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Home > Encyclopedia > Tris(2-methoxyphenyl)phosphine

Tris(2-methoxyphenyl)phosphine

Tris(2-methoxyphenyl)phosphine structure

Tris(2-methoxyphenyl)phosphine 

structure
  • CAS No:

    4731-65-1

  • Formula:

    C21H21O3P

  • Chemical Name:

    Tris(2-methoxyphenyl)phosphine

  • Synonyms:

    Phosphine,tris(2-methoxyphenyl)-;Phosphine,tris(o-methoxyphenyl)-;Tris(2-methoxyphenyl)phosphine;Tris(o-anisyl)phosphine;Tri-o-anisylphosphine;Tris(o-methoxyphenyl)phosphine;Tri(o-methoxyphenyl)phosphine;Tri(2-methoxyphenyl)phosphine;NSC 93545;Tris(2-methoxylphenyl)phosphine;(o-Meoph)3p

  • Categories:

    Organic Chemistry  >  Phosphines

Description

white powder or crystals

Tris(2-methoxyphenyl)phosphine Basic Attributes

352.36

352.36

2776186

225-235-8

H64XF7T8LW

93545

DTXSID90197099

29319090

Characteristics

27.7

4.5

Colorless to yellow or pale orange Liquid

204 °C

477.3°C at 760 mmHg

302.5±27.6 °C

Slightly soluble in water.

Safety Information

NONH for all modes of transport

3

36/37/38-22

37/39-26

Xn,Xi

P261-P305 + P351 + P338

H315-H319-H335-H413

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, 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 46 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

tris(2-methoxyphenyl)phosphine

Tris(2-methoxyphenyl)phosphine Use and Manufacturing

Methods of Manufacturing

General procedure: To a solution of [Fe2(CO)6(m-SCH2CH2CH2S)] (0.039 g, 0.10 mmol) and methyl diphenylphosphinite(0.022 g, 0.10 mmol) in CH2Cl2 (5 mL) was added a solution ofMe3NO2H2O (0.011 g, 0.10 mmol) in MeCN (5 mL). The mixture was stirred at roomtemperature for 1 h and then the solvent was reduced on a rotary evaporator. Theresidue was subjected to TLC using CH2Cl2/petroleum ether 1:5 (v/v) as eluent.From the main red band, 0.045 g (78%) of 2 was obtained as a red solid. IR (CH2Cl2, cm1): mCO 2045 (vs), 1983 (vs), 1933 (m). 1H NMR (500 MHz, CDCl3): 7.78 (s, 4H, PhH), 7.45 (s, 6H, PhH), 3.61 (d, J12.5 Hz, 3H, CH3), 1.88 (s, 2H, CH2), 1.63 (s, 4H, 2SCH2)ppm. 31Pf1Hg NMR (200 MHz, CDCl3, 85% H3PO4): 167.75 (s) ppm. 13Cf1Hg NMR(125 MHz, CDCl3): 213.67 (d, JP-C 13.7 Hz, PFeCO), 209.61 (s, FeCO), 139.22 (d, JP-C 42.9 Hz, i-PhC), 131.07 (d, JP-C 12.2 Hz, o-PhC), 130.73 (s, p-PhC), 128.43 (d, JP-C 9.7 Hz, m-PhC), 53.16 (s, CH3), 30.09 (s, SCH2), 22.01 (s, CH2) ppm. Anal. Calcd. forC21H19Fe2O6PS2: C, 43.93; H, 3.34. Found: C, 44.06; H, 3.52%.General procedure: To a solution of 2 (0.053 g, 0.0996 mmol) and tris(4-fluorophenyl)phosphine (0.032 g, 0.101 mmol) in CH2Cl2 (5 mL) was added a solution of Me3NO*2H2O (0.011 g, 0.0990 mmol) as the decarbonylating agent in MeCN (5 mL). The mixture was stirred atroom temperature for 1 h and then the solvent was reduced on a rotary evaporator.The residue was subjected to TLC separation using CH2Cl2/petroleum ether . 1:3 (v/v)as eluent. From the main red band, 0.065 g (79percent) of 3 was obtained as a red solid.A solution of 0.39 g(1.10 mmol) of phosphine 3 in 10 mL of DCM wasadded dropwise to a suspension of 0.26 g (1.10 mmol)of naphthoquinone 1 in 5 mL of H2Cl2 underbubbling of argon. The reaction mixture graduallyacquired a black color, and the formation of a greencrystalline precipitate was observed. After 30 min theprecipitate was filtered off and dried in a vacuum(14 mmHg). Yield 0.35 g (54percent), mp 250'253°C. IRspectrum, nu, cm'1: 3564 (), 1655 (), 1588, 1574, 1573, 1347, 1322, 1281, 1249, 1211, 1140, 1110, 1080, 1044, 986, 964, 799, 730, 698, 612, 551, 523, 486. 31 NMR spectrum (DMSO-d6 : DMF-d7 = 1 : 1):delta 17.9 ppm. Found, percent: 63.15; 4.47; Br 13.50; 5.22. C31H26BrO5P. Calculated, percent: C 63.17; H 4.45; Br13.56; P 5.25.

Uses

suzuki reaction

Computed Properties

Molecular Weight:352.4
XLogP3:4.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:352.12283153
Monoisotopic Mass:352.12283153
Topological Polar Surface Area:27.7
Heavy Atom Count:25
Complexity:334
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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