4-(2-Naphthyl)butanoic acid

Base Information

• Chemical Name: 4-(2-Naphthyl)butanoic acid
• CAS No.: 782-28-5
• Molecular Formula: C14H14O2
• Molecular Weight: 214.264
• Hs Code.: 2916399090
• European Community (EC) Number: 800-204-7
• NSC Number: 3036
• DSSTox Substance ID: DTXSID50277604
• Nikkaji Number: J819.467J
• Wikidata: Q72493729
• ChEMBL ID: CHEMBL1741827
• Mol file: 782-28-5.mol

Synonyms:2-Naphthalenebutyricacid (6CI,7CI,8CI);4-(2-Naphthyl)butanoic acid;4-(2-Naphthyl)butyric acid;NSC 3036;g-(2-Naphthyl)butyric acid;

Chemical Property of 4-(2-Naphthyl)butanoic acid

Chemical Property:

• Vapor Pressure: 5.71E-07mmHg at 25°C
• Melting Point: 94-95 °C
• Refractive Index: 1.618
• Boiling Point: 395.6 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 292.5 °C
• PSA: 37.30000
• Density: 1.164 g/cm³
• LogP: 3.24710
• Solubility.: Chloroform, DCM
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 214.099379685
• Heavy Atom Count: 16
• Complexity: 237

Purity/Quality:

98% ^*data from raw suppliers

2-NaphthalenebutanoicAcid ^*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)CCCC(=O)O
• Uses: 2-Naphthalenebutanoic Acid is an intermediate in the synthesis of 4-Phenanthrol (P295015), a metabolite of Phenanthrene.

Technology Process of 4-(2-Naphthyl)butanoic acid

There total 27 articles about 4-(2-Naphthyl)butanoic 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: 99.0%

but-3-enoic acid (625-38-7) + naphthalene-2-boronic acid (32316-92-0) → 4-(2-naphthyl)butyric acid (782-28-5)

Guidance literature:

With propan-1-ol; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium tert-butylate; 4,4-dibenzyl-2-(pyridin-2-yl)-4,5-dihydrooxazole; at 60 ℃; regioselective reaction; Sealed tube;

DOI:10.1002/anie.202010840

Reference yield: 97.0%

γ-(2-naphthyl)-γ-butyrolactone (180037-65-4) → 4-(2-naphthyl)butyric acid (782-28-5)

Guidance literature:

With palladium on activated carbon; hydrogen; In methanol; at 20 ℃; for 1h; under 760.051 Torr; Schlenk technique;

DOI:10.1021/acs.orglett.9b02673

Reference yield: 96.0%

4-(2-naphthyl)-4-oxobutyric acid (1590-22-3) → 4-(2-naphthyl)butyric acid (782-28-5)

Guidance literature:

With hydrazine; In ethylene glycol; Heating;

DOI:10.1039/P29810000286

upstream raw materials:

ethyl 4-(naphthalen-2-yl)butanoate

4-(2-naphthyl)-4-oxobutyric acid

4-oxo-4-(5,6,7,8-tetrahydro-[2]naphthyl)-butyric acid methyl ester

methyl 4-(naphthalen-2-yl)butanoate

Downstream raw materials:

1-methylanthracene

4-Phenanthrylacetic acid

phenanthrene

4-phenanthrol

Refernces

• 1、 Tran, Quan H.,Wang, Xiqu,Brookhart, Maurice,Daugulis, Olafs. "Cationic α-Diimine Nickel and Palladium Complexes Incorporating Phenanthrene Substituents: Highly Active Ethylene Polymerization Catalysts and Mechanistic Studies of syn/ anti Isomerization". supporting information. p. 4704 - 4716. Retrieved 2021/01/09.
• 2、 Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng. "Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals". supporting information. p. 5699 - 5703. Retrieved 2019/08/01.