20668-26-2

Basic information

• Product Name: 3,6-dimethylquinoline
• Synonyms: 3,6-DIMETHYLQUINOLINE; quinoline, 3,6-dimethyl-
• CAS NO: 20668-26-2
• Molecular Formula: C₁₁H₁₁N
• Molecular Weight: 157.2117
• Mol File: 20668-26-2.mol

Chemical Properties

• Boiling Point: 270.5°C at 760 mmHg
• Flash Point: 114.4°C
• Density: 1.052g/cm³
• Vapor Pressure: 0.0113mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: 3,6-dimethylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-dimethylquinoline(20668-26-2)
• EPA Substance Registry System: 3,6-dimethylquinoline(20668-26-2)

Safety Data

• Hazardous Substances Data: 20668-26-2(Hazardous Substances Data)

Upstream product

• 78-85-3 2-methylpropenal 
• 106-49-0 p-toluidine 
• 10476-95-6 methallylidene diacetate 
• 105688-79-7 α-methyl-β-(p-toluidino)acrolein 
• 2163-42-0 2-methyl-1.3-propanediol 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 501-60-0 1,2-di(p-tolyl)diazene 
• 105688-77-5 2-methyl-1-(p-methylphenylamino)-3-(p-methylphenylimino)-1-propene 
• 50840-21-6 C₁₈H₂₀N₂*ClH 

Downstream Products

• 74212-55-8 6-methyl-3-phenacylquinoline 
• 53636-65-0 5-methyl-pyridine-2,3-dicarboxylic acid 
• 212568-45-1 (+)-(3R)-N-(4-bromobenzenesulfonyl)-1,2,3,4-tetrahydro-3,6-dimethylquinoline 
• 74212-56-9 1,6-dimethyl-3-phenacylquinolinium iodide 

Relevant articles and documents

Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N=N Bond Cleavage for the Regioselective Synthesis of Quinolines

A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.

Ruthenium-catalysed synthesis of 2- and 3-substituted quinolines from anilines and 1,3-diols

A straightforward synthesis of substituted quinolines is described by cyclocondensation of anilines with 1,3-diols. The reaction proceeds in mesitylene solution with catalytic amounts of RuCl3·xH 2O, PBu3 and MgBr2·OEt2. The transformation does not require any stoichiometric additives and only produces water and dihydrogen as byproducts. Anilines containing methyl, methoxy and chloro substituents as well as naphthylamines were shown to participate in the heterocyclisation. In the 1,3-diol a substituent was allowed in the 1- or the 2-position giving rise to 2- and 3-substituted quinolines, respectively. The best results were obtained with 2-alkyl substituted 1,3-diols to afford 3-alkylquinolines. The mechanism is believed to involve dehydrogenation of the 1,3-diol to the 3-hydroxyaldehyde which eliminates water to the corresponding α,β-unsaturated aldehyde. The latter then reacts with anilines in a similar fashion as observed in the Doebner-von Miller quinoline synthesis.

Chiral polymethine dyes. Part 6: Synthesis, absolute configuration, UV/Vis spectroscopic, and chiroptical properties of chiral tri- and pentamethinium cyanine dyes with 1,2,3,4-tetrahydro-3,6-dimethylquinolyl end groups

Starting with monochiral 1,2,3,4-tetrahydro-3,6-dimethyl quinoline 14a,b (Schemes 1 and 2), we have synthesized the new chiral, symmetrical and unsymmetrical, tri-and pentamethinium streptocyanine dyes 2a (Scheme 8), 4a (Scheme 5), and 5a,b (Scheme 4), resp. 9a (Scheme 6), 10a,b (Scheme 4), and 11a (Scheme 7) with one or two stereogenic centers in the two heterocyclic end groups. The absolute configuration of 14a,b, and thus the absolute configuration of all monochiral polymethinium dyes derived from 14a,b has been determined by a single-crystal X-ray analysis of its 4-bromobenzenesulfonyl derivative 17a (Scheme 1 and Fig. 1). The UV/Vis spectroscopic and chiroptical properties of the new polymethinium dyes have been studied for the first time and compared with that of similar streptocyanine dyes synthesized earlier (Tables 1 and 2) in order to find possible correlations between chiroptical properties and molecular structure.

PREPARATION OF 3-SUBSTITUTED QUINOLINES. II. PREPARATION AND CYCLODEHYDRATION OF α-ALKYL- AND α-PHENYL-β-ARYLAMINOACROLEIN DERIVATIVES

α-Methyl-β-arylaminoacroleins were prepared by the hydrolysis of 2-methyl-1-arylamino-3-arylimino-1-propene derivatives. α-Ethyl- and α-phenyl-β-arylaminoacroleins were prepared by the reaction of arylamine and 2-substituted 1,1,3,3-tetraethoxypropane derivatives. 3-Methyl, 3-ethyl- and 3-phenylquinolines were obtained from α-methyl-, α-ethyl and α-phenyl-β-arylaminoacroleins on heating with aluminum bromide in good yields. α-Bromo-β-anilinoacrolein (9b) was prepared by the reaction of β-anilinoacrolein (6b) and N-bromosuccinimide.Reaction of 9b and aluminum bromide did not afford 3-bromoquinoline.

Preparation of quinolines

Quinoline and substituted quinolines are prepared by reacting aniline or a substituted aniline with an α, β-monounsaturated aldehyde in a high-boiling mineral oil by a method in which the high-boiling mineral oil is replaced when it becomes enriched with by-products, and the said mineral oil enriched with by-products is removed.