| Identification | Back Directory | [Name]
(XYL)2P(O)H | [CAS]
187344-92-9 | [Synonyms]
(XYL)2P(O)H
Bis(3,5-diMethylphenyl)phosphi
BIS(3,5-DIMETHYLPHENYL)PHOSPHINE OXIDE
bis(3,5-dimethylphenyl)-oxophosphanium
Bis(3,5-dimethylphenyl)phosphineOxide>
Phosphine oxide,bis(3,5-diMethylphenyl)-
Bis(3,5-dimethylphenyl)phosphine oxide ,97%
1-[(3,5-diMethylphenyl)phosphoryl]-3,5-diMethylbenzene | [EINECS(EC#)]
805-024-2 | [Molecular Formula]
C16H19OP | [MDL Number]
MFCD08458884 | [MOL File]
187344-92-9.mol | [Molecular Weight]
258.3 |
| Chemical Properties | Back Directory | [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 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Ethanol-->Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->Magnesium-->Phosphorus trichloride-->Lithium-->5-Bromo-m-xylene-->Diethyl phosphite-->1,2-Dibromoethane | [Preparation Products]
Bis(3,5-dimethylphenyl)phosphine-->Phosphine oxide, 1,1'-(1R)-tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene-5,11-diylbis[1,1-bis(3,5-dimethylphenyl)- |
| Hazard Information | Back Directory | [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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