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ChemicalBook > CAS DataBase List > 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

Application
Product Name
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
CAS No.
161265-03-8
Chemical Name
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
Synonyms
XANT PHOS;(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane);9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE;Dimethylbisdiphenylphosphinoxanthene;[5-(diphenylphosphanyl)-9,9-diMethyl-9H-xanthen-4-yl]diphenylphosphane;Bis(diphenylphosphino)-9,9-diMethylxanthene;4,5-Bis(diphenylphosphino)-9,9;4,5-Bis(diphenylphosphino)-9,9-dimethyl;4,5-BIS(DIPHENYLPHOSPHINO)-9,9-DIMETHYLX;9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene, XANTPHOS
CBNumber
CB0141028
Molecular Formula
C39H32OP2
Formula Weight
578.62
MOL File
161265-03-8.mol
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4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene Property

Melting point:
224-228 °C(lit.)
Boiling point:
665.7±55.0 °C(Predicted)
Flash point:
450℃
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
Soluble in organic solvents.
form 
Crystals
color 
White to light yellow
InChIKey
CXNIUSPIQKWYAI-UHFFFAOYSA-N
SMILES
C12=C(OC3=C(C1(C)C)C=CC=C3P(C1C=CC=CC=1)C1C=CC=CC=1)C(P(C1C=CC=CC=1)C1C=CC=CC=1)=CC=C2
CAS DataBase Reference
161265-03-8(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
37-20/22
Safety Statements 
37/39-26
WGK Germany 
3
TSCA 
No
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
526460
Product name
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
Purity
97%
Packaging
1g
Price
$63.06
Updated
2025/07/31
Sigma-Aldrich
Product number
526460
Product name
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
Purity
97%
Packaging
5g
Price
$195
Updated
2025/07/31
Sigma-Aldrich
Product number
928356
Product name
Xantphos ChemBeads
Packaging
1g
Price
$127.88
Updated
2025/07/31
TCI Chemical
Product number
B2709
Product name
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
Purity
>98.0%(HPLC)
Packaging
1g
Price
$57
Updated
2025/07/31
TCI Chemical
Product number
B2709
Product name
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
Purity
>98.0%(HPLC)
Packaging
5g
Price
$169
Updated
2025/07/31
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4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene Chemical Properties,Usage,Production

Application

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene is an organophosphorus compound derived from the heterocycle xanthene. It is used as a bidentate ligand and is noteworthy for having a particularly wide bite angle. Such ligands are useful in the hydroformylation of alkenes.

Chemical Properties

White to light yellow crystals

Uses

suzuki reaction

Uses

4,5-Bis(diphenylphosphino)-9, 9-dimethylxanthene is used as a bidentate ligand, which finds application in hydroformylation of alkenes.

Uses

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenyl-phosphine is an organophosphorus compound derived from the heterocycle xanthene. It is used as a bidentate ligand and is noteworthy for having a particularly wide bite angle. Such ligands are useful in the hydroformylation of alkenes.

Reactions

  1. Ligand used for the hydroformylation of alkenes.
  2. Ligand used in the intermolecular coupling of amides and hydrazones with aryl halides.
  3. Ligand used in the intermolecular coupling of amides with aryl halides or triflates.
  4. Ligand used in the coupling of heteroarylamines and aryl halides.
  5. Ligand used in the hydrophosphinylation of alkenes and alkynes.
  6. Ligand used for the Au(I)-catalyzed dehydrogenative silation of alcohols.
  7. Ligand used for the sulfinylation of aryl iodides.
  8. Ligand used for the Pd-catalyzed carbonylation reaction of aryl bromides and amines.
  9. Ligand used for the Ni-cataltzed alkynylcyanation of alkynes.
  10. Ligand used for the Pd-catalyzed N-arylation of 3-amino-1H-pyrazole.
  11. Ligand used for the Rh-catalyzed dehydrogenation borylation of cyclic alkenes.
  12. Ligand used for the Pd-catalyzed intermolecular coupling of H-Phosphonate diesters with benzyl halides.
  13. Ligand used for the Pd-catalyzed one pot synthesis of 4-aryl-1H-1,2,3-triazoles.
  14. Ligand used for the Pd-catalyzed intermolecular addition of formamides to alkynes.
  15. Ligand used for the Pd-catalyzed decarboxylative couplings of 2-(2-azaaryl)acetates with aryl halides and triflates.
  16. Ligand used for the Pd-catalyzed benzylic arylation of 2-methyl azaarenes
  17. Ligand used for the Pd-catalyzed α-arylation of heteroaromatic ketones.
  18. Ligand used for the Pd-catalyzed direct alkynlation of both azoles and azolines.
  19. Ligand used for the Cu-catalyzed intermolecular coupling of alkynes with aryl iodides.
  20. Ligand used for the Pd-catalyzed ene-type reaction of aldehydes with 1,3-diene.
  21. Ligand used for the Ru-catalyzed intermolecular addition of 2-phenylbenzoic acid onto unactivated olefins.
  22. Ligand used for the Pd/Cu-catalyzed direct arylation of heteroarenes.
  23. Ligand used for the Pd-catalyzed reaction of propargyl-substituted malonate esters with aryl halides.
  24. Ligand used for the Pd-catalyzed decarboxylative coupling of tertiary cyanoacetate salts with aryl halides and triflates.
  25. Ligand used for the Pd-catalyzed hydroesterification of alkynes.
  26. Ligand used for the Cu-catalyzed arylation of arylboronic acids with aldehydes.
  27. Ligand used for the Ru-catalyzed oxidative synthesis of heterocycles from alcohols.
  28. Ligand used for the Rh-catalyzed borylation of nitriles.
  29. Ligand used in the Pd-catalyzed α-arylation of benzylic phosphine oxides.
  30. Ligand used in the Pd-Catalyzed Oxidative Coupling of Enamides and Alkynes.
  31. Ligand used in the Pd-catalyzed difunctionalization of enol ethers to amino acetals with aminals and alcohols.
  32. Ligand used in the Pd-catalyzed alkoxycarbonylation of α-chloroketones.

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

Synthesis

19814-75-6

1079-66-9

161265-03-8

Example 2A Preparation of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (Xantphos): To a 5L round bottom flask was added methyl tert-butyl ether (MTBE, 2.5L), 9,9-dimethylxanthene (131.4 g, 0.60 mol) and N,N,N',N'-tetramethylethylenediamine (TMEDA, 155 g, 1.32 mol). After degassing the solution, sec-butyl lithium (s-BuLi, 1.11 L, 1.3 M in cyclohexane, 1.44 mol) was loaded into a dropping funnel, and then slowly added dropwise over a period of 60 min while controlling the reaction temperature at 6-10 °C. After the dropwise addition, the mixture was stirred at room temperature for 14 hours. Subsequently, diphenylphosphonium chloride (Ph2PCl) was slowly added through the dropping funnel while controlling the reaction temperature at 10-20°C to maintain a mild exothermic reaction. About 60% diphenylphosphonium chloride (175 mL, 0.93 mol) was added over 0.5 hr. The mixture was stirred for 10 minutes and then the remaining diphenylphosphonium chloride (120 mL, 0.63 mol) was added. The reaction mixture was continued to be stirred at room temperature for 5 hours before the reaction was quenched with methanol (MeOH, 9.9 mL, 0.24 mol). Filtration yielded a pale yellow solid product, which was washed sequentially with methyl tert-butyl ether (MTBE, 250 mL), methanol (2 x 250 mL), water (2 x 300 mL), methanol (2 x 250 mL) and methyl tert-butyl ether (250 mL), and dried to give an off-white solid product (304.2 g, 88% yield).

References

[1] Patent: US2004/23979, 2004, A1. Location in patent: Page/Page column 9; 10
[2] Patent: US2004/23979, 2004, A1. Location in patent: Page/Page column 9
[3] Dalton Transactions, 2018, vol. 47, # 11, p. 3745 - 3754
[4] Tetrahedron Letters, 1995, vol. 36, # 1, p. 75 - 78
[5] Patent: US7612241, 2009, B1. Location in patent: Page/Page column 4-5

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene Preparation Products And Raw materials

Raw materials

N,N,N',N'-Tetramethylethylenediamine Xanthone Toluene Diphenyl ether Trimethylaluminium Chlorodiphenylphosphine Tetrahydrofuran Ethyl acetate Hydrochloric acid Magnesium sulfate PETROLEUM ETHER n-Butyllithium

Preparation Products

4-(2-KETO-1-BENZIMIDAZOLINYL)PIPERIDINE
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View Lastest Price from 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene manufacturers

Hebei Fengjia New Material Co., Ltd
Product
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene 161265-03-8
Price
US $8.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
100000
Release date
2024-08-14
Hebei Chuanghai Biotechnology Co., Ltd
Product
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene 161265-03-8
Price
US $30.00-10.00/KG
Min. Order
50KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-24
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene 161265-03-8
Price
US $55.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/week
Release date
2024-06-03

161265-03-8, 4,5-Bis(diphenylphosphino)-9,9-dimethylxantheneRelated Search:

Triphenylphosphine oxide Diphenylsilane tert-Butylchlorodiphenylsilane Dimethyl sulfate Dimethyl ether Dimethyl sulfoxide Dimethyl fumarate Dimethyl sulfide Dacthal 3,4'-DIAMINODIPHENYLMETHANE Chlorodiphenylphosphine (OXYDI-2,1-PHENYLENE)BIS(DIPHENYLPHOSPHINE) Xanthene N,N-Dimethylformamide Dimethyl carbonate 1,5-Diphenylcarbazide TRIMETHYLPHOSPHINE OXIDE Diphenylmethane

  • XANT PHOS
  • 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE
  • (9,9-DIMETHYL-9H-XANTHENE-4,5-DIYL)BIS[DIPHENYL PHOSPHINE]
  • 4,5-BIS-DIPHENYLPHOSPHANYL-9,9-DIMETHYL-9H-XANTHENE
  • 4,5-BIS(DIPHENYLPHOSPHINO)-9,9-DIMETHYLXANTHENE
  • Dimethylbisdiphenylphosphinoxanthene
  • 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene, XANTPHOS
  • 4,5-BIS(DIPHENYLPHOSPHINO)-9,9-DIMETHYLX
  • 4,5-Bis(diphenylphosphino)-9,9
  • 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene,min.98%XANTPHOS
  • 9,9-DiMethyl-4,5-bis(diphenylphosphiNA)xanthene
  • Phosphine, (9,9-diMethyl-9H-xanthene-4,5-diyl)bis[diphenyl- (9CI)
  • 9,9-DiMethyl-4,5-bis(diphenylp
  • [5-(diphenylphosphanyl)-9,9-diMethyl-9H-xanthen-4-yl]diphenylphosphane
  • Xantphos, (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane)
  • 4,5-Bis(diphenylphosphino)-9,9-diMethylxanthene 97%
  • 4,5-Bis(diphenylphosphino)-9,9-diMethylxanthene, 97+%
  • DiMethylbisdiphenylphosphinoxanthene SynonyMs 9,9-DiMethyl-4,5-bis(diphenylphosphino)xanthene
  • 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene,98% XantPhos
  • 4,5- two -9,9- two methyl oxygen hetero
  • Xantphos 97%
  • (2,3-dimethyl-9H-xanthene-1,9-diyl)bis(diphenylphosphine)
  • 4,5-Bis(diphenylphosphino)-9,9-dimethyl-xanthene, Dimethylbisdiphenylphosphinoxanthene
  • (5-diphenylphosphanyl-9,9-dimethylxanthen-4-yl)-diphenylphosphane
  • (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane)
  • 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
  • 4,5-Bis(diphenylphosphino)-9,9-dimethyl xanthenes
  • 4,5-Bis(diphenylphosphino)-9,9-dimethyl
  • 4,5-Bis(diphenylphosphino)-9,9-dimethyl Xantphos
  • Xantphos / 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene
  • Xantphos, 4,5-Bis(diphenylphosphino)-9,9-diMethylxanthene
  • 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthenes
  • 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene 99%
  • 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE99%
  • 9,9-Dimethyl m-4,5-bis(Diphenylphosphino)xanthene
  • 4,5-Bis(diphenylphospheno)-9,9-dimethyl
  • 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene ,98%
  • 9,9-dimethyl-4,5-bis(diphenylphosphino)-9H-xanthene
  • 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene,98%
  • 4,5-Bis(diphenylphospheno)-9,9-dimethylxanthene
  • 9,10a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-8aH-xanthene
  • Dimethylbisdiphenylphosphinoxanthene,98%
  • 4,5-Bis (diphenylphosphino )-9,9-dimethylxanthene（Xantphos）
  • 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene, 99% XANTPHOS
  • 4,5-Bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene
  • Bis(diphenylphosphino)-9,9-diMethylxanthene
  • 9,9-DiMethyl-4,5-bis(diphenylphosphino)xanthene, 98% 1GR
  • 9,9-DiMethyl-4,5-bis(diphenylphosphino)xanthene, 98% 25GR
  • 9,9-DiMethyl-4,5-bis(diphenylphosphino)xanthene, 98% 5GR
  • 5-bis(diphenylphosphino)-9H-xanthene
  • 9-diMethyl-4
  • 98% XantPhos
  • 4,5-Bis(diphenyL
  • phosphino)-9,9-dimethyL
  • 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene &gt
  • 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenyl-phosphine
  • Phosphine, 1,1'-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenyl-
  • 4,5-Bis(diphenylphosphino)-9,9-dimethylxantane (Xantphos)