Naphthalene-2-carbonyl fluoride

Base Information

• Chemical Name: Naphthalene-2-carbonyl fluoride
• CAS No.: 37827-83-1
• Molecular Formula: C11H7 F O
• Molecular Weight: 174.174
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID20567024
• Nikkaji Number: J500.364D
• Wikidata: Q82452809
• Mol file: 37827-83-1.mol

Synonyms:37827-83-1;2-Naphthoyl fluoride;naphthalene-2-carbonyl fluoride;2-Naphthalenecarbonyl fluoride (9CI);2-NAPHTHALENECARBONYL FLUORIDE;starbld0011074;SCHEMBL8344284;DTXSID20567024;F87958

Chemical Property of Naphthalene-2-carbonyl fluoride

Chemical Property:

• Boiling Point: 283.0±9.0 °C(Predicted)
• PSA: 17.07000
• Density: 1.209±0.06 g/cm3(Predicted)
• LogP: 2.94950
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 174.048093005
• Heavy Atom Count: 13
• Complexity: 202

Purity/Quality:

99%min ^*data from raw 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)F

Technology Process of Naphthalene-2-carbonyl fluoride

There total 4 articles about Naphthalene-2-carbonyl fluoride 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:

benzyl (Z)-2-(hydroxyimino)-3-(naphthalen-2-yl)-3-oxopropanoate → benzyl cyanoformate (5532-86-5) + naphthalene-2-carbonyl fluoride (37827-83-1)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2021.153116

Reference yield:

benzyl 3-(naphthalen-2-yl)-3-oxopropanoate → benzyl cyanoformate (5532-86-5) + naphthalene-2-carbonyl fluoride (37827-83-1)

Guidance literature:

Multi-step reaction with 2 steps

1: n-Butyl nitrite; hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

2: diethylamino-sulfur trifluoride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With hydrogenchloride; n-Butyl nitrite; diethylamino-sulfur trifluoride; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1016/j.tetlet.2021.153116

Reference yield:

C29H22O2P(1+)*Br(1-) + (trifluoromethyl)trimethylsilane (81290-20-2) → naphthalene-2-carbonyl fluoride (37827-83-1) + 2-naphthyl trifluoromethyl ketone (1800-42-6)

Guidance literature:

(trifluoromethyl)trimethylsilane; With copper(l) iodide; cesium fluoride; In acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere; Sealed tube;

C₂₉H₂₂O₂P⁽¹⁺⁾*Br^(1-); In tetrahydrofuran; acetonitrile; at 20 ℃; for 2h; Concentration; Solvent; chemoselective reaction; Inert atmosphere;

DOI:10.1002/chem.202102854

upstream raw materials:

naphthalene-2-carboxylate

(trifluoromethyl)trimethylsilane

Downstream raw materials:

tributyl(naphthalene-2-yl)stannane

4-methylphenyl 2-naphthyl sulfide

2-naphthalenecarbonitrile

Refernces

• 1、 Ispizua-Rodriguez, Xanath,Munoz, Socrates B.,Krishnamurti, Vinayak,Mathew, Thomas,Prakash. "Direct Synthesis of Tri-/Difluoromethyl Ketones from Carboxylic Acids by Cross-Coupling with Acyloxyphosphonium Ions". . p. 15908 - 15913. Retrieved 2021/10/07.