4190-06-1

Basic information

• Product Name: 1,5-DIMETHYL-1,4-CYCLOHEXADIENE
• Synonyms: 1,5-DIMETHYL-1,4-CYCLOHEXADIENE;2,4-Dimethyl-1,4-cyclohexadiene;1,5-dimethylcyclohexa-1,4-diene
• CAS NO: 4190-06-1
• Molecular Formula: C₈H₁₂
• Molecular Weight: 108.18
• Mol File: 4190-06-1.mol

Chemical Properties

• Boiling Point: 133.2°Cat760mmHg
• Flash Point: 16.8°C
• Appearance: /
• Density: 0.838g/cm³
• Vapor Pressure: 10.5mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: 1,5-DIMETHYL-1,4-CYCLOHEXADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIMETHYL-1,4-CYCLOHEXADIENE(4190-06-1)
• EPA Substance Registry System: 1,5-DIMETHYL-1,4-CYCLOHEXADIENE(4190-06-1)

Safety Data

• Hazardous Substances Data: 4190-06-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
1,5-DIMETHYL-1,4-CYCLOHEXADIENE is used as a building block for the synthesis of various organic compounds due to its reactive nature and ability to form multiple types of chemical bonds.

InChI:InChI=1/C8H12/c1-7-4-3-5-8(2)6-7/h4-5H,3,6H2,1-2H3

Upstream product

• 108-38-3 m-xylene 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 71-43-2 benzene 
• 95-47-6 o-xylene 

Downstream Products

• 114300-83-3 methyl (1α,5β,6β)-5-methoxy-2,6-dimethyl-2-cyclohexene-1-carboxylate 
• 114300-84-4 methyl (1α,4β,5β)-5-methoxy-2,4-dimethyl-2-cyclohexene-1-carboxylate 
• 108-38-3 m-xylene 
• 115436-60-7 2,4-dimethylbenzene-1,3,5-tricarboxaldehyde 
• 123-54-6 acetylacetone 
• 412021-38-6 1a,3-dimethyl-1a,2,5,5a-tetrahydrobenzo[b]oxirene 
• 412021-39-7 1a,2a-dimethyl perhydro oxireno[2',3':4,5]benzo[b]oxirene 
• 542-78-9 Malondialdehyde 
• 717888-68-1 (3R,5R)-5-Methoxy-3,5-dimethyl-[1,2]dioxolan-3-ol 
• 717888-68-1 (3S,5R)-5-Methoxy-3,5-dimethyl-[1,2]dioxolan-3-ol 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 638-04-0 cis-1,3-dimethylcyclohexane 
• 890651-76-0 (1S)-trans-1,3-dimethyl-cyclohexane 
• 69685-68-3 trans-1,3-dimethylcyclohexane 

Relevant articles and documents

Rhodium(I)-Catalyzed Enantioselective C(sp3)—H Functionalization via Carbene-Induced Asymmetric Intermolecular C—H Insertion?

Transition-metal-catalyzed C—H insertion of metal-carbene represents an excellent and powerful approach for C—H functionalization. However, despite remarkable advances in metal-carbene chemistry, transition metal catalysts that are capable of enantioselective intermolecular carbene C—H insertion are mainly constrained to dirhodium(II) and iridium(III)-based complexes. Herein, we disclose a new version of asymmetric carbene C—H insertion reaction with rhodium(I) catalyst. A highly enantioselective rhodium(I) complex-catalyzed C(sp3)—H functionalization of 1,4-cyclohexadienes with α-aryl-α-diazoacetates was successfully developed. By using chiral bicyclo[2.2.2]-octadiene as ligand, rhodium(I)-carbene-induced asymmetric intermolecular C—H insertion proceeds smoothly at room temperature, allowing access to a diverse variety of α-aryl-α-cyclohexadienyl acetates and gem-diaryl-containing acetates in good yields with good to excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the reaction was highlighted by facile synthesis of a novel cannabinoid CB1 receptor ligand. This method may offer a new opportunity for the development of therapeutically exploitable cannabinoid receptor type ligands in medicinal chemistry.

Sequential Birch reaction and asymmetric Ir-catalyzed hydrogenation as a route to chiral building blocks

A range of 1,2,4-trisubstituted cyclohexadienes obtained from the Birch reaction were hydrogenated asymmetrically to produce synthetically valuable chiral compounds in high enantio- and diastereoselectivity. The Royal Society of Chemistry.

Ozonolysis of 1,4-cyclohexadienes in the presence of methanol and acid. Mechanism and intermediates in the conversion of 1,4-cyclohexadiene derivatives to β-keto esters

Conditions for the preparation of β-keto esters directly from 1,4-cyclohexadiene derivatives are described. This procedure is a further step in the application of the synthetic methodology, which consists of the combination of Birch reduction of available benzene derivatives followed by ozonolysis. In this work, the syntheses of derivatives of dimethyl γ-keto-α-aminoadipate and dimethyl β-keto glutamate from the corresponding 1,4-cyclohexadiene derivatives are described. The latter compounds are prepared from phenylalanine and phenylglycine, respectively. The study of the ozonolysis of simple alkyl derivatives of 1,4-cyclohexadiene in the presence of methanol, both in the presence and absence of acid, helped to establish the mechanism of this reaction. The proximity of the two double bonds, which are cleaved, leads to the intermediate formation of 1,2-dioxolane derivatives that could be identified by NMR spectroscopy. It is shown that regardless of the regioselectivity of the cleavage of the primary ozonide, which is formed, all 1,2-dioxolane derivatives can lead to β-keto esters. This is due to the equilibrium between these dioxolanes in the presence of methanol and acid.

Desymmetrization of cyclohexa-1,4-dienes - A straightforward route to cyclic and acyclic polyhydroxylated systems

A straightforward route to polyols, amino polyols, polysubstituted lactols and lactones from readily available arenes has been devised. It uses a three- or four-step sequence involving a Birch reduction of the arene, followed by desymmetrization through d

Desymmetrisation and ring opening of cyclohexa-1,4-dienes. An access to highly functionalised cyclic and acyclic systems

Acyclic and cyclic synthons are readily available in three steps starting from substituted arenes. Birch reduction of the latter followed by desymmetrisation through Sharpless AD reaction then ozonolysis thus afforded five-membered ring lactols and acycli

A novel synthetic method for halogenated cyclohexane derivatives from m-xylene

The synthesis of halogenated cyclohexane derivatives 7-10 starting from m-xylene is described.

Composition of Mixtures of Hydrocarbons after BIRCH-Reduction of Substituted Benzenes and Acid Catalyzed Addition of Alcohols to Alkylsubstituted Cyclohexenes and Carbohexa-1,4-dienes

10 different benzene hydrocarbons 1, indane, tetraline, anisol and phenol are reduced by sodium in liquid ammonia in the presence of methanol to the BIRCH products 2.The product mixture compositions are determined through capillary GLC.On storage at +6 deg C some rearomatization of the 1,4-cyclohexadienes 2 occurs.Data of the 1H- and 13C-.n.m.r. spectra and also mass spectra of the BIRCH 1,4-dienes 2 are given.For comparison 4-alkoxycyclohexenes 4 and 1-alkoxy-1-methylcyclohexanes 8 are prepared and spectroscopically characterized.Acid-catalyzed addition of alcohols to the 1,4-cyclohexadienes systems is a slow process and gives the 4-alkoxy-4-alkylcyclohex-1-enes (4) only in moderate yields up to 30percent.Most of the products are dimers 5 and also oligomers 6 of the parent hydrocarbons 2.

Novel Dimerisation Reaction of Hydrocarbons with Cs-K-Na Alloy

m-Xylene undergoes dimerisation with Cs-K-Na alloy at -48 deg C to give 1,1',4,4'-tetrahydro-3,3',5,5'-tetramethylbiphenyl (3) while o- and p-xylenes do not follow such a reaction under identical conditions.

REVERSAL OF THE REGIOSELECTIVITY OF THE BIRCH REDUCTION OF XYLENES

The "Photo-Birch" reduction of o-, m-, and p-xylene, using NaBH4, 1,3-dicyanobenzene, and photolysis, gives 1,4-dienes as products.The regioselectivity of these reactions is greatly different from the normal Birch reduction.

A SAFE AND CONVENIENT NEW PROCEDURE FOR REDUCING AROMATIC COMPOUNDS TO BIRCH-TYPE PRODUCTS

Aromatic compounds can be reduced by a calcium-amine-t-butyl alcohol system to products which are identical to those obtained by a Birch reduction of the same substrates.