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Details

Stereochemistry ACHIRAL
Molecular Formula C6H8
Molecular Weight 80.1277
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,3-CYCLOHEXADIENE

SMILES

C1CC=CC=C1

InChI

InChIKey=MGNZXYYWBUKAII-UHFFFAOYSA-N
InChI=1S/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2

HIDE SMILES / InChI

Molecular Formula C6H8
Molecular Weight 80.1277
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Electrophilic aromatic substitution and single-electron transfer (SET) by the phenylium ion in the gas phase: characterization of a long-lived SET intermediate.
2009-01
Generation and detection of the cyclohexadienyl radical in phosphonium ionic liquids.
2008-10-21
Transition states for the dimerization of 1,3-cyclohexadiene: a DFT, CASPT2, and CBS-QB3 quantum mechanical investigation.
2008-10-03
Catalytic tuning of a phosphinoethane ligand for enhanced C-H activation.
2008-10-01
Emergence and visualization of an interface state during contact formation with a single molecule.
2008-08-29
Multiphoton control of the 1,3-cyclohexadiene ring-opening reaction in the presence of competing solvent reactions.
2008-07-31
Does an ethene/benzenium ion complex exist? A discrepancy between B3LYP and MP2 predictions.
2008-07-24
Ligand-tuned regioselectivity of a cobalt-catalyzed Diels-Alder reaction. A theoretical study.
2008-07-16
Cobalt-catalyzed intermolecular [2 + 2 + 2] cycloaddition for the synthesis of 1,3-cyclohexadienes.
2008-07-04
Nickel-catalyzed addition of C-H bonds of terminal alkynes to 1,3-dienes and styrenes.
2008-04-23
Iridium-catalyzed C-C coupling via transfer hydrogenation: carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene.
2008-03-06
Mechanism of the palladium-catalyzed carbohydroxylation of allene-substituted conjugated dienes: rationalization of the recently observed nucleophilic attack by water on a (pi-allyl)palladium intermediate.
2008
Revealing phenylium, phenonium, vinylenephenonium, and benzenium ions in solution.
2008
New insights into the reaction mechanisms of phenylium ions with benzene.
2007-12-13
Energetics of the allyl group.
2007-11-09
Role of surface dimer dynamics in creating ordered organic-semiconductor interfaces.
2007-10-10
Aqueous Ti(IV)-catalyzed Diels-Alder reaction.
2007-08-04
Enhancement of a Lewis acid-base interaction via solvation: ammonia molecules and the benzene radical cation.
2007-07-12
Degradation of H-acid and its derivative in aqueous solution by ionising radiation.
2007-06
Pyrene-benzoylthiophene exciplexes as selective catalysts for the [2+2] cycloaddition between cyclohexadiene and styrenes.
2007-05-24
Radical transfer hydroamination with aminated cyclohexadienes using polarity reversal catalysis: scope and limitations.
2007-04-11
Local ordering in liquids: solvent effects on the hyperfine couplings of the cyclohexadienyl radical.
2007-01-11
Direct estimate of conjugation and aromaticity in cyclic compounds with the EDA method.
2007
Cationic rare-earth polyhydrido complexes: synthesis, structure, and catalytic activity for the cis-1,4-selective polymerization of 1,3-cyclohexadiene.
2006-12-11
Radical additions of aryl iodides to arenes are facilitated by oxidative rearomatization with dioxygen.
2006-10-25
Dynamics of surface catalyzed reactions; the roles of surface defects, surface diffusion, and hot electrons.
2006-10-12
Spectroscopy and femtosecond dynamics of the ring opening reaction of 1,3-cyclohexadiene.
2006-10-07
Studies of the generation and pericyclic behavior of cyclic pentadienyl carbanions. Alkylation reactions as an efficient route to functionalized cis-bicyclo[3.3.0]octenes.
2006-09-20
The enantioselective step in the nickel-catalyzed hydrocyanation of 1,3-cyclohexadiene.
2006-09-06
Measuring the force of interaction between a metallic probe and a single molecule.
2006-09-01
Thermal reactions of 7-d- and 8-d-bicyclo[4.2.0]oct-2-enes.
2006-08-09
Solvent dependent conformational relaxation of cis-1,3,5-hexatriene.
2006-08-03
Contact formation dynamics: Mapping chemical bond formation between a molecule and a metallic probe.
2006-08
Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes.
2006-07-05
Sonochemical cycloadditions in ionic liquids. Lessons from model cases involving common dienes and carbonyl dienophiles.
2006-07
Hydrogen transfer in the formation and destruction of retrograde products in coal conversion.
2006-06-01
Hydrogenation of arenes over silica-supported catalysts that combine a grafted rhodium complex and palladium nanoparticles: evidence for substrate activation on Rh(single-site)-Pd(metal) moieties.
2006-05-31
Infrared and electronic spectroscopy of a model system for the nucleophilic substitution intermediate in the gas phase: the C-N valence bond formation in the benzene-ammonia cluster cation.
2006-05-25
Biochemical characterization and crystal structure of Synechocystis arogenate dehydrogenase provide insights into catalytic reaction.
2006-04
Spectral phase effects on nonlinear resonant photochemistry of 1,3-cyclohexadiene in solution.
2006-03-21
Concise synthesis of the neo-clerodane skeleton of teucrolivin A using a pericyclic reaction cascade.
2006-03-03
Photoactivated h/d exchange in tyrosine: involvement of a radical anion intermediate.
2006-02-22
A new approach to promoting sluggish Diels-Alder reactions: dihapto-coordination of the diene.
2006-02-08
Doubly protonated benzene in the gas phase.
2006-02-02
Spectroscopic analysis of small organic molecules: a comprehensive near-edge x-ray-absorption fine-structure study of C6-ring-containing molecules.
2006-01-21
A novel approach in analyzing aromaticity by homo- and isostructural reactions: an ab initio study of fluorobenzenes.
2005-11-24
Chemo-, regio-, and stereoselective cobalt-mediated [2+2+2] cycloaddition of alkynyl boronates to alkenes: 1,3- and 1,4-diboryl-1,3-cyclohexadienes.
2005-11-04
Evolution of functional cyclohexadiene-based synthetic reagents: the importance of becoming aromatic.
2005-10
Silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines.
2005-09-02
Simulation of scanning tunneling microscope images of 1,3-cyclohexadiene bound to a silicon surface.
2005-02-03
Patents

Patents

Substance Class Chemical
Created
by admin
on Mon Mar 31 18:53:38 GMT 2025
Edited
by admin
on Mon Mar 31 18:53:38 GMT 2025
Record UNII
JV5W0EG5BP
Record Status Validated (UNII)
Record Version
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Name Type Language
1,3-CYCLOHEXADIENE
Systematic Name English
BENZENE, DIHYDRO-
Preferred Name English
Code System Code Type Description
MESH
C034005
Created by admin on Mon Mar 31 18:53:38 GMT 2025 , Edited by admin on Mon Mar 31 18:53:38 GMT 2025
PRIMARY
ECHA (EC/EINECS)
209-764-1
Created by admin on Mon Mar 31 18:53:38 GMT 2025 , Edited by admin on Mon Mar 31 18:53:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID30862259
Created by admin on Mon Mar 31 18:53:38 GMT 2025 , Edited by admin on Mon Mar 31 18:53:38 GMT 2025
PRIMARY
CAS
592-57-4
Created by admin on Mon Mar 31 18:53:38 GMT 2025 , Edited by admin on Mon Mar 31 18:53:38 GMT 2025
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PUBCHEM
11605
Created by admin on Mon Mar 31 18:53:38 GMT 2025 , Edited by admin on Mon Mar 31 18:53:38 GMT 2025
PRIMARY
WIKIPEDIA
1,3-CYCLOHEXADIENE
Created by admin on Mon Mar 31 18:53:38 GMT 2025 , Edited by admin on Mon Mar 31 18:53:38 GMT 2025
PRIMARY
FDA UNII
JV5W0EG5BP
Created by admin on Mon Mar 31 18:53:38 GMT 2025 , Edited by admin on Mon Mar 31 18:53:38 GMT 2025
PRIMARY
CHEBI
37610
Created by admin on Mon Mar 31 18:53:38 GMT 2025 , Edited by admin on Mon Mar 31 18:53:38 GMT 2025
PRIMARY