6-(2-Naphthyl)-6-oxohexanoic acid

Base Information

• Chemical Name: 6-(2-Naphthyl)-6-oxohexanoic acid
• CAS No.: 132104-10-0
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.301
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID30598768
• Wikidata: Q82494571
• Mol file: 132104-10-0.mol

Synonyms:6-(2-NAPHTHYL)-6-OXOHEXANOIC ACID;132104-10-0;6-naphthalen-2-yl-6-oxohexanoic acid;6-(NAPHTHALEN-2-YL)-6-OXOHEXANOIC ACID;MFCD01320091;SCHEMBL8780100;DTXSID30598768;AKOS016022473;2-Naphthalenehexanoic acid, epsilon-oxo-;6-(2-NAPHTHYL)-6-OXOHEXANOICACID

Chemical Property of 6-(2-Naphthyl)-6-oxohexanoic acid

Chemical Property:

• Vapor Pressure: 5.45E-10mmHg at 25°C
• Melting Point: 69 °C
• Boiling Point: 479.1°C at 760 mmHg
• PKA: 4.69±0.10(Predicted)
• Flash Point: 257.7°C
• PSA: 54.37000
• Density: 1.188g/cm³
• LogP: 3.66750
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 256.109944368
• Heavy Atom Count: 19
• Complexity: 324

Purity/Quality:

99% ^*data from raw suppliers

6-(2-Naphthyl)-6-oxohexanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)C(=O)CCCCC(=O)O

Technology Process of 6-(2-Naphthyl)-6-oxohexanoic acid

There total 4 articles about 6-(2-Naphthyl)-6-oxohexanoic 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: 55.0%

2-(naphthalen-2-yl)cyclohexan-1-one (54367-97-4) → 6-(naphthalen-2-yl)-6-oxohexanoic acid (132104-10-0)

Guidance literature:

With aurin; water; copper(II) bis(trifluoromethanesulfonate); In acetonitrile; for 48h; Schlenk technique; Irradiation;

DOI:10.1021/acs.joc.1c00708

Reference yield:

ethyl 6-chloro-6-oxohexanoate (1071-71-2) + naphthalene (91-20-3,71998-51-1,72931-45-4) → 6-[1]naphthyl-6-oxo-hexanoic acid (132104-09-7) + 6-(naphthalen-2-yl)-6-oxohexanoic acid (132104-10-0)

Guidance literature:

With aluminium trichloride; nitrobenzene; Hydrolyse des Reaktionsprodukts;

Reference yield:

naphthalene-2-boronic acid (32316-92-0) + 2-Chlorocyclohexanone (822-87-7) → 6-(naphthalen-2-yl)-6-oxohexanoic acid (132104-10-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate; nickel(II) nitrate hexahydrate; 4,4'-di-tert-butyl-2,2'-bipyridine; sodium iodide / 1,4-dioxane / 12 h / 80 °C / Sealed tube; Inert atmosphere

2: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 8 h / -5 - 20 °C

With hydrogenchloride; nickel(II) nitrate hexahydrate; potassium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; sodium iodide; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/acs.orglett.1c02327

upstream raw materials:

ethyl 6-chloro-6-oxohexanoate

naphthalene

butane-1,1,4-tricarboxylic acid

2-naphthaloyl chloride

Refernces

• 1、 He, Tianyu,Chen, Dengfeng,Qian, Shencheng,Zheng, Yu,Huang, Shenlin. "Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl". supporting information. p. 6525 - 6529. Retrieved 2021/09/02.