Isoprene

Base Information

• Chemical Name: Isoprene
• CAS No.: 78-79-5
• Deprecated CAS: 78006-92-5,823271-95-0,2378489-72-4,9041-64-9,9041-65-0,51731-84-1,37231-42-8
• Molecular Formula: C5H8
• Molecular Weight: 68.1185
• Hs Code.: 4002601000
• European Community (EC) Number: 201-143-3,614-502-8
• ICSC Number: 0904
• NSC Number: 9237
• UN Number: 1218
• UNII: 0A62964IBU
• DSSTox Substance ID: DTXSID2020761
• Nikkaji Number: J1.958E
• Wikipedia: Isoprene
• Wikidata: Q271943,Q83056853
• NCI Thesaurus Code: C29824
• RXCUI: 1364275
• Metabolomics Workbench ID: 55076
• ChEMBL ID: CHEMBL1566132
• Mol file: 78-79-5.mol

Synonyms:2-methyl-1,3-butadiene;isoprene

Chemical Property of Isoprene

Chemical Property:

• Appearance/Colour: colourless liquid with an aromatic odour
• Melting Point: 323-329 °C(lit.)
• Refractive Index: n20/D 1.422(lit.)
• Boiling Point: 34.059 °C at 760 mmHg
• Flash Point: -40.843 °C
• PSA: 0.00000
• Density: 0.674 g/cm³
• LogP: 1.74850
• Water Solubility.: 0.07 g/100 mL
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 68.062600255
• Heavy Atom Count: 5
• Complexity: 51.1

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s): F+,T
• Hazard Codes: F+:Highly flammable
• Statements: R12:; R45:; R52/53:; R68:
• Safety Statements: S45:; S53:; S61:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: UVCB,Plastics & Rubber -> Other Monomers,Plastics & Rubber -> Polymers
• Canonical SMILES: CC(=C)C=C
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance and the vapour are moderately irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system. This may result in respiratory depression and lowering of consciousness. If swallowed the substance easily enters the airways and could result in aspiration pneumonitis.
• Effects of Long Term Exposure: Repeated or prolonged inhalation may cause effects on the lungs. This substance is possibly carcinogenic to humans. May cause heritable genetic damage to human germ cells.
• Use Description: Isoprene, a volatile organic compound, has multiple applications across various fields. In the rubber and polymer industry, it serves as a key monomer for the production of synthetic rubber, particularly polyisoprene, which is used in the manufacturing of tires, footwear, and various rubber products. In the field of biochemistry, isoprene is produced by plants and some microorganisms as a precursor for the synthesis of essential compounds like sterols and carotenoids. Additionally, in the atmospheric sciences, isoprene emissions from plants play a significant role in the formation of aerosols and tropospheric ozone, impacting air quality and climate. Furthermore, in the field of chemistry, isoprene can be employed as a starting material for the synthesis of various organic compounds and as a volatile solvent for chemical reactions. Its multifaceted contributions underscore its significance in rubber production, biochemistry, atmospheric science, and organic chemistry, offering versatile applications and impacts across these diverse fields.

Technology Process of Isoprene

There total 410 articles about Isoprene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + isobutene (115-11-7,15220-85-6) → 4-methyl-3,6-dihydro-2H-pyran (16302-35-5) + 4-methyl-3,4-dihydro-2H-pyran (2270-61-3) + 3-methyl-butane-1,3-diol (2568-33-4) + methylcyclopentadiene (96-39-9) + 3,4,4-trimethylcyclohexene (219811-94-6) + isovaleraldehyde (590-86-3) + isoprene (78-79-5,9003-31-0)

Guidance literature:

With niobium phosphate; at 299.84 ℃; for 3.33333h; Temperature;

DOI:10.1016/j.apcata.2012.06.034

Reference yield: 37.0%

carbon monoxide (201230-82-2) + isoprene epoxide (1838-94-4) → 5-methyl-3,6-dihydro-pyran-2-one (60920-98-1) + 2-methylbut-2-enal (497-03-0) + isoprene (78-79-5,9003-31-0)

Guidance literature:

With dicobalt octacarbonyl; at 85 ℃; under 150012 Torr;

DOI:10.1016/S0040-4039(00)82036-5

Reference yield: 32.0%

3-chloro-3-methyl-1-butene (2190-48-9) → 3,3-dimethyl-allyl chloride (503-60-6) + isoprene (78-79-5,9003-31-0)

Guidance literature:

In dimethylsulfoxide-d6; for 96h; Product distribution; Rate constant; Ambient temperature; in NMR tube, estimated rate: 1.8E-6 s^-1; further solv.;

DOI:10.1021/ja00240a029

upstream raw materials:

2-ethyl-2-methyloxirane

4,4-dimethyl-1,3-dioxane

quinoline

Dimethylallene

Downstream raw materials:

2-(4-methyl-3-cyclohexenyl)pyridine

4-(4-methyl-cyclohex-3-enyl)-pyridine

4-methyl-1,2,3,6-tetrahydrophthalic anhydride

cis-3a,4,7,7a-tetrahydro-5-methyl-1,3-isobenzofurandione

Refernces

• 1、 Wang, SaiSai,Chen, Xingkun,Tan, Yuan,Zhao, Ziang,Yang, Wenshao,Huang, Chuanqi,Wang, Xuepeng,Chen, MiaoMiao,Du, Zhongnan,Ding, Yunjie. "Highly efficient synthesis of isoprene from methyl tert-butyl ether and formaldehyde over activated carbon supported silicotungstic acid catalysts". . . Retrieved 2020.
• 2、 Ponomarev,Zaliznyi,Dvorko. "Kinetics and mechanism of monomolecular heterolysis of commercial organohalogen compounds: XLII. Effect of aprotic solvent on the rate of 3-methyl-3-chloro-1-butene dehydrochlorination. Correlation analysis of solvation effects". . p. 1517 - 1523. Retrieved 2005.
• 3、 Ryabova,Osipova,Librovich. "The kinetics of transformation of isopentenols in the presence of the Nafion-H catalyst". . p. 2034 - 2036. Retrieved 1998.
• 4、 Boonstra,van Amerongen. "". . p. 161. Retrieved 1949.
• 5、 Behnke, Dirk,Hamm, Stefan,Hennig, Lothar,Welzel, Peter. "An allylic isoprenoid C5 nucleophile for the synthesis of forskolin". . p. 7059 - 7062. Retrieved 1997.
• 6、 Balandin et al.. "-". . . Retrieved 1958.
• 7、 Ponomareva,Chistov,Kots,Ivanova. "Isoprene Synthesis from Formaldehyde and Isobutylene over Zeolite Catalysts". . p. 711 - 718. Retrieved 2019.
• 8、 Munyemana, Fran?ois,Patiny, Luc,Ghosez, Léon. "A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols". . . Retrieved 2021/06/07.
• 9、 -. "Method for preparing isoprene". Paragraph 0039-0111. . Retrieved 2021/04/14.