185449-86-9

Basic information

• Product Name: (S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE
• Synonyms: (S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE;(S)-(+)-(2,6-Dimethyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)dimethylamine,min.98%;(S)-(+)-(2,6-Dimethyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a:3,4-a']dinaphthalen-4-yl)dimethylamine, min. 98%;3,4-a']dinaphthalen-4-yl)dimethylamine, min. 98%;N,N,2,6-Tetramethyldinaphtho-[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine;(11bS)-N,N,2,6-tetraMethyl-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-aMine;3,4-a']dinaphthalen-4-yl)dimethylamine,98%
• CAS NO: 185449-86-9
• Molecular Formula: C24H22NO2P
• Molecular Weight: 387.41
• Product Categories: Chiral Phosphine;CPN
• Mol File: 185449-86-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 228-229°C
• Boiling Point: 571.0±53.0 °C(Predicted)
• Appearance: off-white/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.32±0.20(Predicted)
• Sensitive: moisture sensitive
• CAS DataBase Reference: (S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE(185449-86-9)
• EPA Substance Registry System: (S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE(185449-86-9)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 185449-86-9(Hazardous Substances Data)

Usage

Description

(S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE is a complex organic compound that serves as a versatile ligand in various enantioselective catalytic reactions. It is characterized by its unique structure, which allows it to selectively influence the outcome of chemical reactions, leading to the preferential formation of one enantiomer over the other.

Uses

Used in Pharmaceutical Industry:
(S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE is used as a ligand for the enantioselective, rhodium-catalyzed hydrogenation of substituted olefins, such as N-acetyldihydroamino acids, enamides, and unsaturated acids. This application is crucial for the synthesis of chiral pharmaceuticals, as it enables the production of single-enantiomer drugs with desired biological activities and reduced side effects.
Used in Chemical Synthesis:
In the field of chemical synthesis, (S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE is used as a ligand for the enantioselective, iridium-catalyzed allylic substitution of allyl acetates containing only a single substituent in the 1 or 3 position. This reaction is important for the preparation of various chiral compounds, including pharmaceuticals, agrochemicals, and natural products.
Used in Asymmetric Hydroboration Reactions:
(S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE is also used as a ligand in the rhodium-catalyzed, amide directed, asymmetric hydroboration reaction. This reaction is a key step in the synthesis of enantiomerically pure alcohols, which are important building blocks in the pharmaceutical and fine chemical industries.
Used in Conjugate Addition Reactions:
In the field of organic chemistry, (S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE is used as a ligand for the asymmetric conjugate addition of aryl boronic acids to dihydronitronaphthalenes. This reaction is significant for the synthesis of chiral biaryl compounds, which are common structural motifs in various pharmaceuticals and agrochemicals.
Used in Intramolecular 1,4 Addition Reactions:
(S)-(+)-(2,6-DIMETHYL-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE is utilized as a ligand in the rhodium-catalyzed asymmetric intramolecular 1,4 addition. This reaction is essential for the construction of complex molecular architectures, such as carbocycles and heterocycles, which are found in many biologically active compounds and pharmaceuticals.