781637-36-3

Basic information

• Product Name: 2-Propenoic acid, 2-methyl-, 3,5-bis[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]cyclohexyl ester
• Synonyms: MA-3,5-HFA-CHOH
• CAS NO: 781637-36-3
• Molecular Formula: C16H16F12O4
• Molecular Weight: 500.281
• Mol File: 781637-36-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 2-methyl-, 3,5-bis[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 2-methyl-, 3,5-bis[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]cyclohexyl ester(781637-36-3)
• EPA Substance Registry System: 2-Propenoic acid, 2-methyl-, 3,5-bis[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]cyclohexyl ester(781637-36-3)

Safety Data

• Hazardous Substances Data: 781637-36-3(Hazardous Substances Data)

Usage

General Description

2-Propenoic acid, 2-methyl-, 3,5-bis[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]cyclohexyl ester is a chemical compound with the molecular formula C24H25F12O4. It is a cyclohexyl ester derivative of 2-methyl-2-propenoic acid and contains multiple trifluoromethyl and hydroxy functional groups. 2-Propenoic acid, 2-methyl-, 3,5-bis[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]cyclohexyl ester is commonly used in the production of coatings, adhesives, sealants, and elastomers, as well as in the formulation of agricultural and industrial chemicals. It is also employed as a chemical intermediate in the synthesis of various organic compounds. Due to its unique chemical structure and properties, 2-Propenoic acid, 2-methyl-, 3,5-bis[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]cyclohexyl ester is valued for its versatility and wide range of applications in different industries.

Synthetic route

poly(methacrylic acid) (79-41-4) + 3,5-HFA-CHOH (669768-29-0) → 3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3)

Conditions	Yield
With methanesulfonic acid In toluene at 130℃; for 3.5h;

3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3) + di-tert-butyl dicarbonate (24424-99-5) → C26H32F12O8 (1181818-33-6)

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 70℃; Reflux;	80%

1-ethylcyclopentyl methacrylate + 3-hydroxy-1-adamantyl methacrylate (115372-36-6) + ethyl 2-hydroxypropionate (97-64-3, 2676-33-7) + diphenylether (101-84-8) + propylene glycol methyl ether acetate (108-65-6) + 3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3) + 4-diacetoxyiodobiphenyl + alpha-(gamma-butyrolactone) methacrylate + 2-isopropyl-2-adamantyl methacrylate (297156-50-4) + gamma-butyrolactone methacrylate + potassium nonaflate (29420-49-3) → Biphenyl-4-yl(4-phenoxyphenyl)iodonium 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

Conditions	Yield
With toluene-4-sulfonic acid In methanol; dichloromethane; water; acetonitrile

...Expand

2-methyl-2-adamantyl methacrylate (177080-67-0) + 2,2'-azobis-(2,4-dimethylvaleronitrile) (4419-11-8) + 3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3) + alpha-(gammabutyrolactone)methacrylate + (t-butylphenyl)(phenyl)iodonium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonate + triphenylsulfonium 2,3,5,6-tetrafluoro-4-(methacryloyloxy)benzene sulfonate → methyltertbutyl ether (67000-01-5)

Conditions	Yield
In tetrahydrofuran; acetonitrile	39.6 g (54%)

3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3) → C14H11F14O7S(1-)*C12H10I(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 36.5 h / 23 - 90 °C 2.1: chlorobenzene / 0.5 h / 23 °C 2.2: 3 h / 130 °C / Molecular sieve View Scheme

3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3) → C14H11F14O7S(1-)*C12H15OS(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 36.5 h / 23 - 90 °C 2.1: chlorobenzene / 0.5 h / 23 °C 2.2: 3 h / 130 °C / Molecular sieve View Scheme

3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3) → C14H13ClF12O4

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; water / 1,4-dioxane / 36.5 h / 23 - 90 °C 2: pyridine / tetrahydrofuran / 4 h / 40 °C View Scheme

3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3) → C16H13F14O9S(1-)*C18H15S(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 36.5 h / 23 - 90 °C 2.1: pyridine / tetrahydrofuran / 4 h / 40 °C 3.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1.5 h / 23 - 40 °C 3.2: 7 h / 40 °C View Scheme

3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3) → 3,5-HFA-CHOH (669768-29-0)

Conditions	Yield
With water; sodium hydroxide In 1,4-dioxane at 23 - 90℃; for 36.5h;

3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3) → C14H11F14O7S(1-)*C18H15S(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 36.5 h / 23 - 90 °C 2.1: chlorobenzene / 0.5 h / 23 °C 2.2: 3 h / 130 °C / Molecular sieve View Scheme

3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl methacrylate (781637-36-3) → C14H11F14O7S(1-)*C21H21S(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 36.5 h / 23 - 90 °C 2.1: chlorobenzene / 0.5 h / 23 °C 2.2: 3 h / 130 °C / Molecular sieve View Scheme

Upstream product

• 79-41-4 poly(methacrylic acid) 
• 669768-29-0 3,5-HFA-CHOH 

Downstream Products

• 669768-29-0 3,5-HFA-CHOH 
• 1181818-33-6 C₂₆H₃₂F₁₂O₈ 

Relevant articles and documents

Polymerizable Fluorine-Containing Compound

A polymerizable fluorine-containing compound represented by formula (1), wherein R1 represents a polymerizable double-bond containing group, R2 represents an acid-labile protecting group, R3 represents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein R2, R3 and W are defined as above, each of R4, R5 and R6 independently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R4, R5 and R6 may be combined to form a ring. This polymer compound can provide a resist composition capable of forming a pattern that is transparent to exposure light and superior in rectangularity.