30364-38-6

Basic information

• Product Name: 1,1,6-TRIMETHYL-1,2-DIHYDRONAPHTHALENE
• Synonyms: naphthalene,1,2-dihydro-1,1,6-trimethyl-;TDN;1,1,6-TRIMETHYL-1,2-DIHYDRONAPHTHALENE;DEHYDRO-AR-IONENE;dehydro-ar-ionene,1,2-dihydro-1,1,6-trimethylnaphthalene,1,1,6-trimethyl-1,2-dihydronaphthalene;NAPHTHALENE,1,2-DIHYDRO-1,1,6;1,1,6-trimethyl-1,2-dihydronaphtalene;1,1,6-Trimethyl-1,2-dihydro-naphthalene (dehydro-ar-ionene)
• CAS NO: 30364-38-6
• Molecular Formula: C₁₃H₁₆
• Molecular Weight: 172.27
• EINECS: 250-150-8
• Mol File: 30364-38-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 242.2 °C at 760 mmHg
• Flash Point: 94.8 °C
• Appearance: /
• Density: 0.935 g/cm³
• Vapor Pressure: 0.0536mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1,1,6-TRIMETHYL-1,2-DIHYDRONAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,6-TRIMETHYL-1,2-DIHYDRONAPHTHALENE(30364-38-6)
• EPA Substance Registry System: 1,1,6-TRIMETHYL-1,2-DIHYDRONAPHTHALENE(30364-38-6)

Safety Data

• Hazardous Substances Data: 30364-38-6(Hazardous Substances Data)

Usage

Description

1,1,6-Trimethyl-1,2-dihydronaphthalene is an organic compound with a molecular structure characterized by a naphthalene ring, which is a fused pair of benzene rings, and three methyl groups attached to specific carbon atoms. 1,1,6-Trimethyl-1,2-dihydronaphthalene is known for its distinct chemical properties and is found in various natural and industrial settings.

Uses

Used in the Wine Industry:
1,1,6-Trimethyl-1,1-dihydronaphthalene is used as a chemical compound responsible for imparting a "kerosene note" or "petrol" aroma in aged Riesling wines. This characteristic aroma is often considered a desirable quality in certain types of aged wines, adding complexity and depth to their flavor profile.

Synthesis Reference(s)

Synthetic Communications, 20, p. 1853, 1990 DOI: 10.1080/00397919008053110

InChI:InChI=1/C13H16/c1-10-6-7-12-11(9-10)5-4-8-13(12,2)3/h4-7,9H,8H2,1-3H3

Synthetic route

1,2,3,4-tetrahydro-1,1,6-trimethylnaphthalene (475-03-6) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6)

Conditions	Yield
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane
With N-Bromosuccinimide; N,N-diethylaniline; dibenzoyl peroxide

(E)-β-ionone (79-77-6) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6) + 4-(2,3,6-trimethyl-phenyl)-butan-2-one (58720-40-4)

Conditions	Yield
With tetrachloromethane; N-Bromosuccinimide Erhitzen des Reaktionsprodukts mit ueberschuessigem N.N-Diaethyl-anilin auf Temperaturen oberhalb 100grad;

5,6-epoxy-trans-β-ionone (36340-49-5) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6)

Conditions	Yield
With formic acid

alpha-ionone (127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6)

Conditions	Yield
With N-Bromosuccinimide; Perbenzoic acid; N,N-diethylaniline 1.) CCl4, 70 deg C, 15 min, 2.) 120 deg C; Yield given. Multistep reaction;

1.1.3-trimethyl-2-<3-oxo-buten-(1)-yl>-cyclohexene-(2) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6) + 1.2.4-trimethyl-3-<3-oxo-butyl>-benzene

Conditions	Yield
With tetrachloromethane; N-Bromosuccinimide Kochen des Reaktionsprodukts mit N.N-Diaethyl-anilin;

tetrachloromethane (56-23-5) + N-Bromosuccinimide (128-08-5) + (E)-β-ionone (79-77-6) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6) + 1-<2.3.6-trimethyl-phenyl>-butanone-(3)

Conditions	Yield
Erhitzen des Reaktionsprodukts mit ueberschuessigem N.N-Diaethyl-anilin auf Temperaturen bei >100grad;

tetrachloromethane (56-23-5) + N-Bromosuccinimide (128-08-5) + alpha-ionone (127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6) + 1-<2.3.6-trimethyl-phenyl>-butanone-(3)

Conditions	Yield
Erhitzen des Reaktionsprodukts mit ueberschuessigem N.N-Diaethyl-anilin auf Temperaturen oberhalb 100grad;

(R)-α-ionone (24190-29-2) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: iodine 2: N-Bromosuccinimide; N,N-diethylaniline; dibenzoyl peroxide View Scheme

toluene (108-88-3) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6)

Conditions

Yield

Multi-step reaction with 6 steps 1: aluminum (III) chloride / Milling 2: hydrogenchloride / water / 4 h / 20 °C 3: trimethylsilyl trifluoromethanesulfonate / dichloromethane; hexane / 15 h / 0 - 20 °C / Inert atmosphere 4: trifluoroacetic acid; trifluoroacetic anhydride / 4 h / 0 - 20 °C 5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.5 h / 20 °C 6: calcium chloride; toluene-4-sulfonic acid / cyclohexane / 2 h / 50 °C View Scheme

3-(4-methylbenzoyl)propionic acid (4619-20-9) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6)

Conditions

Yield

Multi-step reaction with 5 steps 1: hydrogenchloride / water / 4 h / 20 °C 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane; hexane / 15 h / 0 - 20 °C / Inert atmosphere 3: trifluoroacetic acid; trifluoroacetic anhydride / 4 h / 0 - 20 °C 4: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.5 h / 20 °C 5: calcium chloride; toluene-4-sulfonic acid / cyclohexane / 2 h / 50 °C View Scheme

ethyl 4-oxo-4-(p-tolyl)butanoate (6942-61-6) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; hexane / 15 h / 0 - 20 °C / Inert atmosphere 2: trifluoroacetic acid; trifluoroacetic anhydride / 4 h / 0 - 20 °C 3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.5 h / 20 °C 4: calcium chloride; toluene-4-sulfonic acid / cyclohexane / 2 h / 50 °C View Scheme

4-methyl-4-p-tolyl-valeric acid (40663-79-4) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: trifluoroacetic acid; trifluoroacetic anhydride / 4 h / 0 - 20 °C 2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.5 h / 20 °C 3: calcium chloride; toluene-4-sulfonic acid / cyclohexane / 2 h / 50 °C View Scheme

4,4,7-trimethyl-3,4-dihydronaphthalen-1(2H)-one (70358-65-5) → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.5 h / 20 °C 2: calcium chloride; toluene-4-sulfonic acid / cyclohexane / 2 h / 50 °C View Scheme

C13H18O → 1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6)

Conditions	Yield
With toluene-4-sulfonic acid; calcium chloride In cyclohexane at 50℃; for 2h;

1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6) → 4,4,7-trimethyl-3,4-dihydronaphthalen-1(2H)-one (70358-65-5)

Conditions	Yield
With hydrogenchloride Erwaermen des Reaktionsprodukts mit CrO3 in wss. Essigsaeure;

1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6) → 4-(2-carboxy-1,1-dimethyl-ethyl)-isophthalic acid (855641-95-1)

Conditions	Yield
With sodium hydroxide; potassium permanganate

1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6) + KMnO4 + aqueous alkaline solution → 4-(2-carboxy-1,1-dimethyl-ethyl)-isophthalic acid (855641-95-1)

1,2-dihydro-1,1,6-trimethyl-naphthalene (30364-38-6) → 5,5-dimethyl-1,3-dioxo-1,3,4,5-tetrahydro-benz[c]oxepin-8-carboxylic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH solution; potassium permanganate 2: Sublimation im Hochvakuum View Scheme

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 127-41-3 alpha-ionone 
• 108-88-3 toluene 
• 4619-20-9 3-(4-methylbenzoyl)propionic acid 
• 6942-61-6 ethyl 4-oxo-4-(p-tolyl)butanoate 
• 40663-79-4 4-methyl-4-p-tolyl-valeric acid 
• 70358-65-5 4,4,7-trimethyl-3,4-dihydronaphthalen-1(2H)-one 
• 24190-29-2 (R)-α-ionone 
• 79-77-6 (E)-β-ionone 
• 36340-49-5 5,6-epoxy-trans-β-ionone 
• 475-03-6 1,2,3,4-tetrahydro-1,1,6-trimethylnaphthalene 

Downstream Products

• 855641-95-1 4-(2-carboxy-1,1-dimethyl-ethyl)-isophthalic acid 
• 70358-65-5 4,4,7-trimethyl-3,4-dihydronaphthalen-1(2H)-one 

Relevant articles and documents

Synthesis of Deuterium-Labeled 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) and Quantitative Determination of TDN and Isomeric Vitispiranes in Riesling Wines by a Stable-Isotope-Dilution Assay

The C13-norisoprenoid aroma compounds 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) and isomeric 2,10,10-trimethyl-6-methylene-1-oxaspiro[4.5]dec-7-enes, so-called vitispiranes, are considered to be biosynthetically related. They occur at higher concentrations in bottle-aged Riesling wines especially and are important contributors to the varietal aroma of Riesling wines. Because of the variation of the quantitative methods and data reported in the literature, a redetermination of concentration levels for both free and total TDN and isomeric vitispiranes, especially in German Riesling wines, was performed using a stable-isotope-dilution assay (SIDA). For this purpose, a novel six-step synthetic route to TDN and deuterium-labeled TDN was developed. A standardized sample preparation for TDN and vitispiranes and a rapid acid-hydrolysis method at genuine wine-pH conditions for the conversion of the precursors into TDN and vitispiranes were also developed. Automated HS-SPME was applied to 250 wine samples from two wine competitions, and analysis was performed by gas chromatography-mass spectrometry with selected-ion monitoring (GC-SIM-MS) as well as selected-reaction monitoring (GC-SRM-MS).

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.