100478-25-9

Basic information

• Product Name: 4,6-BIS(DIFLUOROMETHOXY)-2-(METHYLTHIO)PYRIMIDINE
• Synonyms: 4,6-BIS(DIFLUOROMETHOXY)-2-(METHYLTHIO)PYRIMIDINE;4,6-Bis(difluoromethoxy)-2-methyltniopyrimidine
• CAS NO: 100478-25-9
• Molecular Formula: C7H6F4N2O2S
• Molecular Weight: 258.19
• Mol File: 100478-25-9.mol

Chemical Properties

• Melting Point: 48 °C
• Boiling Point: 302.442ºC at 760 mmHg
• Flash Point: 136.712ºC
• Appearance: /
• Density: 1.494g/cm3
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.469
• Solubility: soluble in Methanol
• CAS DataBase Reference: 4,6-BIS(DIFLUOROMETHOXY)-2-(METHYLTHIO)PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-BIS(DIFLUOROMETHOXY)-2-(METHYLTHIO)PYRIMIDINE(100478-25-9)
• EPA Substance Registry System: 4,6-BIS(DIFLUOROMETHOXY)-2-(METHYLTHIO)PYRIMIDINE(100478-25-9)

Safety Data

• Hazardous Substances Data: 100478-25-9(Hazardous Substances Data)

Usage

Uses

This compound was a reagent in the synthesis of the herbicide, primisulfuron-Me.

InChI:InChI=1/C7H6F4N2O2S/c1-16-7-12-3(14-5(8)9)2-4(13-7)15-6(10)11/h2,5-6H,1H3

Upstream product

• 593-81-7 trimethylamine hydrochloride 
• 111810-91-4 4-hydroxy-6-difluoromethoxy-2-methylthiopyrimidine 

Relevant articles and documents

Process for producing a 4,6-bis(difluoromethoxy)-2-alkylthiopyrimidine

A process for producing a 4,6-bis(difluoromethoxy)-2-alkylthiopyrimidine, which comprises reacting a 2-alkylthiobarbituric acid and monochlorodifluoromethane in the presence of a base in an inert solvent, wherein, for a first reaction, after charging a part of the base, the rest of the base and the monochlorodifluoromethane are simultaneously introduced to obtain a mixture of a 4-difluoromethoxy-6-hydroxy-2-alkylthiopyrimidine and a 4,6-bis(difluoromethoxy)-2-alkylthiopyrimidine, and then, for a second reaction, to this mixture, the base and the monochlorodifluoromethane are again simultaneously introduced, or the base is charged first and then the monochlorodifluoromethane is introduced.

Process for producing a 4,6-bis(difluoromethoxy)-2-alkylthiopyrimidine

A process for producing a 4,6-bis(difluoromethoxy)-2-alkylthiopyrimidine, which comprises reacting a 2-alkylthiobarbituric acid and monochlorodifluoromethane in the presence of a base in an inert solvent, wherein, for a first reaction, after charging a part of the base, the rest of the base and the monochlorodifluoromethane are simultaneously introduced to obtain a mixture of a 4-difluoromethoxy-6-hydroxy-2-alkylthiopyrimidine and a 4,6-bis(difluoromethoxy)-2-alkylthiopyrimidine, and then, for a second reaction, to this mixture, the base and the monochlorodifluoromethane are again simultaneously introduced, or the base is charged first and then the monochlorodifluoromethane is introduced.

Process for the preparation of pyrimidine derivatives

4,6-Bis(difluoromethoxy)pyrimidines of formula I STR1 wherein R is C1 -C4 alkyl or unsubstituted or substituted phenyl or benzyl, are prepared by reacting a 4,6-dihydroxypyrimidine dialkali metal salt of formula II STR2 wherein R is as defined for formula I and Me is an alkali metal, with chlorodifluoromethane in a solvent selected from the group consisting of ketones and alkyl cyanides, in the presence of 0.05 to 1.1 mol of water per mol of dialkali metal salt of formula II.

Process for the preparation of pyrimidine derivatives

The present invention relates to a process for the preparation of 2-mercapto-4,6-bis-fluoroalkoxypyrimidines of the formula STR1 wherein R1 is C1 -C4 alkyl, phenyl or benzyl and each of T1 and T2 independently of the other is hydrogen or a --CHX1 X2 group, wherein each of X1 and X2 independently of the other is trifluoromethyl, fluorine, chlorine or bromine. In accordance with this process, 2-mercapto-4-halo-6-hydroxy-pyrimidines of the formula STR2 wherein R1 is as defined above and Y is chlorine or bromine, are reacted with chlorodifluoromethane or a 1,1-difluoroalkene of the formula STR3 wherein each of the X1 and X2 independently of the other is trifluoromethyl, fluorine, chlorine or bromine, in an inert solvent and in the presence of a strong base, to give a 2-mercapto-4-halo-6-fluoro-alkoxypyrimidine of the formula STR4 wherein R1, Y and T1 are as defined above, said 2-mercapto-4-halo-6-fluoroalkoxypyrimidine is converted by subsequent reaction with an alkali metal nitrite or an alkaline earth metal nitrite into a 2-mercapto-4-hydroxy-6-fluoroalkoxypyrimidine of the formula STR5 wherein R1 and T1 are as defined above, and then said 2-mercapto-4-hydroxy-6-fluoroalkoxypyrimidine is converted by reaction with chlorodifluoromethane or a 1,1-difluoroalkene of the above formula into a 2-mercapto-4,6-bix-fluoroalkoxypyrimidine of the above formula. The 2-mercapto-4,6-bis-fluoroalkoxypyrimidines of the above formula are intermediates for the preparation of herbicidally effective sulfonylureas.

Process for producing fluoroalkoxyaminopyrimidines

A novel process for producing fluoroalkoxyaminopyrimidines of the formula I STR1 wherein R is hydrogen, C1 -C4 -alkyl, C1 -C4 -alkoxy or benzyl, X is halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkyl, C1 -C4 -haloalkoxy, C1 -C4 -alkylamino or di-C1 -C4 -alkylamino, and T is hydrogen, chlorofluoromethyl, bromofluoromethyl, difluoromethyl or 1,2,2,2-tetrafluoroethyl, characterized in that a thiopyrimidine of the formula II STR2 wherein Y has the meaning given for X under the formula I or is hydroxyl, A is hydrogen, sodium, potassium or an equivalent of calcium or magnesium, and Q is C1 -C4 -alkyl, phenyl or benzyl, is reacted with difluorochloromethane, difluorobromomethane, tetrafluoroethylene, perfluoropropylene, trifluorobromoethylene or trifluorochloroethylene in the presence of a base; the resulting compound of the formula III STR3 is converted by oxidation into a compound of the formula IV STR4 wherein n is the number one or two; and this compound is treated with an amine of the formula V