3642-21-5

Basic information

• Product Name: 3,4-dimethylidenehexa-1,5-diene
• Synonyms: 2,3-Divinylbutadiene
• CAS NO: 3642-21-5
• Molecular Formula: C₈H₁₀
• Molecular Weight: 106.165
• Mol File: 3642-21-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 138.1°C at 760 mmHg
• Flash Point: 19.9°C
• Density: 0.755g/cm³
• Vapor Pressure: 8.49mmHg at 25°C
• Refractive Index: 1.448
• CAS DataBase Reference: 3,4-dimethylidenehexa-1,5-diene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dimethylidenehexa-1,5-diene(3642-21-5)
• EPA Substance Registry System: 3,4-dimethylidenehexa-1,5-diene(3642-21-5)

Safety Data

• Hazardous Substances Data: 3642-21-5(Hazardous Substances Data)

Upstream product

• 93155-51-2 1,6-diacetoxy-3,4-bis-acetoxymethyl-hexane 
• 3642-10-2 1,2,6,7-Octatetraene 
• 32657-89-9 1,3-butadien-2-ylmagnesium chloride 
• 126-99-8 chloroprene 
• 102845-28-3 6,7-bis(4-tolylsulfonyloxymethyl)-3-thiabicyclo<3.2.0>heptane 3,3-dioxide 
• 102845-27-2 6,7-Dimethylene-3-thiabicyclo<3.2.0>heptane-3,3-dioxide 
• 42464-53-9 5,6-dimethylene-2,3-diaza-bicyclo[2.2.2]oct-2-ene 
• 40117-13-3 2,3-Dimethylenbicyclo<2.2.0>hexan 
• 106-99-0 buta-1,3-diene 
• 37343-83-2 2,3-dimethylenecyclohexa-1,3-diene 
• 42206-10-0 Bicyclo<4.2.0>octa-1,5-dien 
• 42206-11-1 1,2-Divinyl-1-cyclobuten 
• 69573-29-1 1,1'-Bicyclobutenyl 
• 65656-54-4 1'-acetoxy-bicyclobutyl-1-ene 

Downstream Products

• 583-48-2 3,4-dimethylhexane 
• 42206-11-1 1,2-Divinyl-1-cyclobuten 
• 42206-10-0 Bicyclo<4.2.0>octa-1,5-dien 

Relevant articles and documents

Practical synthesis and Diels-Alder chemistry of [4]dendralene

Spectacular new atom efficient domino cycloaddition sequences involving [4]dendralene, the simplest cross-conjugated tetraene, are reported. Up to eight stereocenters, three new rings, and six C-C bonds are generated in one synthetic operation. The site s

Molecular Structure of 3,4-Dimethylenehexa-1,5-diene ([4]Dendralene), C8H10, in the Gas Phase As Determined by Electron Diffraction and ab Initio Calculations

The molecular structure of 3,4-dimethylenehexa-1,5-diene ([4]dendralene), C8H10, has been determined in the gas phase. A single conformer with C2 symmetry, having two almost planar, anti butadiene groups orientated with a dihedral angle C(2)C(3)C(4)C(5) of 71.7(19) °, is detected by electron diffraction employing flexible restraints derived from ab initio computations. Other experimental structural parameters (rα/pm, ∠α/°) are: C(1)=C(2) 133.4(1), C(3)=C(7) (not in main chain) 134.0(1), C(2)-C(3) 147.4(2), C(3)-C(4) 149.6(3), C(1)C(2)C(3) 124.4(3), C(2)C(3)C(4) 119.2(5), C(4)C(3)C(7) 117.6(7), and C(7)C(3)C(2)C(1) -174.8(28). Ab initio computations at the MP2/6-311G* level predict that the vapor consists of ca. 90percent of the conformer found experimentally, the other 10percent comprising four other conformers.

First synthesis of the dendralene family of fundamental hydrocarbons

A neglected group of highly unsaturated hydrocarbons was how the dendralenes were described 16 years ago in a review in Angewandte Chemie. These compounds are neglected no more ! The hitherto unknown [5]-, [6]- (see scheme), and [8]dendralenes are synthesized by thermolysis of masked sulfolene derivatives which, in turn, are prepared by Stille coupling. The same approach offers an improved route to pure samples of [3]- and [4]dendralene, the full spectroscopic details of which are reported for the first time.