627-97-4

Basic information

• Product Name: 2-METHYL-2-HEPTENE
• Synonyms: 2-Heptene, 2-methyl-;2-methyl-hept-2-ene;2-Methylhept-2-ene;2-METHYL-2-HEPTENE;2-BUTYL-1,1-DIMETHYLETHYLENE;2-Methyl-2-heptene 98%
• CAS NO: 627-97-4
• Molecular Formula: C₈H₁₆
• Molecular Weight: 112.21
• EINECS: 211-022-7
• Product Categories: Acyclic;Alkenes;Organic Building Blocks
• Mol File: 627-97-4.mol

Chemical Properties

• Melting Point: −122 °C(lit.)
• Boiling Point: 122 °C(lit.)
• Flash Point: 48 °F
• Appearance: /
• Density: 0.726 g/mL at 20 °C
• Vapor Pressure: 16.8mmHg at 25°C
• Refractive Index: n20/D 1.417(lit.)
• Storage Temp.: 2-8°C
• BRN: 1732139
• CAS DataBase Reference: 2-METHYL-2-HEPTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-2-HEPTENE(627-97-4)
• EPA Substance Registry System: 2-METHYL-2-HEPTENE(627-97-4)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-65
• Safety Statements: 16-62
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 627-97-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-METHYL-2-HEPTENE is used as a reactant in the Alder Ene reaction for the functionalization of ethylene/5,7-dimethyl-1,6-diene copolymer with maleic anhydride. This application takes advantage of the compound's reactivity in the Alder Ene reaction, which is a powerful method for the formation of carbon-carbon bonds.
Used in Oxidation Processes:
In the field of organic chemistry, 2-METHYL-2-HEPTENE is used as a substrate for oxidation reactions. It undergoes oxidation by singlet oxygen generated by the excitation of thiazine dyes cation to form hydroperoxides. This process is significant for the synthesis of various oxygen-containing compounds and can be applied in the development of new materials and pharmaceuticals.
Used in Polymer Industry:
2-METHYL-2-HEPTENE is utilized in the polymer industry for the functionalization of copolymers, which can lead to the creation of materials with improved properties, such as enhanced mechanical strength, thermal stability, or chemical resistance. The functionalization of copolymers with maleic anhydride, as mentioned in the provided materials, is an example of how 2-METHYL-2-HEPTENE can be used to modify polymers for specific applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 609, 1983 DOI: 10.1021/jo00152a042

InChI:InChI=1/C8H16/c1-4-5-6-7-8(2)3/h7H,4-6H2,1-3H3

Upstream product

• 625-25-2 2-Methyl-2-heptanol 
• 4325-49-9 2-chloro-2-methylheptene 
• 60-29-7 diethyl ether 
• 693-04-9 butyl magnesium bromide 
• 563-47-3 3-Chloro-2-methylpropene 
• 78-79-5 isoprene 
• 917-64-6 methyl magnesium iodide 
• 106-70-7 methyl hexanoate 
• 109-65-9 1-bromo-butane 
• 13222-26-9 2-chloroisobutyryl chloride 
• 693-03-8 n-butyl magnesium bromide 
• 917-93-1 2-chloroisobutyraldehyde 
• 109-72-8 n-butyllithium 
• 513-37-1 2-methylprop-1-enyl chloride 

Downstream Products

• 592-27-8 2-methylheptane 
• 15870-10-7 2-methylhept-1-ene 
• 76589-15-6 3-methoxy-2-methylheptane 
• 76589-14-5 3-methoxy-2-methyl-1-heptene 
• 1068-81-1 rac-2-methyl-heptane-2,3-diol 
• 996-60-1 2-hydroxy-2-methyl-heptan-3-one 
• 109-52-4 valeric acid 
• 65405-68-7 3-hydroxymethyl-heptan-2-one 
• 65822-42-6 2-amino-N-(1,1-dimethylhexyl)acetamide 
• 1198339-72-8 C₂₄H₄₄OSi 
• 1198339-67-1 4-desoxytrisporin A 
• 1198339-66-0 trisporin A 
• 13019-19-7 2-methylhept-1-en-3-ol 
• 116668-45-2 C₈H₁₆O 

Relevant articles and documents

FRAGRANCE MATERIAL

Fragrance compounds having a unique chemical structure are provided, including 2-methoxy-2-methylheptane and derivatives thereof. The fragrance compounds can have fruity, radish, and/or herbaceous odor notes with a strong top note. The fragrance compounds can be used alone or incorporated into a fragrance composition and/or consumer product to modify or enhance the odor of the fragrance composition and/or consumer product.

γ-Alumina-supported [60]fullerene catalysts: Synthesis, properties and applications in the photooxidation of alkenes

Immobilization of [60]fullerene onto γ-Al2O3 surface provides new heterogeneous photocatalysts for the oxidation of organic compounds under oxygen atmosphere. These catalysts have been prepared by simple or successive incipient wetness impregnation (using an organic solvent) followed by air-heating at 180 °C. In the C60/Al2O3 system, C60 loading was varied in the range of 1-4% (w/w). Several experimental techniques including BET, XRD, DRS, TGA, microelectrophoresis, photoluminescence and kinetic extraction, have been used to characterize these catalytic materials. It was found that the quite high surface exposed by the supported C60 increases with the amount of the supported C60, while the dispersion of the supported C60 decreases. The quite stable supported [60]fullerene phase is comprised from C60 clusters, small and large aggregates. This non-uniform size distribution is reflected to a non-uniform distribution concerning the 'supported phase-support' interactions. These interactions decrease with the amount of the supported C60. The photocatalysts prepared may be safely used up to 200 °C. Above this temperature the supported C60 is sublimated/combusted in air. The photocatalytic activity of the so-obtained catalytic systems has been evaluated in terms of substrate conversion in the singlet oxygen 'ene' reaction of alkenes. The photooxygenation of 2-methyl-2-heptene has been examined as a probe reaction. It was found that the catalytic activity increases with the increasing amount of the supported C60 up to the value of 3% (w/w) and then decreases. The intrinsic activity expressed as TON or TOF decreased monotonically with C60. In all cases, however, the photocatalytic activity of the Al2O3-supported C60 catalysts was substantially increased compared to the unsupported C60 precursor, exhibiting quantitative conversion yields after short reaction times. The catalytic behavior was attributed to the aforementioned opposite trends which follow the surface exposed by the supported C60 on one hand and the 'supported C60-support' interactions and the C60 dispersion on the other hand. The easy separation of these solid catalysts from the reaction mixture, the high activity and stability as well as the retained activity in subsequent catalytic cycles, make these supported catalysts suitable for a small-scale synthesis.

Palladium nanoparticles stabilized by alkylated polyethyleneimine as aqueous biphasic catalysts for the chemoselective stereocontrolled hydrogenation of alkenes

Palladium nanoparticles were prepared, stabilized, and dispersed in water by alkylated branched polyethyleneimine. The palladium nanoparticles were effective aqueous biphasic catalysts for the chemoselective hydrogenation of alkenes with preferential reduction of less hindered double bonds, such as reduction of 3-methylcyclohexene in the presence of 1-methylcyclohexene and 1-octene in the presence of 2-methyl-2-heptene.

ESTER SYNTHESIS

Process for making lower aliphatic ester, especially ethyl acetate, by reacting a lower olefin with a saturated lower aliphatic mono-carboxylic acid in the vapor phase using a heteropolyacid catalyst, wherein the reaction pressure is 11 to 20 barg (1100 to 2000 KPa), more preferably 12 to 15 barg (1200 to 1500 KPa). The reaction temperature is 140 to 250°C, more preferably 160 to 195°C. The process reduces the level of by-products, for example methyl ethyl ketone and/or acetaldehyde.

Polysulfones: Catalysts for alkene isomerization

A radical intermediate is generated when methylidenecyclopentane (1) is isomerized by SO2 into 1-methylcyclopentene (3) through the formation of a polysulfone polymer (PS), which first abstracts a hydrogen atom from the alkene. The allyl radical intermediate 2 abstracts a hydrogen atom from another alkene molecule 1, to yield the isomerized alkene and regenerating the allyl radical. Polysulfones are organic catalysts.

Biocatalytic asymmetric and enantioconvergent hydrolysis of trisubstituted oxiranes

Asymmetric biohydrolysis of trialkyl oxiranes (±)-1a-3a using the epoxide hydrolase activity of whole bacterial cells proceeded in an enantioconvergent fashion and thus led to the corresponding (R)-configurated vicinal diols 1b-3b in up to 97% enantiomeric excess (e.e.) as the sole product. The mechanism of this enantioconvergence was investigated by 18O-labelling experiments and it was found that both enantiomers were hydrolysed with opposite regioselectivity.

Reactions of Saturated and Unsaturated Tertiary Alkyl Halides and Saturated Secondary Alkyl Iodides with Lithium Aluminum Deuteride. Convincing Evidence for a Single-Electron-Transfer Pathway

Reactions of saturated secondary and tertiary alkyl halides with LiAlH4 (LAH) and LiAlD4 (LAD) have been carried out, and convincing evidence for a single-electron-transfer (SET) pathway has been obtained. Reactions involving saturated alkyl halides with LAD provide a model system in which a halogen-atom radical chain process is not possible, and therefore, the observation of large quantities (in some cases >90 percent) of protium in the reduction product provides strong evidence for a radical intermediate and a SET pathway. Specifically, the reaction of 2-iodooctane (10) with LAD produced octane with a deuterium content as low as 21 percent. Also, the reaction of the tertiary halide 2-iodo-2-methylheptane (15) with LAD produced 2-methylheptane (16) with a deuterium content as low as 8 percent. The effect of stoichiometry, halogen type, and reaction vessel surface on these reactions was studied. Reaction of the unsaturated tertiary halide 6-iodo-6-methyl-1-heptene (25) with LAD was also studied and was found to proceed predominantly by a SET process involving a halogen-atom radical chain process. The possibility of a carbocation intermediate in all of these reactions is discussed.

The reaction of 1-chloro-2-methyl-2-propenyllithium with a selection of organolithiums. The development and synthetic utility of novel base/nucleophile combinations

The title compound was generated by and reacted with (1) a series of reagents which have basic as well as nucleophilic properties and (2) a series of base/nucleophile combinations.Product yields of the isobutenyl derivative were generally low to very good, and the best results (89percent) were obtained by using a 1:2 ratio (3 equiv total) of nBuLi:LiPPh2.Synthetic utility of the reaction is optimized as it approaches a situation in which the base/nucleophile combination is composed of one compound which is both a strong base and a poor nucleophile and another compound which is both a weak base and a good nucleophile.

Free-radical-mediated Carbonylative Cyclization of Alk-4-enyl Halides Leading to Cyclopentanone

Alk-4-enyl bromides and iodides 1, when treated with the tributyltin hydride/CO sustem, undergo carbonylative cyclization to give cyclopentanones in good yields (AIBN cat., benzene, 79-90 atm, = 0.025-0.05 mol dm-3, 80 deg C.

The Synthetic Potential of the Isocyanide-Cyanide Rearrangement

Excellent chemical and optical yields (>96percent retention) of cyanides are achieved by vapor phase thermolysis or short contact flow thermolysis of isocyanides. trans-2-Butenyl isocyanide rearranges without concomitant allylic isomerization to trans-2-butenyl cyanide.Optically active 1-(formyloxymethyl)-2-phenylethyl cyanide is obtained from optically active L-phenylalanine as a new type of chiral pool synthon.