Cas no 83724-41-8 (Tris(2-methoxyphenyl)bismuthine)

Tris(2-methoxyphenyl)bismuthine is an organobismuth compound featuring three 2-methoxyphenyl groups bonded to a central bismuth atom. This compound is of interest in synthetic and coordination chemistry due to the electron-donating methoxy groups, which influence its reactivity and stability. It serves as a precursor for bismuthine-based catalysts and ligands, particularly in reactions requiring mild Lewis acidity or redox-active behavior. The methoxy substituents enhance solubility in organic solvents, facilitating its use in homogeneous systems. Its well-defined structure makes it suitable for mechanistic studies in bismuth-mediated transformations. Careful handling is advised due to potential sensitivity to air and moisture.
Tris(2-methoxyphenyl)bismuthine structure
83724-41-8 structure
Product Name:Tris(2-methoxyphenyl)bismuthine
CAS No:83724-41-8
MF:C21H21BiO3
MW:530.370023488998
MDL:MFCD00092705
CID:720549
PubChem ID:87577565
Update Time:2025-05-20

Tris(2-methoxyphenyl)bismuthine Chemical and Physical Properties

Names and Identifiers

    • Bismuthine,tris(2-methoxyphenyl)-
    • Tris(2-methoxyphenyl)bismuthine
    • tris(2-methoxyphenyl)bismuthane
    • tris-(2-methoxyphenyl)bismuthane
    • VFWRGMGLLNCHIA-UHFFFAOYSA-N
    • Tris(2-methoxyphenyl)bismuthine (ACI)
    • Tris(2-methoxyphenyl)bismuth
    • T72981
    • DTXSID00370098
    • MFCD00092705
    • T1838
    • SCHEMBL1539178
    • AKOS015851741
    • 83724-41-8
    • DB-056738
    • MDL: MFCD00092705
    • Inchi: 1S/3C7H7O.Bi/c3*1-8-7-5-3-2-4-6-7;/h3*2-5H,1H3;
    • InChI Key: VFWRGMGLLNCHIA-UHFFFAOYSA-N
    • SMILES: O(C)C1C([Bi](C2C(OC)=CC=CC=2)C2C(OC)=CC=CC=2)=CC=CC=1

Computed Properties

  • Exact Mass: 530.12900
  • Monoisotopic Mass: 530.12947g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 6
  • Complexity: 334
  • 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: 27.7
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing

Experimental Properties

  • Color/Form: solid
  • Melting Point: 160.0 to 163.0 deg-C
  • PSA: 27.69000
  • LogP: 4.48620
  • Solubility: Not determined

Tris(2-methoxyphenyl)bismuthine Security Information

Tris(2-methoxyphenyl)bismuthine Pricemore >>

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Tris(2-methoxyphenyl)bismuthine Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Bismuth trichloride Solvents: Tetrahydrofuran ;  0 °C; 1 h, rt; 30 min, rt → 65 °C; 65 °C → rt
1.2 Reagents: Sodium chloride ;  rt
Reference
High efficient copper-promoted N-arylation of secondary and primary amines with triarylbismuth reagents under mild conditions
Zhou, Xuehao; et al, Journal of Molecular Structure, 2023, 1294,

Production Method 2

Reaction Conditions
1.1 Reagents: Bismuth trichloride
Reference
Estimation of the magnitude of quadrupole relaxation enhancement in the context of magnetic resonance imaging contrast
Kruk, Danuta ; et al, Journal of Chemical Physics, 2019, 150(18), 184306/1-184306/9

Production Method 3

Reaction Conditions
1.1 Reagents: Calcium carbonate ,  Copper ,  Bismuth ,  Cuprous iodide ;  12 h, rt
Reference
A novel dry route to ortho-functionalized triarylbismuthanes that are difficult to access by conventional wet routes
Urano, Mika; et al, Chemical Communications (Cambridge, 2003, (10), 1202-1203

Production Method 4

Reaction Conditions
1.1 Solvents: Dichloromethane ;  30 min, rt
Reference
Diverse Structures and Remarkable Oxidizing Ability of Triarylbismuthane Oxides. Comparative Study on the Structure and Reactivity of a Series of Triarylpnictogen Oxides
Matano, Yoshihiro; et al, Organometallics, 2004, 23(23), 5471-5480

Production Method 5

Reaction Conditions
1.1 Solvents: Chloroform-d
Reference
Dimeric Triarylbismuthane Oxide: A Novel Efficient Oxidant for the Conversion of Alcohols to Carbonyl Compounds
Matano, Yoshihiro; et al, Journal of the American Chemical Society, 2001, 123(26), 6443-6444

Production Method 6

Reaction Conditions
1.1 Solvents: Chloroform-d
Reference
Dimeric Triarylbismuthane Oxide: A Novel Efficient Oxidant for the Conversion of Alcohols to Carbonyl Compounds
Matano, Yoshihiro; et al, Journal of the American Chemical Society, 2001, 123(26), 6443-6444

Production Method 7

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide ,  Water Solvents: Dichloromethane ;  2 h, 0 °C
2.1 Solvents: Dichloromethane ;  30 min, rt
Reference
Diverse Structures and Remarkable Oxidizing Ability of Triarylbismuthane Oxides. Comparative Study on the Structure and Reactivity of a Series of Triarylpnictogen Oxides
Matano, Yoshihiro; et al, Organometallics, 2004, 23(23), 5471-5480

Production Method 8

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: Dichloromethane
1.2 Solvents: Acetonitrile
2.1 Solvents: Chloroform-d
Reference
Dimeric Triarylbismuthane Oxide: A Novel Efficient Oxidant for the Conversion of Alcohols to Carbonyl Compounds
Matano, Yoshihiro; et al, Journal of the American Chemical Society, 2001, 123(26), 6443-6444

Production Method 9

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide ,  Water Solvents: Dichloromethane ;  2 h, 0 °C
2.1 Solvents: Dichloromethane ;  30 min, rt
Reference
Diverse Structures and Remarkable Oxidizing Ability of Triarylbismuthane Oxides. Comparative Study on the Structure and Reactivity of a Series of Triarylpnictogen Oxides
Matano, Yoshihiro; et al, Organometallics, 2004, 23(23), 5471-5480

Production Method 10

Reaction Conditions
1.1 Solvents: Dichloromethane
2.1 -
Reference
Stabilized bismuthonium ylides bearing a highly cross-conjugated ylidic carbon atom: synthesis, structures, and reactions
Matano, Yoshihiro; et al, Journal of Organometallic Chemistry, 2000, 611(1-2), 89-99

Production Method 11

Reaction Conditions
1.1 Solvents: Dichloromethane
2.1 -
Reference
Stabilized bismuthonium ylides bearing a highly cross-conjugated ylidic carbon atom: synthesis, structures, and reactions
Matano, Yoshihiro; et al, Journal of Organometallic Chemistry, 2000, 611(1-2), 89-99

Production Method 12

Reaction Conditions
1.1 Solvents: Benzene
Reference
Dimeric Triarylbismuthane Oxide: A Novel Efficient Oxidant for the Conversion of Alcohols to Carbonyl Compounds
Matano, Yoshihiro; et al, Journal of the American Chemical Society, 2001, 123(26), 6443-6444

Production Method 13

Reaction Conditions
1.1 Reagents: Zinc Catalysts: Trifluoroacetic acid ,  Allyl chloride ,  Cobalt dibromide Solvents: Acetonitrile ;  15 min, 20 °C
1.2 20 °C
1.3 Reagents: Bismuth trichloride Solvents: Acetonitrile ;  18 h, 20 °C
Reference
Advanced preparation of functionalized triarylbismuths and triheteroaryl-bismuths: new scope and alternatives
Urgin, Karene; et al, Tetrahedron Letters, 2012, 53(15), 1894-1896

Production Method 14

Reaction Conditions
1.1 Reagents: Bismuth trichloride Solvents: Tetrahydrofuran
Reference
Aryl bismuth phosphinates [BiAr2(O(O)PRR')]: structure-activity relationships for antibacterial activity and cytotoxicity
Herdman, Megan E.; et al, Dalton Transactions, 2022, 51(24), 9323-9335

Production Method 15

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: Dichloromethane
1.2 Solvents: Acetonitrile
2.1 Solvents: Benzene
Reference
Dimeric Triarylbismuthane Oxide: A Novel Efficient Oxidant for the Conversion of Alcohols to Carbonyl Compounds
Matano, Yoshihiro; et al, Journal of the American Chemical Society, 2001, 123(26), 6443-6444

Production Method 16

Reaction Conditions
Reference
Stabilized bismuthonium ylides bearing a highly cross-conjugated ylidic carbon atom: synthesis, structures, and reactions
Matano, Yoshihiro; et al, Journal of Organometallic Chemistry, 2000, 611(1-2), 89-99

Production Method 17

Reaction Conditions
Reference
Stabilized bismuthonium ylides bearing a highly cross-conjugated ylidic carbon atom: synthesis, structures, and reactions
Matano, Yoshihiro; et al, Journal of Organometallic Chemistry, 2000, 611(1-2), 89-99

Production Method 18

Reaction Conditions
1.1 Solvents: Dichloromethane ;  30 min, rt
Reference
Diverse Structures and Remarkable Oxidizing Ability of Triarylbismuthane Oxides. Comparative Study on the Structure and Reactivity of a Series of Triarylpnictogen Oxides
Matano, Yoshihiro; et al, Organometallics, 2004, 23(23), 5471-5480

Production Method 19

Reaction Conditions
1.1 Solvents: Chloroform-d
Reference
Dimeric Triarylbismuthane Oxide: A Novel Efficient Oxidant for the Conversion of Alcohols to Carbonyl Compounds
Matano, Yoshihiro; et al, Journal of the American Chemical Society, 2001, 123(26), 6443-6444

Production Method 20

Reaction Conditions
1.1 Solvents: Dichloromethane ;  30 min, rt
Reference
Diverse Structures and Remarkable Oxidizing Ability of Triarylbismuthane Oxides. Comparative Study on the Structure and Reactivity of a Series of Triarylpnictogen Oxides
Matano, Yoshihiro; et al, Organometallics, 2004, 23(23), 5471-5480

Production Method 21

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: Dichloromethane
1.2 Solvents: Acetonitrile
2.1 Solvents: Chloroform-d
Reference
Dimeric Triarylbismuthane Oxide: A Novel Efficient Oxidant for the Conversion of Alcohols to Carbonyl Compounds
Matano, Yoshihiro; et al, Journal of the American Chemical Society, 2001, 123(26), 6443-6444

Production Method 22

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide ,  Water Solvents: Dichloromethane ;  2 h, 0 °C
2.1 Solvents: Dichloromethane ;  30 min, rt
Reference
Diverse Structures and Remarkable Oxidizing Ability of Triarylbismuthane Oxides. Comparative Study on the Structure and Reactivity of a Series of Triarylpnictogen Oxides
Matano, Yoshihiro; et al, Organometallics, 2004, 23(23), 5471-5480

Production Method 23

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: Dichloromethane
1.2 Solvents: Acetonitrile
2.1 Solvents: Chloroform-d
Reference
Dimeric Triarylbismuthane Oxide: A Novel Efficient Oxidant for the Conversion of Alcohols to Carbonyl Compounds
Matano, Yoshihiro; et al, Journal of the American Chemical Society, 2001, 123(26), 6443-6444

Production Method 24

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide ,  Water Solvents: Dichloromethane ;  2 h, 0 °C
2.1 Solvents: Dichloromethane ;  30 min, rt
Reference
Diverse Structures and Remarkable Oxidizing Ability of Triarylbismuthane Oxides. Comparative Study on the Structure and Reactivity of a Series of Triarylpnictogen Oxides
Matano, Yoshihiro; et al, Organometallics, 2004, 23(23), 5471-5480

Production Method 25

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide ,  Water Solvents: Dichloromethane ;  2 h, 0 °C
2.1 Solvents: Dichloromethane ;  30 min, rt
Reference
Diverse Structures and Remarkable Oxidizing Ability of Triarylbismuthane Oxides. Comparative Study on the Structure and Reactivity of a Series of Triarylpnictogen Oxides
Matano, Yoshihiro; et al, Organometallics, 2004, 23(23), 5471-5480

Production Method 26

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide ,  Water Solvents: Dichloromethane ;  2 h, 0 °C
2.1 Solvents: Dichloromethane ;  30 min, rt
Reference
Diverse Structures and Remarkable Oxidizing Ability of Triarylbismuthane Oxides. Comparative Study on the Structure and Reactivity of a Series of Triarylpnictogen Oxides
Matano, Yoshihiro; et al, Organometallics, 2004, 23(23), 5471-5480

Tris(2-methoxyphenyl)bismuthine Raw materials

Tris(2-methoxyphenyl)bismuthine Preparation Products

Additional information on Tris(2-methoxyphenyl)bismuthine

Exploring the Potential of Tris(2-Methoxyphenyl)Bismuthine: A Comprehensive Overview

Tris(2-Methoxyphenyl)Bismuthine (CAS No. 83724-41-8) is a fascinating compound that has garnered significant attention in the fields of materials science, organic synthesis, and catalysis. This compound, with its unique structure and properties, offers a wide range of applications and continues to be a subject of extensive research. In this article, we delve into the intricacies of Tris(2-Methoxyphenyl)Bismuthine, exploring its chemical composition, physical properties, applications, and the latest advancements in its utilization.

The molecular structure of Tris(2-Methoxyphenyl)Bismuthine is characterized by a central bismuth atom surrounded by three 2-methoxyphenyl groups. This arrangement imparts the compound with distinctive electronic and optical properties. Recent studies have highlighted its potential as a versatile building block in the synthesis of advanced materials. For instance, researchers have demonstrated its ability to form stable coordination complexes with transition metals, which can be employed in catalytic processes for organic transformations.

One of the most promising applications of Tris(2-Methoxyphenyl)Bismuthine lies in its role as a precursor for the synthesis of bismuth-based nanoparticles. These nanoparticles exhibit unique optical properties, making them ideal candidates for applications in sensing, imaging, and drug delivery systems. A groundbreaking study published in *Advanced Materials* revealed that nanoparticles derived from Tris(2-Methoxyphenyl)Bismuthine exhibit enhanced biocompatibility and stability under physiological conditions, paving the way for their use in biomedical applications.

In addition to its role in materials science, Tris(2-Methoxyphenyl)Bismuthine has also found utility in organic synthesis as a ligand or catalyst. Its ability to stabilize reactive intermediates makes it an invaluable tool in asymmetric catalysis. Recent advancements have shown that when used as a chiral ligand, it can significantly enhance the enantioselectivity of certain reactions, opening new avenues for the production of chiral pharmaceuticals.

The physical properties of Tris(2-Methoxyphenyl)Bismuthine are equally intriguing. Its melting point and solubility characteristics make it suitable for various industrial processes. Moreover, its thermal stability under high-temperature conditions has been leveraged in the development of novel thermoelectric materials. A study conducted at Stanford University demonstrated that composites incorporating Tris(2-Methoxyphenyl)Bismuthine exhibit improved thermoelectric performance, offering potential solutions for energy harvesting applications.

Looking ahead, the future of Tris(2-Methoxyphenyl)Bismuthine seems bright as researchers continue to unlock its full potential. Collaborative efforts between academia and industry are expected to drive innovation in its application across diverse sectors. As sustainability becomes a critical focus globally, the development of eco-friendly synthesis routes for Tris(2-Methoxyphenyl)Bismuthine will be paramount. Researchers are actively exploring green chemistry approaches to minimize waste and reduce environmental impact during its production.

In conclusion, Tris(2-Methoxyphenyl)Bismuthine (CAS No. 83724-41-8) stands out as a multifaceted compound with immense potential across various scientific disciplines. Its unique structure, coupled with cutting-edge research advancements, positions it as a key player in shaping future technologies. As we continue to unravel its capabilities, one can only anticipate further breakthroughs that will redefine its role in materials science and beyond.

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