1-(1,3-Benzodioxol-5-YL)-2,2,2-trifluoro-ethanone

Base Information

• Chemical Name: 1-(1,3-Benzodioxol-5-YL)-2,2,2-trifluoro-ethanone
• CAS No.: 102124-73-2
• Molecular Formula: C9H5 F3 O3
• Molecular Weight: 218.132
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID60445736
• Nikkaji Number: J1.585.378F
• Wikidata: Q82264259
• Mol file: 102124-73-2.mol

Synonyms:102124-73-2;1-(Benzo[d][1,3]dioxol-5-yl)-2,2,2-trifluoroethanone;1-(1,3-BENZODIOXOL-5-YL)-2,2,2-TRIFLUORO-ETHANONE;1-(1,3-benzodioxol-5-yl)-2,2,2-trifluoroethanone;Ethanone, 1-(1,3-benzodioxol-5-yl)-2,2,2-trifluoro- (9CI);1-(1,3-Dioxaindan-5-yl)-2,2,2-trifluoroethan-1-one;SCHEMBL9000245;DTXSID60445736;5-(Trifluoroacetyl)-1,3-benzodioxole;AKOS017344705;CS-0238705;EN300-1996685;1-Benzo[1,3]dioxol-5-yl-2,2,2-trifluoroethanone;trifluoromethyl (3,4-methylenedioxyphenyl)-methanone;Trifluoromethyl(3,4-methylenedioxyphenyl) methanone;3',4'-(Methylenedioxy)-2,2,2-trifluoroacetophenone;1-(2H-1,3-benzodioxol-5-yl)-2,2,2-trifluoroethan-1-one

Chemical Property of 1-(1,3-Benzodioxol-5-YL)-2,2,2-trifluoro-ethanone

Chemical Property:

• PSA: 35.53000
• LogP: 2.16030
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 218.01907850
• Heavy Atom Count: 15
• Complexity: 264

Purity/Quality:

99% ^*data from raw suppliers

1-Benzo[1,3]dioxol-5-yl-2,2,2-trifluoroethanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C(=O)C(F)(F)F

Technology Process of 1-(1,3-Benzodioxol-5-YL)-2,2,2-trifluoro-ethanone

There total 11 articles about 1-(1,3-Benzodioxol-5-YL)-2,2,2-trifluoro-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: 97.0%

1-(benzo[d][1,3]dioxol-5-yl)-2,2,2-trifluoroethan-1-ol → α,α,α-trifluoro-3,4-methylenedioxyacetophenone (102124-73-2)

Guidance literature:

With 2,6-dimethylpyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; In dichloromethane; at 20 ℃; Sealed tube;

DOI:10.1021/jo301477s

Reference yield: 89.0%

((Z)-2-(1-(benzo[d][1,3]dioxol-5-yl)-2,2,2-trifluoroethylidene)-1,1-dimethylhydrazine) → α,α,α-trifluoro-3,4-methylenedioxyacetophenone (102124-73-2)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201300782

Reference yield: 68.0%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + ethyl trifluoroacetate, (383-63-1) → α,α,α-trifluoro-3,4-methylenedioxyacetophenone (102124-73-2)

Guidance literature:

1,2-(methylenedioxy)-4-bromobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

ethyl trifluoroacetate,; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201916129

upstream raw materials:

ethyl trifluoroacetate,

(3,4-methylenedioxy)phenylmagnesium bromide

1,2-(methylenedioxy)-4-bromobenzene

N-(trifluoroacetyl)piperidine

Downstream raw materials:

1-benzo[1,3]dioxol-5-yl-2,2-difluoro-ethanone

4-methoxy-6,7-methylenedioxy-4-trifluoromethyl-1-[4-(trifluoromethyl)styryl]-3,4-dihydroisoquinoline

N-[2-methoxy-2-(3,4-methylenedioxyphenyl)-2-(trifluoromethyl)ethyl]-4-(trifluoromethyl)cinnamic amide

6,7-methylenedioxy-4-(trifluoromethyl)-1-[(4-trifluoromethyl)styryl]isoquinoline

Refernces

• 1、 Barber, David M.,Dixon, Darren J.,Thomson, Connor J.. "Catalytic Enantioselective Direct Aldol Addition of Aryl Ketones to α-Fluorinated Ketones". . p. 5359 - 5364. Retrieved 2020.
• 2、 Liu, Xue,Liu, Long,Huang, Tianzeng,Zhang, Jingjing,Tang, Zhi,Li, Chunya,Chen, Tieqiao. "Trifluoromethylation of Benzoic Acids: An Access to Aryl Trifluoromethyl Ketones". supporting information. p. 4930 - 4934. Retrieved 2021/06/30.