2-(Diphenylphosphino)-2′-(N,N-dimethylamino)biphenyl
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2-(Diphenylphosphino)-2′-(N,N-dimethylamino)biphenyl
structure -
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CAS No:
240417-00-9
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Formula:
C26H24NP
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Chemical Name:
2-(Diphenylphosphino)-2′-(N,N-dimethylamino)biphenyl
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Synonyms:
[1,1′-Biphenyl]-2-amine,2′-(diphenylphosphino)-N,N-dimethyl-;2′-(Diphenylphosphino)-N,N-dimethyl[1,1′-biphenyl]-2-amine;2-(Dimethylamino)-2′-(diphenylphosphino)biphenyl;2′-(Diphenylphosphino)-N,N′-dimethyl(1,1′-biphenyl)-2-amine;2-(Diphenylphosphino)-2′-(N,N-dimethylamino)biphenyl;PhDavePhos;2-(Dimethylamino)-2′-(diphenylphosphino)-[1,1′-biphenyl];2-(2-Diphenylphosphanylphenyl)-N,N-dimethylaniline
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CAS No:
2-(Diphenylphosphino)-2′-(N,N-dimethylamino)biphenyl Basic Attributes
381.45
381.45
1312995-182-4
DTXSID50370588
29310099
Characteristics
3.2
6.4
White to yellow Powder, Crystals, Crystalline Powder and/or Chunks
124-126 °C
514.6°C at 760 mmHg
265.0±28.2 °C
H2O: insoluble
1.06E-10mmHg at 25°C
Safety Information
IRRITANT
NONH for all modes of transport
3
36/37/38
37/39-26-36/37/39
NM1880000
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 75 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-(Diphenylphosphino)-2′-(N,N-dimethylamino)biphenyl Use and Manufacturing
General procedure: Complex (S, S)-5 (29.6mg, 0.0510mmol) was transferred into an Ar-filled 10-mL Schlenk flask. The flask was placed under vacuum, then filled with Ar followed by the addition of THF (3.0mL) using a syringe. Then a 0.5M solution of LiPPhThe compound was prepared using the reported procedure for the methylation of similar aromatic amines [36] in 47percent yield. R25 mL of Schlenk tube, and 2-diphenylphosphino-2 '- (N, N-dimethylamino) biphenyl was added to a solution of 76.3 mg (0.2 mmol), (1, 5-cyclooctadiene) chloride2.5 mg of rhodium (I) dimer (2.5% of moles of raw material), and 32 mg of lithium tert-butoxide (0.4 mmol), argon was replaced three times, and 1 mL of 1, 4-dioxane and 47.1 mg (0.3 mmol) of bromobenzene were added under argon. 120 C for 36 hours, cooled to room temperature and evaporated under reduced pressure. The solvent was separated on a 200-300 mesh silica gel column. The petroleum ether: Ester = 100: 1 and dried in vacuo to give 56.9 mg of product as a white solid in 62% yield, In a nitrogen-purged glove box, a jar equipped with a stir bar was charged with 2- diphenylphosphino-2'-(N, N-dimethylamino)biphenyl (PhDavePhos, 0.75 g, 1.96 mmol) and toluene (20 mL). Mesitylcopper(I) (0.35 g, 1.92 mmol), dissolved in toluene (10 mL), was then added. After stirring at room temperature for about 5 minutes, pyrazole (0.14 g, 2.05 mmol) was added as a solid. The resulting mixture was at 100C, for 2 hours, with stirring. The solvent was mostly removed in vacuo, and the resulting mixture, in about 2 mL toluene, was precipitated with 40 mL hexanes. The solid was collected by filtration, and rinsed with hexanes. The white solid was dried under vacuum to yield the title complex (0.42 g), as an off white solid.General procedure: Complex (S, S)-5 (29.6mg, 0.0510mmol) was transferred into an Ar-filled 10-mL Schlenk flask. The flask was placed under vacuum, then filled with Ar followed by the addition of THF (3.0mL) using a syringe. Then a 0.5M solution of LiPPh2 in THF (0.46mL, 0.23mmol) was introduced dropwise for 5min. The mixture appeared yellow, dark red, and finally dark yellow. The reaction mixture was stirred under Ar for 18h at rt. After the solvent was removed on a rotary evaporator, the crude mixture was dissolved in CH2Cl2 (0.5mL) and the concentrated mixture was placed on a preparative TLC (silica gel, 10:1 benzene-acetone). Compound (S)-6 was isolated as a light yellow liquid in 46% yield (15.6mg).The compound was prepared using the reported procedure for the methylation of similar aromatic amines [36] in 47% yield. Rf 0.35 (hexane). Spectral data of the synthesized product were identical to those reported previously [37].
suzuki reaction
Computed Properties
Molecular Weight:381.4
XLogP3:6.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:5
Exact Mass:381.164636767
Monoisotopic Mass:381.164636767
Topological Polar Surface Area:3.2
Heavy Atom Count:28
Complexity:433
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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2-(Diphenylphosphino)-2′-(N,N-dimethylamino)biphenyl
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