19550-88-0

Usage

Uses

Used in Organic Synthesis:
3,4-Dimethyl-3-hexene is used as a building block in organic synthesis for the production of various other compounds. Its unique structure allows it to be a valuable intermediate in the synthesis of complex organic molecules.
Used in Fragrance and Flavoring Industry:
3,4-Dimethyl-3-hexene is used as a chemical intermediate in the production of fragrances and flavorings. Its ability to impart specific scents and tastes makes it a valuable component in the creation of various consumer products.
Used in Plastics and Rubber Industry:
In the plastics and rubber industry, 3,4-dimethyl-3-hexene is utilized in the manufacture of various types of plastics and rubber. Its properties contribute to the development of materials with specific characteristics, such as flexibility, durability, and resistance to certain conditions.
Used in Pharmaceutical and Agrochemical Production:
3,4-Dimethyl-3-hexene also serves as a chemical intermediate in the production of pharmaceuticals and agrochemicals. Its role in the synthesis of these compounds highlights its importance in the development of new drugs and agricultural products.
Although 3,4-dimethyl-3-hexene is considered a relatively low-risk chemical with no known significant toxic effects, it is essential to follow proper handling and storage practices to ensure safety.

InChI:InChI=1/C8H16/c1-5-7(3)8(4)6-2/h5-6H2,1-4H3/b8-7+

Upstream product

• 19550-08-4 3,4-dimethyl-3-hexanol 
• 18265-39-9 (E,E)-3,4-dimethylhexa-2,4-diene 
• 2417-88-1 (E,Z)-3,4-dimethylhexa-2,4-diene 
• 928-49-4 hex-3-yne 
• 16356-05-1 2,3-diethyl-1,3-butadiene 
• 19550-87-9 cis-3,4-Dimethyl-3-hexene 
• 32388-99-1 (Z)-2-ethyl-3-methyl-penta-1,3-diene 
• 32388-98-0 (E)-2-ethyl-3-methyl-penta-1,3-diene 
• 117139-79-4 (3aS,7aR)-3a,7a-Dimethyl-2-phenyl-hexahydro-benzo[1,3]oxathiole 
• 77-78-1 dimethyl sulfate 
• 1185-02-0 3,4-dimethyl-3,4-hexanediol 
• 134881-81-5 r-3,t-5-diethyl-t-3,c-5-dimethyl-4-(methylimino)-3,5-dihydro-4H-pyrazole 
• 134881-82-6 r-3,c-5-diethyl-t-3,t-5-dimethyl-4-(methylimino)-3,5-dihydro-4H-pyrazole 
• 74097-35-1 r-3,t-5-Diethyl-3,5-dihydro-t-3,c-5-dimethyl-4H-pyrazol-4-on 

Downstream Products

• 118112-36-0 cis-3,5-dimethyl-3,5-diethyl-1,2,4-trioxolane 
• 118112-36-0 trans-3,5-dimethyl-3,5-diethyl-1,2,4-trioxolane 
• 123-72-8 butyraldehyde 

Relevant academic research and scientific papers

Thermal decomposition of meso- and d,l-3,4-diethyl-3,4-dimethyldiazetine N,N′-dioxide

Two stereochemically defined diazetine N,N′-dioxides were synthesized. Thermal decomposition at 200 °C resulted in 95% retention of stereochemistry in the alkene product relative to the starting stereochemistry. These results suggest that decomposition occurs via cleavage of the two C-N bonds either simultaneously or in rapid succession.

Stereoselective synthesis of vicinal dilithioalkenes by addition of lithium metal, to carbon-carbon triple bonds

The reaction of various cyclic and acyclic alkynes with lithium dust (2% sodium) to form vicinal dilithioalkenes has been investigated. Aliphatic alkynes, e.g. 3-hexyne (27a), exclusively afford the corresponding (E)-dilithioalkenes, insoluble solids which are stable at room temperature and allow access to a variety of tetrasubstituted olefins in acceptable yields.

Retention of Configuration in Two Photochemical Reactions: Formation of Cyclopropanimines by Extrusion of Molecular Nitrogen from Tetraalkyl-4-imino-1-pyrazolines and Cycloreversion of Cyclopropanimines to Isocyanides and Alkenes

The 1-pyrazolin-4-ones 7 and 9 and the pyrazolidin-4-one 13 are condensed with alkanamines 8 to produce the imines 3, 10 and 12 in high yields.Direct irradiation of 3 with 350-nm light at 90 deg C in deuterated hydrocarbon solvents affords the cyclopropanimines 4 in almost quantitative yields besides molecular nitrogen and small amounts of the imines 12 as a result of photoreduction.In acetone, the cyclopropanimine 4b isomerizes in part of the α,β-unsaturated imine 14.Direct irradiation of 3 with the unfiltered light of the high-pressure mercury lamp results in quantitative cycloreversion of the primary photoproducts 4 into the alkene 6 and an isocyanide 5.At low temperature (10 deg C), photolysis of 3 occurs much more slowly giving rise to photoextrusion of nitrogen (-> 4) and photoreduction (-> 12) to about the same extent. - Photolysis of the stereochemically labelled iminopyrazolines cis- and trans-10 (d. e. 99percent) at 90 deg C produces the cyclopropanimines cis- and trans-16 (d. e. 94percent) with high stereospecifity.The configuration of cis- and trans-16 is established by a comparison with the corresponding methylenecyclopropanes cis- and trans-19 and the quantitative and completely stereospecfic cycloreversion into methyl isocyanide (5a) and the 3,4-dimethyl-3-hexenes (Z)- and (E)-17 on irradiation with the unfiltered light of the mercury arc.The necessity of thermal activation for efficient nitrogen extrusion from the 1(n, ?*) state of 3 and 10 is indicative of a considerable energy barrier towards the transition into a dissociative state.At low temperature, hydrogen abstraction from the solvent or other molecules becomes important for the deactivation of the 1(n, ?*) state, in addition to decay and fluorescence.The stereospecific formation of cis- and trans-16 is interpreted in terms of diastereomeric bis-orthogonal azatrimethylenemethane diradicals as intermediates which retain the configuration on cyclization.The minor non-stereospecific path may involve mono-orthogonal azatrimethylenemethane diradicals.Thus, mechanisms that involve the same types of diradical intermediates can rationalize the photolysis of the iminopyrazolines 3, 10 and of the methylenetriazoline 1 as well.The cycloreversion of cis- and trans-16 into the alkenes (Z)- and (E)-17 and methyl isocyanide (5a) demonstrates for the first time that such photoreactions can be entirely stereospecific. Key Words: 4H-pyrazoles, 3,3,5,5-tetraalkyl-4-imino-3,5-dihydro- / cyclopropanes, 2,2,3,3-tetraalkyl-1-(alkylimino)- / alkanamines, 2,2,3,3-tetraalkylcyclopropylidene- / photolysis / extrusion of molecular nitrogen / photoreduction / configuration, retention of / azatrimethylenemethanes / cycloreversion, stereospecific, photochemical

Rotational Barriers of Strained Olefines

For the olefins 1-8 heats of formation have been derived from heats of hydrogenation and force-field calculations, respectively.From the kinetics of their geometrical isomerisation the corresponding values for the transition states were obtained.The rotational barriers, which vary by nearly 30 kcal/mol, can be described by a unique torsional potential (65.9 +/- 0.9 kcal/mol), which is independent of the degree of substitution, if a correction is made for the steric energy contribution in the ground- and transition-states. - Key Words: Rotational barriers / Olefins, strained / Heat of Hydrogenation / Force-field calculation

α-Thio-substituted Ketones as Precursors of Olefins via Oxathiolanes: Benzyl as Protecting Group

The feasibility of a regiospecific synthesis of tetrasubsituted olefins starting from protected α-thiol substituted ketones has been demonstrated by three examples.The approach (see Scheme) involves: S-activated alkylation (i), carbonyl addition of an organometallic reagent (ii), deprotection (iii), formation of a 2-phenyloxathiolane (iv), and base-promoted cycloelimination (v).An unsatisfactory feature is the lack of stereochemical control in step (ii).An attempt to telescope steps (iii) and (iv) by sequential Pummerer reaction-cyclisation at the β-benzylthio alcohol stage was unsuccessful.

Reduction of Alkyl-Substituted Butadienes by Sodium in Liquid Ammonia

Six alkyl-substituted butadienes have been reduced by sodium in liquid ammonia to determine the relative importance of 1,2 and 1,4 reduction pathways and, for the latter, whether the cisoid or transoid state of the butadiene preferentially is reduced.The 1,4 reduction predominates in all cases and especially so when a terminal methylene is present.For alkylbutadienes which have no steric constraints preventing the cisoid conformation, 1,4 reduction of the cisoid conformation is preferred.