Prodan

Base Information

• Chemical Name: Prodan
• CAS No.: 70504-01-7
• Molecular Formula: C₁₅H₁₇NO
• Molecular Weight: 227.306
• Hs Code.: 2922399090
• UNII: 3KRL7R0ZB7
• DSSTox Substance ID: DTXSID60990711
• Nikkaji Number: J665.702H
• Wikipedia: Prodan_(dye)
• Wikidata: Q27122985
• Metabolomics Workbench ID: 57963
• Mol file: 70504-01-7.mol

Synonyms:6-propionyl-2-dimethylaminonaphthalene;prodan

Chemical Property of Prodan

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 137 °C(lit.)
• Refractive Index: 1.614
• Boiling Point: 386.157 °C at 760 mmHg
• PKA: 4.31±0.40(Predicted)
• Flash Point: 150.15 °C
• PSA: 20.31000
• Density: 1.085 g/cm³
• LogP: 3.49850
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: DMF: soluble
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 227.131014166
• Heavy Atom Count: 17
• Complexity: 274

Purity/Quality:

98%,99%, ^*data from raw suppliers

Prodan ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(=O)C1=CC2=C(C=C1)C=C(C=C2)N(C)C
• Uses: When prodan is incorporated into membranes, its fluorescence spectra are sensitive to the physical state of the surrounding phospholipids. Prodan is widely used as a fluorescent molecule probe because of its significant Stokes shift in polar solvents.

Technology Process of Prodan

There total 6 articles about Prodan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

ethyl 1-propenyl ether (928-55-2) + 6?bromo?N,N?dimethylnaphthalen?2?amine (5043-03-8) → prodan (70504-01-7)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine; In 1,2-dimethoxyethane; at 145 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201909536

Reference yield:

1-(1H-pyrrol-1-yl)propan-1-one (59303-16-1) + 6?bromo?N,N?dimethylnaphthalen?2?amine (5043-03-8) → prodan (70504-01-7)

Guidance literature:

6?bromo?N,N?dimethylnaphthalen?2?amine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

1-(1H-pyrrol-1-yl)propan-1-one; In tetrahydrofuran; hexane; at -45 ℃; for 1.5h;

DOI:10.1080/00304940509354992

Reference yield:

6-(methylamino)-2-bromonaphthalene (305835-80-7) → prodan (70504-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 80 percent / K₂CO₃ / dimethylformamide / 20 °C

2.1: 82 percent / ethanolamine / 1 h / 150 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 580 mg / tetrahydrofuran; hexane / 1.5 h / -45 °C

With n-butyllithium; potassium carbonate; ethanolamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1080/00304940509354992

upstream raw materials:

1-(1H-pyrrol-1-yl)propan-1-one

6?bromo?N,N?dimethylnaphthalen?2?amine

6-(methylamino)-2-bromonaphthalene

6-bromo-naphthalen-2-ol

Refernces

• 1、 Fleming, Cassandra L.,Sandoz, Patrick A.,Inghardt, Tord,?nfelt, Bj?rn,Gr?tli, Morten,Andréasson, Joakim. "A Fluorescent Kinase Inhibitor that Exhibits Diagnostic Changes in Emission upon Binding". . p. 15000 - 15004. Retrieved 2019/09/17.