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{{chembox |
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| verifiedrevid = 408448831 |
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| Name = Trifluorotoluene |
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| verifiedrevid = 444991574 |
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| ImageFileL1 = benzotrifluoride.png |
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| Name = Trifluorotoluene |
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| ImageSizeL1=160px |
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| ImageFileL1 = benzotrifluoride.png |
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| ImageFileR1 = Trifluorotoluene-3D-balls.png |
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| ImageFileR1 = Trifluorotoluene-3D-balls.png |
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| ImageSizeR1 = 120 |
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| PIN = (Trifluoromethyl)benzene |
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| OtherNames = Benzotrifluoride<br>α,α,α-Trifluorotoluene |
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| OtherNames = Benzotrifluoride (BTF)<br>α,α,α-Trifluorotoluene <br> CF3Ph<br> PhCF3 |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 98-08-8 |
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| CASNo = 98-08-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 49R6421K89 |
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| PubChem = 7368 |
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| EINECS = 202-635-0 |
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| InChI = 1S/C7H5F3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H |
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| InChIKey = GETTZEONDQJALK-UHFFFAOYSA-N |
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| SMILES = C1=CC=C(C=C1)C(F)(F)F |
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| ChemSpiderID = 7090 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>5</sub>CF<sub>3</sub> |
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| Formula = C<sub>6</sub>H<sub>5</sub>CF<sub>3</sub> |
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| MolarMass = 146.11 g/mol |
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| MolarMass = 146.11 g/mol |
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| Appearance = colorless liquid |
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| Appearance = colorless liquid |
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| Density = 1.19 g/mL at 20 °C |
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| Odor = aromatic |
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| Density = 1.19 g/mL at 20 °C |
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| MeltingPt = -29 °C |
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| MeltingPtC = -29.05 |
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| BoilingPt = 102 °C |
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| BoilingPtC = 103.46 |
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| Solubility = <0.1 g/100 mL at 21 °C |
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| SolubleOther = soluble in ], ], ], ] <br> miscible in ], ] |
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| RefractIndex = 1.41486 (13 °C) |
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|Section7={{Chembox Hazards |
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| FlashPtC = 12 |
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| NFPA-H = 0 | NFPA-F = 3 | NFPA-R = 0 |
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'''Trifluorotoluene''' is an ] with the formula of C<sub>6</sub>H<sub>5</sub>CF<sub>3</sub>. This colorless ] is used as a specialty ] in ] and an intermediate in the production of pesticides and pharmaceuticals.<ref name=Banks>Banks, R.E. Organofluorine Chemicals and their Industrial Applications, Ellis Horwood LTD, Chichester, 1979.</ref> |
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'''Trifluorotoluene''' is an ] with the formula of C<sub>6</sub>H<sub>5</sub>CF<sub>3</sub>. This colorless ] is used as a specialty ] in ] and an intermediate in the production of pesticides and pharmaceuticals.<ref name=Banks>Banks, R.E. Organofluorine Chemicals and their Industrial Applications, Ellis Horwood LTD, Chichester, 1979.</ref> |
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==Synthesis== |
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==Synthesis== |
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For small-scale laboratory preparations, trifluorotoluene is synthesized by coupling an aromatic halide and ] in the presence of a copper catalyst:<ref>Ogawa, Akiya; Tsuchii, Kaname “α,α,α-Trifluorotoluene” in Encyclopedia of Reagents for Organic Synthesis 2005, John Wiley and Sons. {{DOI| 10.1002/047084289X.rn00653}}</ref> |
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For small-scale laboratory preparations, trifluorotoluene is synthesized by coupling an aromatic halide and ] in the presence of a copper catalyst:<ref>Ogawa, Akiya; Tsuchii, Kaname "α,α,α-Trifluorotoluene" in Encyclopedia of Reagents for Organic Synthesis 2005, John Wiley and Sons. {{doi| 10.1002/047084289X.rn00653}}</ref> |
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:ArX + CF<sub>3</sub>I → Ar-CF<sub>3</sub> + CuXI (where X = I, Br, Cl) |
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:PhX + CF<sub>3</sub>I → PhCF<sub>3</sub> (where X = I, Br) |
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For large scale preparations using batch or continuous processes, ] is treated with ] under pressure.<ref name=Ullmann>Siegemund, Günter “Aromatic Compounds with Fluorinated Side-Chains” in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH. {{DOI|10.1002/14356007.a11_349}}.</ref> |
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Industrial production is done by reacting ] with ] in a pressurized reactor.<ref name=Ullmann>Siegemund, Günter "Aromatic Compounds with Fluorinated Side-Chains" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH. {{doi|10.1002/14356007.a11_349}}.</ref> |
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:C<sub>6</sub>H<sub>5</sub>CCl<sub>3</sub> + 3 HF → C<sub>6</sub>H<sub>5</sub>CF<sub>3</sub> + 3 HCl |
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:PhCCl<sub>3</sub> + 3 HF → PhCF<sub>3</sub> + 3 HCl |
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==Uses== |
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==Uses== |
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Trifluorotoluene has a variety of niche uses. |
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Trifluorotoluene has a variety of niche uses. |
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===Solvent alternative to dichloromethane=== |
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===Low toxicity alternative to dichloromethane=== |
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According to Ogawa and Curran, trifluorotoluene is similar to ] in standard ], ], and ] reactions.<ref>Ogawa, Akiya; Curran, Dennis P. “Benzotrifluoride: A Useful Alternative Solvent for Organic Reactions Currently Conducted in Dichloromethane and Related Solvents” Journal of Organic Chemistry 1997, volume 62, pp. 450-451. {{DOI|10.1021/jo9620324}}</ref> The ]s for dichloromethane and trifluorotoluene are 9.04 and 9.18, respectively, indicative similar solvating properties. Dipole moments compare less favorably: 1.89 and 2.86 D for dichloromethane and trifluorotoluene, respectively. Replacing dichloromethane is advantageous when conditions require higher boiling solvents since trifluorotoluene boils 62 °C higher than dichloromethane (b.p. 40 °C). |
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According to Ogawa and Curran, trifluorotoluene is similar to ] in standard ], ], and ] reactions.<ref>{{cite journal | last1 = Ogawa | first1 = Akiya | author-link2 = Dennis Patrick Curran | last2 = Curran | first2 = Dennis P. | year = 1997 | title = Benzotrifluoride: A Useful Alternative Solvent for Organic Reactions Currently Conducted in Dichloromethane and Related Solvents | journal = Journal of Organic Chemistry | volume = 62 | issue = 3| pages = 450–451 | doi = 10.1021/jo9620324 | pmid = 11671431 }}</ref> The ]s for dichloromethane and trifluorotoluene are 9.04 and 9.18, respectively, indicating similar solvating properties. Dipole moments compare less favorably: 1.89 and 2.86 D for dichloromethane and trifluorotoluene, respectively. Replacing dichloromethane is advantageous when conditions require higher boiling solvents, since trifluorotoluene boils at 103 °C it has a higher boiling point than dichloromethane, which has a boiling point of ~40 °C. |
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As a solvent, trifluorotoluene is useful in mild Lewis-acid catalyzed reactions, such as the Friedel-Crafts preparations. The most common catalyst, ] reacts with trifluorotoluene at room temperature; however, ] does not. |
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As a solvent, trifluorotoluene is useful in mild Lewis-acid catalyzed reactions, such as the Friedel-Crafts preparations. The most common catalyst, ] reacts with trifluorotoluene at ]; however, ] does not. |
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===Synthetic intermediate=== |
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===Synthetic intermediate=== |
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A second and perhaps more valuable use of trifluorotoluene is as a synthetic intermediate. A derivative of trifluorotoluene, ], is the precursor to the herbicide ].<ref name=Ullmann/> It is synthesized via ] followed by reduction to meta-H<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>CF<sub>3</sub>. This ] is then converted to the urea. |
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A second and perhaps more valuable use of trifluorotoluene is as a synthetic intermediate. A derivative of trifluorotoluene, ], is the precursor to the herbicide ].<ref name=Ullmann/> It is synthesized via ] followed by reduction to meta-H<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>CF<sub>3</sub>. This ] is then converted to the urea. |
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Flumetramide (6-morpholin-3-one), a skeletal muscle relaxant, is also prepared from trifluorotoluene.<ref name=Banks/> |
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Flumetramide (6-morpholin-3-one), a ] relaxant, is also prepared from trifluorotoluene.<ref name=Banks/> |
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==Analytics== |
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Trifluorotoluene appears in ] as a singlet at -63.2 ppm.<ref>{{cite journal|last1=Denmark|first1=Scott E.|last2=Smith|first2=Russell C.|title=Mechanistic Duality in Palladium-Catalyzed Cross-Coupling Reactions of Aryldimethylsilanolates. Intermediacy of an 8-Si-4 Arylpalladium(II) Silanolate (Supplementary Material, referenced as PhCF<sub>3</sub>) |journal=Journal of the American Chemical Society|date=3 February 2010|volume=132|issue=4|pages=1243–1245|doi=10.1021/ja907049y|pmc=2812642|pmid=20058920}}</ref> |
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==References== |
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==References== |
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