[ CAS No. 564483-18-7 ]

Name: 564483-18-7|2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl|97%
Brand: Ambeed
SKU: A167774
Price: 5.0 USD
Availability: InStock
Rating: 98 (28 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 564483-18-7 * Storage: {[proInfo.prStorage]}

Cart0 Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 88K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 564483-18-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 564483-18-7 ]

SDS

Alternatived Products of [ 564483-18-7 ]

Product Details of [ 564483-18-7 ]

CAS No. :	564483-18-7	MDL No. :	MFCD04117682
Formula :	C₃₃H₄₉P	Boiling Point :	569.8°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	476.72 g/mol	Pubchem ID :	11155794
Synonyms :

Safety of [ 564483-18-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 564483-18-7 ]

Upstream synthesis route of [ 564483-18-7 ]
Downstream synthetic route of [ 564483-18-7 ]

[ 564483-18-7 ] Synthesis Path-Upstream 1~8

1
[ 21524-34-5 ]
[ 16523-54-9 ]
[ 583-53-9 ]
[ 564483-18-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: With n-butyllithium In tetrahydrofuran at 0℃; for 1 h; Inert atmosphere Stage #2: at 0℃; for 1 h; Inert atmosphere	Under the protection of nitrogen, 200 ml of THF and 31g of 2, 4, 6-tri-isopropyl-bromobenzene was added to 1L three-mouth bottle. The temperature was cooled down to 0 °C, and 46 ml of 2.5M n-butyl lithiumwas added dropwise. The reaction was continued for 1 hour after the addition. At 0 °C, 24.6g O-dibromobenzene was added dropwise. The reaction was continued for 1 hour after the addition. At0 °C, 42 ml of 2.5M n-butyl lithiumwas added dropwise to the reaction liquid.After the addition, the reaction was continued for 1 hour. 26.7g of dicyclohexyl phosphine was added dropwise, and the temperature was naturally warmed to react at room temperature for 2 hours. 200 ml saturated ammonium chloride aqueous solution was added dropwsie to the reaction liquid under the ice bath to quench the reaction. After phase separation, the organic phase was precipitated, and methanol was added for crystallization. Byfiltering, 44.5g white product of 2’-dicyclohexyl phosphino-2, 4, 6-tri-isopropyl biphenyl was obtained, with a yield of 89percent.

Reference： [1] Patent: CN105273006, 2016, A, . Location in patent: Paragraph 0069; 0070

2
[ 16523-54-9 ]
[ 564483-18-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: at 0℃; for 1 h; Stage #2: at 20℃; for 2 h;	At 0 °C,42 ml of 2.5M n-butyl lithium was added dropwise to the reaction liquid. After the addition, the reaction was continued for 1 hour.26.7g of dicyclohexyl phosphine was added dropwise, and the temperature was naturally warmed to react at room temperature for 2 hours. 200 ml saturated ammonium chloride aqueous solution was added dropwsie to the reaction liquid under the ice bathto quench the reaction.After phase separation, the organic phase was precipitated,and methanol was added for crystallization. Byfiltering,45g white product of 2’-dicyclohexyl phosphino-2, 4, 6-tri-isopropyl biphenyl was obtained, with a yield of 90percent.

Reference： [1] Patent: CN105273006, 2016, A, . Location in patent: Paragraph 0059

3
[ 694-80-4 ]
[ 21524-34-5 ]
[ 16523-54-9 ]
[ 564483-18-7 ]

Reference： [1] Journal of the American Chemical Society, 2003, vol. 125, # 22, p. 6653 - 6655
[2] Chemistry - A European Journal, 2011, vol. 17, # 39, p. 10828 - 10831
[3] Organic Process Research and Development, 2004, vol. 8, # 6, p. 1065 - 1071

4
[ 694-80-4 ]
[ 21524-34-5 ]
[ 100384-03-0 ]
[ 564483-18-7 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 39, p. 10828 - 10831

5
[ 13078-80-3 ]
[ 564483-18-7 ]
[ 1028206-56-5 ]

Reference： [1] Journal of the American Chemical Society, 2008, vol. 130, # 21, p. 6686 - 6687

6
[ 13078-80-3 ]
[ 14267-08-4 ]
[ 917-54-4 ]
[ 564483-18-7 ]
[ 1028206-56-5 ]

Reference： [1] Journal of the American Chemical Society, 2008, vol. 130, # 21, p. 6686 - 6687

7
[ 3375-31-3 ]
[ 90-41-5 ]
[ 564483-18-7 ]
[ 1310584-14-5 ]

Reference： [1] Journal of the American Chemical Society, 2010, vol. 132, # 40, p. 14073 - 14075

8
[ 564483-18-7 ]
[ 1445085-55-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	at 20℃; for 0.75 h; Inert atmosphere	A 300-mL round-bottomed flask equipped with a stir bar and rubber septum was charged with μ-OMs dimer 3 (11.92 g, 15.25 mmol, 0.50 eq) and XPhos (14.52 g, 30.5 mmol, 1.00 eq). The flask was evacuated under vacuum and backfilled with argon (this procedure was repeated twice), after which THF (120 mL) was added. The reaction mixture was stirred at room temperature for 45 min. After removal of 90percent of the solvent under vacuum the product was precipitated from pentane to afford the title compound as an off-white solid as the 1:1 THF complex. THF could be removed by dissolving the solid in DCM and reprecipitating with pentane. Yield: 25.5 g, 92percent. FIG. 7. [0295] FIG. 8 tabulates the percent yield of various precatalysts formed using the procedures outlined above.

Reference： [1] Patent: US2013/331566, 2013, A1, . Location in patent: Paragraph 0294

[ 564483-18-7 ] Synthesis Path-Downstream 1~24

1
[ 564483-18-7 ]
2'-dicyclohexylphosphanyl-2,6-diisopropyl-biphenyl-4-sulfonic acid [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 6173 - 6177

2
[ 564483-18-7 ]
dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine oxide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 5096 - 5101
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 5272 - 5276
Angew. Chem.,2017,vol. 129,p. 5356 - 5360,5
[3]Chemistry - A European Journal,2019,vol. 25,p. 6980 - 6987

3
[ 564483-18-7 ]
sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		To an oven-dried 25 mL round bottom flask equipped with a Teflon-coated magnetic stir bar and rubber septum was added dicyclohexyl-(2',4',6'-triisopropyl-biphenyl-2-yl)-phosphane (476 mg, 1.00 mmol) and CH2Cl2 (1.0 mL). The solution was cooled to 0 C. using an ice/water bath and then concentrated H2SO4 (1.00 mL) and fuming sulfuric acid (3.0 mL, 20% SO3) were added dropwise. The solution was allowed to warm to room temperature and stir for 24 h. At this time it was cooled to 0 C. using an ice/water bath and crushed ice (10 g) was added. The solution turned cloudy and white in color. An aqueous solution of NaOH (6.0 M, 20.0 mL) was then added dropwise to the cooled solution until it became neutral (pH 7.0 as judged by pH paper). The aqueous solution was extracted with CH2Cl2 (3×50 mL) and concentrated under reduced pressure to give a beige solid. The crude material was then dissolved in a minimum amount of cold methanol (20 mL), filtered and concentrated (this cycle was repeated) to give sodium 2'-(dicyclohexyl-phosphanyl)-2,6-diisopropyl-biphenyl-4-sulfonate (4) as a beige solid (503 mg, 94%). Mp=>250 C. 1H NMR (400 MHz, CD3OD) delta: 7.52 (s, 2H), 7.46 (m, 1H), 7.22 (m, 2H), 6.90 (m, 1H), 2.24 (m, 1H), 0.71-1.83 (34H). 13C NMR (125 MHz, CD3OD) delta: 148.4, 147.9, 147.8, 147.5, 145.6, 142.8, 137.4, 137.2, 133.92, 133.91, 132.43, 132.42, 129.3, 128.1, 121.3, 121.0, 40.1, 39.9, 39.7, 39.5, 39.3, 38.8, 35.8, 35.7, 32.5, 32.3, 31.9, 30.8, 30.6, 28.7, 28.6, 28.4, 28.3, 27.7, 26.0, 25.9, 23.3, 23.1. 31P NMR (162 MHz, CD3OD) delta: -10.7. IR (neat, cm-1): 3459, 2927, 2851, 1634, 1463, 1447, 1184, 1078, 1040. Anal. Calcd for C30H42NaO3PS: C, 67.14; H, 7.89. Found: C, 66.93; H, 7.77.

Reference： [1]Patent: US2006/173186,2006,A1 .Location in patent: Page/Page column 27; Sheet 1
[2]Journal of the American Chemical Society,2018,vol. 140,p. 13570 - 13574

4
[ 120-72-9 ]
potassium phosphate [ No CAS ]
[ 890315-75-0 ]
[ 131274-22-1 ]
[ 564483-18-7 ]
[ 890313-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; citric acid;tris-(dibenzylideneacetone)dipalladium(0); In ethyl acetate; toluene;	Example 407 33 mg of 1H-indole, 0.12 g of cesium carbonate, 5.1 mg of tris(dibenzylideneacetone)dipalladium(0), 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 4.4 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, 33 mg of 1H-indole, 79 mg of tripotassium phosphate, 5.1 mg of tris (dibenzylideneacetone) dipalladium (0), 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 4.4 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10percent citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 20:1] to obtain 45 mg of tert-butyl 2-(benzamido)-4-(1H-indol-1-yl)benzoate as colorless oil. 1H-NMR (CDCl3) delta: 1. 67 (9H, s), 6.73 (1H, d, J = 3.4 Hz), 7.18-7.22 (1H, m), 7.25-7.33 (2H, m), 7.48 (1H, d, J = 3.4 Hz), 7.51-7.62 (3H, m), 7.66-7.70 (1H, m), 7.83 (1H, d, J = 8.3 Hz), 8.06-8.10 (2H, m), 8.17 (1H, d, J = 8.8 Hz), 9.22 (1H, d, J = 2.2 Hz), 12.35 (1H, s).

Reference： [1]Patent: EP1820795,2007,A1

5
[ 496-15-1 ]
[ 890315-75-0 ]
[ 564483-18-7 ]
tert-butyl 2-(benzamido)-4-(indolin-1-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; citric acid;tris-(dibenzylideneacetone)dipalladium(0); palladium diacetate; In ethyl acetate; toluene;	Example 253 0.031 mL of indoline, 0.12 g of cesium carbonate, 1.7 mg of tris(dibenzylideneacetone)dipalladium(0), 0.8 mg of palladium acetate and 4.4 mg of 2-dicyclohexylphosphino -2',4',6'-triisopropylbiphenyl were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 3 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 10:1] to obtain 77 mg of tert-butyl 2-(benzamido)-4-(indolin-1-yl)benzoate as yellow oil. 1H-NMR (CDCl3) delta: 1.63 (9H, s), 3. 17 (2H, t, J = 8.4 Hz), 4.10 (2H, t, J = 8.4 Hz), 6.86 (1H, td, J = 7.4, 0.8 Hz), 6.96 (1H, dd, J = 8.9, 2.5 Hz), 7.16-7.24 (2H, m), 7.46-7.57 (4H, m), 7.97 (1H, d, J = 8.9 Hz), 8.06-8.10 (2H, m), 8.81 (1H, d, J = 2.5 Hz), 12.40 (1H, s).

Reference： [1]Patent: EP1820795,2007,A1

6
[ 890315-75-0 ]
[ 88-74-4 ]
[ 564483-18-7 ]
[ 890313-98-1 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; citric acid;tris-(dibenzylideneacetone)dipalladium(0); palladium diacetate; In ethyl acetate; toluene;	Example 412 55 mg of 2-nitroaniline, 0.17 g of cesium carbonate, 2.4 mg of tris(dibenzylideneacetone)dipalladium(0), 1.2 mg of palladium acetate and 6.3 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added to 2.0 mL of toluene solution containing 0.10 g of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 1:1] to obtain 94 mg of tert-butyl 2-(benzamido)-4-(2-nitroanilino)benzoate as yellow solid. 1H-NMR (CDCl3) delta: 1.64 (9H, s), 6.90-6.96 (2H, m), 7.50-7.60 (4H, m), 7.66 (1H, dd, J = 8.5, 1.2 Hz), 8.02 (1H, d, J = 8.5 Hz), 8.02-8.08 (2H, m), 8.22 (1H, dd, J = 8.7, 1.6 Hz), 8.94 (1H, d, J = 2.2 Hz), 9.53 (1H, s), 12.33 (1H, s).

Reference： [1]Patent: EP1820795,2007,A1

7
[ 109-97-7 ]
[ 890315-75-0 ]
[ 131274-22-1 ]
[ 564483-18-7 ]
[ 890313-92-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; citric acid;tris-(dibenzylideneacetone)dipalladium(0); In ethyl acetate; toluene;	Example 406 0.019 mL of 1H-pyrrole, 0.12 g of cesium carbonate, 5.1 mg of tris(dibenzylideneacetone)dipalladium(0), 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 4.4 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 3 hours. After the reaction mixture was cooled to room temperature, 5.1 mg of tris(dibenzylideneacetone)dipalladium(0), 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 4.4 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 3 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10percent citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 10:1] to obtain 60 mg of tert-butyl 2-(benzamido)-4-(1H-pyrrol-1-yl)benzoate as white solid. 1H-NMR (CDCl3) delta: 1.65 (9H, s), 6.38 (2H, t, J = 2.2 Hz), 7.12 (1H, dd, J = 8.6, 2.3 Hz), 7.25-7.28 (2H, m), 7.51-7.61 (3H, m), 8.05-8.10 (3H, m), 9.16 (1H, d, J = 2.3 Hz), 12.36 (1H, s).

Reference： [1]Patent: EP1820795,2007,A1

8
[ 771-99-3 ]
[ 890315-75-0 ]
[ 564483-18-7 ]
[ 890316-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; citric acid;tris-(dibenzylideneacetone)dipalladium(0); tris(dibenzylideneacetone)dipalladium (0); palladium diacetate; In ethyl acetate; toluene;	Example 584 86 mg of 4-phenylpiperidine, 0.22 g of cesium carbonate, 2.4 mg of tris(dibenzylideneacetone)dipalladium(0), 1.2 mg of palladium acetate and 6.3 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added to 3.0 mL of toluene solution containing 0.10 g of tert-butyl 2-(benzamido)-4-bromobenzoate, and the resulting mixture was heated to reflux for 2 hours. After the reaction mixture was cooled to room temperature, 2.4 mg of tris(dibenzylideneacetone)dipalladium(O), 1.2 mg of palladium acetate and 6.3 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added and the resulting mixture was heated to reflux for 6 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 10:1] to obtain tert-butyl 2-(benzamido)-4-(4-phenylpiperidin-1-yl)benzoate as pale yellow solid.

Reference： [1]Patent: EP1820795,2007,A1

9
[ 39929-21-0 ]
[ 564483-18-7 ]
[ 854045-94-6 ]

Reference： [1]Australian Journal of Chemistry,2014,vol. 67,p. 481 - 499
[2]Organometallics,2008,vol. 27,p. 28 - 32
[3]Chemistry - A European Journal,2016,vol. 22,p. 5909 - 5913
[4]Chemistry - A European Journal,2016,vol. 22,p. 11587 - 11592
[5]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 572 - 576

10
[ 100-01-6 ]
[ 55052-28-3 ]
[ 564483-18-7 ]
(4-Nitrophenyl)-1H-pyrrolo[2,3-b]pyridine-4-amine [ No CAS ]