1,3-Cyclohexadiene - ≥95%, contains 0.1% BHT as stabilizer , CAS No.592-57-4

CAS: 592-57-4 Cat. No.: C189164 Molecular Weight: 80.13 Beilstein Registry Number: 506024 EC Number: 209-764-1

GRADE & PURITY ≥95%, contains 0.1% BHT as stabilizer

Synonyms

1,3-CYCLOHEXADIENE|Cyclohexa-1,3-diene|592-57-4|CYCLOHEXADIENE|1,2-dihydrobenzene|JV5W0EG5BP|29797-09-9|1165952-91-9|Cyclohexadiene-1,3|EINECS 209-764-1|UNII-JV5W0EG5BP|MFCD00001532|cyclohexa-1|1,3 cyclohexadiene|2,4-cyclohexadiene|EINECS 249-853-2|1,-3-c

Storage

Store at 2-8°C

Shipped In

Wet ice,FedEx DG Service

Overview

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.

Specifications

Synonyms

1, 3-CYCLOHEXADIENE | Cyclohexa-1, 3-diene | 592-57-4 | CYCLOHEXADIENE | 1, 2-dihydrobenzene | JV5W0EG5BP | 29797-09-9 | 1165952-91-9 | Cyclohexadiene-1, 3 | EINECS 209-764-1 | UNII-JV5W0EG5BP | MFCD00001532 | cyclohexa-1 | 1, 3 cyclohexadiene | 2, 4-cyclohexadiene | EINECS 249-853-2 | 1, -3-c

Specifications & Purity

≥95%, contains 0.1% BHT as stabilizer

Storage

Store at 2-8°C

Shipped In

Wet ice, FedEx DG Service

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

• Canonical Smiles: C1CC=CC=C1
• IUPAC Name: cyclohexa-1,3-diene
• InChIKey: MGNZXYYWBUKAII-UHFFFAOYSA-N
• INCHI: 1S/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2
• Isomeric SMILES: C1CC=CC=C1
• WGK Germany: 3
• Molecular Weight: 80.13
• Beilstein: 506024
• Reaxy-Rn: 506024
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=506024&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Hydrocarbons
    • Class Unsaturated hydrocarbons
      • Subclass Olefins

• Kingdom: Organic compounds
• Superclass: Hydrocarbons
• Class: Unsaturated hydrocarbons
• Subclass: Olefins
• Intermediate Tree Nodes: Not available
• Direct Parent: Cyclic olefins
• Alternative Parents: Unsaturated aliphatic hydrocarbons
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclic olefin - Unsaturated aliphatic hydrocarbon - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as cyclic olefins. These are olefins that contain at least one ring in their structure.
• External Descriptors: cyclohexadiene

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Slightly miscible with methanol. Immiscible with water
• Sensitivity: heat sensitive
• Refractive Index: 1.474
• Flash Point(°F): 17.6 °F
• Flash Point(°C): -8 °C
• Boil Point(°C): 80 °C
• Molecular Weight: 80.130 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 80.0626 Da
• Monoisotopic Mass: 80.0626 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 66.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jinxiu Hu, Xianlong Liu, Yi Liu, Kang Xue, Chengxiang Shi, Xiangwen Zhang, Li Wang, Ji-Jun Zou, Lun Pan.  (2023)  Photoinduced transposed Paternò-Büchi reaction for effective synthesis of high-performance jet fuel.  CHINESE JOURNAL OF CHEMICAL ENGINEERING,      [PMID:] [10.1016/j.cjche.2023.09.014]

2. Junjian Xie, Xiangwen Zhang, Chengxiang Shi, Lun Pan, Fang Hou, Genkuo Nie, Jiawei Xie, Qing Liu, Ji-Jun Zou.  (2019)  Self-photosensitized [2 + 2] cycloaddition for synthesis of high-energy-density fuels.  Sustainable Energy & Fuels,  4  (2): (911-920).  [PMID:] [10.1039/C9SE00863B]

3. Qiong Wu, Tianfeng Chen, Zhao Zhang, Siyan Liao, Xiaohui Wu, Jian Wu, Wenjie Mei, Yanhua Chen, Weili Wu, Lingli Zeng, Wenjie Zheng.  (2014)  Microwave-assisted synthesis of arene ruthenium(II) complexes [(η6-RC6H5)Ru(m-MOPIP)Cl]Cl (R = -H and -CH3) as groove binder to c-myc G4 DNA.  DALTON TRANSACTIONS,  43  (24): (9216-9225).  [PMID:24818221] [10.1039/C3DT53635A]