Cas no 21854-95-5 (1,2-Bis(2-chlorophenyl)-1,2-ethanedione)

1,2-Bis(2-chlorophenyl)-1,2-ethanedione is a chlorinated aromatic diketone with applications in organic synthesis and pharmaceutical intermediates. Its structure, featuring two ortho-chlorophenyl groups bonded to a central ethanedione moiety, enhances reactivity in cross-coupling and cyclization reactions. The compound's electron-withdrawing chlorine substituents contribute to its stability and selectivity in forming heterocyclic compounds. It is particularly useful in the synthesis of complex molecules due to its predictable reactivity and compatibility with various catalysts. The high purity and well-defined crystalline form of this diketone ensure consistent performance in research and industrial processes. Proper handling is advised due to its potential sensitivity to light and moisture.
1,2-Bis(2-chlorophenyl)-1,2-ethanedione structure
21854-95-5 structure
Product Name:1,2-Bis(2-chlorophenyl)-1,2-ethanedione
CAS No:21854-95-5
MF:C14H8Cl2O2
MW:279.11812210083
MDL:MFCD00018263
CID:88294
PubChem ID:24882282
Update Time:2025-08-05

1,2-Bis(2-chlorophenyl)-1,2-ethanedione Chemical and Physical Properties

Names and Identifiers

    • 2,2'-Dichlorobenzil
    • 2,2-Dichlorodibenzoyl
    • 1,2-bis(2-chlorophenyl)ethane-1,2-dione
    • 2,2′-Dichlorobenzil
    • 2,2'-DIADAMANTYLAMINE HYDROCHLORIDE
    • 2,2'-Dichlor-benzil
    • 2,2'-dichlorobenzyl
    • 2,2'-Dichlorodibenzoyl
    • Benzil,2,2'-dichloro
    • Benzil,2'-dichloro
    • AKOS015913690
    • J-014315
    • Benzil,2'-dichloro-
    • bis(2-chlorophenyl)ethane-1,2-dione
    • Benzil-based compound, 10
    • PD129614
    • 1,2-Ethanedione, 1,2-bis(2-chlorophenyl)-
    • DTXSID1066736
    • CS-0199369
    • BDBM22732
    • AS-76455
    • E79189
    • SCHEMBL2156567
    • NSC114829
    • NSC-114829
    • AE-562/43458948
    • FT-0609210
    • Ethanedione, bis(2-chlorophenyl)-
    • CHEMBL365392
    • NSC 114829
    • 1,2-Bis(2-chlorophenyl)-1,2-ethanedione #
    • 2,2-dichlorobenzil
    • VOSNNSVWVJFJCR-UHFFFAOYSA-N
    • 21854-95-5
    • Benzil, 2,2'-dichloro-
    • A878909
    • 2,2'-Dichlorobenzil, 97%
    • ZB1725
    • MFCD00018263
    • 2,2//'-Dichlorobenzil
    • 1,2-Bis(2-chlorophenyl)-1,2-ethanedione
    • DB-045715
    • 2,2''-Dichlorobenzil
    • 2,2 inverted exclamation marka-Dichlorobenzil
    • MDL: MFCD00018263
    • Inchi: 1S/C14H8Cl2O2/c15-11-7-3-1-5-9(11)13(17)14(18)10-6-2-4-8-12(10)16/h1-8H
    • InChI Key: VOSNNSVWVJFJCR-UHFFFAOYSA-N
    • SMILES: ClC1C=CC=CC=1C(C(C1C=CC=CC=1Cl)=O)=O
    • BRN: 2120689

Computed Properties

  • Exact Mass: 277.99000
  • Monoisotopic Mass: 277.99
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 3
  • Complexity: 298
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 4.2
  • Topological Polar Surface Area: 34.1A^2

Experimental Properties

  • Color/Form: {"from":"zh","to":"en","trans_result":[{"src":"\u672a\u786e\u5b9a","dst":"Not determined"},{"src":"2.\u00a0\u5bc6\u5ea6\uff08g\/mL,25\/4\u2103\uff09","dst":"2. density (g\/ml, 25\/4 \u2103)"}]}
  • Density: 1.366
  • Melting Point: 132-136?°C (lit.)
  • Boiling Point: 426.9°C at 760 mmHg
  • Flash Point: 180.2°C
  • Refractive Index: 1.612
  • PSA: 34.14000
  • LogP: 4.05900

1,2-Bis(2-chlorophenyl)-1,2-ethanedione Security Information

  • Symbol: GHS07 GHS09
  • Signal Word:Warning
  • Hazard Statement: H319-H400
  • Warning Statement: P273-P305+P351+P338
  • Hazardous Material transportation number:UN 3077 9/PG 3
  • WGK Germany:3
  • Hazard Category Code: 36-50/53
  • Safety Instruction: S22-S24/25
  • Hazardous Material Identification: Xi N
  • TSCA:Yes
  • Risk Phrases:R36; R50/53
  • Safety Term:S22;S24/25

1,2-Bis(2-chlorophenyl)-1,2-ethanedione Customs Data

  • HS CODE:2914700090
  • Customs Data:

    China Customs Code:

    2914700090

    Overview:

    2914700090 Halogenation of other ketones and quinones\Sulfonated derivative(Including nitrated and nitrosative derivatives). VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:5.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, Acetone declared packaging

    Summary:

    HS: 2914700090 halogenated, sulphonated, nitrated or nitrosated derivatives of ketones and quinones, whether or not with other oxygen function Tax rebate rate:9.0% Supervision conditions:none VAT:17.0% MFN tariff:5.5% General tariff:30.0%

1,2-Bis(2-chlorophenyl)-1,2-ethanedione Pricemore >>

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1,2-Bis(2-chlorophenyl)-1,2-ethanedione Production Method

1,2-Bis(2-chlorophenyl)-1,2-ethanedione Related Literature

Additional information on 1,2-Bis(2-chlorophenyl)-1,2-ethanedione

1,2-Bis(2-chlorophenyl)-1,2-ethanedione: A Comprehensive Overview

1,2-Bis(2-chlorophenyl)-1,2-ethanedione (CAS No. 21854-95-5) is a versatile organic compound with significant applications in various fields of chemistry and materials science. This compound, often referred to as DDQ analog, has garnered attention due to its unique structural properties and potential uses in drug design, material synthesis, and environmental chemistry. The molecule consists of two chlorophenyl groups attached to a central ethanedione core, which imparts it with distinctive electronic and steric characteristics.

Recent advancements in computational chemistry have enabled researchers to delve deeper into the electronic structure of 1,2-Bis(2-chlorophenyl)-1,2-ethanedione. Studies utilizing density functional theory (DFT) have revealed that the compound exhibits a high degree of conjugation across its aromatic rings and the diketone moiety. This conjugation not only enhances its stability but also contributes to its ability to act as a redox-active species in various chemical reactions. The presence of electron-withdrawing chlorine atoms further modulates the electronic properties of the molecule, making it an attractive candidate for applications in organic electronics.

The synthesis of 1,2-Bis(2-chlorophenyl)-1,2-ethanedione typically involves multi-step organic reactions. One common approach involves the Friedel-Crafts acylation of chlorobenzene derivatives followed by oxidation to form the diketone structure. Recent optimizations in this synthesis pathway have focused on improving yield and reducing reaction times by employing catalytic systems such as transition metal catalysts or enzymatic methods. These advancements have made the compound more accessible for large-scale production and research purposes.

In terms of applications, 1,2-Bis(2-chlorophenyl)-1,2-ethanedione has found utility in the field of drug discovery. Its ability to act as a chelating agent has been leveraged in designing metalloenzyme inhibitors and anti-inflammatory agents. Additionally, the compound has been explored as a building block for constructing bioactive molecules with potential anticancer properties. Recent studies have demonstrated that derivatives of this compound can induce apoptosis in cancer cells by targeting specific signaling pathways.

The environmental impact of 1,2-Bis(2-chlorophenyl)-1,2-ethanedione has also been a topic of interest. Research into its biodegradation pathways has revealed that under aerobic conditions, the compound undergoes microbial transformation through hydroxylation and ring-opening mechanisms. These findings are crucial for assessing its ecological safety and guiding its responsible use in industrial settings.

From a materials science perspective, 1,2-Bis(2-chlorophenyl)-1,2-ethanedione has been investigated as a precursor for synthesizing advanced materials such as conductive polymers and coordination polymers. Its ability to coordinate with metal ions makes it a valuable component in designing functional materials for energy storage devices and sensors.

In conclusion, 1,2-Bis(2-chlorophenyl)-1,2-ethanedione (CAS No. 21854-95-5) is a multifaceted compound with diverse applications across various scientific domains. Ongoing research continues to uncover new insights into its properties and potential uses, solidifying its position as an important molecule in modern chemistry.

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