78-80-8

Usage

Uses

Used in Organic Synthesis:
2-Methyl-1-butene-3-yne is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the creation of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2-Methyl-1-butene-3-yne is used as a key intermediate in the production of various pharmaceuticals, contributing to the development of new medications and therapies.
Used in Agrochemical Production:
2-Methyl-1-butene-3-yne is also utilized in the manufacturing of agrochemicals, playing a role in the development of products that protect and enhance crop yields.
Used in Plastics and Rubber Manufacturing:
This alkyne is employed in the production of plastics and rubber, where it contributes to the formation of materials with specific properties for various applications.
Used in the Production of Fine Chemicals:
2-Methyl-1-butene-3-yne is a valuable intermediate in the synthesis of fine chemicals, which are used in a wide range of applications, including fragrances, dyes, and other specialty products.
Overall, 2-Methyl-1-butene-3-yne's applications span across multiple industries, highlighting its importance as a versatile and essential component in the synthesis of a broad spectrum of products.

InChI:InChI=1/C5H6/c1-4-5(2)3/h1H,2H2,3H3

Upstream product

• 2696-26-6 2,5-dimethylhex-5-en-3-yn-2-ol 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 56184-83-9 (2-Methyl-buta-2,3-dienyl)-dipropyl-amine 
• 78-79-5 isoprene 
• 7487-88-9 magnesium sulfate 
• 7732-18-5 water 
• 86119-84-8 phosphoric acid 
• 108-95-2 phenol 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 64-17-5 ethanol 
• 21678-37-5 N,N,2-trimethylpropionamide 
• 26189-59-3 1-chloro-1-(dimethylamino)-2-methyl-1-propene 
• 335-03-5 1,1-difluoro-2,2-dimethylcyclopropane 
• 115-11-7 isobutene 

Downstream Products

• 13152-68-6 1-(3-methyl-but-3-en-1-ynyl)-cyclohexanol 
• 96870-99-4 4-methyl-1,1,1,6,6,6-hexaphenyl-hexa-2,3-diene 
• 814-78-8 3-Methyl-3-buten-2-one 
• 13152-69-7 4-methyl-1-(3-methyl-but-3-en-1-ynyl)-cyclohexanol 
• 2696-26-6 2,5-dimethylhex-5-en-3-yn-2-ol 
• 7595-75-7 3-ethoxy-4-methyl-penta-2,4-dienoic acid ethyl ester 
• 54701-07-4 3,3-diethoxy-4-methyl-pent-4-enoic acid ethyl ester 
• 14539-67-4 4-methoxy-3-methyl-butan-2-one 
• 1124-20-5 2-(3-methylphenyl)propene 
• 408338-20-5 3-methyl-4-propoxy-butan-2-one 
• 99852-06-9 1-(4-chloro-phenyl)-2-methyl-but-1-en-3-yne 
• 99983-99-0 3-chloro-4-(4-chloro-phenyl)-3-methyl-but-1-yne 
• 20082-32-0 (+/-)-2,5-dimethyl-7t-(2,2,6-trimethyl-cyclohexen-⁽⁶⁾-yl)-heptadien-(1,6)-yn-⁽³⁾-ol-⁽⁵⁾ 
• 174833-99-9 3,7-dimethyl-1-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-2,7-dien-5-yn-4-ol 

Relevant academic research and scientific papers

CATALYZED HYDROSILYLATION OF 2-METHYL-1-BUTEN-3-YNE WITH METHYLDICHLOROSILANE; PROMOTIONAL EFFECT IMPARTED BY THE PRESENCE OF A DIFFERENT CHLOROSILANE

Chloroplatinic acid catalyzed hydrosilylation of 2-Methyl-1-buten-3-yne with chlorosilanes is reinvestigated; the results can't be satisfactorily explained by Chalk and Harrod mechanism.

A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols

A study of the deoxyhalogenation of allylic and propargylic alcohols with tetramethyl-α-halo-enamines is reported. Primary allylic and primary and secondary propargylic alcohols gave the corresponding halides in high yields. Secondary allylic and propargylic alcohols yielded the corresponding secondary halides but the reaction also produced some rearranged primary halides (I > Br > Cl). The reactions with tertiary allylic and tertiary propargylic alcohols gave several products and was therefore of little synthetic value. However, the addition of triethylamine to the reaction mixture or the use of lithium alkoxide instead of alcohol brought about a major change of the course of the reaction which led to amides carrying an allyl or an allenyl group at C2. This was shown to result from a Claisen-Eschenmoser rearrangement of an intermediate α-allyloxy- or propargyloxy-enamine.

Total Synthesis and Biological Investigation of (?)-Artemisinin: The Antimalarial Activity of Artemisinin Is not Stereospecific

Here, we describe an efficient and diversity-oriented entry to both (?)-artemisinin (1) and its natural antipode (+)-artemisinin, starting from commercially and readily available S-(+)- and R-(?)-citronellene, respectively. Subsequently, we answered the still open question regarding the specificity of artemisinins action. By using a drug-sensitive Plasmodium falciparum NF54 strain, we showed that the antimalarial activity of artemisinin is not stereospecific. Our straightforward and biomimetic approach to this natural endoperoxide enables the synthesis of artemisinin derivatives that are not accessible through applying current methods and may help to address the problem of emerging resistance of Plasmodium falciparum towards artemisinin.

A new tactic for tocopherol synthesis using intramolecular benzyne trapping by an alcohol

A formal total synthesis of (S)-α-Tocopherol, the major component of natural Vitamin E has been achieved using intramolecular benzyne trapping as a key step to form the chroman ring. The synthesis also features an efficient new method for benzotriazole N-Amination using an oxaziridine; chiral, nonracemic intermediates are generated using asymmetric dihydroxylation.

Aluminum oxide-induced gas-phase ring-opening in methyl substituted gem-difluorocyclopropanes, leading to 2-fluorobuta-1,3-dienes and vinylacetylenes

A gas-phase pyrolysis of methyl-substituted gem-difluorocyclopropanes in a flow-tube reactor in the presence of Al2O3 at 185 - 250 °C gives 2-fluorobuta-1,3-dienes and vinylacetylenes.

Reaction rate and isomer-specific product branching ratios of C 2H + C4H8: 1-butene, cis -2-butene, trans -2-butene, and isobutene at 79 K

The reactions of C2H radicals with C4H8 isomers 1-butene, cis-2-butene, trans-2-butene, and isobutene are studied by laser photolysis-vacuum ultraviolet mass spectrometry in a Laval nozzle expansion at 79 K. Bimolecular-reaction rate constants are obtained by measuring the formation rate of the reaction product species as a function of the reactant density under pseudo-first-order conditions. The rate constants are (1.9 ± 0.5) × 10-10, (1.7 ± 0.5) × 10 -10, (2.1 ± 0.7) × 10-10, and (1.8 ± 0.9) × 10-10 cm3 s-1 for the reaction of C2H with 1-butene, cis-2-butene, trans-2-butene, and isobutene, respectively. Bimolecular rate constants for 1-butene and isobutene compare well to values measured previously at 103 K using C2H chemiluminescence. Photoionization spectra of the reaction products are measured and fitted to ionization spectra of the contributing isomers. In conjunction with absolute-ionization cross sections, these fits provide isomer-resolved product branching fractions. The reaction between C2H and 1-butene yields (65 ± 10)% C4H4 in the form of vinylacetylene and (35 ± 10)% C5H6 in the form of 4-penten-1-yne. The cis-2-butene and trans-2-butene reactions yield solely 3-penten-1-yne, and no discrimination is made between cis- and trans-3-penten-1-yne. Last, the isobutene reaction yields (26 ± 15)% 3-penten-1-yne, (35 ± 15)% 2-methyl-1-buten-3-yne, and (39 ± 15)% 4-methyl-3-penten-1-yne. The branching fractions reported for the C2H and butene reactions indicate that these reactions preferentially proceed via CH3 or C2H3 elimination rather than H-atom elimination. Within the experimental uncertainties, no evidence is found for the formation of cyclic species.

Bimolecular rate constant and product branching ratio measurements for the reaction of C2H with ethene and propene at 79 K

The reactions of the ethynyl radical (C2H) with ethene (C 2H4) and propene (C3H6) are studied under low temperature conditions (79 K) in a pulsed Laval nozzle apparatus. Ethynyl radicals are formed by 193 nm photolysis of acetylene (C 2H2) and the reactions are studied in nitrogen as a carrier gas. Reaction products are sampled and subsequently photoionized by the tunable vacuum ultraviolet radiation of the Advanced Light Source (ALS) at Lawrence Berkeley National Laboratory. The product ions are detected mass selectively and time-resolved by a quadrupole mass spectrometer. Bimolecular rate coefficients are determined under pseudo-first-order conditions, yielding values in good agreement with previous measurements. Photoionization spectra are measured by scanning the ALS photon energy while detecting the ionized reaction products. Analysis of the photoionization spectra yields-for the first time-low temperature isomer resolved product branching ratios. The reaction between C2H and ethene is found to proceed by H-loss and yields 100% vinylacetylene. The reaction between C2H and propene results in (85 ± 10)% C4H4 (m/z = 52) via CH3-loss and (15 ± 10)% C5H6 (m/z = 66) by H-loss. The C 4H4 channel is found to consist of 100% vinylacetylene. For the C5H6 channel, analysis of the photoionization spectrum reveals that (62 ± 16)% is in the form of 4-penten-1-yne, (27 ± 8)% is in the form of cis-and trans-3-penten-1-yne and (11 ± 10)% is in the form of 2-methyl-1-buten-3-yne.

A synthesis of α-tocopherol featuring benzyne trapping by an alcohol

A formal total synthesis of α-tocopherol, the main component of Vitamin E, has been achieved in which a central step is the intramolecular trapping of a highly substituted benzyne by an alcohol group to establish the pyran ring.

Synthesis and characterization of solid acid in system SnO 2/B2O3

SnO2/B2O3 materials with Sn/B molar ratio 1:1; 1:2 and 1:3 were synthesized from SnCl4, H3BO 3 and (NH2)2CO. The samples contain SnO 2 with different cristallinity and an amorphous borate phase. Their thermal transformations were investigated by DTA method. The surface acidity was investigated by TPR method using conversion of 2-methyl-3-butyn-2-ol (MBOH). The temperature maximum of MBOH dehydration for SnO2/B 2O3 materials is close to that for ZrO2/ SiO2 catalyst. On the surface of SnO2/B2O 3 mainly strong acid sites were detected. In the case of B 2O3/SiO2 (aerosil), samples have mainly weak acid sites. The surface of pure SnO2 has amphoteric sites. IR spectroscopy and MAS NMR spectra of 11B showed that SnO 2/B2O3 materials had three-and four-coordinated B atoms.

Selective oxidation of light alkanes on transition metal promoted vanadyl pyrophosphate (VPO) catalysts

Vanadyl diphosphate (= vanadyl pyrophosphate) promoted with Bi, Cs, Co and Te was studied as catalyst in the oxidation of propane, n-butane and n-pentane. The additives modified the surface P/V ratio as determined by XPS, and Brinsted and Lewis acidity, determined by TPD of ammonia and transformation of 2-methyl-3-butyn-2-ol. The specific rate of the oxidation of hydrocarbons correlated with the nucleophilicity of surface oxygen ions. With increase of Lewis acidity the selectivity to maleic anhydride in oxidation of n-butane increased, whereas in oxidation of n-pentane the selectivity to phthalic anhydride increased and that to maleic anhydride decreased. The mechanism is discussed.