1,5-Hexadiene

Last updated
1,5-Hexadiene
1,5-hexadienestick.png
Names
Preferred IUPAC name
Hexa-1,5-diene
Other names
diallyl, biallyl, α,ω-Hexadiene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.869 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-754-7
PubChem CID
UNII
  • InChI=1S/C6H10/c1-3-5-6-4-2/h3-4H,1-2,5-6H2
    Key: PYGSKMBEVAICCR-UHFFFAOYSA-N
  • C=CCCC=C
Properties
C6H10
Molar mass 82.146 g·mol−1
Appearancecolorless liquid
Boiling point 59–60 °C (138–140 °F; 332–333 K)
Hazards
GHS pictograms GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
GHS Signal word Danger
H225, H302, H305, H315, H319, H335, H336
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301+310, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P331, P332+313, P337+313, P362, P370+378, P403+233, P403+235, P405
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,5-Hexadiene is the organic compound with the formula (CH2)2(CH=CH2)2. It is a colorless, volatile liquid. It is used as a crosslinking agent and precursor to a variety of other compounds.

Synthesis

1,5-Hexadiene is produced commercially by the ethenolysis of 1,5-cyclooctadiene: [1]

(CH2CH=CHCH2)2 + 2 CH2=CH2 → 2 (CH2)2CH=CH2

The catalyst is derived from Re2O7 on alumina.

A laboratory-scale preparation involves reductive coupling of allyl chloride using magnesium: [2]

2 ClCH2CH=CH2 + Mg → (CH2)2(CH=CH2)2 + MgCl2

Related Research Articles

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Magnesium chloride Inorganic salt: MgCl2 and its hydrates

Magnesium chloride is the name for the chemical compound with the formula MgCl2 and its various hydrates MgCl2(H2O)x. Anhydrous MgCl2 contains 25.5% elemental magnesium by mass. These salts are typical ionic halides, being highly soluble in water. The hydrated magnesium chloride can be extracted from brine or sea water. In North America, magnesium chloride is produced primarily from Great Salt Lake brine. It is extracted in a similar process from the Dead Sea in the Jordan Valley. Magnesium chloride, as the natural mineral bischofite, is also extracted (by solution mining) out of ancient seabeds, for example, the Zechstein seabed in northwest Europe. Some magnesium chloride is made from solar evaporation of seawater. Anhydrous magnesium chloride is the principal precursor to magnesium metal, which is produced on a large scale. Hydrated magnesium chloride is the form most readily available.

Allyl chloride Chemical compound

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.

Lead(II) chloride Chemical compound

Lead(II) chloride (PbCl2) is an inorganic compound which is a white solid under ambient conditions. It is poorly soluble in water. Lead(II) chloride is one of the most important lead-based reagents. It also occurs naturally in the form of the mineral cotunnite.

Caesium chloride Chemical compound

Caesium chloride or cesium chloride is the inorganic compound with the formula CsCl. This colorless salt is an important source of caesium ions in a variety of niche applications. Its crystal structure forms a major structural type where each caesium ion is coordinated by 8 chlorine ions. Caesium chloride dissolves in water. CsCl changes to NaCl structure on heating. Caesium chloride occurs naturally as impurities in carnallite, sylvite and kainite. Less than 20 tonnes of CsCl is produced annually worldwide, mostly from a caesium-bearing mineral pollucite.

18-Crown-6 Chemical compound

18-Crown-6 is an organic compound with the formula [C2H4O]6 and the IUPAC name of 1,4,7,10,13,16-hexaoxacyclooctadecane. It is a white, hygroscopic crystalline solid with a low melting point. Like other crown ethers, 18-crown-6 functions as a ligand for some metal cations with a particular affinity for potassium cations (binding constant in methanol: 106 M−1). The point group of 18-crown-6 is S6. The dipole moment of 18-crown-6 varies in different solvent and under different temperature. Under 25 °C, the dipole moment of 18-crown-6 is 2.76 ± 0.06 D in cyclohexane and 2.73 ± 0.02 in benzene. The synthesis of the crown ethers led to the awarding of the Nobel Prize in Chemistry to Charles J. Pedersen.

Titanocene dichloride Chemical compound

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Petasis reagent Chemical compound

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Grignard reagent Grignard reagents are extremely useful organometallic compounds in the field of organic chemistry

A Grignard reagent or Grignard Compound is a chemical compound with the generic formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH
3
and phenylmagnesium bromide (C
6
H
5
)−Mg−Br
. They are a subclass of the organomagnesium compounds.

Diphenyl diselenide Chemical compound

Diphenyl diselenide is the chemical compound with the formula (C6H5)2Se2, abbreviated Ph2Se2. This orange-coloured solid is the oxidized derivative of benzeneselenol. It is used as a source of the PhSe unit in organic synthesis.

Titanocene dicarbonyl Chemical compound

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Organonickel

Organonickel chemistry is a branch of organometallic chemistry that deals with organic compounds featuring nickel-carbon bonds. They are used as a catalyst, as a building block in organic chemistry and in chemical vapor deposition. Organonickel compounds are also short-lived intermediates in organic reactions. The first organonickel compound was nickel tetracarbonyl Ni(CO)4, reported in 1890 and quickly applied in the Mond process for nickel purification. Organonickel complexes are prominent in numerous industrial processes including carbonylations, hydrocyanation, and the Shell higher olefin process.

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Tributylphosphine Chemical compound

Tributylphosphine is the organophosphorus compound with the formula P(C
4
H
9
)
3
. Abbreviated or PBu
3
, it is a tertiary phosphine. It is an oily liquid at room temperature, with a nauseating odor. It reacts slowly with atmospheric oxygen, and rapidly with other oxidizing agents, to give the corresponding phosphine oxide. It is usually handled using air-free techniques.

Methyldichloroarsine Chemical compound

Methyldichloroarsine, sometimes abbreviated “MD” and also known as methyl Dick, is an organoarsenic compound with the formula CH3AsCl2. This colourless volatile liquid is a highly toxic vesicant that has been used in chemical warfare.

Magnesium acetate Chemical compound

Anhydrous magnesium acetate has the chemical formula Mg(C2H3O2)2 and in its hydrated form, magnesium acetate tetrahydrate, it has the chemical formula Mg(CH3COO)2 • 4H2O. In this compound magnesium has an oxidation state of 2+. Magnesium acetate is the magnesium salt of acetic acid. It is deliquescent and upon heating, it decomposes to form magnesium oxide. Magnesium acetate is commonly used as a source of magnesium in biological reactions.

Organogallium chemistry

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Isopropylmagnesium chloride Chemical compound

Isopropylmagnesium chloride is an organometallic compound with the general formula (CH3)2HCMgCl. This highly flammable, colorless, and moisture sensitive material is the Grignard reagent derived from isopropyl chloride. It is commercially available, usually as a solution in tetrahydrofuran. This reagent is used to prepare Grignard reagents by transmetalation reactions as well as installing isopropyl groups. An illustrative generic reaction involves the generation of the Grignard reagent derived from bromo-3,5-bis(trifluoromethyl)benzene:

References

  1. Lionel Delaude; Alfred F. Noels (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01.
  2. Amos Turk; Henry Chanan (1947). "Biallyl". Org. Synth. 27: 7. doi:10.15227/orgsyn.027.0007.