[ CAS No. 161265-03-8 ]

Name: 161265-03-8|(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)|98%
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Product Details of [ 161265-03-8 ]

CAS No. :	161265-03-8	MDL No. :	MFCD00233866
Formula :	C₃₉H₃₂OP₂	Boiling Point :	665.7°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	578.62 g/mol	Pubchem ID :	636044
Synonyms :

Safety of [ 161265-03-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 161265-03-8 ]

Upstream synthesis route of [ 161265-03-8 ]
Downstream synthetic route of [ 161265-03-8 ]

[ 161265-03-8 ] Synthesis Path-Upstream 1~8

1
[ 4175-77-3 ]
[ 161265-03-8 ]
[ 141305-40-0 ]

Reference： [1] Chemistry - A European Journal, 2015, vol. 21, # 23, p. 8471 - 8482

2
[ 19814-75-6 ]
[ 1079-66-9 ]
[ 161265-03-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tert-butyl methyl ether; cyclohexane at 6 - 10℃; Stage #2: at 20℃; for 14 h; Stage #3: at 10 - 20℃; for 5.16667 h;	Example 2A Preparation of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, Xantphos To a 5L round bottom flask (RBF) are added MTBE (2.5 L), 9,9-dimethylxanthene (131.4 g, 0.60 mole) and TMEDA (155 g, 1.32 mole). After degassing the solution, s-BuLi (1.11 L, 1.3 M in cyclohexane, 1.44 mole) is cannulated into a dropping funnel and then slowly added over 60 min while maintaining the batch temperature at 6-10° C. The mixture is then aged for 14 h at room temperature. Ph₂PCl is added slowly via a dropping funnel while maintain the mildly exothermic reaction at 10-20° C. ~60percent of the Ph₂PCl (175 mL, 0.93 mole) is added in 0.5 hour. The mixture is aged for 10 minutes before addition of the remaining Ph₂PCl (120 mL, 0.63 mole). After aged for 5 h at room temperature, the reaction is quenched with MeOH (9.9 mL, 0.24 mole). The product is filtered and the slightly yellow solid is washed consecutively with MTBE (250 mL), MeOH (2250 mL), water (2300 mL), MeOH (2*250 mL) and MTBE (250 mL) and dried to give an off-white solid as product (304.2 g, 88percent yield).
77%	Stage #1: With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tert-butyl methyl ether; cyclohexane at 10 - 20℃; for 16 h; Stage #2: at 20℃; for 5.75 h;	Example 2 Preparation of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, Xantphos To a 1L round bottom flask (RBF) are added MTBE (500 mL), 9,9-dimethylxanthene (26.65 g) and TMEDA (30.6 g). After degassing the solution, s-BuLi (155 g, 1.3 M in cyclohexane) is cannulated into a dropping funnel and then slowly added over 30 min while maintaining the batch temperature at 10-20° C. The mixture is then aged for 16 h at room temperature. Ph₂PCl is added slowly via a dropping funnel while maintain the mildly exothermic reaction at 10-20° C. ~60percent of the Ph₂PCl (30 mL) is added in 0.5 hour. The mixture is aged for 15 minutes before addition of the remaining Ph₂PCl. After aged for 5.5 h at room temperature, the reaction is quenched with MeOH (2.0 mL). The product is filtered and the slightly yellow solid is washed consecutively with MeOH (200 mL), water (200 mL), MeOH (200 mL) and MTBE (200 mL) and dried to give an off-white solid as product (54.8 g, 77percent yield).

Reference： [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
[6] Patent: US2004/23978, 2004, A1, . Location in patent: Page/Page column 15;16
[7] Patent: US2004/23981, 2004, A1, . Location in patent: Page/Page column 17
[8] Dyes and Pigments, 2012, vol. 94, # 3, p. 561 - 569

3
[ 19814-75-6 ]
[ 161265-03-8 ]

Reference： [1] Patent: US2004/23980, 2004, A1, . Location in patent: Page/Page column 15

4
[ 808142-24-7 ]
[ 161265-03-8 ]

Reference： [1] ChemCatChem, 2017, vol. 9, # 24, p. 4460 - 4464
[2] Chemistry - A European Journal, 2017, vol. 23, # 58, p. 14434 - 14438

5
[ 21264-30-2 ]
[ 161265-03-8 ]
[ 205319-10-4 ]

Reference： [1] Organic Syntheses, 2016, vol. 93, p. 341 - 351
[2] Organic Syntheses, 2016, vol. 93, p. 341 - 351
[3] Journal of the American Chemical Society, 2015, vol. 137, # 39, p. 12490 - 12493

6
[ 15617-18-2 ]
[ 161265-03-8 ]
[ 205319-10-4 ]

Reference： [1] European Journal of Inorganic Chemistry, 1998, # 2, p. 155 - 157

7
[ 161265-03-8 ]
[ 205319-10-4 ]

Reference： [1] Journal of Organometallic Chemistry, 2012, vol. 696, # 26, p. 4293 - 4297

8
[ 1435520-65-2 ]
[ 161265-03-8 ]
[ 1445085-97-1 ]

Reference： [1] Chemical Science, 2013, vol. 4, # 3, p. 916 - 920

[ 161265-03-8 ] Synthesis Path-Downstream 1~24

1
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[ 161265-03-8 ]
[ 205319-10-4 ]

Reference： [1]European Journal of Inorganic Chemistry,1998,p. 155 - 157

2
[ 14104-20-2 ]
[ 161265-03-8 ]
[ 39069-02-8 ]
Ag⁽¹⁺⁾*BF₄^(1-)*C₁₂H₆Br₂N₂*C₃₉H₃₂OP₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To 1 mL of the solution of silver(I) tetrafluoroborate (1.17 mg, 0.00601 mmol) in dichloromethane was added 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.48 mg, 0.00601 mmol), and the mixture was stirred at room temperature for 15 minutes. Then, f23 (2.03 mg, 0.00601 mmol) was added to the reaction solution, which was stirred at 40C for five minutes. The reaction solution was subjected to recrystallization by slow diffusion of dichloromethane-ether and dried to provide 5.40 mg of the complex of the pale yellow crystal. [Show Image] The NMR data of the obtained complex is provided below. 1H NMR (300 MHz, CDCl3) delta 8.50 (brd, 2H), 8.13 (brs, 2H), 7.84 (brd, 2H), 7.62 (brd, 2H), 7.26-7.04 (m, 22H), 6.78 (br, 2H), 1.71 (s, 6H); 31P NMR (122 MHz, CDCl3); 31P NMR (122 MHz, CDCl3) delta -4.9 (d, J (31P-107Ag, 109Ag) = 392, 451 Hz). The composition of the obtained complex was determined according to the same method as in Example 15. The present complex corresponds to the above composition formula (5).

Reference： [1]Patent: EP2360162,2011,A1 .Location in patent: Page/Page column 44

3
[ 161265-03-8 ]
palladium dichloride [ No CAS ]
[ 205319-10-4 ]

Reference： [1]Journal of Organometallic Chemistry,2012,vol. 696,p. 4293 - 4297

4
[ 64443-05-6 ]
[ 4733-39-5 ]
[ 161265-03-8 ]
[ 1421057-42-2 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 419 - 423
Angew. Chem.,2013,vol. 125,p. 437 - 441,5
[2]Chemistry - A European Journal,2013,vol. 19,p. 15972 - 15978

5
[ 1435520-65-2 ]
[ 161265-03-8 ]
[ 1445085-97-1 ]

Reference： [1]Chemical Science,2013,vol. 4,p. 916 - 920

6
[ 52522-40-4 ]
[ 591-50-4 ]
[ 161265-03-8 ]
[(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)palladium(II)(phenyl)iodine] [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2015,vol. 10,p. 321 - 324

7
[ 4175-77-3 ]
[ 161265-03-8 ]
[ 141305-40-0 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 8471 - 8482

8
[ 21264-30-2 ]
[ 161265-03-8 ]
[ 205319-10-4 ]

Reference： [1]Organic Syntheses,2016,vol. 93,p. 341 - 351
[2]Organic Syntheses,2016,vol. 93,p. 341 - 351
[3]Journal of the American Chemical Society,2015,vol. 137,p. 12490 - 12493

9
[ 64443-05-6 ]
[ 161265-03-8 ]
[ 56100-22-2 ]
[copper(I)(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)(6-methyl-2,2'-bipyridine)](hexafluorophosphate) [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 3857 - 3871

10
tetrakis(acetonitrile)copper(I)tetrafluoroborate [ No CAS ]
[ 17217-57-1 ]
[ 161265-03-8 ]
C₅₁H₄₄CuN₂O₃P₂⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 5477 - 5481
Angew. Chem.,2018,vol. 130,p. 5575 - 5579,5

11
[ 52522-40-4 ]
[ 161265-03-8 ]
p-anisoyl iodide [ No CAS ]
(Xantphos)Pd(CO(C₆H₄OCH₃))(I) [ No CAS ]