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544-25-2

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544-25-2 Usage

Chemical Properties

Cycloheptatriene is a clear yellow to brownish liquid. Insoluble in water and less dense than water. Vapors heavier than air. Inhalation of high concentrations may have a narcotic effect. It is a ligand in organometallic chemistry and as a building block in organic synthesis. Cycloheptatriene is not aromatic, as reflected by the nonplanarity of the methylene bridge with respect to the other atoms.

Uses

1,3,5-Cycloheptatriene functions as a ligand in organometallic chemistry and also as a building block in organic synthetic processes. 1,3,5-Cycloheptatriene is applied in cycloheptatrienyl transition zirconium complexes formation and in other organic complex formation processes.

Definition

ChEBI: A cycloheptatriene with unsaturation at positions 1, 3 and 5.

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 5009, 1959 DOI: 10.1021/ja01527a075Tetrahedron, 21, p. 1673, 1965 DOI: 10.1016/S0040-4020(01)98637-5

General Description

A colorless liquid. Insoluble in water and less dense than water. Flash point 35°F. Vapors heavier than air. Inhalation of high concentrations may have a narcotic effect. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Cycloheptatriene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions.

Health Hazard

TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Poison by ingestion and skin contact. Mutation data reported. A very dangerous fire hazard when exposed to heat, flame, or oxidzers. Potentially violent reaction with nitrogen monoxide. Whenheated to decomposition it emits acrid smoke and fumes.

Purification Methods

Wash the triene with alkali, then fractionally distil it. Store it under N2 or Ar as it resinifies in air. [Dryden J Am Chem Soc 76 2814 1954, Kohler et al. J Am Chem Soc 61 1057 1939, Beilstein 5 IV 280.]

Check Digit Verification of cas no

The CAS Registry Mumber 544-25-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 4 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 544-25:
(5*5)+(4*4)+(3*4)+(2*2)+(1*5)=62
62 % 10 = 2
So 544-25-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H8/c1-2-4-6-7-5-3-1/h1-6H,7H2

544-25-2 Well-known Company Product Price

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  • TCI America

  • (C0572)  1,3,5-Cycloheptatriene  >95.0%(GC)

  • 544-25-2

  • 25mL

  • 405.00CNY

  • Detail
  • Alfa Aesar

  • (A17064)  Cycloheptatriene, 95%   

  • 544-25-2

  • 50ml

  • 673.0CNY

  • Detail
  • Alfa Aesar

  • (A17064)  Cycloheptatriene, 95%   

  • 544-25-2

  • 250ml

  • 2581.0CNY

  • Detail
  • Aldrich

  • (C99205)  Cycloheptatriene  95%

  • 544-25-2

  • C99205-100ML

  • 866.97CNY

  • Detail
  • Aldrich

  • (C99205)  Cycloheptatriene  95%

  • 544-25-2

  • C99205-1L

  • 7,166.25CNY

  • Detail

544-25-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name cyclohepta-1,3,5-triene

1.2 Other means of identification

Product number -
Other names 1,3,5-Cycloheptatriene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:544-25-2 SDS

544-25-2Relevant articles and documents

-

Anastassiou,Cellura

, p. 1521 (1969)

-

Pulse Radiolysis Study of the Cycloheptatriene Triplet State: Lifetime, Relaxation, and Nonvertical Excitation

Gorman, A. A.,Hamblett, I.,Irvine, M.,Raby, P.,Standen, M. C.,Yeates, S.

, p. 4404 - 4411 (1985)

The triplet state of cycloheptatriene (CHT) has been produced by pulse radiolysis in toluene.Its lifetime of 6 +/- 1 μs is considerably longer than for acyclic trienes, ca. 300 ns, despite a smaller energy gap between the relaxed T1 and S0 surfaces.It is proposed that relaxation is from the boatlike spectroscopic state to an approximately planar species within which spin-orbit coupling factors are minimized.Plots of log ket vs. donor triplet energy for endothermic triplet energy transfer to both CHT and the acyclic neo-alloocimene (NA) show that, whereas the latter is close to being a vertical acceptor of triplet energy, CHT exhibits clear "nonvertical" character.In this respect, NA and CHT mimic trans- and cis-stilbene, respectively.It would appear that, for olefinic systems, established "nonvertical" behavior is currently restricted to nonplanar ? systems, and the possibility is raised that such behavior may, at least in part, reflect higher vibrational level densities in such systems.

Photolysis of two tricyclic nonenediones. Direct observation of norcaradiene

Rubin, Mordecai B.

, p. 7791 - 7792 (1981)

-

Synthesis of 1,2,3,4,5,6,7-Heptasubstituted Cycloheptatrienes through Cycloaddition Reactions of Substituted Cyclopentadienones

Platonov, Dmitry N.,Belyy, Aleksandr Yu.,Ananyev, Ivan V.,Tomilov, Yury V.

, p. 4105 - 4110 (2016)

Two schemes for synthesizing heptasubstituted cycloheptatrienes with various substituents in the ring are suggested. The first method is based on cycloaddition of 2,5-dimethoxycarbonyl-3,4-diphenylcyclopentadienone with substituted cyclopropenes and allows cycloheptatrienes containing two or three electron-withdrawing substituents in the molecule to be obtained. The second method employs a cascade reaction between a substituted cyclopentadienone and appropriate vinyldiazoacetates. It allows the number of electron-withdrawing substituents to be increased to five. In all cases, heptasubstituted cycloheptatrienes are formed as just one of the possible isomers.

Synthesis and characterization of manganese triple-decker complexes

Heinl, Sebastian,Balázs, Gábor,Bodensteiner, Michael,Scheer, Manfred

, p. 1962 - 1966 (2016)

The use of the highly sterically demanding CpBIG ligand (CpBIG = C5(4-nBuC6H4)5) and white phosphorus (P4) enables the synthesis of new P-rich derivatives of the rare Pn ligand complexes of manganese. The obtained complexes, [{CpBIGMn}2(μ,η5:5-P5)] (2) and [{CpBIGMn}2(μ,η2:2-P2)2] (3), exhibit the highest number of P atoms in this class of manganese compounds identified by X-ray structure analyses. The EPR spectrum of the 29 VE triple-decker complex 2 shows one unpaired electron coupling with two 5/2 spin Mn nuclei.

-

Gassman,P.G.,Creary,X.

, p. 2729 - 2731 (1973)

-

Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement

Cheng, Mu-Jeng,Kardile, Rahul Dadabhau,Kuo, Tung-Chun,Liu, Rai-Shung,More, Sayaji Arjun

supporting information, p. 5506 - 5511 (2021/07/31)

Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.

Gold(I) Carbenoids: On-Demand Access to Gold(I) Carbenes in Solution

Sarria Toro, Juan M.,García-Morales, Cristina,Raducan, Mihai,Smirnova, Ekaterina S.,Echavarren, Antonio M.

supporting information, p. 1859 - 1863 (2017/02/05)

Chloromethylgold(I) complexes of phosphine, phosphite, and N-heterocyclic carbene ligands are easily synthesized by reaction of trimethylsilyldiazomethane with the corresponding gold chloride precursors. Activation of these gold(I) carbenoids with a variety of chloride scavengers promotes reactivity typical of metallocarbenes in solution, namely homocoupling to ethylene, olefin cyclopropanation, and Buchner ring expansion of benzene.

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