1-[4-(Diethylamino)-2-hydroxyphenyl]-2,2,2-trifluoro-1-ethanone

Base Information

• Chemical Name: 1-[4-(Diethylamino)-2-hydroxyphenyl]-2,2,2-trifluoro-1-ethanone
• CAS No.: 333303-11-0
• Molecular Formula: C₁₂H₁₄F₃NO₂
• Molecular Weight: 261.244
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID40444808
• Nikkaji Number: J3.566.144A
• Wikidata: Q82263080
• ChEMBL ID: CHEMBL4928463
• Mol file: 333303-11-0.mol

Synonyms:333303-11-0;1-[4-(diethylamino)-2-hydroxyphenyl]-2,2,2-trifluoro-1-ethanone;1-(4-(Diethylamino)-2-hydroxyphenyl)-2,2,2-trifluoroethanone;1-[4-(diethylamino)-2-hydroxyphenyl]-2,2,2-trifluoroethanone;1-[4-(diethylamino)-2-hydroxyphenyl]-2,2,2-trifluoroethan-1-one;1-(4-(Diethylamino)-2-hydroxyphenyl)-2,2,2-trifluoroethan-1-one;CHEMBL4928463;DTXSID40444808;OAVOCVYNBQRORC-UHFFFAOYSA-N;MFCD08056623;AKOS005070165;SB81647;CS-0363523;J3.566.144A;3T-0029;J-503204;2'-Hydroxy-4'-(diethylamino)-alpha,alpha,alpha-trifluoroacetophenone

Chemical Property of 1-[4-(Diethylamino)-2-hydroxyphenyl]-2,2,2-trifluoro-1-ethanone

Chemical Property:

• Melting Point: 51-52°
• PSA: 40.54000
• LogP: 2.98340
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 261.09766318
• Heavy Atom Count: 18
• Complexity: 290

Purity/Quality:

98%min ^*data from raw suppliers

1-[4-(Diethylamino)-2-hydroxyphenyl]-2,2,2-trifluoro-1-ethanone >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C1=CC(=C(C=C1)C(=O)C(F)(F)F)O

Technology Process of 1-[4-(Diethylamino)-2-hydroxyphenyl]-2,2,2-trifluoro-1-ethanone

There total 3 articles about 1-[4-(Diethylamino)-2-hydroxyphenyl]-2,2,2-trifluoro-1-ethanone 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: 40.0%

3-(diethylamino)phenyl acetate (18997-95-0) + trifluoroacetic anhydride (407-25-0) → 4-(dimethylamino)-1′,1′,1′-trifluoro-2-hydroxyacetophenone (333303-11-0)

Guidance literature:

3-(diethylamino)phenyl acetate; trifluoroacetic anhydride; In diethyl ether; for 3h; Reflux;

With hydrogenchloride; In tetrahydrofuran; Dimethyl ether; at 20 ℃; for 24h;

DOI:10.1021/acs.joc.6b00981

Reference yield:

3-(diethylamino)phenyl acetate (18997-95-0) → 4-(dimethylamino)-1′,1′,1′-trifluoro-2-hydroxyacetophenone (333303-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / 3 h / Heating

2: 2 M aq. NaOH / tetrahydrofuran / 20 °C

With sodium hydroxide; In tetrahydrofuran; diethyl ether;

DOI:10.1002/jhet.5570370608

Reference yield:

3-diethylaminophenol (91-68-9) → 4-(dimethylamino)-1′,1′,1′-trifluoro-2-hydroxyacetophenone (333303-11-0)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; triethylamine / dichloromethane / 12 h / 20 °C

2: diethyl ether / 3 h / Reflux

3: hydrogenchloride / water; tetrahydrofuran / 24 h / 20 °C

With hydrogenchloride; dmap; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; 2: |Friedel-Crafts Acylation;

DOI:10.1021/acs.joc.5b00077

upstream raw materials:

3-(diethylamino)phenyl acetate

3-diethylaminophenol

trifluoroacetic anhydride

Downstream raw materials:

7-diethylamino-4-trifluoromethylcoumarin-3-carboxylic acid

Refernces

• 1、 Niu, Guangle,Liu, Weimin,Wu, Jiasheng,Zhou, Bingjiang,Chen, Jianhong,Zhang, Hongyan,Ge, Jiechao,Wang, Ying,Xu, Haitao,Wang, Pengfei. "Aminobenzofuran-fused rhodamine dyes with deep-red to near-infrared emission for biological applications". . p. 3170 - 3175. Retrieved 2015/03/30.