laoqianxiu
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2-(Tifluoromethyl)acrylic acid
hi
does anybody have an idea how to create 2-(Tifluoromethyl)acrylic acid ?
thx and greets
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Sauron
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This is what you want, right?
Beilstein, 2,III,1296
CAS 381-298-6
Lithography resist polymer. Commercially available. For lithographic nanopatterning. Sounds like chipmaking tech.
[Edited on 1-3-2007 by Sauron]
[Edited on 2-3-2007 by Sauron]
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unionised
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Would an adaptation of the methyl methacrylate process work? That starts from acetone and hydrogen cyanide. If you used trifluoroacetone I think you
could get the desired product.
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Sauron
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Trifluoroacetone (b.p. 22 C) is a commercial product so I think this is a really good suggestion. Aldrich sells it so others are likely to.
If trichloroacetone exists then Swarts type fluorination could produce the trifluoroacetone. There are probably other, better methods. I think this
fellow needs to hit the lit.
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Ozone
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Sauron,
It looks like other neat molecules could easily be made from this as well...
Hmm,
O3
-Anyone who never made a mistake never tried anything new.
--Albert Einstein
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Sauron
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?? Drop me a PM and give me a clue. I can' think of anything particularly "interesting" Maybe I should go take my stupid pill for the day.
1,1,1-trichloroacetone is one of Aldrich's "rare chemicals" and that means expensive, and to me that means look for a better route.
[Edited on 2-3-2007 by Sauron]
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laoqianxiu
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Right! This is i want,
Beilstein, 2,III,1296
CAS 381-298-6
Does anybody have interrelated article about how to product 2-(Tifluoromethyl)acrylic acid ?
I can't search Beilstein and CA.
thx and greets
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Sauron
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You can search Google.
You can try Org.Syn.
We are sympathetic but this is a commercial chemical that you can just order. And we already told yoiu that, like methylacrylic acid, its parent
structure, it can be produced from the (substituted acetone and good old HCN. 1,1,1-Trifluoroacetone is likewise a commercial chemical.
Locate the Advanced Search page of Journal of Organic Chemistry and (seperately) Journal of the American Chemical Society (online). From your desktop
with the same facility that I could do it you can search about 115 years of JACS and half that many for JOC. That will get you (free) detailed
citations with DOI numbers, and first pages with abstracts.
If those searches are fruitful, then take the citations and DOI numbers and post them with a polite request for the articles in References on this
forum, you will need a password if you don't have one already.
Ask a moderator for that. I am not a moderator, so I can't give it to you.
You can do the same with many many other online journals.
These are the very same steps I would take if I were researching this compound for myself, or for you.
If for some reason you get stuck, come back here again and ask for help, but, I for one would be a whole lot more willing to exert myself for you if
you first did what you can do to help yourself. Okay?
Advice: don't ask th References guys for articles till you have full citation and DOI number or url.
Good hunting!
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Sauron
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To get you started, I ran a search in all ACS journals for last 106 years for 2-trifluoromethylacrylic acid and got 63 hits.
The 13 that I deem most likely to have synthetic details, or at least a reference to those, are listed below.
The entire 63 citations are attached as TFMAA2.txt
Just in case I might have missed something.
Note that only citations 1996-present have DOI numbers, For the rest you need to go to the webpage of the particular journal and find the issue with
the articles one by one; the citations there will include DOI.
You can also obtain abstracts (for current articles) or first pages (for pre 1996 "legacy" articles for free and often these will help you decide on
how to prioritize which articles to request from References.
DO NOT ASK FOR ALL 63 articles from References! Pick your best candidates only. Preparation of .alpha.-trifluoromethyl esters from malonic esters
T. Stephen Everett, Suzanne T. Purrington, Carl L. Bumgardner
J. Org. Chem.; 1984; 49(20); 3702-3706
Synthesis and reactions of substituted alkyl trifluoromethyl ethers
Wan Ahmad Kamil, Fritz Haspel-Hentrich, Jeanne M. Shreeve
Inorg. Chem.; 1986; 25(3); 376-380
Preparation and reactions of lithium derivatives of trifluoropropene and trifluoropropyne
F. G. Drakesmith, Oliver John Stewart, Paul Tarrant
J. Org. Chem.; 1968; 33(1); 280-285
Unimolecular Reactions of Chemically Activated Species Produced in Systems of Methylene with Propene, Butene-1, 3,3,3-Trifluoropropene, and
4,4,4-Trifluorobutene-11
F. H. Dorer, B. S. Rabinovitch
Anti-Michael addition and fluoride ion elimination on .beta.,.beta.-bis(trifluoromethyl)acrylic esters. Preparation of .alpha.-perfluoroisopropenyl
.alpha.-substituted acetic acid esters
Valerie Martin, Huguette Molines, Claude Wakselman
J. Org. Chem.; 1992; 57(20); 5530-5532.
Fluorinated Aromatic Amino Acids.1,2 II. 2- and 3-Trifluoromethyltyrosines. Hydrolytic Stability of the Trifluoromethyl Group on the Aromatic Nucleus
ROBERT FILLER, HERMAN NOVAR
J. Org. Chem.; 1961; 26(8); 2707-2710.
Aza-Michael Addition of Nosyloxycarbamates to 2-(Trifluoromethyl)acrylates
Colantoni, D.; Fioravanti, S.; Pellacani, L.; Tardella, P. A.
Org. Lett.; (Letter); 2004; 6(2); 197-200. DOI: 10.1021/ol0361554
Ultrasound-promoted synthesis of .alpha.-difluoromethylated carboxylic acids
Tomoya Kitazume, Takeshi Ohnogi, Hirofumi Miyauchi, Takashi Yamazaki, Shoji Watanabe
J. Org. Chem.; 1989; 54(23); 5630-5632.
Anodic trifluoromethylation of acrylic acid. Synthesis of diethyl (2,2,2-trifluoroethyl)malonate and trifluorinated analogs of barbital and
amobarbital
Norbert Muller
J. Org. Chem.; 1986; 51(2); 263-265.
Molecularly Imprinted Fluorescent-Shift Receptors Prepared with 2-(Trifluoromethyl)acrylic Acid
Matsui, J.; Kubo, H.; Takeuchi, T.
Anal. Chem.; (Article); 2000; 72(14); 3286-3290. DOI: 10.1021/ac000106c
J. Phys. Chem.; 1965; 69(6); 1964-1972.
General Method for the Preparation of 2,2-Difluoroacrylates Using BrF3
Hagooly, A.; Rozen, S.
J. Org. Chem.; (Article); 2004; 69(25); 8786-8788.
DOI: 10.1021/jo0485280
Photochemical transformations. XI. Photochemical and thermal rearrangements of some .beta.-substituted allylic systems
Stanley J. Cristol, Roger P. Micheli
J. Org. Chem.; 1975; 40(6); 667-672.
Photocatalyzed reaction of trifluoromethyl iodide with steroidal dienones
Gary H. Rasmusson, Ronald D. Brown, Glen E. Arth
J. Org. Chem.; 1975; 40(6); 672-675.
.alpha.- and .beta.-(Trifluoromethylthio)acrylic acid derivatives
J. F. Harris, , Jr.
J. Org. Chem.; 1972; 37(9); 1340-1346
[Edited on 2-3-2007 by Sauron]
Attachment: TFMAA2.txt (14kB)
This file has been downloaded 766 times
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laoqianxiu
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Thx
About this product,I have finished production,but haveing some problems.so,i comes here to discuss it.i would like hear anything about it
I come from China, and is willing to share.
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laoqianxiu
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why?
I ran a search in all ACS journals for last 106 years for 2-trifluoromethylacrylic acid and only got 3 hits
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laoqianxiu
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thx Sauron
Very grateful
i can obtain all fulltext in all ACS journals，and i would find the articles one by one
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Sauron
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No problem.
There are a few tricks to getting good results out of the ACS journals search engine. Mainly, you should set the Boolean operators to OR rather than
AND up near the top of page (author/title/anywhere in text)
Also don't select a journal, in which case the engine searches all of them.
Please let us know what you find.
I thought I had a good prep spotted but it can't be applied to a methylene on the beta carbon of malonic ester. So you can skip that reference.
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