tris(2,6-dimethoxyphenyl)phosphane

• ChemBase ID: 145259
• Molecular Formular: C24H27O6P
• Molecular Mass: 442.441341
• Monoisotopic Mass: 442.15452521
• SMILES: COc1cccc(c1P(c1c(cccc1OC)OC)c1c(cccc1OC)OC)OC
• Canonical SMILES: COc1cccc(c1P(c1c(OC)cccc1OC)c1c(OC)cccc1OC)OC
• InChI: 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
• InChIKey: CMLWFCUAXGSMBB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tris(2,6-dimethoxyphenyl)phosphane
• IUPAC Traditional name: tris(2,6-dimethoxyphenyl)phosphane
• Synonyms: DMPP; Tris(2,6-dimethoxyphenyl)phosphine; TDMPP; 三(2,6-二甲氧基苯)膦; 三(2,6-二甲氧基苯基)磷

Database IDs

• CAS Number: 85417-41-0
• EC Number: 000-000-0
• MDL Number: MFCD00192558
• PubChem SID: 162239467; 24864518
• PubChem CID: 2734597

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.5904
• LogD (pH = 7.4): 3.5904
• Log P: 3.5904
• Molar Refractivity: 120.4021 cm^3
• Polarizability: 47.338394 Å^3
• Polar Surface Area: 55.38 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 145-147 °C(lit.); 145-147°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Linear Formula: [(CH3O)2C6H3]3P

DETAILS

Sigma Aldrich - 393436

Packaging
5 g in glass bottle
Application
Catalyst for:
• Preparation of chiral building blocks via hydroalkynylation reactions or ynolates1
• Three-component aza-Morita-Baylis-Hillman reactions (aza-MBH)2
• Atom-economic synthesis of nitrogen heterocycles and ynenoates from alkynes3
• Oxycylizations of allendiols4
• Enantioselective aldol reactions5
• Pd-mediated cross-coupling, Pd- and Cu-mediated benzannulation reactions and copper-mediated dimerization reactions6

REFERENCES

• Preferred ligand employed by Trost in directed tandem Pd-catalyzed reactions as an approach to furans and butenolides: J. Am. Chem. Soc., 117, 7255 (1995).