IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data
Identification
Product Name1,5-HEXADIENEIUPAC Namehexa-1,5-diene Molecular StructureCAS Registry Number 592-42-7EINECS Number209-754-7MDL NumberMFCD00008666Synonyms1,5-HEXADIENE592-42-7Hexa-1,5-dieneDiallylBiallylHexadiene (DOT)alpha,omega-Hexadiene.alpha.,.omega.-HexadieneEINECS 209-754-7UNII-4MTZ4764FINSC 606904MTZ4764FIDTXSID4049323NSC-60690CH2=CHCH2CH2CH=CH2DTXCID9029279alpha,omegaHexadieneinchi=1/c6h10/c1-3-5-6-4-2/h3-4h,1-2,5-6hpygskmbevaiccr-uhfffaoysa-nun24581,5-Hexadiene, 97%CHEMBL31747BCP08456NSC60690Tox21_202852MFCD00008666AKOS015960557NCGC00260398-01CAS-592-42-7H0084NS00020101EN300-105621F14840A832222Q16155125067-96-3Molecular FormulaC6H10 Molecular Weight82.14InChIInChI=1S/C6H10/c1-3-5-6-4-2/h3-4H,1-2,5-6H2 InChI KeyPYGSKMBEVAICCR-UHFFFAOYSA-N SMILESC=CCCC=C
Patent InformationPatent IDTitlePublication DateCN110981836Method for preparing diepoxide by one-pot method2020US2018/282866RUTHENIUM PRECURSOR, PREPARATION METHOD THEREFOR AND METHOD FOR FORMING THIN FILM USING SAME2018CN103588807A double ( alkane oxygen silicon-based ) alkane preparation method2016WJP5652360Method of manufacturing Organoxysilane compd.2015US2013/35451Solid State Polymerization Process for Polyester with Phosphinic Acid Compounds2013US8772533Organoleptic compound2014US6870068Synthesis of pentafluorosulfuranyl substituted alkanes2005US2004/82803Trichlorosilyl groups containing organochlorosilanes and their preparation methods by the double-silylation of olefins with trichlorosilane2004
Physical Data
AppearanceColorless to light yellow transparent liquid
Melting Point, °C -139.5-141.2-140.8-140.68
Boiling Point, °CPressure (Boiling Point), Torr59.99750.07559 - 6058.5 - 59.559.760 - 6259.5760
Density, g·cm-3Reference Temperature, °CMeasurement Temperature, °C0.6886250.69094200.69254250.69114200.69144200.7031420
Spectra
Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Chemical shifts, Spectrum1Hbenzene-d625Chemical shifts1HacetonitrileChemical shifts13CacetonitrileSpectrum1HChemical shifts1Htetrahydrofuran-d8Chemical shifts13Ctetrahydrofuran-d8Chemical shifts1Hacetone
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Temperature (IR Spectroscopy), °CSpectrumSpectrumgasSpectrumneat (no solvent)Spectrumneat (no solvent)Bandssolid matrix-163.2Spectrumgaseous matrix-261.2
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Spectrum165 - 195 nm, Dampf.SpectrumRatio of solv200 - 215 nmSpectrumcyclohexane
Route of Synthesis (ROS)
Route of Synthesis (ROS) of 1,5-HEXADIENE CAS 592-42-7
ConditionsYieldWith 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16h;Experimental Procedure(±)-((2S,5S)-tetrahydrofuran-2,5-diyl) dimethanol 6a,((2R,5R)-tetrahydrofuran-2,5-diyl) dimethanol 6b: and((2R,5S)-tetrahydrofuran-2,5-diyl) dimethanol 6c from 1,5-hexadiene 17 through the 1,5-diepoxide 18:3-Chloroperoxybenzoicacid (57-60%, 48.6 g, 281 mmol) was addedin five portions to a mechanically-stirred solution of 1,5-hexadiene 17 (4.84 g, 59 mmol) in CH2Cl2 (150 mL) whilecooling (0°C). The reaction mixture was allowed to warm toroom temperature then stirring was continued (16h). Saturatedaqueous sodium bicarbonate (100 mL) was then addedto the reaction mixture while stirring followed by separationof the organic layer and washing with 1M aqueous KOH (7 x50 mL). The organic layer was then dried over anhydrousMgSO4, filtered and concentrated to provide the racemic/meso 1, 5-diepoxides 18 (6.8 g, >99%). A mixture ofaqueous NaOH (18 mL, 0.1M) and the diepoxide 18 (1.0 g,8.7 mmol) was stirred at room temperature (16 h). Water wasthen removed and the oily residue was flushed through asilica gel column giving the mixture of oily (2S,5S)-6a,(2R,5R)-6b and (2S,5R)-6c diols (0.8 g, 70%). The mixturewas then submitted to gravity-column chromatography(CHCl3/tert-butanol, 7/3) which separated the more mobile(2S,5R)-6c from the racemic mixture of 6a/6b. Acetylation(Ac2O/pyridine) of a portion of the 6a/6b/6c mixture followedby flash chromatography gave a mixture of the threecorresponding stereoisomeric diacetates. The diacetates weresubmitted to chiral HPLC (ChiracelOJ, 4.6 x 250 mm, 10;mobile phase 80% hexane/20% ethanol; 0.7 mL/min, 22°C)and indicated that the ratio of racemic: meso diacetates was54:46.99%With 3-chloro-benzenecarboperoxoic acid at 10 - 20℃; for 19h;Experimental Procedure1 A one-pot method for preparing diepoxide includes the following steps:S1. Epoxidation reaction: At a low temperature, add 10.04g1,5-hexadiene to the reactor, slowly add m-chloroperoxybenzoic acid solution dropwise, control the drop acceleration to make the system temperature around 10 , and maintain after the dropwise addition The reaction was carried out at a low temperature for 4h, and then the temperature was raised to 20°C, the reaction was continued for 15h, and the reaction was completed to obtain a crude diepoxyhexane solution, in which the molar ratio of diene to m-chlorobenzoyl chloride was 1:2.45;S2. Separation and purification: add 125g of 20% mass fraction sodium sulfite aqueous solution to the crude diepoxyhexane solution, keep the system temperature at 20°C, reduce the reaction for 2h, extract and separate the organic phase. To the organic phase, add 165g of a 20% sodium bicarbonate mass fraction, maintain the system at 20°C, neutralize the reaction for 3 hours, and extract the organic phase. The organic phase was washed three times with water (150 mL×3), the organic phase was extracted and separated, dried over anhydrous sodium sulfate, the solid filter residue was filtered off, the filtrate was distilled under reduced pressure, the solvent methylene chloride was recovered, and the product was collected to obtain diepoxyhexane.Among them, the preparation method of m-chloroperoxybenzoic acid solution is as follows:Add 50.4g of potassium hydroxide, 260mL of water, 100g of 30% hydrogen peroxide solution, 1.5g of magnesium sulfate heptahydrate to the reactor, stir to dissolve, then add 300mL of dioxane, control the feeding temperature at 15 , in the fierce Under stirring, 52.5 g of m-chlorobenzoyl chloride was added all at once, maintaining the reaction temperature at 20° C., and stirring for 20 min. Cool down, add 20% sulfuric acid solution, control the temperature of the system at 10 , acidify to pH 2, add 400mL of dichloromethane, extract and separate the organic phase, dry with anhydrous potassium sulfate, filter off the solid filter residue to obtain m-chloroperoxy Benzoic acid / dichloromethane solution,The molar ratio of chlorobenzoyl chloride, potassium hydroxide and hydrogen peroxide is 1: 3: 2.93.The yield of diepoxyhexane is 95.1% and the purity is 93.4%.95.1%With 3-chloro-benzenecarboperoxoic acid In dichloromethane87%
Safety and Hazards
Pictogram(s)SignalDangerGHS Hazard StatementsH225 (100%): Highly Flammable liquid and vapor H304 (90.4%): May be fatal if swallowed and enters airways H315 (28.1%): Causes skin irritation H319 (30%): Causes serious eye irritation H335 (37.8%): May cause respiratory irritation Precautionary Statement CodesP210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P331, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501(The corresponding statement to each P-code can be found at the GHS Classification page.)
Other Data
TransportationUnder the room temperature and away from lightStorageUnder the room temperature and away from lightShelf Life
DruglikenessLipinski rules componentMolecular Weight82.1454logP3.022HBA0HBD0Matching Lipinski Rules4Veber rules componentPolar Surface Area (PSA)0Rotatable Bond (RotB)3Matching Veber Rules2
Toxicity/Safety PharmacologyQuantitative Results https://www.chemwhat.com/15-hexadiene-cas-592-42-7/
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