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C100005

Sigma-Aldrich

1,3-Cyclohexadiene

contains 0.05% BHT as inhibitor, 97%

Synonym(s):

1,2-Dihydrobenzene

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About This Item

Empirical Formula (Hill Notation):
C6H8
CAS Number:
592-57-4
Molecular Weight:
80.13
Beilstein:
506024
EC Number:
209-764-1
MDL number:
MFCD00001532
UNSPSC Code:
12352100
PubChem Substance ID:
24892292
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

contains

0.05% BHT as inhibitor

refractive index

n20/D 1.474 (lit.)

bp

80 °C (lit.)

density

0.841 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C1CC=CC=C1

InChI

1S/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2

InChI key

MGNZXYYWBUKAII-UHFFFAOYSA-N

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Application

1,3-Cyclohexadiene can undergo:
  • C-C coupling with aromatic alcohols via iridium-catalyzed hydrogen auto-transfer and with aldehydes via transfer hydrogenation mediated by isopropanol to form carbonyl addition products.
  • Living anionic polymerization with n-BuLi/TMEDA system to form polycyclohexadiene.
  • Platinum-catalyzed silaboration to form (1R,4S)-1-(dimethylphenylsilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclohexene.
  • Aerobic palladium-catalyzed 1,4-diacetoxylation in the presence of cobalt tetra(hydroquinone)porphyrin as an electron transfer reagent.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H335

Hazard Classifications

Flam. Liq. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

66.0 °F

Flash Point(C)

18.9 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nicolas J Saettel et al.
Journal of the American Chemical Society, 124(38), 11552-11559 (2002-09-19)
The electron-transfer-catalyzed Diels-Alder reaction of indole and 1,3-cyclohexadiene was studied by a combination of experimental and theoretical methods. The (13)C kinetic isotope effects were determined at natural abundance by NMR methodology. B3LYP/6-31G* calculations allow for the first time a quantitatively
Takumi Oshima et al.
Organic & biomolecular chemistry, 10(9), 1730-1734 (2012-01-13)
The first CH/π solute-solvent interaction of C(60) was evidenced by the kinetic solvent effects in the Diels-Alder reaction with 1,3-cyclohexadiene based on the evaluation of linear free energy relationship of log k(2) with empirical solvent polarity and basicity parameters, E(T)(30)
Synthesis of polymers with an alicyclic structure in the main chain. Living anionic polymerization of 1, 3-cyclohexadiene with the n-butyllithium/N, N, N ′, N′-tetramethyl-ethylenediamine system.
Natori I.
Macromolecules, 30(12), 3696-3697 (1997)
B Naydenov et al.
Physical review letters, 97(9), 098304-098304 (2006-10-10)
Precision current measurements are recorded at 5 K during the approach and contact between a Pt-inked probe and the carbon-carbon double-bond region of an isolated 1,3-cyclohexadiene molecule chemisorbed on a Si(100) surface. Scanning tunneling spectroscopic data reveal systematic features in
J L White et al.
The Journal of chemical physics, 136(5), 054303-054303 (2012-02-11)
We use spectral unmixing to determine the number of transient photoproducts and to track their evolution following the photo-excitation of 1,3-cyclohexadiene (CHD) to form 1,3,5-hexatriene (HT) in the gas phase. The ring opening is initiated with a 266 nm ultraviolet
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