SPANphos

Base Information

Chemical Name:SPANphos
CAS No.:556797-94-5
Molecular Formula:C47H46O2P2
Molecular Weight:704.829
Hs Code.:
European Community (EC) Number:814-334-7
DSSTox Substance ID:DTXSID501336643
Nikkaji Number:J1.897.832F
Wikipedia:SPANphos
Mol file:556797-94-5.mol

Synonyms:SPANphos;556797-94-5;racemic-8,8'-Bis(diphenylphosphino)-3,3',4,4'-tetrahydro-4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[2H-1-benzopyran];SCHEMBL15327029;DTXSID501336643;MFCD18827638;CS-0108218;(8'-diphenylphosphanyl-4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[3H-chromene]-8-yl)-diphenylphosphane

Suppliers and Price of SPANphos

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Strem Chemicals
racemic-8,8'-Bis(diphenylphosphino)-3,3',4,4'-tetrahydro-4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[2H-1-benzopyran], min. 95% SPANphos
500mg
$ 422.00

Strem Chemicals
racemic-8,8'-Bis(diphenylphosphino)-3,3',4,4'-tetrahydro-4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[2H-1-benzopyran], min. 95% SPANphos
100mg
$ 105.00

Total 6 raw suppliers

Chemical Property of SPANphos

Chemical Property:

Boiling Point:766.7±60.0 °C(Predicted)
PSA：45.64000
LogP:9.33650
XLogP3:12.2
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:704.29730470
Heavy Atom Count:51
Complexity:1000

Purity/Quality:

97% ^*data from raw suppliers

racemic-8,8'-Bis(diphenylphosphino)-3,3',4,4'-tetrahydro-4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[2H-1-benzopyran], min. 95% SPANphos ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1=CC2=C(C(=C1)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5(CC2(C)C)CC(C6=C(O5)C(=CC(=C6)C)P(C7=CC=CC=C7)C8=CC=CC=C8)(C)C
Uses A binucleating diphosphine ligand used as a trans-spanning ligand which rigidly links mutually trans coordination sites via phosphorous atoms separated by a large distance to form a cavity over the face of square planar mono and di-metallic complexes, e.g. in MCl2(SPANphos) (M = Pd, Pt), Rh2(μ-Cl)2(CO)2(SPANphos), the latter useful in, for example, the homogeneous catalytic carbonylation of methanol to acetic acid.

Technology Process of SPANphos

There total 2 articles about SPANphos 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: 89.0%

: 1079-66-9,74391-44-9
chloro-diphenylphosphine

: 8,8'-dibromo-4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[chroman]

: 556797-94-5
4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[chroman]-8,8'-diylbis(diphenylphosphane)

Guidance literature:: 8,8'-dibromo-4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[chroman]; With n-butyllithium; In tetrahydrofuran; hexane; Heating;

chloro-diphenylphosphine; In tetrahydrofuran; hexane; at 20 ℃; for 16h;
DOI:10.1002/anie.200390330

Reference yield:

: 7595-11-1
4,4,4',4',6,6'-hexamethylspiro-2,2'-bi(chroman)

: 556797-94-5
4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[chroman]-8,8'-diylbis(diphenylphosphane)

Guidance literature:: Multi-step reaction with 2 steps

1.1: 84 percent / M-bromosuccinimide / dimethylformamide / 120 h

2.1: n-BuLi / hexane; tetrahydrofuran / Heating

2.2: 89 percent / hexane; tetrahydrofuran / 16 h / 20 °C

With N-Bromosuccinimide; n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200390330

Reference yield: 95.0%

: 109-99-9,24979-97-3,77392-70-2
tetrahydrofuran

: bis(norbornadiene)rhodium(l)tetrafluoroborate

: 556797-94-5
4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[chroman]-8,8'-diylbis(diphenylphosphane)

Guidance literature:: In tetrahydrofuran; byproducts: norbornadiene; (Ar); stirring a soln. of rhodium complex and ligand in THF at room temp. for 1 h; evapn., recrystn. (CH2Cl2/THF/hexane);
DOI:10.1039/b513870c