9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE

9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE - Names and Identifiers

Name	9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene
Synonyms	Xantphos Xant-phos XANT PHOS Dimethylbisdiphenylphosphinoxanthene 4,5-BIS(DIPHENYLPHOSPHINO)-9,9-DIMETHYLX 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE 4,5-BIS(DIPHENYLPHOSPHINO)-9,9-DIMETHYLXANTHENE 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene 4,5-BIS-DIPHENYLPHOSPHANYL-9,9-DIMETHYL-9H-XANTHENE 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene, XANTPHOS (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (9,9-DIMETHYL-9H-XANTHENE-4,5-DIYL)BIS[DIPHENYL PHOSPHINE] (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[diphenyl phosphine]
CAS	161265-03-8
EINECS	605-249-4
InChI	InChI=1/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
InChIKey	CXNIUSPIQKWYAI-UHFFFAOYSA-N

9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE - Physico-chemical Properties

Molecular Formula	C39H32OP2
Molar Mass	578.62
Melting Point	224-228°C(lit.)
Boling Point	665.7±55.0 °C(Predicted)
Flash Point	450℃
Solubility	Soluble in organic solvents.
Vapor Presure	7.61E-17mmHg at 25°C
Appearance	White to yellow crystals
Color	White to light yellow
Storage Condition	Keep in dark place,Sealed in dry,Room Temperature
MDL	MFCD00233866

9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE - Risk and Safety

Hazard Symbols	Xn - Harmful
Risk Codes	R37 - Irritating to the respiratory system R20/22 - Harmful by inhalation and if swallowed.
Safety Description	S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany	3
TSCA	No
HS Code	29319090

9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE - Reference Information

Open Data Unverified Data

overview	4, 5-didiphenylphosphine -9, 9-dimethyloxanthracene (xantphos) compounds due to their special electron-rich properties and large steric hindrance, it has high reactivity in palladium-catalyzed coupling reactions such as Suzuki, Negishi, Stille, Heck, etc.
preparation	under the protection of argon, add 538g of bis (2-diphenylphosphine phenyl) ether (compound 2) and 700mL of toluene solvent to the reaction kettle, trifluoromethanesulfonic acid 8.8mL (the molar ratio of bis (2-diphenylphosphine phenyl) ether (compound 2) to trifluoromethanesulfonic acid is 1:0.1), acetone 150mL, the reaction system is heated to 150oC, and after 16h of reaction, it is reduced to room temperature. After extraction, drying, and recrystallization, the target product 4, 5-bisdiphenylphosphine -9 is obtained, 9-dimethyloxanthracene (xantphos)(compound 1)520g (yield 90%).
Main applications	Xantphos metal chelating ligands that can be used for catalytic reactions. Used as a ligand for the synthesis of heterocyclic rings by palladium-catalyzed C- N cross-coupling reactions of 3-bromothiophene and 2-aminopyridine. It can also be used for ruthenium-catalyzed alkylation reactions involving active methylene compounds and alcohols. Buchwald-Hartwig aromatic amination reaction is a very commonly used reaction to prepare aromatic amines from aryl halides or aryl sulfonates. The commonly used palladium catalysts for Buchwald reactions are: Pd2(dba)3,Pd(OAc)2, and the commonly used ligands are: P(t-Bu)3,BINAP, P(o-tolyl)3, Xantphos. There is no fixed match between catalyst and ligand, and the commonly used ligands with better effect are Xantphos and BINAP.
Use	As a ligand, used in coupling reactions such as Buchwald and Suzuki Organic reagents, pharmaceutical intermediates. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene The complex with transition metals can be used as organic synthesis catalysts such as carbonylation reactions; in palladium-catalyzed 3-brominated thiophene and 2-aminopyridine C- N Cross-coupled heterocyclic synthesis of ligands; also used in ruthenium-catalyzed activation of alkylation of methylene compounds with ethanol; metal chelate ligand for catalysis

Last Update：2024-04-09 19:43:38

9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE - Overview

4, 5-didiphenylphosphine -9, 9-dimethyloxanthracene (xantphos) compounds are used in palladium-catalyzed Suzuki, Negishi, Stille, Heck and other coupling reactions due to their special electron-rich properties and large steric hindrance. Has high reactivity.