763-30-4

Usage

Uses

Used in Chemical Industry:
2-METHYL-1,4-PENTADIENE is used as a key chemical intermediate for the production of synthetic rubbers and resins, which are essential components in various industrial applications, including tires, hoses, and belts.
Used in Adhesive and Coating Industry:
2-METHYL-1,4-PENTADIENE is used as a raw material in the manufacturing of adhesives and coatings, providing properties such as adhesion, flexibility, and durability to the final products.
Used in Environmental Processes:
As a naturally occurring compound, 2-METHYL-1,4-PENTADIENE plays a role in the formation of atmospheric aerosols and acts as a precursor to the formation of ozone and other secondary pollutants, highlighting its significance in environmental processes.

InChI:InChI=1/C6H10/c1-4-5-6(2)3/h4H,1-2,5H2,3H3

Upstream product

• 4798-45-2 4-methyl-pent-1-en-3-ol 
• 624-97-5 2-methylpent-4-en-2-ol 
• 67845-37-8 acetic acid-(1,3-dimethyl-but-3-enyl ester) 
• 1826-67-1 vinyl magnesium bromide 
• 563-47-3 3-Chloro-2-methylpropene 
• 593-60-2 Vinyl bromide 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 16862-21-8 dimethyl-(2-methyl-pent-4-enyl)-amine 
• 34242-17-6 1,5-dimethyl-3-(4-methyl-penta-1,4-dienyl)-3-bora-bicyclo[3.3.1]non-6-ene 
• 115-11-7 isobutene 
• 74-86-2 acetylene 
• 929-12-4 5-Acetoxy-2-methyl-2-pentene 
• 10555-46-1 3-methylenecyclobutylmethyl bromide 
• 22600-85-7 (tetrahydro-5,5-dimethylfuran-3-yl)methanol 

Downstream Products

• 926-56-7 4-methyl-1,3-pentadiene 
• 1118-58-7 1,3-Dimethyl-1,3-butadien 
• 80698-49-3 1-((E)-2-Methyl-5-phenyl-pent-1-enyl)-piperidine 
• 82123-64-6 1,1-dimethyl-3-butenylphenylphosphinic chloride 
• 64-18-6 formic acid 
• 144-62-7 oxalic acid 
• 64-19-7 acetic acid 
• 591-24-2 3-Methylcyclohexanone 
• 107-83-5 2-Methylpentane 
• 1501-60-6 (Z)-2-methyl-1,3-pentadiene 
• 926-54-5 trans-2-methyl-1,3-pentadiene 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 2004-67-3 4-methyl-4-penten-2-ol 
• 76638-82-9 3,3,5-Trimethyl-[1,2]dioxolane 

Relevant academic research and scientific papers

3-Methylenecyclobutyl, Cyclopent-3-enyl, and 3-Methylenecyclobutylmethyl Radicals; Absence of Homoallylic Conjugation

The 3-methylenecyclobutyl radical and the cyclopent-3-enyl radicals show such small e.s.r. hyperfine splittings from the δ- and γ-hydrogens respectively that homoallylic conjugation can be ruled out.Semiempirical SCF-MO calculations indicated that the through-space interaction of the p-orbital at Cα with the ?-orbitals is negligible because they are >2 Angstroem apart.The 3-methylenecyclobutylmethyl radical rearranges by β-scission to give the 2-allylallyl radicals.The Arrhenius parameters of the rearrangement were determined by kinetic e.s.r. spectroscopy and by study of the reduction of 3-methylenecyclobutylmethyl bromide with tri-n-butyltin hydride.The resonance stabilisation of the rearranged radical causes no significant lowering of the activation energy for β-scission.

Synthesis, characterization, and rearrangements of [(1-methylcyclobutyl)methyl]platinum(II) complexes. Very mild ring-strain-induced carbon-carbon activation

Complexes trans-Pt(PMe3)2ClR, where R = (1-methylcyclobutyl)methyl (mcbm, 1), (adamantyl)methyl (adm, 8), 4-methylpentyl-1,1-d2 (9), and 4-methyl-4-pentenyl (10), and also PtCl(dmpe)(mcbm) [dmpe = 1,2-bis(dimethylphosphmo)ethane] (2) have been prepared. Pyrolysis of 1 or 2 at 140°C yields 2-methyl-1,4-pentadiene (12) as the only organic product, and trans-HPt(PMe3)2Cl (13) is isolated in high yield in the case of 1. Added PMe3 retards the pyrolysis of 1, leading to formation of [HPt(PMe3)3]Cl (14) and exhibiting kinetics consistent with initial PMe3 dissociation. Decomposition of 8 requires heating at 240°C for hours. Pyrolysis of 9 at 140°C forms 13 and 4-methyl-1-pentene-1,1-d2 with very little rearrangement of the deuterium label. Treatment of 1 with Ag+ in acetone at -80°C forms [trans-Pt(PMe3)2(mcbm)(acetone)]+ (15) that rearranges above -40°C to {cis-Pt(PMe3)2[1,4,5-n-(CH2) 3C(Me)=CH2]}+ (16) and above -10°C to a mixture of [Pt(PMe3)2(2-4-n-2-methylpentenyl)]+ (17a) and [Pt(PMe3)2(1-3-n-2-methylpentenyl)]+ (17b), which is isolated as the PF6- salt. Reaction of 1 with Ag+ in CD2Cl2 at -80 °C leads within 30 min to direct formation of 16, representing an extremely mild C-C activation step. Reaction of 10 with Ag+ at -80°C followed by warming to -20°C also generates 16. In contrast, 8 and Ag+ from [Pt(PMe3)2(adm)(acetone)]+ which is isolable at ambient temperature. Mechanistic implications of these reactions are discussed.

Gas-Phase Pyrolysis Kinetics of 5-Acetoxy-2-methylpent-2-ene

The kinetics of the gas-phase pyrolysis of 5-acetoxy-2-methylpent-2-ene has been measured over the temperature range 330-380 deg C and pressure range 53-210 torr.The reaction, in a static system seasoned with allyl bromide, and in the presence of propene inhibitor, is homogeneous, obeys a first-order law, and is unimolecular.The rate constants are given by the Arrhenius equation log k(s-1) = (13.21+/-0.14)-(199.6+/-1.7)kJ mol-1(2.303RT)-1.The presence of the (CH3)2C=CH group at the β-carbon atom of ethyl acetate does not provide anchimeric assistence in the elimination of this ester.A simultaneous effect of both steric acceleration and the allylic weakening of the β hydrogen appears to cause a slight rate enhancement of the Z=(CH3)2C=CH group relative to Z=CH2=CH group in the pyrolysis of ZCH2CH2OAc.

Etude des transformations catalytiques sur alumine de β-tetrahydrofurylmethanols

The products obtained by treatment of β-tetrahydrofurylmethanols at 310-330 deg C, using alumina as catalyst are studied.The nature of the products-furans, tetrahydrofurans, aliphatic and cyclic dienes-shows that beside the simple dehydration side reactions take place leading, as the case may be, to dehydrogenation, raduction, ring opening and fragmentation.