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393436

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

393436-5G:
393436-BULK:
393436-25G:
393436-VAR:

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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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
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)
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
Takio Kitazawa et al.
General and comparative endocrinology, 274, 106-112 (2019-01-25)
Motilin (MLN), a 22-amino-acid peptide hormone, is generally present in the mucosa of the upper gastrointestinal (GI) tract, mainly the duodenum of mammals, and it regulates GI motility, especially that related to interdigestive migrating contraction. However, MLN and its receptor
Sigrid Jall et al.
Diabetologia, 63(6), 1236-1247 (2020-03-07)
Treatment with the α3β4 nicotinic acetylcholine receptor (nAChR) agonist, 1,1-dimethyl-4-phenylpiperazinium iodide (DMPP), improves glucose tolerance in diet-induced obese (DIO) mice, but the physiological and molecular mechanisms are unknown. DMPP (10 mg/kg body weight, s.c.) was administered either in a single injection
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