1,5-HEXADIENE CAS#: 592-42-7 • ChemWhat | Database of Chemicals & Biologicals + AI Chemist

1,5-HEXADIENE CAS#: 592-42-7; ChemWhat Code: 32392

Identification	Physical Data	Spectra
Route of Synthesis (ROS)	Safety and Hazards	Other Data

Identification

15-Hexadiene-CAS-592-42-7

Patent Information
Patent ID	Title	Publication Date
CN110981836	Method for preparing diepoxide by one-pot method	2020
US2018/282866	RUTHENIUM PRECURSOR, PREPARATION METHOD THEREFOR AND METHOD FOR FORMING THIN FILM USING SAME	2018
CN103588807	A double ( alkane oxygen silicon-based ) alkane preparation method	2016
WJP5652360	Method of manufacturing Organoxysilane compd.	2015
US2013/35451	Solid State Polymerization Process for Polyester with Phosphinic Acid Compounds	2013
US8772533	Organoleptic compound	2014
US6870068	Synthesis of pentafluorosulfuranyl substituted alkanes	2005
US2004/82803	Trichlorosilyl groups containing organochlorosilanes and their preparation methods by the double-silylation of olefins with trichlorosilane	2004

Physical Data

Appearance

Colorless to light yellow transparent liquid

Melting Point, °C

-139.5

-141.2

-140.8

-140.68

Boiling Point, °C	Pressure (Boiling Point), Torr
59.99	750.075
59 – 60
58.5 – 59.5
59.7
60 – 62
59.5	760

Density, g·cm^-3	Reference Temperature, °C	Measurement Temperature, °C
0.6886		25
0.6909	4	20
0.6925	4	25
0.6911	4	20
0.6914	4	20
0.7031	4	20

Spectra

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Solvents (NMR Spectroscopy)	Temperature (NMR Spectroscopy), °C
Chemical shifts, Spectrum	1H	benzene-d6	25
Chemical shifts	1H	[D3]acetonitrile
Chemical shifts	13C	[D3]acetonitrile
Spectrum	1H
Chemical shifts	1H	tetrahydrofuran-d8
Chemical shifts	13C	tetrahydrofuran-d8
Chemical shifts	1H	[(2)H6]acetone

Description (IR Spectroscopy)	Solvent (IR Spectroscopy)	Temperature (IR Spectroscopy), °C
Spectrum
Spectrum	gas
Spectrum	neat (no solvent)
Spectrum	neat (no solvent)
Bands	solid matrix	-163.2
Spectrum	gaseous matrix	-261.2

Description (UV/VIS Spectroscopy)	Solvent (UV/VIS Spectroscopy)	Comment (UV/VIS Spectroscopy)
Spectrum		165 – 195 nm, Dampf.
Spectrum		Ratio of solv200 – 215 nm
Spectrum	cyclohexane

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 1,5-HEXADIENE CAS 592-42-7

Conditions	Yield
With 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 Procedure 1 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 dichloromethane	87%

Safety and Hazards

Pictogram(s)
Signal	Danger
GHS Hazard Statements	H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids] H304 (90.4%): May be fatal if swallowed and enters airways [Danger Aspiration hazard] H315 (28.1%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (30%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (37.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statement Codes	P210, 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

Transportation	Under the room temperature and away from light
Storage	Under the room temperature and away from light
Shelf Life

Druglikeness
Lipinski rules component
Molecular Weight	82.1454
logP	3.022
HBA	0
HBD	0
Matching Lipinski Rules	4
Veber rules component
Polar Surface Area (PSA)	0
Rotatable Bond (RotB)	3
Matching Veber Rules	2

Toxicity/Safety Pharmacology

Quantitative Results


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