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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)

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Sarah J Ryan et al.
Journal of the American Chemical Society, 133(13), 4694-4697 (2011-03-12)
Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with α,β-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr >20:1) while demonstrating a new type of reaction cascade exploiting
Borislav Naydenov et al.
Nano letters, 6(8), 1752-1756 (2006-08-10)
We present a study that maps out chemical bond formation between a Pt-inked probe and a single 1,3-cyclohexadiene (1,3-CHD) molecule on Si(100). By separating the mechanical and electronic contributions to the current during the approach to contact, we show that
Enantioselective Platinum?Catalyzed Silicon?Boron Addition to 1, 3?Cyclohexadiene.
Gerdin M and Moberg C
Advanced Synthesis & Catalysis, 347(6), 749-753 (2005)
Marija Kotur et al.
The Journal of chemical physics, 130(13), 134311-134311 (2009-04-10)
We demonstrate the use of shaped ultrafast laser pulses in the deep ultraviolet to control the ring opening isomerization of 1,3-cyclohexadiene to form 1,3,5-hexatriene. The experiments are performed with a gas phase sample and the isomerization yield is probed with
Chemo-, regio-, and stereoselective cobalt-mediated [2+2+2] cycloaddition of alkynyl boronates to alkenes: 1,3- and 1,4-diboryl-1,3-cyclohexadienes.
Vincent Gandon et al.
Angewandte Chemie (International ed. in English), 44(43), 7114-7118 (2005-10-12)
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