(XYL)2P(O)H Chemical Properties

Melting point:

82-84℃

Boiling point:

414.8±55.0 °C(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Powder

color 

White

InChI

InChI=1S/C16H19OP/c1-11-5-12(2)8-15(7-11)18(17)16-9-13(3)6-14(4)10-16/h5-10,18H,1-4H3

InChIKey

AWAYSUMOANJULO-UHFFFAOYSA-N

SMILES

P(=O)(C1=CC(C)=CC(C)=C1)C1=CC(C)=CC(C)=C1

Safety Information

Risk Statements 

20/21/22

Safety Statements 

26-36/37/39

HS Code 

29319090

(XYL)2P(O)H Usage And Synthesis

Chemical Properties

White powder

Uses

suzuki reaction

Synthesis

General procedure for the synthesis of bis(3,5-dimethylphenyl)phosphine oxide from 3,5-dimethylbromobenzene: 1-bromo-3,5-dimethylbenzene (129.5 g, 3.5 eq.) was slowly added to a suspension of magnesium shavings (17.0 g, 3.5 eq.) in tetrahydrofuran (THF, 770 mL) while controlling the internal temperature to maintain at 40-50 °C. The reaction mixture was stirred continuously at 40-50 °C for 1 h and subsequently cooled to 0 °C. Triethyl phosphate ((EtO)3PO, 27.7 g, 0.200 mol) was added dropwise over 30 min and stirring was continued for 1 h at 0 °C. Upon completion of the reaction, the reaction was quenched with 6 M aqueous hydrochloric acid (260 mL) and the mixture was extracted with dichloromethane (CH2Cl2, 260 mL x 3) and washed with water (H2O, 130 mL x 2). After concentration under vacuum, the residue was purified by silica gel column chromatography to afford bis(3,5-dimethylphenyl)phosphine oxide (49.7 g, 96% yield) as a light yellow solid.

References

[1] Chemistry Letters, 2013, vol. 42, # 9, p. 1035 - 1037
[2] Chemical Communications, 2013, vol. 49, # 82, p. 9425 - 9427
[3] Patent: WO2014/196930, 2014, A1. Location in patent: Page/Page column 21; 22
[4] Patent: EP1452537, 2004, A1. Location in patent: Page 25
[5] Zeitschrift fur Anorganische und Allgemeine Chemie, 2016, vol. 642, # 6, p. 508 - 514

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