1-Tetralone

changed changed 361749842 1-tetralone.png 120 Structural formula of 1-tetralone 1-Tetralone 3D ball.png 155 Ball-and-stick model of the 1-tetralone molecule 3,4-Dihydronaphthalen-1(2H)-one α-Tetralone; 1-Tetralone correct CAS 529-34-0 correct FDA 6VT52A15HY 10724 C1CC2=CC=CC=C2C(=O)C1 193373 changed chemspider 10273 208-460-6 1/C10H10O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6H,3,5,7H2 XHLHPRDBBAGVEG-UHFFFAOYAD changed chemspider 1S/C10H10O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6H,3,5,7H2 changed chemspider XHLHPRDBBAGVEG-UHFFFAOYSA-N 10 10 1 colorless liquid 1.099 g·cm−3 (25 °C)T19003 α-Tetralon 25. November 2017 2–7 °C 255–257 °CWilliam M. Haynes CRC Handbook of Chemistry and Physics, 97th Edition CRC Press Boca Raton, FL, U.S.A. 3–504 978-1-4987-5429-3 2016 113–116 °C (8 hPa) insolublehttp://www.tcichemicals.com/eshop/de/de/commodity/T0134 alpha-Tetralone 529-34-0 TCI Deutschland GmbH www.tcichemicals.com de 2017-12-17 soluble in organic solvents 2.7 Pa (20 °C) 1.5672 1-Tetralone https://pubchem.ncbi.nlm.nih.gov/compound/10724#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov en 07 Warning 302 264 270 301+317 330 501 1-Tetralone is a bicyclic aromatic hydrocarbon and a ketone. In terms of its structure, it can also be regarded as benzo-fused cyclohexanone. It is a colorless oil with a faint odor. It is used as starting material for agricultural and pharmaceutical agents. The carbon skeleton of 1-tetralone is found in natural products such as Aristelegone A (4,7-dimethyl-6-methoxy-1-tetralone) from the family of Aristolochiaceae used in traditional Chinese medicine.P.-C. Kuo Y.-C. Li T.-S. Wu EJTCM Chemical constituents and pharmacology of the Aristolochia species 2 4 249–266 2012 10.1016/S2225-4110(16)30111-0 24716140 3942903 free Preparation By oxidation of 1,2,3,4-tetrahydronaphthalene As already described in 1933 by Heinrich Hock, 1,2,3,4-tetrahydronaphthalene tends to autoxidize and gradually forms the 1-hydroperoxide with atmospheric oxygen.H. Hock W. Susemihl Ber. Dtsch. Chem. Ges. Autoxydation von Kohlenwasserstoffen: Über ein durch Autoxydation erhaltenes Tetrahydro-naphthalin-peroxyd (I. Mitteil.) 66 1 61–68 1933 German 10.1002/cber.19330660113 The heavy metal ion catalyzed air oxidation of 1,2,3,4-tetrahydronaphthalene with Cr3+S. Bhattacharjee Y.-R. Lee W.-S. Ahn Korean J. Chem. Eng. Oxidation of tetraline to 1-tetralone over CrAPO-5 34 3 701–705 2017 German 10.1007/s11814-016-0310-4 100124813 or Cu2+ in the liquid phase leads via the hydroperoxide to a mixture of the intermediate 1-tetralol and the final product 1-tetralone. US 4473711 Liquid-phase process for oxidation of tetralin 1984-09-25 1981-08-06 R.W. Coon Union Carbide Corp. 300px|center|Oxidation von Tetraloin zu 1-Tetralon The boiling points of the main component 1-tetralone (255-257 °C) and the minor component 1-tetralol (255 °C) are virtually identical, the latter is therefore removed by a chemical reaction.C.E. Olson, A.R. Bader α-Tetralone 1955 35 95 Org. Synth. 10.15227/orgsyn.035.0095 free By Friedel-Crafts reactions The starting compound 4-phenylbutanoic acid is accessible from 3-benzoylpropanoic acid via catalytic hydrogenation, using a palladium contact catalyst.10.15227/orgsyn.020.0094 free H.R. Snyder, F.X. Werber α-Tetralone 1940 20 94 Org. Synth. 3-Benzoylpropanoic acidL. F. Somerville, C. F. H. Allen Org. Synth. β-Benzoylpropionic acid 1933 13 12 10.15227/orgsyn.013.0012 free itself can be obtained by a Haworth reaction (a variant of the Friedel-Crafts reaction) from benzene and succinic anhydride. The intramolecular cyclization of 4-phenylbutanoic acid to 1-tetralone is catalyzed by polyphosphoric acid and methanesulfonic acid.V. Premasagar V.A. Palaniswamy E.J. Eisenbraun J. Org. Chem. Methanesulfonic acid catalyzed cyclization of 3-arylpropanoic and 4-arylbutanoic acids to 1-indanones and 1-tetralones 46 14 2974–2976 1981 10.1021/jo00325a028350px|center|Cyclisierung von 4-Phenylbuttersäure zu 1-Tetralon It has been described as a teaching experiment for chemistry lessons.M.S. Holden R.D. Crouch K.A. Barker J. Chem. Educ. Formation of α-tetralone by intramolecular Friedel-Crafts acylation 82 6 934–935 2005 10.1021/ed082p934 2005JChEd..82..934H 4-Phenylbutanoic acid can also be quantitatively converted into 1-tetralone by heating in the presence of a strong Lewis acid catalyst such as bismuth(III)bis(trifluoromethanesulfonyl)amideS. Antoniotti E. Dunach Chem. Commun. Facile preparation of metallic triflates and triflimidates by oxidative dissolution of metal powders 8 8 993–995 2008 10.1039/B717689A 18283360 [Bi(NTf2)3], which is relatively easily accessible.D.-M. Cui M. Kawamura S. Shimada T. Hayashi M. Tanaka Tetrahedron Lett. Synthesis of 1-tetralones by intramolecular Friedel-Crafts reaction of 4-arylbutyric acids using Lewis acid catalysts 44 21 4007–4010 2003 10.1016/S0040-4039(03)00855-4 The use of the acid chloride and tin(IV) chloride (SnCl4) allows significantly shorter reaction times than the Friedel-Crafts acylation with 4-phenylbutanoic acid. 500px|center|Synthese von 1-Tetralon über 4-Phenylbuttersäurechlorid 4-Phenylbutanoic acid chlorides with electron-donating groups can be cyclized to 1-tetralones under mild reaction conditions in yields greater than 90% using the strong hydrogen-bonding solvent hexafluoroisopropanol (HFIP).H. Motiwala R.H. Vekariya J. Aubé Org. Lett. Intramolecular Friedel-Crafts acylation reaction promoted by 1,1,1,3,3,3-hexafluoro-2-propanol 17 21 5484–5487 2015 German 10.1021/acs.orglett.5b02851 26496158 The AlCl3-catalyzed acylation of benzene with γ-butyrolactone produces 1-tetralone.350px|center|Synthesis of 1-tetralone using butyrolactone. Reactions 1-Tetralone can be reduced via a Birch reduction with lithium in liquid ammonia to 1,2,3,4-tetrahydronaphthalene.S.S. Hall S.D. Lipsky F.J. McEnroe A.P. Bartels J. Org. Chem. Lithium-ammonia Reduction of Aromatic Ketones to Aromatic Hydrocarbons 38 18 2588–2591 1971 10.1021/jo00817a004 The keto group can also be reduced to a secondary alcohol giving 1-tetralol, when a modified process is applied, using the addition of aqueous ammonium chloride solution after evaporation of the ammonia.Z. Marcinow P.W. Rabideau J. Org. Chem. Metal-Ammonia Reduction of α-Tetralone. Competition Between Ring Reduction, Carbonyl Reduction, and Dimer Formation 53 9 2117–2119 1988 10.1021/jo00244a054 500px|center|Reaktionen von 1-Tetralon mit Li in Ammoniak With calcium in liquid ammonia, 1-tetralone is reduced to 1-tetralol at −33 °C in 81% yield.J.R. Hwu Y.S. Wein Y.-J. Leu J. Org. Chem. Calcium metal in liquid ammonia for selective reduction of organic compounds 61 4 1493–1499 1996 German 10.1021/jo951219c The methylene group in α-position to the keto group is particularly reactive and can be converted with formaldehyde (in the form of the trimeric trioxane) to 2-methylene-1-tetralone in the presence of the trifluoroacetic acid salt of N-methylaniline with yields up to 91% . 500px|center|Synthese von 2-Methylen-1-tetralon aus 1-Tetralon The 2-methylene ketone is stable at temperatures below −5 °C, but fully polymerizes at room temperature within 12 hours.CV7P0332 J.-L. Gras Methylene ketones and aldehydes by simple, direct methylene transfer: 2-Methylene-1-oxo-1,2,3,4-tetrahydronaphthalene 1981 60 88 7 332 10.15227/orgsyn.060.0088 In the Pfitzinger reaction of 1-tetralone with isatin, a compound called tetrofan (3,4-dihydro-1,2-benzacridine-5-carboxylic acid) is formed.450px|center|Synthese von Tetrophan The reactivity of the α-methylene group is also exploited in the reaction of 1-tetralone with methanol at 270-290 °C, which produces via dehydrogenation and formation of the aromatic naphthalene ring system 2-methyl-1-naphthol in 66% yield.I. Yuranov L. Kiwi-Minsker A. Renken Appl. Catal. A One-step vapour-phase synthesis of 2-methyl-1-naphthol from 1-tetralone 226 1–2 193–198 2002 German 10.1016/S0926-860X(01)00902-4 http://infoscience.epfl.ch/record/84417 450px|center|Synthese von 2-Methyl-1-naphthol The oxime of 1-tetralone reacts with acetic anhydride leading to aromatization of the cycloalkanone ring. The resulting N-(1-naphthyl)acetamideM.S. Newman W.M. Hung J. Org. Chem. An improved aromatization of α-tetralone oximes to N-(1-naphthyl)acetamides 38 23 4073–4074 1973 German 10.1021/jo00987a029 has biological properties akin to those of 2-(1-Naphthyl)acetic acid as a synthetic auxin. 450px|center|Synthese von N-(1-Naphthyl)acetamid The tertiary alcohol formed in the Grignard reaction of 1-tetralone with phenylmagnesium bromide reacts with acetic anhydride upon elimination of water to 1-phenyl-3,4-dihydronaphthalene, which is dehydrated with elemental sulfur in an overall yield of about 45% to 1-phenylnaphthalene.CV3P0729 R. Weiss 1-Phenylnaphthalene 1944 24 84 3 729 10.15227/orgsyn.024.0084 350px|center|Synthese von 1-Phenylnaphthalin aus 1-Tetralon The ruthenium(II)-catalyzed arylation of 1-tetralone using phenyl boronic acid neopentyl glycol ester gives 8-phenyl-1-tetralone in up to 86% yield.V87P0209 K. Kitazawa, T. Kochi, F. Kakiuchi Ruthenium-catalyzed arylation of ortho C-H bond in an aromatic with an arylboronate: 8-Phenyl-1-tetralone 2009 87 209–217 11 1210–1216 10.15227/orgsyn.087.0209 550px|center|Synthese von 8-Phenyl-1-tetralon aus 1-Tetralon With 5-aminotetrazole and an aromatic aldehyde, 1-tetralone reacts in a multi-component reaction under microwave irradiation to form a four-membered heterocyclic ring system.G.P. Kantin M. Krasavin Chem. Heterocycl. Compd. Reaction of α-tetralone, 1H-tetrazol-5-amine, and aromatic aldehydes upon microwave irradiation – a convenient method for the synthesis of 5,6,7,12-tetrahydrobenzo[h]tetrazolo[5,1-b]quinazolines 52 11 918–922 2016 German 10.1007/s10593-017-1985-0 99144245 550px|center|Multikomponentenreaktion von 1-Tetralon mit Aminotetrazol und aromatischem Aldehyd Applications By far the most important application of 1-tetralone is in the synthesis of 1-naphthol by aromatization, e.g. upon contact with platinum catalysts at 200 to 450 °C. DE 2421745 Verfahren zur Herstellung von α-Naphthol durch katalytische Dehydrierung von α-Tetralon 1975-11-20 1974-05-06 K. Kudo, T. Ohmae, A. Uno Sumitomo Chemical Co., Ltd. 300px|center|Synthese von 1-Naphthol aus 1-Tetralon 1-Naphthol is the starting material for the insecticides carbaryl and the beta-blockers propranolol. A known application of 1-tetralone is in the synthesis of RAC-109 [17592-97-1] & RAC-421 [139085-58-8].((Castañer, J.)), ((Kolwas, J.)) Drugs of the Future RAC-109 and RAC-421 7 7 489 1982 http://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=1000241&p_IsPs=N 0377-8282 10.1358/dof.1982.007.07.1000241 subscription Tenthorey PA, Ronfeld RA, Feldman HS, Sandberg RV, McMaster PD, Smith ER New antiarrhythmic agents. 4. 1'-(Aminoalkyl)-1,2,3,4-tetrahydronaphthalene-1-spiro-3'-pyrrolidine-2',5'-dione derivatives Journal of Medicinal Chemistry 24 1 47–53 January 1981 7205874 10.1021/jm00133a011 Safety Toxicological studies were dermally performed with rabbits, with an LD50 of 2192 mg·kg−1 body weight being observed. References Category:Tetralones