513-81-5

Basic information

• Product Name: 2,3-Dimethyl-1,3-butadiene
• Synonyms: 2,3-Dimethyl-1,3-butadiene; 2,3-dimethylbuta-1,3-diene
• CAS NO: 513-81-5
• Molecular Formula: C₆H₁₀
• Molecular Weight: 82.14
• EINECS: 208-172-0
• Mol File: 513-81-5.mol
• Article Data: 83

Chemical Properties

• Boiling Point: 68.8°Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 0.699g/cm³
• Vapor Pressure: 150mmHg at 25°C
• Refractive Index: 1.408
• CAS DataBase Reference: 2,3-Dimethyl-1,3-butadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethyl-1,3-butadiene(513-81-5)
• EPA Substance Registry System: 2,3-Dimethyl-1,3-butadiene(513-81-5)

Safety Data

• Statements: R11:Highly flammable.; R65:Harmful: may cause lung damage if swallowed.
• Safety Statements: S16:Keep away from sources of ignition - No smoking.; S23:Do not inhale gas/fumes/vapour/spray.; S33:Take precauti
• Hazardous Substances Data: 513-81-5(Hazardous Substances Data)

Usage

General Description

2,3-Dimethyl-1,3-butadiene is a chemical compound classified as a hydrocarbon diene. It has the molecular formula C6H10 and is primarily used in the industrial production of chemical products where it serves as an important reactive intermediate. Its exact nature involves two double bonds, indicating its potential for reactions. It appears as a clear, colorless to light yellow liquid and has a characteristic, strong odor. As a chemical substance, it needs to be handled with care due to potential harm which may include skin and eye irritation or respiratory issues. Additionally, it poses particular risks in relation to fire and explosion hazards.

InChI:InChI=1/C6H10/c1-5(2)6(3)4/h1,3H2,2,4H3

Upstream product

• 110-86-1 pyridine 
• 60-29-7 diethyl ether 
• 814-78-8 3-Methyl-3-buten-2-one 
• 463-51-4 Ketene 
• 50-00-0 formaldehyd 
• 513-35-9 2-methyl-but-2-ene 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 120-18-3 naphthalene-2-sulfonate 
• 542-11-0 aniline hydrobromide 
• 557-98-2 2-chloropropene 
• 1826-67-1 vinyl magnesium bromide 
• 21326-63-6 2,3-dimethyl-3-chloro-2-butanol 
• 594-81-0 2,3-dibromo-2,3-dimethylbutane 

Downstream Products

• 4717-64-0 (3aRS,7aSR)-5,6-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxol-2-one 
• 66483-45-2 (+/-)-4,5-dimethyl-1-phenyl-cyclohex-4-ene-1r,2c-dicarboxylic acid 
• 106213-83-6 3,4-dimethyl-6-phenyl-1,2-dihydropyridine 
• 108774-33-0 3,4-dimethyl-6t-phenyl-cyclohex-3-ene-r-carboxylic acid methyl ester 
• 128352-65-8 1-(3,4-dimethylcyclohex-3-enyl)ethanone 
• 27063-84-9 4,5-dimethyl-2-phenylpyridine 
• 13616-69-8 4,5-dimethyl-2-phenyl-3,6-dihydro-2H-[1,2]thiazine 1-oxide 
• 61309-42-0 (+/-)-6.7-dimethyl-2-phenyl-(4arH.8acH)-4a.5.8.8a-tetrahydro-naphthoquinone-(1.4) 
• 95157-11-2 4,5-dimethyl-1,2-bis-(4-nitro-phenyl)-1,2,3,6-tetrahydro-pyridazine 
• 18022-66-7 3,4-dimethylcyclohex-3-ene-1-carboxaldehyde 
• 1122-39-0 2,4,5-trimethylpyridine 
• 975-70-2 trans dibenzoyl-4,5 dimethyl-1,2 cyclohexene 
• 91965-39-8 ethyl 3,4-dimethylcyclohex-3-ene-1-carboxylate 
• 130442-99-8 (+/-)-1.2-dimethyl-4r.5t-di-p-toluoyl-cyclohexene-⁽¹⁾ 

Relevant articles and documents

Stable vapor-phase catalytic conversion of pinacolone into 2,3-dimethyl-1,3-butadiene

In the vapor-phase synthesis of 2,3-dimethyl-1,3-butadiene from pinacolone over modified alumina catalysts, it was found that alumina modified with transition metals such as Co stabilized the conversion of pinacolone and produced 2,3- dimethyl-1,3-butadiene selectively under hydrogen flow conditions, whereas the catalytic activity of pure alumina was seriously deteriorated irrespective of its high initial activity.

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Control of Polymorphisms and Functions in All-Inorganic Ionic Crystals Based on Polyaluminum Hydroxide and Polyoxometalates

Two kinds of polymorphs of all-inorganic ionic crystals were obtained by the combination of oppositely charged molecular ions (macroions) with Td symmetry, Keggin-type polyaluminum hydroxide [?-Al13O4(OH)24(H2O)12]7+ (Al13) and polyoxometalates (POMs) [α-CoW12O40]6- (POM6), [α-1,2,3-SiVV3W9O40]7- (POM7), or [α-1,2,3-SiVIVVV2W9O40]8- (POM8) in aqueous solutions. The needle-type crystals were grown by dissolution-recrystallization of the precipitates, which formed immediately by combining Al13 and POMs. On the other hand, the plate-type crystals were grown by adding inorganic salts (e.g., NaCl) into the aqueous solution containing the needle-type crystals: Dissolution of the needle-type crystals occurred followed by precipitation of the plate-type crystals, which is the more insoluble and stable polymorph with larger numbers of hydrogen bonds between the constituent ions. The plate-type crystals possess one-dimensional channels with large apertures (ca. 12 ? × 6 ?) and showed high activities as heterogeneous solid acid catalysts in pinacol rearrangement.

CYCLOADDITION REACTIONS OF 2,3-DIDEHYDROTHIOPHENE GENERATED BY FLOW VACUUM THERMOLYSIS OF THIOPHENE-2,3-DICARBOXYLIC ANHYDRIDE

Flow vacuum thermolysis (FVT) of thiophene-2,3-di-carboxylic anhydride (2) in the presence of 2,3-dimethylbutadiene (6) gives, in addition to 5,6-dimethylthianaphthene (9), small quantities of a dihydrodimethylthianaphthene (12) and another dimethylthianaphthene (13) which is probably also formed by dehydrogenation of 12 with chloranil.The partial structures of these minor products are consistent with their being formed by a -cycloaddition between 6 and an intermediate aryne, 2,3-didehydrothiophene (1), followed by a rearrangement of the resulting adduct 11 and dehydrogenation.FVT of 2 in the presence of 2,5- (17b) or 3,4-dimethylthiophene (17c) also gave a mixture of the dimethylthianaphthenes (18, 22, 23) which can be rationalized as arising by a - and two -cycloadditions of the aryne 1 to the thiophenes 17 with subsequent desulfurization.The lack of equilibration of the products 18, 22, and 23 was demonstrated and their origin as a function of the structure and reactivity of the aryne 1 discussed.

The Tetramethyleneethane Radical Cation. An ESR and ENDOR Study

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Isomeric effects on the acidity of Al13Keggin clusters in porous ionic crystals

We demonstrate a facile synthesis method of a porous ionic crystal (PIC) composed of the little-known δ-Keggin-type cationic polyoxoaluminum cluster ([δ-Al13O4(OH)24(H2O)12]7+, δ-Al13) with an oppositely-charged polyoxometalate, which enabled us to investigate the activity as a solid acid. The δ-Al13based PIC exhibited much higher activity in pinacol rearrangement, a typical acid-catalyzed reaction, than the PIC based on the well-known and thermodynamically stable rotational isomer (ε-Al13). This work is a rare example of rotational isomers of polyoxoaluminum clusters exhibiting remarkably different catalytic activities.

1,1-Dimetallagermacyclopent-3-enes: Precursors to Transition Metal Substituted Germylenes (Germanediyls)

Transition metal substituted germylenes have been generated by pyrolysis of 1,1-dimetallagermacyclopent-3-enes and by the metathesis reaction between GeI2 and -(Cp = C5H5).

Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides

Facile construction of 1,3-dienes building upon cross-electrophile coupling of two open-chain vinyl halides is disclosed in this work, showing moderate chemoselectivities between the terminal bromoalkenes and internal vinyl bromides. The present method is mild and tolerates a range of functional groups and can be applied to the total synthesis of a tobacco fragrance solanone.