Triisopropylphosphine

Base Information

• Chemical Name: Triisopropylphosphine
• CAS No.: 6476-36-4
• Molecular Formula: C9H21P
• Molecular Weight: 160.239
• Hs Code.: 29310099
• European Community (EC) Number: 229-333-1
• NSC Number: 244304
• UNII: MDE86CLL2B
• DSSTox Substance ID: DTXSID80215074
• Nikkaji Number: J125.178C
• Wikipedia: Triisopropylphosphine
• Wikidata: Q7841934
• Mol file: 6476-36-4.mol

Synonyms:Triisopropylphosphine;6476-36-4;TRI-I-PROPYLPHOSPHINE;tri(propan-2-yl)phosphane;Phosphine, tris(1-methylethyl)-;Phosphine, triisopropyl-;MDE86CLL2B;EINECS 229-333-1;MFCD00015029;tri-isopropylphosphine;NSC-244304;triisopropylphosphane;trisisopropylphosphine;NSC244304;triisopropyl phosphine;PPr(i)3;UNII-MDE86CLL2B;Tris(1-methylethyl)phosphine;SCHEMBL103207;DTXSID80215074;TRIS(PROPAN-2-YL)PHOSPHANE;AMY11701;P(C(C)C)(C(C)C)C(C)C;Triisopropylphosphine, technical grade;AKOS015910600;NSC 244304;SC11083;AS-57529;FT-0652047;Q7841934;PHOSPHORUS TRIISOPROPYL;TRIISOPROPYLPHOSPHINE

Chemical Property of Triisopropylphosphine

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 1.18mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Boiling Point: 181 °C at 760 mmHg
• Flash Point: 62.9 °C
• PSA: 13.59000
• Density: 0.839 g/cm³
• LogP: 3.69350
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive
• Solubility.: Soluble in alkanes.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 160.138087668
• Heavy Atom Count: 10
• Complexity: 65.7

Purity/Quality:

98% ^*data from raw suppliers

Tri-i-propylphosphine, 98% (10 wt% in hexanes) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Statements: 17-34
• Safety Statements: 17-26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)P(C(C)C)C(C)C
• Uses: Triisopropylphosphine is used as a ligand in organometallic chemistry. It is an important raw material and intermediate used in organic Synthesis, pharmaceuticals and agrochemicals. It is also used to produce Chlor(triisopropyl)phosphonium-dimesylamid at temperature of 40°C.

Technology Process of Triisopropylphosphine

There total 26 articles about Triisopropylphosphine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

tris(isopropyl)phosphonium tetrafluoroborate (121099-07-8) → tris(1-methylethyl)phosphine (6476-36-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; Glovebox; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01116

Reference yield: 84.0%

trans-[RhCl(PhCCPh)(PiPr3)2] (131564-13-1,85944-35-0) + sodium cyclopentadienide → (C5H5)Rh(P(CH(CH3)2)3)(C6H5CCC6H5) (81423-53-2) + tris(1-methylethyl)phosphine (6476-36-4)

Guidance literature:

In tetrahydrofuran; under Ar, soln. of Rh complex in THF mixed with NaC5H5, stirred at room temp. for 3 h; evapd., residue extracted with hexane, evapd. in vac., dried in vac. for 6 h, dissolved in hexane, chromd., evapd., recrystd. from THF/pentane,elem. anal.;

DOI:10.1016/S0022-328X(00)98566-8

Reference yield: 70.0%

cis-dihydrido(bicarbonato)bis(triisopropylphosphine)rhodium(III) (71380-76-2) + diphenyl acetylene (501-65-5) → (E)-1,2-diphenyl-ethene (103-30-0) + dihydrido(carbonato)(diphenylacetylene)tris(triisopropylphosphine)rhodium(III) (86747-89-9) + tris(1-methylethyl)phosphine (6476-36-4)

Guidance literature:

In toluene; byproducts: CO2; to Rh complex in toluene added diphenylacetylene (molar ratio 1:3) at room temp. for 3 h; washed with hexane, recrystd. from toluene/hexane, elem. anal.;

DOI:10.1021/ja00358a015

upstream raw materials:

2-iodo-propane

di-isopropylphosphine

isopropylmagnesium bromide

dithiocarboxy-triisopropyl-phosphonium betaine

Downstream raw materials:

trimethylphosphane

diisopropylmethylphosphine

triethylphosphine

tributylphosphine

Refernces

• 1、 Scott, Thomas A.,Zhou, Hong-Cai. "The first all-cyanide Fe4S4 cluster: [Fe 4S4(CN)4]3-". . p. 5628 - 5631. Retrieved 2004.
• 2、 Wang, Chengpeng,Rago, Alexander J.,Dong, Guangbin. "Direct β-Alkenylation of Ketones via Pd-Catalyzed Redox Cascade". supporting information. p. 3377 - 3381. Retrieved 2019/05/10.
• 3、 Thomas, Andy A.,Wang, Hao,Zahrt, Andrew F.,Denmark, Scott E.. "Structural, Kinetic, and Computational Characterization of the Elusive Arylpalladium(II)boronate Complexes in the Suzuki-Miyaura Reaction". supporting information. p. 3805 - 3821. Retrieved 2017/03/20.