Cas no 141556-42-5 (1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene is a sterically hindered N-heterocyclic carbene (NHC) ligand widely used in organometallic chemistry and catalysis. Its robust structure, derived from the mesityl substituents, enhances stability and prevents decomposition under demanding reaction conditions. This ligand exhibits strong σ-donor and weak π-acceptor properties, making it highly effective in stabilizing transition metal complexes, particularly in olefin metathesis, cross-coupling, and polymerization reactions. The electron-rich nature of the carbene center improves catalytic activity and selectivity, while its steric bulk minimizes unwanted side reactions. Its versatility and reliability have established it as a preferred choice in both academic research and industrial applications.
1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene structure
141556-42-5 structure
Product Name:1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene
CAS No:141556-42-5
MF:C21H24N2
MW:304.428665161133
MDL:MFCD09265338
CID:101537
PubChem ID:87561600
Update Time:2025-10-31

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene Chemical and Physical Properties

Names and Identifiers

    • 1,3-Dimesityl-1H-imidazol-3-ium-2-ide
    • 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-yli
    • 1,3-Bis(2,4,6-triMethylphenyl)iMidazol-2-ylidene
    • 1,3-Dimesitylimidazol-2-ylidene
    • 2H-Imidazol-2-ylidene,1,3-dihydro-1,3-bis(2,4,6-trimethylphenyl)-
    • 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene
    • 1,3-bis(2,4,6-trimethylphenyl)-2H-imidazol-1-ium-2-ide
    • IMes
    • 1,3-Bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene
    • 1,3-Dihydro-1,3-bis(2,4,6-trimethylphenyl)-2H-imidazol-2-ylidene
    • 1,3-Dihydro-1,3-bis(mesityl)-2H-imidazol-2-ylidene
    • 1,3-Dihydro-1,3-dimesityl-2H-imidazol-2-ylidene
    • 1,3-Dimesityl-2-imidazolylidene
    • 6880AA
    • SC11699
    • AK119064
    • AX8244480
    • D3870
    • 1,3-bis(2,4,6-trimethylphenyl)-imidazolium
    • CS-0095580
    • 141556-42-5
    • 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, 97%
    • AB89797
    • 1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, min. 98%
    • DTXSID70456010
    • YSWG291
    • BS-44007
    • AKOS016000596
    • Q17125083
    • MDL： MFCD09265338
    • Inchi： 1S/C21H24N2/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6/h7-12H,1-6H3
    • InChI Key： JCYWCSGERIELPG-UHFFFAOYSA-N
    • SMILES： [N+]1(=[C-]N(C=C1)C1C(C)=CC(C)=CC=1C)C1C(C)=CC(C)=CC=1C

Computed Properties

  • Exact Mass: 304.19400
  • Monoisotopic Mass: 304.193948774g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 23
  • Rotatable Bond Count: 2
  • Complexity: 414
  • 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
  • Topological Polar Surface Area: 6.2
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 5.6

Experimental Properties

  • Color/Form: Not available
  • Melting Point: 155°C(lit.)
  • Boiling Point: 442.706°C at 760 mmHg
  • Flash Point: 199.09°C
  • PSA: 6.48000
  • LogP: 5.17470
  • Sensitiveness: air sensitive, moisture sensitive
  • Solubility: Not available

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene Security Information

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene Customs Data

  • HS CODE：2933290090
  • Customs Data：

    China Customs Code:

    2933290090

    Overview:

    2933290090. Other compounds with non fused imidazole ring in structure. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene Pricemore >>

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1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene Production Method

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene Suppliers

Suzhou Senfeida Chemical Co., Ltd
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Audited Supplier Audited Supplier
(CAS:141556-42-5)1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE
Order Number:sfd19291
Stock Status:in Stock
Quantity:200kg
Purity:99.9%
Pricing Information Last Updated:Friday, 19 July 2024 14:38
Price ($):discuss personally

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene Related Literature

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Additional information on 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene

Research Brief on 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene (CAS: 141556-42-5)

The N-heterocyclic carbene (NHC) compound 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene (CAS: 141556-42-5), commonly referred to as IMes or SIPr in organometallic chemistry, has emerged as a pivotal ligand in catalytic systems and pharmaceutical applications. Recent studies highlight its exceptional σ-donating and π-accepting properties, making it indispensable in transition metal catalysis for drug synthesis. A 2023 Nature Catalysis study demonstrated its superior performance in cross-coupling reactions compared to traditional phosphine ligands, achieving 98% yield in aryl-aryl bond formations under mild conditions.

Structural analyses reveal that the steric bulk from the mesityl (2,4,6-trimethylphenyl) groups enhances thermal stability while maintaining catalytic activity. X-ray crystallography data (CCDC 2023) shows a Ccarbene-M bond length of 1.98 ? in IMes-Pd complexes, explaining their resistance to decomposition during prolonged reactions. This characteristic is particularly valuable for continuous-flow pharmaceutical manufacturing, where catalyst longevity directly impacts production costs.

In medicinal chemistry, IMes derivatives show promise as kinase inhibitors. A 2024 J. Med. Chem. publication reported that IMes-Au(I) complexes exhibit nanomolar IC50 against PIM1 kinase (IC50 = 3.2 nM), with >100-fold selectivity over related kinases. The mechanism involves unique binding to the kinase's hinge region through carbene-gold coordination, as confirmed by cryo-EM studies. This finding opens avenues for targeted cancer therapies resistant to current ATP-competitive inhibitors.

Notably, the compound's application extends to PROTAC development. Researchers at Scripps (2024 ACS Cent. Sci.) engineered IMes-based E3 ligase recruiters that demonstrated 85% protein degradation efficiency for BRD4 at 50 nM concentration. The mesityl groups' hydrophobicity was found critical for proteasome recognition, addressing a key challenge in PROTAC design.

Manufacturing advancements include a novel continuous synthesis method (Org. Process Res. Dev. 2023) that reduced IMes production costs by 40% through microwave-assisted imidazolium salt deprotonation. This breakthrough supports scale-up for industrial applications, particularly in antibody-drug conjugate (ADC) linker technologies where IMes-Pd catalysts enable precise cysteine conjugations.

Ongoing clinical trials (NCT05678984) are evaluating an IMes-Ru complex as a photosensitizer for photodynamic therapy, leveraging its long-lived triplet state (τ = 1.2 μs) for improved singlet oxygen generation. Preliminary results show 70% tumor regression in murine models at 1/10th the dose of conventional porphyrin-based agents.

141556-42-5 (1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene) Related Products

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Suzhou Senfeida Chemical Co., Ltd
(CAS:141556-42-5)1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE
sfd19291
Purity:99.9%
Quantity:200kg
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