Xantphos - ≥98% , CAS No.161265-03-8

CAS: 161265-03-8 Cat. No.: X111327 Molecular Weight: 578.62 EC Number: 605-249-4 PubChem CID: 636044

GRADE & PURITY ≥98%

Synonyms

4,5-Bis(diphenylphospheno)-9,9-dimethyl xanthene | dimethyl bisdiphenylphosphinoxanthene | 4,5-Bis(diphenylphosphino)-9,9-dimethyl xanthene | Phosphine, 1,1'-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenyl- | [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xa

Storage

Room temperature

Shipped In

Normal

Overview

Xantphos is a bidentate ligand that is employed in various metal-catalyzed reactions, including cross-couplings, Buchwald-Hartwig cross-coupling reactions, C-X bond formation, hydroformylation, Miyaura borylation reaction, Stille coupling, Suzuki-Miyaura coupling, (hetero)arylation, amination, and amidation.
Application
Ligand used in a synthesis of heterocycles by palladium-catalyzed C-N cross coupling of 3-bromothiophenes with 2-aminopyridines. Also used in a ruthenium-catalyzed alkylation of active methylene compounds with alcohols. 
Metal chelating ligand for catalysis.

Specifications

Synonyms

4, 5-Bis(diphenylphospheno)-9, 9-dimethyl xanthene | dimethyl bisdiphenylphosphinoxanthene | 4, 5-Bis(diphenylphosphino)-9, 9-dimethyl xanthene | Phosphine, 1, 1'-(9, 9-dimethyl-9H-xanthene-4, 5-diyl)bis[1, 1-diphenyl- | [5-(diphenylphosphanyl)-9, 9-dimethyl-9H-xa

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488190834
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488190834
• Canonical Smiles: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
• IUPAC Name: (5-diphenylphosphanyl-9,9-dimethylxanthen-4-yl)-diphenylphosphane
• InChIKey: CXNIUSPIQKWYAI-UHFFFAOYSA-N
• INCHI: 1S/C39H32OP2/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3
• Isomeric SMILES: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
• WGK Germany: 3
• PubChem CID: 636044
• Molecular Weight: 578.62
• Reaxy-Rn: 7085968

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Phenylphosphines and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Phenylphosphines and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylphosphines and derivatives
• Alternative Parents: Xanthenes Diarylethers Organic phosphines and derivatives Oxacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Triphenylphosphine - Dibenzopyran - Xanthene - Diaryl ether - Benzopyran - 1-benzopyran - Phenylphosphine - Phosphine - Ether - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organophosphorus compound - Organopnictogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylphosphines and derivatives. These are compounds containing a phenylphosphine, which consists of phosphine substituent bound to a phenyl group.
• External Descriptors: Not available

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: Soluble in organic solvents
• Melt Point(°C): 226-230°C
• Molecular Weight: 578.600 g/mol
• XLogP3: 9.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 578.193 Da
• Monoisotopic Mass: 578.193 Da
• Topological Polar Surface Area: 9.200 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 731.000
• 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. Xiaoyuan Ma, Kunlong Yang, Jingchao Wang, Siyi Li, Tianyong Zhang, Shuang Jiang, Bin Li.  (2021)  Novel bioinspired diiron core complexes with rigid chelating diphosphine ligands for highly efficient catalytic phenol hydroxylation.  Molecular Catalysis,      [PMID:] [10.1016/j.mcat.2021.112088]

2. Jian Chen, Kai Chen, Baichuan Han, Yunting Xue, Wanjuan Chen, Zhenzhong Gao, Xianfeng Hou.  (2020)  A novel single-fluorophore-based ratiometric fluorescent probe for detection of formaldehyde in air.  TETRAHEDRON,      [PMID:] [10.1016/j.tet.2020.131681]

3. Linfeng Zhang, Changpo Ma, Chenyu Wang, Guangyu Sun, Yongqi Shu, Wenya Zou, Tao Yang, Weiran Yang.  (2022)  Direct conversion of glyceric acid to succinic acid by reductive carbonylation.  GREEN CHEMISTRY,  24  (19): (7644-7651).  [PMID:] [10.1039/D2GC02594A]