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Tris(2,6-dimethoxyphenyl)phosphine
Catalog Number
ACM85417410
Product Name
Tris(2,6-dimethoxyphenyl)phosphine
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/85417-41-0.gif)
CAS
85417-41-0
Synonyms
DMPP; TDMPP
IUPAC Name
tris(2,6-dimethoxyphenyl)phosphane
Molecular Weight
442.44
Molecular Formula
C24H27O6P
Canonical SMILES
COC1=C(C(=CC=C1)OC)P(C2=C(C=CC=C2OC)OC)C3=C(C=CC=C3OC)OC;
InChI
CMLWFCUAXGSMBB-UHFFFAOYSA-N
InChI Key
InChI=1S/C24H27O6P/c1-25-16-10-7-11-17(26-2)22(16)31(23-18(27-3)12-8-13-19(23)28-4)24-20(29-5)14-9-15-21(24)30-6/h7-15H,1-6H3
Boiling Point
566.4±50.0 °C(Predicted)
Melting Point
145-147 °C(lit.)
Purity
98%
Appearance
Solid
Complexity
415
Covalently-Bonded Unit Count
1
Exact Mass
442.155g/mol
H-Bond Acceptor
6
Heavy Atom Count
31
Isomeric SMILES
COC1=C(C(=CC=C1)OC)P(C2=C(C=CC=C2OC)OC)C3=C(C=CC=C3OC)OC
Monoisotopic Mass
442.155g/mol
Rotatable Bond Count
9
Topological Polar Surface Area
55.4A^2
Application
Tris(2,6-dimethoxyphenyl)phosphine serves as a versatile catalyst, characterized by its white to light yellow crystal powder form. Its primary purpose is to facilitate a range of chemical reactions crucial in advanced organic synthesis. This includes the preparation of chiral building blocks through hydroalkynylation reactions or the generation of ynolates. It is pivotal in three-component aza-Morita-Baylis-Hillman (aza-MBH) reactions and supports atom-economic syntheses of nitrogen heterocycles and ynenoates from alkynes. Additionally, it aids in the oxycyclization of allendiols and promotes enantioselective aldol reactions. The product is also instrumental in palladium-mediated cross-coupling, as well as palladium- and copper-mediated benzannulation and copper-mediated dimerization reactions, demonstrating its essential role in modern synthetic chemistry.
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