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Cycloheptatriene information


Cycloheptatriene
Names
Preferred IUPAC name
Cyclohepta-1,3,5-triene[1]
Other names
1,3,5-Cycloheptatriene
1H-[7]Annulene
CHT
Tropilidene
Identifiers
CAS Number
  • 544-25-2 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
506066
ChEBI
  • CHEBI:37519 checkY
ChemSpider
  • 10534 checkY
ECHA InfoCard 100.008.061 Edit this at Wikidata
EC Number
  • 208-866-3
Gmelin Reference
1943
PubChem CID
  • 11000
UNII
  • P58Q106NTF checkY
UN number 2603
CompTox Dashboard (EPA)
  • DTXSID5073909 Edit this at Wikidata
InChI
  • InChI=1S/C7H8/c1-2-4-6-7-5-3-1/h1-6H,7H2 checkY
    Key: CHVJITGCYZJHLR-UHFFFAOYSA-N checkY
  • InChI=1/C7H8/c1-2-4-6-7-5-3-1/h1-6H,7H2
    Key: CHVJITGCYZJHLR-UHFFFAOYAI
SMILES
  • C1=C\C/C=C\C=C1
Properties
Chemical formula
C7H8
Molar mass 92.141 g·mol−1
Appearance Colourless liquid
Density 0.888 g/mL at 25 °C
Melting point −80 °C (−112 °F; 193 K)
Boiling point 116 °C (241 °F; 389 K)
Solubility in water
Insoluble in water
Acidity (pKa) 36
Hazards
GHS labelling:
Pictograms
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Signal word
Danger
Hazard statements
H225, H301, H304, H311, H315, H319, H335
Precautionary statements
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P322, P330, P331, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cycloheptatriene (CHT) is an organic compound with the formula C7H8. It is a closed ring of seven carbon atoms joined by three double bonds (as the name implies) and four single bonds. This colourless liquid has been of recurring theoretical interest in organic chemistry. It is a ligand in organometallic chemistry and a building block in organic synthesis. Cycloheptatriene is not aromatic, as reflected by the nonplanarity of the methylene bridge (-CH2-) with respect to the other atoms; however the related tropylium cation is.

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 223. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

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Cycloheptatriene

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Cycloheptatriene (CHT) is an organic compound with the formula C7H8. It is a closed ring of seven carbon atoms joined by three double bonds (as the name...

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Tropylium cation

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of [C7H7]+. Its name derives from the molecule tropine from which cycloheptatriene (tropylidene) was first synthesized in 1881. Salts of the tropylium...

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Cycloheptatrienemolybdenum tricarbonyl

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The compound has no practical value but is a prototypical complex of cycloheptatriene. The compound is prepared by thermal reaction of the triene with molybdenum...

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C7H8

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The molecular formula C7H8 (molar mass: 92.14 g/mol) may refer to: Cycloheptatriene Isotoluenes Norbornadiene Quadricyclane Toluene, or toluol This set...

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Buchner ring expansion

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using both thermal and photochemical pathways in the synthesis of cycloheptatriene derivatives. The resulting product was a mixture of four isomeric carboxylic...

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Azulene

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is usually viewed as resulting from fusion of cyclopentadiene and cycloheptatriene rings. Like naphthalene and cyclodecapentaene, it is a 10 pi electron...

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Methylecgonidine

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with methanol. The scheme by Kline is based on the reaction of 2,4,6-cycloheptatriene-7-carboxylic acid with methylamine. This is a modified version of U...

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Borepin

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with a tricoordinate boron in it. Simple borepins are analogues of cycloheptatriene, which is a seven-membered ring containing three carbon-carbon double...

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Sesquifulvalene

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chemical formula C12H10. It is composed of linked cyclopentadiene and cycloheptatriene rings. In the ground state, which is a singlet state, the central double...

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Cycloheptadiene

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6577-10-2 1,3-Cycloheptadiene 1,4-Cycloheptadiene Cycloheptatriene or its theoretical isomer 1,3,5-Cycloheptatriene Cycloheptene This set index article lists...

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CHT

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Bangladesh Cylinder Head Temperature gauge, an engine control sensor Cycloheptatriene, an organic chemical compound Ford CHT engine, a Compound High Turbulence...

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Carbenium ion

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can be stable, e.g. tropylium tetrafluoroborate. It can be made from cycloheptatriene (tropylidene) and bromine or phosphorus pentachloride. It is a planar...

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Elassovalene

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polycyclic hydrocarbon with chemical formula C12H10, composed of one cycloheptatriene ring and two fused cyclopentene rings. List of chemical compounds with...

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Tropylium tetrafluoroborate

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is a white solid. This compound may be prepared by the reaction of cycloheptatriene with phosphorus pentachloride, followed by tetrafluoroboric acid. Triphenylmethyl...

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Tecovirimat

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Technologies in 2004. It is made in two steps from cycloheptatriene. A Diels–Alder reaction of cycloheptatriene with maleic anhydride forms the main ring system...

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Heptalene

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polycyclic hydrocarbon with chemical formula C12H10, composed of two fused cycloheptatriene rings. It is an unstable, non-planar compound which is non-aromatic...

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Half sandwich compound

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readily cleaved by ligands to give monoRu half-sandwich derivatives. Cycloheptatriene molybdenum tricarbonyl Cp2V2(CO)5 featuring a pair of semi-bridging...

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Triphenylmethane

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(1969). "Electrochemical determinations of pKa's. Triphenylmethanes and cycloheptatriene". Journal of the American Chemical Society. 92 (7): 2165. doi:10.1021/ja00710a077...

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Transition metal alkene complex

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several adjacent carbon centers. Common examples of such ligands are cycloheptatriene and cyclooctatetraene. The bonding is often denoted using the hapticity...

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Aromatization

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hydride. Tropylium, C 7H+ 7 arises by the aromatization reaction of cycloheptatriene with hydride acceptors. C 7H 8 + Br 2 → C 7H+ 7 + Br− + HBr The aromatization...

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Cyclopropene

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also be obtained in about 1% yield by thermolysis of the adduct of cycloheptatriene and dimethyl acetylenedicarboxylate. Allyl chloride undergoes dehydrohalogenation...

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Carbocation

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1891 when G. Merling reported that he added bromine to tropylidene (cycloheptatriene) and then heated the product to obtain a crystalline, water-soluble...

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Dye laser

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laser-pumping source. Adamantane is added to some dyes to prolong their life. Cycloheptatriene and cyclooctatetraene (COT) can be added as triplet quenchers for rhodamine...

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Sigmatropic reaction

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rearrangement is the shift of substituents on tropilidenes (1,3,5-cycloheptatrienes). When heated, the pi-system goes through an electrocyclic ring closing...

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Cyclopentadienylvanadium tetracarbonyl

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CO Protonation of this salt gives Cp2V2(CO)5. Heating a mixture of cycloheptatriene and cyclopentadienylvanadium tetracarbonyl gives...

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Cyclononatetraene

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that exhibits Möbius aromaticity. Cyclopentadiene Cyclooctatetraene Cycloheptatriene Azonine Radlick, Phillip; Alford, Gary (November 1969). "Preparation...

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