4-Pyreneacetic acid

Base Information

• Chemical Name: 4-Pyreneacetic acid
• CAS No.: 22245-55-2
• Molecular Formula: C18H12 O2
• Molecular Weight: 260.292
• Mol file: 22245-55-2.mol

Synonyms:4-Pyrenylaceticacid

Chemical Property of 4-Pyreneacetic acid

Chemical Property:

• Vapor Pressure: 7.93E-11mmHg at 25°C
• Boiling Point: 500.2°Cat760mmHg
• Flash Point: 396.7°C
• PSA: 37.30000
• Density: 1.374g/cm³
• LogP: 4.21110
• Solubility.: Methanol

Purity/Quality:

4-PyreneaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Pyreneacetic Acid is a key intermediate in the synthesis of Acepyrene (A130950), a novel constituent discovered that belongs to the pyrene class of the polycyclic aromatic hydrocarbons.

Technology Process of 4-Pyreneacetic acid

There total 16 articles about 4-Pyreneacetic acid 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: 81.0%

4-pyrenylacetaldehyde (125996-96-5) → pyren-4-ylacetic acid (22245-55-2)

Guidance literature:

With sodium hydroxide; silver nitrate; In ethanol; for 4h; Ambient temperature;

DOI:10.1021/jo00296a065

Reference yield: 72.0%

4,5-dihydropyren-4-ylacetic acid (82243-05-8) → pyren-4-ylacetic acid (22245-55-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 3h; Heating;

Reference yield:

1,2,3,6,7,8-hexahydropyrene (1732-13-4) → pyren-4-ylacetic acid (22245-55-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / trifluoroacetic anhydride, SnCl₄ / CH₂Cl₂ / 0.5 h / 0 °C

2: 69 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / benzene / 2.5 h / Heating

3: 20percent aq. KOH, Zn, CuSO₄*5H₂O, pyridine / 4 h / 90 °C

4: 45percent aq. KOH / methanol / 1.5 h / Heating

With pyridine; potassium hydroxide; tin(IV) chloride; copper(II) sulfate; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In methanol; dichloromethane; benzene;

DOI:10.1021/jo00383a039

upstream raw materials:

pyrene

monosodium iodoacetate

methyl pyren-4-yl acetate

4-pyrenylacetaldehyde

Downstream raw materials:

3-hydroxy-3,4-dihydrocyclopentapyrene

cyclopenta[c,d]pyrene

cyclopentapyrene-3(4H)-one

Refernces

• 1、 Veeraraghavan, Seshadri,Jostmeyer, Scott,Myers, J'ne,Wiley, James C.. "A Convenient Synthesis of Cyclopentapyrene". . p. 1355 - 1357. Retrieved 1987.
• 2、 Tintel, C.,Cornelisse, J.,Lugtenburg, J.. "Convenient synthesis of cyclopentapyrene and 3,4-dihydrocyclopentapyrene. The reactivity of the pyrene dianion". . p. 14 - 20. Retrieved 2007/10/02.