598-25-4

Usage

Uses

Used in Rubber and Elastomer Industry:
3-Methyl-1,2-butadiene is used as a key monomer for the production of synthetic rubber and elastomers, such as butyl rubber and styrene-butadiene rubber. It provides essential properties like elasticity, durability, and resistance to heat and chemicals, making it a crucial component in the manufacturing of tires, hoses, seals, and other rubber products.
Used in Chemical Synthesis:
3-Methyl-1,2-butadiene serves as a precursor to various synthetic chemicals, including pharmaceuticals, agrochemicals, and specialty polymers. Its reactivity allows for the formation of complex molecules and compounds through processes like polymerization, addition, and substitution reactions.
Used in Occupational Settings with Precautions:
Although 3-Methyl-1,2-butadiene is classified as a potential occupational carcinogen, it is still used in certain industries where proper handling and storage precautions are taken to minimize exposure. Workers in these industries are trained to handle the compound safely and are provided with appropriate personal protective equipment to prevent respiratory and skin irritation, as well as potential long-term health effects.

InChI:InChI=1/C5H8/c1-4-5(2)3/h1H2,2-3H3

Upstream product

• 110-86-1 pyridine 
• 594-51-4 2,3-dibromo-2-methylbutane 
• 91-22-5 quinoline 
• 54462-66-7 1,4-dibromo-2-methyl-butane 
• 3017-70-7 2-bromo-3-methylbut-2-ene 
• 141-52-6 sodium ethanolate 
• 123-51-3 i-Amyl alcohol 
• 598-23-2 3-methyl-but-1-yne 
• 100860-89-7 1,2,2-trimethyl-3-methylene-cyclobutanecarbonitrile 
• 78-79-5 isoprene 
• 503-17-3 dimethylacetylene 
• 2229-07-4 methyl radical 
• 4143-42-4 (Z)-azomethane 
• 563-79-1 2,3-Dimethyl-2-butene 

Downstream Products

• 598-23-2 3-methyl-but-1-yne 
• 78-79-5 isoprene 
• 30758-34-0 2,2-dimethyl-3-methylene-cyclobutanecarbonitrile 
• 30758-35-1 3-isopropylidene-cyclobutanecarbonitrile 
• 624-96-4 1,3-dichloro-3-methylbutane 
• 865-58-7 3-bromo-3-methyl-but-1-ene 
• 61845-78-1 β-hydroxy-α-phenylhydrazono-isovaleraldehyde phenylhydrazone 
• 65354-74-7 1-Methyl-2-isopropylidencyclopropancarbonsaeureethylester 
• 65354-75-8 1,2,2-Trimethyl-3-methylene-cyclopropanecarboxylic acid ethyl ester 
• 65108-41-0 1,1-diphenyl-4-methylpent-2,3-dien-1-ol 
• 65108-40-9 2,2-Dimethyl-1,1-diphenyl-but-3-yn-1-ol 
• 65108-50-1 2-(3-Methyl-buta-1,2-dienyl)-cyclohexanol 
• 65108-26-1 2-p-Tolyl-3,3-dimethylmethylenecyclopropane 
• 24578-28-7 2-p-Tolyl-isopropylidenecyclopropane 

Relevant academic research and scientific papers

Silver-Catalyzed Three-Component 1,1-Aminoacylation of Homopropargylamines: α-Additions for Both Terminal Alkynes and Isocyanides

The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent a cyclizative Ugi–Joullié three-component reaction with isocyanides and carboxylic acids to afford functionalized N-acyl proline amides. High diastereoselectivity was observed in the synthesis of 4-alkoxy and 4,5-disubstituted proline derivatives. This work represents the first examples of a three-component cyclizative 1,1-aminoacylation of terminal alkynes.

Azo-coupling and reduction of cyclopropanediazonium ions in the reactions with polyhydroxyarenes and aminophenols

A reaction of cyclopropanediazonium ion, generated by decomposition of N-cyclopropyl-N-nitrosourea upon treatment with potassium or cesium carbonates, with various poly-hydroxyarenes and aminophenols has been studied. The reaction of azo-coupling proceeds with phloroglucinol, resorcinol, 3-methoxy- and 3-aminophenol giving rise to mono-, bis-, and tris(cyclopropylazo)arenes as the major products. Oxidizable phenols such as hydro-quinone, 2-methoxy-, 4-amino-, and 2-aminophenol give products of radical transformations with participation of cyclopropyl radical.

Palladium-mediated intramolecular C-N bond formation involving allyl substituted pyridines. Application to a novel strategy for the synthesis of the skeleton of berberinium derivatives

The insertion of allenes in the Pd-C σ bond of cyclopalladated pyridine derivatives afforded (η3-allyl) Pd complexes. The ideally located imine unit reacted selectively with the allyl functionality to yield a series of new cationic heterocycles. The process opened the route to a novel strategy for the synthesis of berberiniums, a class of molecules of pharmacological interest.

IMIDAZOLE DERIVATIVES AND MEDICINAL COMPOSITION THEREOF

An imidazole derivative represented by the following general formula (I), a salt thereof, a hydrate thereof or a solvate thereof. (Symbols in the formula have the following meanings. A: a lower alkylene group unsubstituted or substituted with a hydroxyl group, an aryl group, a lower alkylidene group or an oxo group (=O), X: a methylene group or a group represented by a formula -NR2-, R1: a hydrogen atom, a lower alkyl group or an aralkyl group, R2: a hydrogen atom or a lower alkyl group). The compounds have a steroid 17-20 lyase inhibiting activity and is useful in treating and preventing diseases such as prostate cancer, benign prostatic hyperplasia, breast cancer, mastopathy, hysteromyoma, endometriosis and the like.

Synthetic Microbial Chemistry, XXVI. - Absolute Configuration of (+)-Xanthocidin as Determined by the Synthesis of Its Enantiomers of Known Stereochemistry

The absolute configuration of the antibiotic (+)-xanthocidin (4,5-dihydroxy-5-isopropyl-4-methyl-2-methylene-3-oxocyclopentane-1-carboxylic acid, 1) was shown to be 1R,4S,5S by the synthesis of its enantiomers.Lipase AK (Amano) was used for the key resolution step, and the absolute configuration of the resolved intermediate (+)-16 was determined by X-ray analysis of its (1S)-camphanic ester (+)-20. - Key Words: Antibiotics / Asymmetric acylation / Lipases / Streptomyces xanthocidicus / Xanthocidin

Kinetic Investigation of the Reactions of Methyl Radicals with But-2-yne

The reactions of methyl radicals with but-2-yne have been studied in a greaseless static vessel in the temperature range 543...583 K.The methyl radicals were generated by thermolysis of azomethane (initial pressures 2.66 kPa and 3.19 kPa) in mixtures with the alkyne (initial pressures 0...7.8 kPa).The primary steps are H-abstractions producing 3-methylpropargyl radicals and additions to the triple bond forming trimethylvinyl radicals.Both radicals were stabilized by hydrogen abstraction from the parent compounds and by combination processes. The temperature dependence of the rate constant k2 for the addition reactio n can be expressed by the equation k2 = 108.65+/-0.20exp(-40300 +/- 1300)Jmol-1/RT M-1s-1 For the rate constant of hydrogen abstraction a value of k1 = 1.65 . 105 M-1s-1 at 573 K was estimated.Therefore the H-abstraction proceeds about two times faster than the addition reaction.

LA PHOTOCHIMIE DE L'ISOPRENE GAZEUX DANS LA REGION DE L'ULTRAVIOLET TRES LOINTAIN

Yields of various products have been measured in the photolysis of isopropene at 184.9, 213.8, and 228.8 nm and at pressures between 1 and 400 Torr.At each wavelength, the major process is the rupture of a C-CH3 bond, which leads to the formation of methyl and CH2=C=CHCH2.The quantum yield for this process is 0.83 +/- 0.08 at 213.8 nm.The lifetime of the intermediate involved in this process is 20 ns at 184.9 nm.Similar quantities of ethylene and C3H4 (φ >/= 0.050) and propene and acetylene (φ >/= 0.023) are measured.All the measured yields decrease with an increase in the pressure.In addition to these fragmentation processes, isomerization reactions are also observed, particularly at 228.8 nm.They lead to the formation of 1,3- and 1,4-pentadiene as well as 3-methyl-1,2-butadiene.The Stern-Volmer plot for each isomer different and each plot shows a strong negative curvature, indicating the coplexity of the reaction process.The lifetime of each intermediate is 2 ns or less.

Gas-phase Kinetics of Pyrolysis of 1,2-Dimethylcyclopropene

The pyrolysis of 1,2-dimethylcyclopropene has been studied in the temperature range 260-300 oC.The sole product is isoprene and material recovery was complete to within +/- 3.5percent.The reaction obeyed first-order kinetics and appeared to be homogeneous in a hexamethyldisilazane-conditioned Pyrex reactor, although surface catalysis could not be eliminated in a packed vessel.At 12 Torr (close to the high-pressure limit) rate constants fitted the Arrhenius equation (i).This study provides further evidence for the log(k/s-1) = (13.63 +/- 0.19) - (183.7 +/- 2.0kJmol-1)/RTln10 (i) deactivating effect of methyl substituents on cyclopropene isomerization.

Isomerisation des radicaux insatures. III. Radicaux α,α,β-, α,β,γ- et α,α,γ-trimethallyles

α,α,β-, α,β,γ-, and α,α,γ-trimethallyl radicals have been generated in the 147.0-nm gas phase photolysis of 2,3,3-trimethyl-1-butene, 3,4-dimethyl-2-pentene, and 2,4-dimethyl-2-pentene, respectively.Under these conditions, the majority of allyl radicals have an internal energy sufficient for further decomposition: they give rise to the formation of various 1,3-dienes and small amounts of either 1,2- or 2,3-dienes.An internal sigmatropic 1,2-hydrogen atom transfer process is part of the proposed mechanism to explain such products.Moreover, the fragmentation of the trimethyl substituted allyl radicals involves the split of one β(C-C) bond, then one β(C-H), and, to a lesser extent, one central C-CH3 bond.

Cyclizations of ω-Allenyl Radicals

Allenyl halides of structure (CH3)2C=C=CH(CH2)nX with n=3-6 have been prepared and reacted with n-Bu3SnH to generate the corresponding radicals for examination of the cyclization reactions of these reactive intermediates.The observed hydrocarbon products indicate that cyclization occurs for the n=3,4, and 5 radicals but not for the n=6 species.The n=3 radical isomerizes very efficiently by intramolecular addition to the sp carbon of the allene group.The n=5 intermediate reacts relatively slowly by attack at the near sp2 carbon.Both cyclization modes are observed for the n=4 species.The details of these radical cyclizations are discussed.