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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:
Molecular Weight:
80.13
Beilstein:
506024
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level

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.[1]
  • Living anionic polymerization with n-BuLi/TMEDA system to form polycyclohexadiene.[2]
  • Platinum-catalyzed silaboration to form (1R,4S)-1-(dimethylphenylsilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclohexene.[3]
  • Aerobic palladium-catalyzed 1,4-diacetoxylation in the presence of cobalt tetra(hydroquinone)porphyrin as an electron transfer reagent.[4]

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

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

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Yasushi Obora et al.
The Journal of organic chemistry, 75(17), 6046-6049 (2010-08-05)
Intermolecular [2+2+2] cycloaddition of tert-butylacetylene with alpha,omega-dienes was successfully achieved by NbCl(3)(DME) catalyst to afford 5-omega-alkenyl-1,4-disubstituted-1,3-cyclohexadienes in excellent yields with high chemo- and regioselectivity.
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)
Cobalt Tetra (hydroquinone) porphyrin: An Efficient Electron Transfer Reagent in Aerobic Pd?Catalyzed 1, 4?Diacetoxylation of 1, 3?Cyclohexadiene.
Grennberg H, et al.
Angewandte Chemie (International Edition in English), 32(2), 263-264 (1993)
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)
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

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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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