[ CAS No. 14221-01-3 ]

Name: 14221-01-3|Tetrakis(triphenylphosphine)palladium|98%
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SKU: A211391
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Product Details of [ 14221-01-3 ]

CAS No. :	14221-01-3	MDL No. :	MFCD00010012
Formula :	C₇₂H₆₀P₄Pd	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	1155.56 g/mol	Pubchem ID :	11979704
Synonyms :

Safety of [ 14221-01-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312+P330-P501	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 14221-01-3 ]

Upstream synthesis route of [ 14221-01-3 ]
Downstream synthetic route of [ 14221-01-3 ]

[ 14221-01-3 ] Synthesis Path-Upstream 1~11

1
[ 6165-69-1 ]
[ 14221-01-3 ]
[ 95-56-7 ]
[ 1003-09-4 ]

Reference： [1] Patent: US2002/137746, 2002, A1,
[2] Patent: US2002/137746, 2002, A1,

2
[ 1003015-89-1 ]
[ 14221-01-3 ]
[ 109299-78-7 ]
[ 26456-59-7 ]
[ 1134120-38-9 ]
[ 98511-61-6 ]

Reference： [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 2009, vol. 131, p. 4174 - 4175

3
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[ 150691-04-6 ]
[ 72459-45-1 ]

Reference： [1] Patent: US5219856, 1993, A,

4
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[ 7440-44-0 ]
[ 159-66-0 ]

Reference： [1] Patent: US2012/32121, 2012, A1,

5
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[ 144-55-8 ]
[ 13589-72-5 ]

Reference： [1] Patent: EP1323713, 2003, A1,

6
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[ 2042-37-7 ]
[ 5720-05-8 ]
[ 497-19-8 ]
[ 64113-85-5 ]

Reference： [1] Patent: EP470795, 1992, A1,

7
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[ 1122-91-4 ]
[ 107834-03-7 ]

Reference： [1] Patent: US5849911, 1998, A,

8
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[ 93777-26-5 ]
[ 146137-79-3 ]

Reference： [1] Patent: US6384080, 2002, B1,

9
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[ 27007-53-0 ]
[ 439117-38-1 ]

Reference： [1] Patent: US2003/13700, 2003, A1,
[2] Patent: US6528503, 2003, B2,
[3] Patent: US2003/158218, 2003, A1,
[4] Patent: US2002/193398, 2002, A1,
[5] Patent: US2002/119992, 2002, A1,

10
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[ 1993-03-9 ]
[ 886444-12-8 ]

Reference： [1] Patent: US2007/37974, 2007, A1, . Location in patent: Page/Page column 23

11
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[ 1007882-04-3 ]
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[ 791-28-6 ]

Reference： [1] Patent: US2008/44380, 2008, A1, . Location in patent: Page/Page column 73

[ 14221-01-3 ] Synthesis Path-Downstream 1~24

1
[ 14221-01-3 ]
[ 74785-02-7 ]
C₂₆H₂₄BrOPPd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In toluene; at 20℃; for 12h;	Example 2: Synthesis of Compound IB; (2-Bromomethyl-phenyl)-methanol (0.25g, 1.24 mmol) wasdissolved in toluene (10cm3), and added dropwise to astirred suspension oftetrakis(triphenylphosphine)palladium(O) (1.43g, 1.24mmol) in toluene (60cm3) . The suspension was degassed andpurged with N2. The mixture was stirred at roomtemperature for 12 hours, and then filtered. The solidproduct was washed with diethyl ether (3 x 20cm3) anddried in vacua to give compound IB as an amorphous, off-white solid (605mg, 86%), this was then recrystallisedfrom dichloromethane and petroleum ether to give yellowcubes, mp 168-171 C (decomp.) (Found: C, 54.96; H,4.28%; C26H24BrOPPd requires C, 54.81; H, 4.28%); NMRassignments made by HMQC, NOE, DEPT, 8H [CDC13] 2.80 (2H,d, 3JH-ia,ib-31p = 2.5 Hz), 4.55 (bs, 2H, H-4), 6.15 (1H, d, Jk-7,8 = 7.68 Hz, H-7), 7.0 (m, 3H, H-8 or 9 or 10), 7.40-7.55 (m, 6H, PPh3), 7.60-7.70, (m, 9H, PPh3) ; 5C [CDC13]30.91 (C-l), 64.18 (C-4), 124.89 (C-8 or 9'or 10), 127.65(C-7), 127.75, (C-8 or 9 or 10), 128.39 (PPh3-C) , 128.54(PPh3-C) , 128.64, (C-8 or 9 or 10), 130.41, (PPh3-C) ,131.0 (PPh3-ipso 4C) , 134.26 (PPh3-C) , 134.47 (PPh3-C) ,138.9 (C-2 or C-3), 141.05 (C-2 / C-3); 8P [CDC13] 42.61(s) ; m/z Electrospray (2M - 79Br)*+, 1058 (47%) C26H24BrOPPdrequires 568; X-ray data, (C-l-Pd, 2.066A) , (O-Pd, 2.124A) ,(P-Pd, 2.194A), (Cl-Pd, 2.5055A) .

Reference： [1]Patent: WO2006/10885,2006,A1 .Location in patent: Page/Page column 21-22

2
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[ 93777-26-5 ]
[ 146137-79-3 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	PREPARATION 88(1) To a solution of 5-bromo-2-fluorobenzaldehyde (10 g) in dimethylformamide (60 mL) were added zinc cyanide (6.92 g) and tetrakis(triphenylphosphine)palladium(O) (2.28 g), and the mixture was stirred at 80° C. for 6 hours. The resulting mixture was diluted with ethyl acetate and washed successively with water and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluding with a mixture of hexane and ethyl acetate (3:1) to give 5-cyano-2-fluorobenzaldehyde (5.3 g) as a solid substance. NMR (DMSO-d6, delta): 7.35 (1H, t, J=9 Hz), 7.91 (1H, m), 8.22 (1H, dd, J=2, 7 Hz), 10.36 (1H, s); Mass m/z: 150 (M++1).

Reference： [1]Patent: US6384080,2002,B1

3
[ 14221-01-3 ]
[ 262444-42-8 ]
[ 330793-35-6 ]
[ 330793-36-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In n-heptane; water; ethyl acetate; N,N-dimethyl-formamide;	-3-fluorophenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate A suspension of ethyl 2-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate (0.790 g, 2.28 mmol), <strong>[262444-42-8]tert-butyl N-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate</strong> (1.08 g, 3.19 mmol), tetrakis(triphenylphosphine) palladium (0.105 g, 0.091 mmol), and sodium bicarbonate (0.478 g, 5.69 mmol) in N,N-dimethylformamide (12 mL) and water (2 mL) was heated at 90° C. for 14 hours under an atmosphere of nitrogen. The solvent was removed under reduced pressure, and the residue was partitioned between saturated aqueous sodium chloride (50 mL) and ethyl acetate (30 mL). The aqueous layer was separated and extracted further with ethyl acetate (330 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by flash column chromatography on silica gel using ethyl acetate/heptane (9:1) as a mobile phase afforded ethyl 2-(4-amino-3-4-[(tert-butoxycarbonyl)amino]-3-fluorophenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate (0.193 g, 0.449 mmol) as a yellow oil: 1H NMR (CDCl3, 400 MHz) delta 8.41 (s, 1H), 8.30 (m, 1H), 7.47 (m, 2H), 6.81 (s, 1H), 5.47 (br, 2H), 5.20 (s, 2H), 4.25 (qt, 2H), 1.55 (s, 9H), 1.27 (t, 3H); RP-HP (25 to 100percent acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at I mL/min using a Hypersil HS C18, 2504.6 mm column) Rt 9.47 min.

Reference： [1]Patent: US2002/156081,2002,A1

4
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[ 14221-01-3 ]
[ 80500-27-2 ]
[ 67-63-0 ]
[ 289470-05-9 ]