

With silver fluoride; at 350 ℃; Product distribution / selectivity; Gas phase;

upstream raw materials:

1-amino-3-methylbenzene

fluorobenzene

Methyl fluoride

Chlorodifluoromethane

Downstream raw materials:

2-(2-fluoro-4-methyl-benzoyl)-benzoic acid

1-tert-butyl-3-fluoro-5-methyl-benzene

5-Fluoro-2-nitrotoluene

2-fluoro-4-methyl-1-nitrobenzene

Refernces

Substituted methyl groups : Substituent effects

10.1016/S0040-4020(01)92493-7

The research investigates the electronic effects of various substituents on methyl groups attached to aromatic rings, specifically focusing on mono-, di-, and trisubstituted methyl groups (CH3, CH2X, and CX3, where X is F, Cl, Br, OMe, SCF3, and CN). The study aims to understand the interaction between the unshared p-electrons of these substituents and the p-system of the aromatic ring, using 19F NMR measurements on corresponding meta- and para-fluorotoluenes. Meta-Fluorotoluene and para-fluorotoluene play crucial roles as the core compounds for studying the substituent effects on methyl groups attached to aromatic rings. The 19F NMR measurements were conducted on these fluorotoluenes to determine the substituent parameters for the series of mono-, di-, and trisubstituted methyl groups. The meta-fluorotoluene (m-fluorotoluene) and para-fluorotoluene (p-fluorotoluene) were used as the base compounds to which various substituents (such as F, Cl, Br, OMe, SCF3, and CN) were introduced to form the substituted methyl groups. The chemical shifts observed in the NMR spectra provided insights into the electronic effects of these substituents on the methyl groups and the aromatic ring system. Specifically, the study found that the substituents influenced the electron density distribution in the aromatic ring, with notable effects observed for different types of substitutions. For instance, the cyano substituent exhibited an additive linear effect, while other substituents like F, Cl, Br, and SCF3 showed saturation effects after disubstitution, indicating through-space interactions with the p-system of the ring. These findings were critical in understanding the electronic interactions between the substituents and the aromatic ring, contributing to the broader knowledge of substituent effects in organic chemistry.