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Sigma-Aldrich

Tris(2,6-dimethoxyphenyl)phosphine

98%

Synonym(s):

DMPP

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About This Item

Linear Formula:
[(CH3O)2C6H3]3P
CAS Number:
85417-41-0
Molecular Weight:
442.44
MDL number:
MFCD00192558
UNSPSC Code:
12352112
PubChem Substance ID:
24864518

Assay

98%

form

powder

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

mp

145-147 °C (lit.)

functional group

phosphine

SMILES string

COc1cccc(OC)c1P(c2c(OC)cccc2OC)c3c(OC)cccc3OC

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

InChI key

CMLWFCUAXGSMBB-UHFFFAOYSA-N

Application

Catalyst for:
  • Preparation of chiral building blocks via hydroalkynylation reactions or ynolates
  • Three-component aza-Morita-Baylis-Hillman reactions (aza-MBH)
  • Atom-economic synthesis of nitrogen heterocycles and ynenoates from alkynes
  • Oxycylizations of allendiols
  • Enantioselective aldol reactions
  • Pd-mediated cross-coupling, Pd- and Cu-mediated benzannulation reactions and copper-mediated dimerization reactions

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jamal Sheikhi et al.
Ecotoxicology and environmental safety, 191, 110243-110243 (2020-02-01)
The use of nitrification inhibitors (NIs) such as 3,4-dimethylpyrazole phosphate (DMPP) has been suggested to diminish agricultural soil nitrate (NO3-) loss and increase nitrogen (N) use efficiency (NUE). However, the yield of ammonium (NH4+)-sensitive plants such as spinach (Spinacia oleracea
Evangelia S Papadopoulou et al.
Frontiers in microbiology, 11, 581283-581283 (2020-12-01)
Nitrification inhibitors (NIs) applied to soil reduce nitrogen fertilizer losses from agro-ecosystems. NIs that are currently registered for use in agriculture appear to selectively inhibit ammonia-oxidizing bacteria (AOB), while their impact on other nitrifiers is limited or unknown. Ethoxyquin (EQ)
Marloes van Hout et al.
Biochemical pharmacology, 174, 113788-113788 (2019-12-31)
α6β2-Containing nicotinic acetylcholine receptors (α6β2* nAChRs) are predominantly expressed in midbrain dopaminergic neurons, including substantia nigra pars compacta (SNc) neurons and their projections to striatal regions, where they regulate dopamine release and nigrostriatal activity. It is well established that nAChR
Jeningsih et al.
Sensors (Basel, Switzerland), 20(7) (2020-03-29)
A DNA micro-optode for dengue virus detection was developed based on the sandwich hybridization strategy of DNAs on succinimide-functionalized poly(n-butyl acrylate) (poly(nBA-NAS)) microspheres. Gold nanoparticles (AuNPs) with an average diameter of ~20 nm were synthesized using a centrifugation-based method and
Ruting Xiao et al.
Journal of chromatography. A, 1617, 460807-460807 (2020-01-01)
Click chemistry has attracted increasing attention for the synthesis of novel stationary phases. Considering the advantage of click chemistry, a strategy based on thiol-Michael addition was developed for the preparation of a new stationary phase herein, and a phenyl vinyl
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