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125415

Sigma-Aldrich

1,4-Cyclohexadiene

97%

Synonym(s):

1,4-Dihydrobenzene

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About This Item

Empirical Formula (Hill Notation):
C6H8
CAS Number:
628-41-1
Molecular Weight:
80.13
Beilstein:
1900733
MDL number:
MFCD00001535
UNSPSC Code:
12352100
PubChem Substance ID:
24847665
NACRES:
NA.22
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Quality Level

100

Assay

97%

form

liquid

contains

~0.1% hydroquinone as stabilizer

impurities

3% benzene

refractive index

n20/D 1.472 (lit.)

bp

88-89 °C (lit.)

density

0.847 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C1C=CCC=C1

InChI

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

InChI key

UVJHQYIOXKWHFD-UHFFFAOYSA-N

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General description

1,4-Cyclohexadiene is an effective hydrogen donor for catalytic hydrogenation reactions[1]. It can rapidly replace benzyl groups of N-benzyloxycarbamates, benzyl esters, benzyl ethers and benzyl amines with hydrogen[1]. It forms benzene at elevated temperatures in the presence of a ruthenium(II)-triphenylphosphine catalyst[2].

Application

1,4-Cyclohexadiene (1,4-CHD) was used to study the formation of parent ion from heavy fragmentation of 1,4-CHD on irradiation with a high-intensity laser pulse[3].
Useful for the reduction of radical intermediates formed in electron-transfer mediated ring-opening reactions

Pictograms

FlameHealth hazard
GHS02,GHS08

Signal Word

Danger

Hazard Statements

H225,H340,H350,H373

Hazard Classifications

Carc. 1A - Flam. Liq. 2 - Muta. 1B - STOT RE 2

Target Organs

Blood

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

19.4 °F - closed cup

Flash Point(C)

-7 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS1790
SHBN8511
SHBK8437
SHBH2723V
29096LKV

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A key factor in parent and fragment ion formation on irradiation with an intense femtosecond laser pulse.
Harada H, et al.
Chemical Physics Letters, 342(5), 563-570 (2001)
Organometallics, 25, 5456-5456 (2006)
Kyung-Bin Cho et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(33), 10444-10453 (2012-06-21)
The experimentally measured bimolecular reaction rate constant, k(2), should in principle correlate with the theoretically calculated rate-limiting free energy barrier, ΔG(≠), through the Eyring equation, but it fails quite often to do so due to the inability of current computational
Kazutada Ikeuchi et al.
Organic letters, 14(23), 6016-6019 (2012-11-15)
Asymmetric bromolactonization of prochiral cyclohexadiene derivatives with N-bromosuccimide proceeded in the presence of (DHQD)(2)PHAL as a chiral catalyst to afford the corresponding bromolactones with up to 93% ee. This reaction was also applicable to the kinetic resolution of a racemic
Enrico Tapavicza et al.
Physical chemistry chemical physics : PCCP, 13(47), 20986-20998 (2011-10-25)
We investigate the photodynamics of vitamin D derivatives by a fully analytical implementation of the linear response time-dependent density functional theory surface hopping method (LR-TDDFT-SH). Our study elucidates the dynamics of the processes involved in vitamin D formation at the
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    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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