630414-85-6

Basic information

• Product Name: 2-Propenoic acid, 2-Methyl-, 4,4,4-trifluoro-3-hydroxy-1-Methyl-3-(trifluoroMethyl)butyl ester
• Synonyms: 2-Propenoic acid, 2-Methyl-, 4,4,4-trifluoro-3-hydroxy-1-Methyl-3-(trifluoroMethyl)butyl ester;2-Hydroxy-1,1,1-trifluoro-2-(trifluoromethyl)-4-pentyl methacrylate;5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate;1,1,1-Trifluoro-2-trifluoromethyl-2- hydroxy-4-pentyl methacrylate
• CAS NO: 630414-85-6
• Molecular Formula: C₁₀H₁₂F₆O₃
• Molecular Weight: 294.1908992
• Mol File: 630414-85-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 291.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.321±0.06 g/cm3(Predicted)
• PKA: 9.32±0.29(Predicted)
• CAS DataBase Reference: 2-Propenoic acid, 2-Methyl-, 4,4,4-trifluoro-3-hydroxy-1-Methyl-3-(trifluoroMethyl)butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 2-Methyl-, 4,4,4-trifluoro-3-hydroxy-1-Methyl-3-(trifluoroMethyl)butyl ester(630414-85-6)
• EPA Substance Registry System: 2-Propenoic acid, 2-Methyl-, 4,4,4-trifluoro-3-hydroxy-1-Methyl-3-(trifluoroMethyl)butyl ester(630414-85-6)

Safety Data

• Hazardous Substances Data: 630414-85-6(Hazardous Substances Data)

Usage

General Description

"2-Propenoic acid, 2-Methyl-, 4,4,4-trifluoro-3-hydroxy-1-Methyl-3-(trifluoroMethyl)butyl ester" is a complex chemical compound. It is categorized as an ester, meaning it is derived from an acid (in this case, 2-Propenoic acid) and an alcohol. Its molecular structure includes several notable groups, such as the trifluoro and hydroxy groups. Trifluoro groups contain three fluorine atoms, making the compound partially fluorinated, something that tends to give the compound unique properties such as resistance to solvents and acids. The hydroxy group implies the presence of a hydroxide ion, giving it potential for varied reactivity. This complex chemical compound is likely to have specialized applications due to the unique combination of structural components.

Synthetic route

methacryloyl anhydride (760-93-0) + 1,1,1-trifluoro-2-(trifluoromethyl)pentane-2,4-diol (34844-48-9) → 5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate (630414-85-6)

Conditions	Yield
With 10H-phenothiazine; methanesulfonic acid In toluene at 50℃; for 4h; Product distribution / selectivity; Heating / reflux;	58.8%
With 10H-phenothiazine; methanesulfonic acid In toluene at 50℃; for 4h; Product distribution / selectivity; Heating / reflux;	94.5 %Chromat.
With 2,6-dimethylpyridine; 2,4-dimethyl-6-tert-butylphenol; 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane In tetrahydrofuran at 40℃; for 5h; Inert atmosphere;
With 2,6-dimethylpyridine; 2,4-dimethyl-6-tert-butylphenol; 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane In tetrahydrofuran at 40℃; for 5h; Reagent/catalyst; Inert atmosphere; Large scale;

poly(methacrylic acid) (79-41-4) + 1,1,1-trifluoro-2-(trifluoromethyl)pentane-2,4-diol (34844-48-9) → 5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate (630414-85-6)

Conditions	Yield
With 10H-phenothiazine; methanesulfonic acid In toluene at 120℃; for 6h; Product distribution / selectivity; Heating / reflux;

1,1,1-trifluoro-2-(trifluoromethyl)pentane-2,4-diol (34844-48-9) + Methacryloyl chloride (920-46-7) → 5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate (630414-85-6)

Conditions	Yield
With 2,6-dimethylpyridine; 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane In toluene at 95 - 100℃; for 6h; Product distribution / selectivity;
With 2,6-dimethylpyridine; 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane In toluene at 95 - 100℃; for 6h; Product distribution / selectivity;	89.0 %Chromat.

poly(methacrylic acid) (79-41-4) + 1,1,1-trifluoro-2-(trifluoromethyl)pent-4-en-2-ol (646-97-9) → 5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate (630414-85-6) + 2-hydroxy-1,1,1-trifluoro-2-trifluoromethylpentan-3-yl methacrylate

Conditions	Yield
tris-(trifluoromethanesulfonyl)methane acid at 110℃; for 7h;

5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate (630414-85-6) + di-tert-butyl oxalate (691-64-5) → C15H20F6O5

Conditions	Yield
Stage #1: 5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate With dmap; triethylamine In tetrahydrofuran at 70℃; Reflux; Stage #2: di-tert-butyl oxalate In tetrahydrofuran for 0.0833333h;	80%

5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate (630414-85-6) + trifluoroacetic anhydride (407-25-0) → 5,5,5-trifluoro-4-(2,2,2-trifluoroacetoxy)-4-(trifluoromethyl)pentane-2-yl methacrylate

Conditions	Yield
at 0 - 20℃; for 2.5h; Inert atmosphere;	44%

Upstream product

• 79-41-4 poly(methacrylic acid) 
• 34844-48-9 1,1,1-trifluoro-2-(trifluoromethyl)pentane-2,4-diol 
• 760-93-0 methacryloyl anhydride 
• 920-46-7 Methacryloyl chloride 
• 646-97-9 1,1,1-trifluoro-2-(trifluoromethyl)pent-4-en-2-ol 

Relevant articles and documents

METHOD FOR PURIFYING POLYMERIZABLE FLUOROMONOMER BY DISTILLATION

To provide a novel method for efficiently purifying a polymerizable fluoromonomer represented by formula (1) by distillation capable of inhibiting polymerization even in an industrial production scale.SOLUTION: The method comprises incorporating a phenolic compound A, e.g., 6-tert-butyl-2,4-xylenol, and a phenolic compound B, e.g., 2,2'-methylenebis(4-methyl-6-tert-butylphenol), as polymerization inhibitors into the polymerizable fluoromonomer, and conducting the distillation for the purification. The use of the phenolic compound A and the phenolic compound B in combination makes it possible to significantly inhibit oligomerization or polymerization during the distillation.SELECTED DRAWING: None

Process for Producing Monomer for Fluorinated Resist

According to the present invention, an α-substituted acrylic ester monomer for a fluorinated resist is produced by direct addition of an α-substituted acrylic acid to a fluorinated alkene in the presence of a specific acid catalyst having a sulfonyl group. By the use of such a specific acid catalyst, it is possible to achieve industrial-scale production of the α-substituted acrylic ester monomer for the fluorinated resist by carrying out the target addition reaction of the fluorinated alkene and the α-substituted acrylic acid efficiently during the occurrence of side reactions such as isomerization of the alkene, generation of a diol and excessive addition of the α-substituted acrylic acid.

Processes for producing fluorine-containing 2,4-diols and their derivatives

A process for producing a fluorine-containing 2,4-diol represented by the formula [4], wherein R1 represents a hydrogen atom or an acyclic or cyclic alkyl group having a carbon atom number of 1 to 7; R2 represents an acyclic or cyclic alkyl group having a carbon atom number of 1 to 7, a phenyl group, or a substituted phenyl group; and R1 and R2 are optionally bonded to each other to form a ring, includes reducing a hydroxy ketone represented by the formula [3], wherein R1 and R2 are defined as above, by hydrogen in the presence of a ruthenium catalyst.