2-(Difluoromethoxy)naphthalene

Base Information

• Chemical Name: 2-(Difluoromethoxy)naphthalene
• CAS No.: 712-79-8
• Molecular Formula: C11H8F2O
• Molecular Weight: 194.181
• DSSTox Substance ID: DTXSID50364063
• Nikkaji Number: J2.420.241K
• Wikidata: Q82147824
• Mol file: 712-79-8.mol

Synonyms:2-(difluoromethoxy)naphthalene;712-79-8;C11H8F2O;SCHEMBL12646813;DTXSID50364063;MFCD05856249;STK663860;AKOS003348442;SB85524;s10100;DS-14953;CS-0155873;A914604

Chemical Property of 2-(Difluoromethoxy)naphthalene

Chemical Property:

• PSA: 9.23000
• LogP: 3.44120
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 194.05432120
• Heavy Atom Count: 14
• Complexity: 184

Purity/Quality:

95% ^*data from raw suppliers

2-(Difluoromethoxy)naphthalene 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)OC(F)F

Technology Process of 2-(Difluoromethoxy)naphthalene

There total 4 articles about 2-(Difluoromethoxy)naphthalene 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: 86.0%

bromodifluoroacetic acid (354-08-5) + β-naphthol (135-19-3) → 2-(difluoromethoxy)naphthalene (712-79-8)

Guidance literature:

With tris[2-phenylpyridinato-C₂,N]iridium(III); caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Solvent; Time; Inert atmosphere; Schlenk technique; Irradiation;

DOI:10.1021/acs.orglett.7b01118

Reference yield: 40.0%

2,2-difluoro-2-(fluorosulfonyl)acetic acid (1717-59-5) + β-naphthol (135-19-3) → trifluoromethan (75-46-7) + 2-(difluoromethoxy)naphthalene (712-79-8)

Guidance literature:

copper(l) iodide; In acetonitrile; at 55 ℃; for 2h;

DOI:10.1016/S0022-1139(00)82808-0

Reference yield:

naphthalene (91-20-3,71998-51-1,72931-45-4) + 1-(difluoromethoxy)-3-methyl-6-nitro-4-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-3-ium trifluoromethanesulfonate → 1-(difluoromethoxy)naphthalene (920981-10-8) + 2-(difluoromethoxy)naphthalene (712-79-8)

Guidance literature:

With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; In acetonitrile; at 23 ℃; for 12h; Overall yield = 72 %Spectr.; Irradiation;

DOI:10.1039/C8SC05390A

upstream raw materials:

2,2-difluoro-2-(fluorosulfonyl)acetic acid

β-naphthol

bromodifluoroacetic acid

naphthalene

Refernces

• 1、 Lee, Johnny W.,Zheng, Weijia,Morales-Rivera, Cristian A.,Liu, Peng,Ngai, Ming-Yu. "Catalytic radical difluoromethoxylation of arenes and heteroarenes". . p. 3217 - 3222. Retrieved 2019/03/21.
• 2、 Yang, Jinyan,Jiang, Min,Jin, Yunhe,Yang, Haijun,Fu, Hua. "Visible-Light Photoredox Difluoromethylation of Phenols and Thiophenols with Commercially Available Difluorobromoacetic Acid". supporting information. p. 2758 - 2761. Retrieved 2017/05/24.