26974-09-4

Usage

Chemical Properties

White to light yellow solid

InChI:InChI=1/C10BrF7/c11-3-4(12)1-2(5(13)8(3)16)7(15)10(18)9(17)6(1)14

Upstream product

• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 594-14-9 guanidinium sulfate 
• 593-85-1 diguanidine carbonate 
• 172032-06-3 1,1,1,2,2-pentafluoro-4-iodo-4-phenyl-3-butene 
• 113-00-8 guanidine nitrate 
• 536-74-3 phenylacetylene 
• 1020540-98-0 4-trifluoromethyl-6-phenyl-2-acetylaminopyrimidine 
• 6048-29-9 triphenylphenacylphosphonium bromide 
• 50-01-1 guanidine hydrochloride 
• 98-86-2 acetophenone 
• 593-85-1 guanidine carbonate 
• 58518-08-4 1,1,1-trifluoro-4-phenylbut-3-yn-2-one 
• 85694-32-2 1-phenyl-4,4,4-trifluoro-1-butyn-3-one 
• 149846-93-5 1-phenyl-4,4,4-trifluorobut-2-yn-1-ol 

Relevant academic research and scientific papers

Fluorinated β-diketo phosphorus ylides: Their cyclocondensation with amidines affording 4-trifluoromethyl- And 4-perfluoroalkyl-substituted pyrimidines

A study is presented for the syntheses of a series of 4-trifluoromethyl- and 4-perfluoroalkyl-substituted pyrimidines from the reaction of trifluoromethyl or perfluoroalkyl β-diketo phosphorus ylides (Ph3P=C(CORF)COR) with amidine hydrochloride.

Facile preparation and conversion of 4,4,4-trifluorobut-2-yn-1-ones to aromatic and heteroaromatic compounds

The concise preparation of 4,4,4-trifluorobut-2-yn-1-ones by the oxidation of the readily accessible corresponding propargylic alcohols as well as their utilization as Michael acceptors for the construction of aromatic and heteroaromatic compounds are rep

One-Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF3-Ynones

A highly efficient synthetic method for the preparation of of 6-trifluoromethylated pyrimidines was developed. The reaction of CF3-substituted ynones and nitrogen 1,3-bis(nucleophile)s was employed for the one-pot assembly of the pyrimidine core. The cascade route proceeded through an aza-Michael addition, intramolecular cyclization, and dehydration reaction sequence to give the target heterocycles in excellent yields (up to 97 %). When acetamidine was used as the bis(nucleophile), the unexpected addition of two equivalents of the CF3-substituted ynone to the acetamidine was observed.

Synthesis, fungicidal activity and mode of action of 4-phenyl-6-trifluoromethyl-2-aminopyrimidines against Botrytis cinerea

Anilinopyrimidines are the main chemical agents for management of Botrytis cinerea. However, the drug resistance in fungi against this kind of compounds is very serious. To explore new potential fungicides against B. cinerea, a series of 4-phenyl-6-trifluoromethyl-2-amino-pyrimidine compounds (compounds III-1 to III-22) were synthesized, and their structures were confirmed by 1H-NMR, IR and MS. Most of these compounds possessed excellent fungicidal activity. The compounds III-3 and III-13 showed higher fungicidal activity than the positive control pyrimethanil on fructose gelatin agar (FGA), and compound III-3 on potato dextrose agar (PDA) indicated high activity compared to the positive control cyprodinil. In vivo greenhouse results indicated that the activity of compounds III-3, III-8, and III-11 was significantly higher than that of the fungicide pyrimethanil. Scanning electron micrography (SEM) and transmission electron micrography (TEM) were applied to illustrate the mechanism of title compounds against B. cinerea. The title compounds, especially those containing a fluorine atom at the ortho-position on the benzene ring, could maintain the antifungal activity against B. cinerea, but their mechanism of action is different from that of cyprodinil. The present study lays a good foundation for us to find more efficient reagents against B. cinerea.

One-pot synthesis of N2-aminoprotected 6-substituted and cycloalka[d] 4-trifluoromethyl-2-acetylaminopyrimidines

(Chemical Equation Presented) The one-pot synthesis of a novel series of amino-protected 6-alkyl-, 6-aryl-, 6-heteroaryl- and 5,6-fused-cycloalkane 4-trifluoromethyl-2-acetylaminopyrimidines, where alkyl = Me; aryl = Ph, 4-CH3Ph, 4-FPh, 4-ClPh, 4-BrPh, 4-OCH3Ph, 4-NO 2Ph, 4,4′-biphenyl, 1-naphthyl; heteroaryl = 2-thienyl, 2-furyl and cycloalkyl = c-C6H4, c-C7H5 from the reaction of substituted 4-methoxy-1,1,1-trifluoroalk-3-en-2-ones with 1-acetylguanidine in acetonitrile or propan-2-ol as solvent, is reported. The acetylamino group of 2-acetylaminopyrimidines was hydrolyzed under three different conditions to afford the corresponding free 2-aminopyrimidines.

Synthesis and evaluation of 2-(2,6-dihalophenyl)-3-pyrimidinyl-1,3-thiazolidin-4-one analogues as anti-HIV-1 agents

A series of 2-(2,6-dihalophenyl)-3-(substituted pyrimidinyl)-1,3-thiazolidin-4-ones were designed on the prediction of quantitative structure-activity relationship (QSAR) studies, synthesized, and evaluated as HIV-1 reverse transcriptase inhibitors. Our attempts in correlating the identified molecular surface features related properties for modeling the HIV-1 RT inhibitory activity resulted in some statistically significant QSAR models with good predictive ability. The results showed that compounds 4m and 4n were highly active in inhibiting HIV-1 replication with EC50 values in the range of 22-28 nM in MT-4 as well as in CEM cells with selectivity indexes of >10,000. The derived models collectively suggest that the compounds should be compact without bulky substitution on its peripheries for better HIV-1 RT inhibitory activity. These models also indicate a preference for hydrophobic compounds to obtain good HIV-1 RT inhibitory activity.

Convenient synthesis of fluoroalkyl-substituted heterocycles from 1-fluoroalkyl-2-iodoalkenes

A convenient synthesis of fluoroalkyl-substituted heterocycles including 3-trifluoromethylpyrazoles 7,5-trifluoromethylisoxazoles 8 and 4-trifluoromethylpyrimidines 9 is described. This two-step sequence consists of a radical addition of fluoroalkyl iodid

Improved Synthesis of Fluoroalkyl and Fluoroaryl Substituted 2-Aminopyrimidines

Fluoroalkyl and fluoroaryl substituted 2-aminopyrimidines have been prepared in good yields by the cyclization of guanidine salts with fluorine substituted β-diketones in sodium isopropoxide/isopropanol at reflux.