475-03-6

Usage

Uses

Used in Flavor and Fragrance Industry:
1,1,6-Trimethyltetralin is used as an intermediate in the synthesis of 1,2-Dihydro-1,1,6-trimethyl-naphthalene, which is responsible for imparting a "kerosene note" or "petrol" aroma in aged Riesling wines. This unique aroma characteristic is highly valued in the production of certain types of wines, adding complexity and depth to their flavor profiles.
Used in Chemical Synthesis:
1,1,6-Trimethyltetralin is also utilized in the synthesis of other organic compounds, particularly those with aromatic properties. Its versatile molecular structure allows it to be a key component in the creation of various fragrances, flavorings, and other specialty chemicals. This makes it an important substance in the development of new products across multiple industries, including pharmaceuticals, cosmetics, and materials science.

InChI:InChI=1/C13H18/c1-10-6-7-12-11(9-10)5-4-8-13(12,2)3/h6-7,9H,4-5,8H2,1-3H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 79-77-6 (E)-β-ionone 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 127-41-3 alpha-ionone 
• 68238-72-2 4-(2,2-dimethyl-6-methylene-cyclohexylidene)-butan-2-one 
• 55728-27-3 1,1,6-trimethyl-1,2,3,7,8,8a-hexahydro-naphthalene 
• 87077-24-5 2-methyl-5-(m-tolyl)pentan-2-ol 
• 70358-65-5 4,4,7-trimethyl-3,4-dihydronaphthalen-1(2H)-one 
• 127-41-3 alpha-ionone 
• 25312-34-9 alpha-ionol 
• 5046-92-4 2,5,5,8a-tetramethyl-6,7,8,8a-tetrahydro-5H-chromene 
• 7553-56-2 iodine 
• 71-43-2 benzene 

Downstream Products

• 575-43-9 1,6-dimethylnaphthalene 
• 34557-54-5 methane 
• 541-31-1 3-methylbutanethiol 
• 30364-38-6 1,2-dihydro-1,1,6-trimethyl-naphthalene 
• 70358-65-5 4,4,7-trimethyl-3,4-dihydronaphthalen-1(2H)-one 
• 857806-41-8 4-(1-carboxy-1-methyl-ethyl)-isophthalic acid 
• 855641-95-1 4-(2-carboxy-1,1-dimethyl-ethyl)-isophthalic acid 
• 87756-40-9 1-(5,6,7,8-tetrahydro-3,8,8-trimethyl-2-naphthalenyl)ethanone 
• 169124-27-0 methyl 4-<(3,8,8-trimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl>benzoate 
• 857803-88-4 4-(2-carboxy-1,1-dimethyl-2-oxo-ethyl)-isophthalic acid 
• 149620-31-5 5,6,7,8-tetrahydro-3,8,8-trimethyl-1-naphthalenamine 
• 149620-39-3 1-(3-ethyl-5,6,7,8-tetrahydro-2,5,5-trimethyl-1-naphthalenyl)ethanone 

Relevant academic research and scientific papers

Ultrasound-Mediated Rearrangement of β-Ionone to 1,1,6-Trimethyl-1,2,3,4-Tetrahydronaphthalene.

The rearrangement of β-ionone in CHBr3 to 1,1,6-trimethyl-1,2,3,4-tetrahydronaphthalene was studied under sonochemical conditions.Trapping experiments showed ultrasound to induce the generation of bromine radicals from CHBr3 that abstracted hydrogen from the solvent to yield HBr.The hydrogen bromide catalyses the cyclisation of β-ionone.

Effects of sulphur nutrition during potato cultivation on the formation of acrylamide and aroma compounds during cooking

Lack of sulphur nutrition during potato cultivation has been shown to have profound effects on tuber composition, affecting in particular the concentrations of free asparagine, other amino acids and sugars. This is important because free asparagine and sugars react at high temperatures to form acrylamide, a suspect carcinogen. Free amino acids and sugars also form a variety of other compounds associated with colour and flavour. In this study the volatile aroma compounds formed in potato flour heated at 180 °C for 20 min were compared for three varieties of potato grown, with and without sulphur fertiliser. Approximately 50 compounds were quantified in the headspace extracts of the heated flour, of which over 40 were affected by sulphur fertilisation and/or variety. Many of the 41 compounds found at higher concentrations in the sulphur-deficient flour were Strecker aldehydes and compounds formed from their condensation, whereas only one compound, benzaldehyde, behaved in the same way as did acrylamide and was found at higher concentrations in the sulphur-sufficient flour. The reasons for these effects are discussed.

Synthesis and Herbicidal Activity of Substituted Tetrahydronaphthalenes: I

This paper reports the synthesis and the biological activity of substituted 6-alkyl-1,2,3,4-tetrahydro-1,1-dimethylnaphthalenes in which the substituents at the 5- and/or 7-position are varied with a multitude of functional groups. These compounds exhibited pre-emergent herbicidal activity which was a function of the electron-withdrawing ability and the size of the groups substituted at the 5- and/or 7-position. Nitro and/or nitrile groups at these positions tended to optimize activity.

Selective syntheses of substituted 6-alkyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalenes

β-ionone is cyclized to 1,1,6-trimethyl-1,2,3,4-tetrahydronaphthalene in 80-95% yield. Selective derivatization at the 5- and/or 7-positions of 6-alkyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalenes was achieved by nitration, acylation, and reduction.

STUDIES IN ACETALIZATION REACTIONS OF SOME TERPENES

The reactions of some terpenic ketones / aldehydes with alcohols were investigated in acidic medium.Some expected and unexpected products have been identified and possible mechanistic pathways leading to the products are discussed.

A Facile Synthesis of 1,1,6-Trimethyl 1,2-Dihydronaphtalene

An easy two-step preparation of 1,1,6-trimethyl 1,2-dihydronaphtalene from α-ionone via 1,1,6-trimethyl 1,2,3,4-tetrahydronaphtalene is described.

Rearrangement of β-Ionone to 1,1,6-Trimethyltetralin

Treatment of β-ionone (I) with p-toluenesulphonic acid in refluxing benzene or with iodine in refluxing carbon tetrachloride affords 1,1,6-trimethyltetralin (IV) in 80-90percent yield.A plausible mechanism for this cyclization is described.

Dehydration Studies of α- and β-Ionol. II With Toluene-p-sulfonic Acid

α-Ionol (2), when made to react with a 5percent solution of toluene-p-sulfonic acid at 20 deg C for 120 h, gave in 20percent yield one major dehydration product (1'E)-6-(buta-1',3'dienyl)-1,5,5-trimethylcyclohex-1-ene (4a) together with trace quantities of the (1'Z)-isomer (4b). β-Ionol (3) under similar conditions gave after 10 min in 84percent yield (6E,2'E)- and (6Z,2'E)-6-(but-2'-enylidene)-1,5,5-trimethylcyclohex-1-ene (1a) and (1b).Minor products from this reaction included the isomeric trienes (1c) and (1d).However, at 80 deg C the alcohols (2) and (3) gave in about 60percent yields complex mixtures of dehydration products which included 1-butyl-2,3,6-trimethylbenzene (7), 1-butyl-2,4,6-trimethylbenzene (8), 1,1,6-trimethyl-1,2,3,4-tetrahydronaphthalene (9), and 1,1,4,4-tetramethyl-2,3,4,5,6,7-hexahydro-1H-indene (10).Minor products obtained at 80 deg C included 1,1,4,4- tetramethyl-2,4,5,6-tetrahydro-1H-indene (11) and 1,4,4,7a-tetramethyl-5,6,7,7a-tetrahydro-4H-indene (12).The trienes (1a-d) and (4a,b) when reacted with toluene-p-sulfonic acid at 80 deg C also yielded the compounds (7), (8), (9) and (10).Reaction pathways are suggested for the formation of all identified compounds