19550-88-0

Basic information

• Product Name: 3,4-DIMETHYL-3-HEXENE
• Synonyms: 3,4-DIMETHYL-3-HEXENE;TRANS-3,4-DIMETHYL-3-HEXENE;(E)-3,4-dimethylhex-3-ene;3-Hexene, 3,4-dimethyl-, (E)-;(E)-3,4-Dimethyl-3-hexene;Einecs 243-158-8
• CAS NO: 19550-88-0
• Molecular Formula: C₈H₁₆
• Molecular Weight: 112.21
• EINECS: 243-158-8
• Mol File: 19550-88-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: -103.01°C (estimate)
• Boiling Point: 120.2°C (estimate)
• Flash Point: 15.6°C
• Appearance: /
• Density: 0.7430
• Vapor Pressure: 17.1mmHg at 25°C
• Refractive Index: 1.4280
• CAS DataBase Reference: 3,4-DIMETHYL-3-HEXENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHYL-3-HEXENE(19550-88-0)
• EPA Substance Registry System: 3,4-DIMETHYL-3-HEXENE(19550-88-0)

Safety Data

• Hazardous Substances Data: 19550-88-0(Hazardous Substances Data)

Usage

General Description

3,4-Dimethyl-3-hexene is a chemical compound with the molecular formula C8H16. It is a colorless liquid that is insoluble in water but soluble in organic solvents. 3,4-DIMETHYL-3-HEXENE is a member of the family of 3,4-dialkyl-3-hexenes and is commonly used in organic synthesis as a building block for the production of various other compounds. It is also used in the production of fragrances and flavorings, as well as in the manufacture of plastics and rubber. Additionally, 3,4-dimethyl-3-hexene has applications as a chemical intermediate in the production of pharmaceuticals and agrochemicals. It is considered to be a relatively low-risk chemical with no known significant toxic effects, but proper handling and storage practices should still be followed to ensure safety.

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

Upstream product

• 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 
• 19550-87-9 cis-3,4-Dimethyl-3-hexene 
• 21293-01-6 (Z,Z)-3,4-dimethylhexa-2,4-diene 
• 134881-82-6 r-3,c-5-diethyl-t-3,t-5-dimethyl-4-(methylimino)-3,5-dihydro-4H-pyrazole 
• 134881-81-5 r-3,t-5-diethyl-t-3,c-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 
• 74097-99-7 r-3,c-5-Diethyl-3,5-dihydro-t-3,t-5-dimethyl-4H-pyrazol-4-on 
• 1185-02-0 3,4-dimethyl-3,4-hexanediol 
• 117139-68-1 4-Benzylsulfanyl-3,4-dimethyl-hexan-3-ol 
• 117139-73-8 4-Mercapto-3,4-dimethyl-hexan-3-ol 
• 117139-61-4 2-(benzylthio)pentan-3-one 
• 117139-65-8 4-benzylthio-4-methylhexan-2-one 

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 articles and documents

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.

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

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.