2144-53-8

Basic information

• Product Name: 2-(Perfluorohexyl)ethyl methacrylate
• Synonyms: 1H,1H,2H,2H-Tridecafluorooct-1-yl methacrylate 99%;2-(Perfluorohex-1-yl)ethyl methacrylate, 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooct-1-yl 2-methylprop-2-enoate;1H,1H,2H,2H-Tridecafluoro-n-octyl Methacrylate (stabilized with MEHQ);3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl methacrylate contains 100 ppm 4-tert-butylcatechol as inhibitor, 97%;1H,1H,2H,2H-Tridecafluoro-n-octyl Methacrylate (stabilized with HQ + MEHQ);2-propenoicacid,2-methyl-,3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylester;2-(PERFLUOROHEXYL)ETHYL METHACRYLATE;3,3,4,4,5,5,6,6,7,7,8,8,8-TRIDECAFLUOROOCTYL METHACRYLATE
• CAS NO: 2144-53-8
• Molecular Formula: C₁₂H₉F₁₃O₂
• Molecular Weight: 432.18
• EINECS: 218-407-9
• Product Categories: monomer;Acrylic Monomers;Fluorinated Acrylics;Monomers
• Mol File: 2144-53-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 92 °C8 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.496 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.116mmHg at 25°C
• Refractive Index: n20/D 1.346(lit.)
• Storage Temp.: Keep Cold
• Water Solubility: 42μg/L at 20℃
• CAS DataBase Reference: 2-(Perfluorohexyl)ethyl methacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Perfluorohexyl)ethyl methacrylate(2144-53-8)
• EPA Substance Registry System: 2-(Perfluorohexyl)ethyl methacrylate(2144-53-8)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: UD3580000
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 2144-53-8(Hazardous Substances Data)

Usage

Uses

Surface structure and outer group orientation in poly(perfluoroalkylethyl methacrylate) consist of Tridecafluorohexylethyl Methacrylate.Semifluorinated diblock copolymers based on Me methacrylate and Tridecafluorohexylethyl Methacrylate were prepared by nucleophilic catalyzed group transfer polymerization.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C12H9F13O2/c1-5(2)6(26)27-4-3-7(13,14)8(15,16)9(17,18)10(19,20)11(21,22)12(23,24)25/h1,3-4H2,2H3

Synthetic route

poly(methacrylic acid) (79-41-4) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8)

Conditions	Yield
With hydroquinone; toluene-4-sulfonic acid In toluene at 115℃; for 5h;	94%
With sulfuric acid; hydroquinone In benzene Heating;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

methacryloyl anhydride (760-93-0) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8)

Conditions	Yield
With dmap; triethylamine In dichloromethane; 1,1,2-Trichloro-1,2,2-trifluoroethane at 30℃; for 18h;	76%

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) + sodium methacrylate (5536-61-8) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8)

Conditions	Yield
With tetra-n-butylphosphonium chloride In o-xylene; water at 100℃; for 12h; Reagent/catalyst;	71.8%

Bromoform (75-25-2) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + acetone (67-64-1) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzonitrile; acetonitrile at 20℃; for 5h;	70%

chloroform (67-66-3) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + acetone (67-64-1) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzonitrile; acetonitrile at 50℃; for 42h;	8.8%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + Methacryloyl chloride (920-46-7) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8)

Conditions	Yield
With triethylamine In tetrahydrofuran Yield given;

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) + potassium methacrylate (6900-35-2) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8)

Conditions	Yield
With 10H-phenothiazine In tert-butyl alcohol at 130 - 170℃; for 6 - 9h;

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) + potassium methacrylate (6900-35-2) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8)

Conditions	Yield
With 10H-phenothiazine In tert-butyl alcohol at 160℃; for 9h;

1H,1H,2H,2H-tridecafluorooctyl 2-chloro-2-methylpropanoate → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8)

Conditions	Yield
at 540℃; for 0.55h; Inert atmosphere;	1.36 g

mercaptopropylmethyldimethoxysilane (31001-77-1) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → Dimethoxy-methyl-[3-(2-pentafluorophenyl-ethylsulfanyl)-propyl]-silane

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In acetonitrile at 80℃; for 4h;	60%

tris-(trimethylsilyl)silane (1873-77-4) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl2-((1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilan-2-yl)methyl)acrylate

Conditions	Yield
With Quinuclidine; pyridine; chloropyridinecobaloxime(III); (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In acetonitrile at 25℃; Schlenk technique; Irradiation; Inert atmosphere;	52%

thiophenol (108-98-5) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → 1,2,3,4,5-Pentafluoro-6-(2-phenylsulfanyl-ethyl)-benzene

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In acetonitrile at 80℃; for 4h;

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → poly(2-perfluorohexylethyl methacrylate)

Conditions	Yield
In acetone at -196℃; Polymerization; γ-Irradiation;
at -196℃; X-irradiation;

2-(dimethylamino)ethyl methacrylate (2867-47-2) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → poly(dimethylamino ethyl methacrylate-block-1H,1H,2H,2H-perfluorooctyl methacrylate); monomer(s): dimethylamino ethyl methacrylate; 1H,1H,2H,2H-perfluorooctyl methacrylate

Conditions	Yield
Stage #1: 2-(dimethylamino)ethyl methacrylate With 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene; tetrabutylammonium bibenzoate In tetrahydrofuran for 1h; Stage #2: 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl methacrylate In tetrahydrofuran for 1h; Further stages.;	5.9 g

styrene (292638-84-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → poly[(tridecafluorooctyl methacrylate)-stat-styrene], miniemulsion copolymerization, particle diameter: 125 nm, Tg: 50 deg C, morphology: homogeneous; monomer: tridecafluorooctyl methacrylate; styrene

Conditions	Yield
With 2,2'-dimethyl-2,2'-azo-di-valeronitrile; acrylic acid anhydride; sodium dodecyl-sulfate In water at 60℃; for 2h;

methacrylic acid methyl ester (80-62-6) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → poly[(tridecafluorooctyl methacrylate)-co-(methyl methacrylate)], miniemulsion copolymerization, morphology: multiblobs, particle diameter: 120 nm, Tg: 50 deg C; monomer: tridecafluorooctyl methacrylate; methyl methacrylate

Conditions	Yield
With 2,2'-dimethyl-2,2'-azo-di-valeronitrile; sodium dodecyl-sulfate In water at 60℃; for 2h;

methacrylic acid methyl ester (80-62-6) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → poly[(tridecafluorooctyl methacrylate)-co-(methyl methacrylate)], miniemulsion copolymerization, morphology: core-shell, particle diameter: 128 nm, Tg: 50 deg C; monomer: tridecafluorooctyl methacrylate; methyl methacrylate

Conditions	Yield
With 2,2'-dimethyl-2,2'-azo-di-valeronitrile; acrylic acid anhydride; sodium dodecyl-sulfate In water at 60℃; for 2h;

methacrylic acid methyl ester (80-62-6) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → poly[(tridecafluorooctyl methacrylate)-co-(methyl methacrylate)], miniemulsion copolymerization, morphology: cups, particle diameter: 170 nm, Tg: 50 deg C; monomer: tridecafluorooctyl methacrylate; methyl methacrylate

Conditions	Yield
With 2,2'-dimethyl-2,2'-azo-di-valeronitrile; cetyltrimethylammonium chloride In water at 60℃; for 2h;

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → poly(tridecafluorooctyl methacrylate), miniemulsion polymerization; monomer: tridecafluorooctyl methacrylate

Conditions	Yield
With 1-perfluoromethyldecaline; 2,2'-dimethyl-2,2'-azo-di-valeronitrile; sodium dodecyl-sulfate In water at 60℃; for 2h; Product distribution; Further Variations:; Reagents;

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) + 2-methyl-butyl acrylate (97-88-1) → poly[(tridecafluorooctyl methacrylate)-co-(n-butyl methacrylate)], miniemulsion copolymerization, morphology: homogeneous, particle diameter: 120 nm; monomer: tridecafluorooctyl methacrylate; n-butyl methacrylate

Conditions	Yield
With 2,2'-dimethyl-2,2'-azo-di-valeronitrile; sodium dodecyl-sulfate In water at 60℃; for 2h;

modified poly(ethylene oxide) monool containing 2-bromopropionyl end group, molar mass of the poly(ethylene oxide) block: 5000 g/mol + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → poly(ethylene oxide)-b-poly(perfluorohexylethyl methacrylate) diblock copolymer, atom-transfer radical polymerized, molar mass of the PEO block: 5000 g/mol, PFMA content: 15 wt percent, average number of FMA units per PEO chain: ca. 1-2, polydispersity: 1.03

Conditions	Yield
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper(I) bromide In various solvent(s) at 85℃;

chemically modified poly(ethylene oxide) diol containing 2-bromopropionyl end groups, molar mass of the poly(ethylene oxide) block: 10000 g/mol + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → poly(perfluorohexylethyl methacrylate)-b-poly(ethylene oxide)-b-poly(perfluorohexylethyl methacrylate) triblock copolymer, atom-transfer radical polymerized, molar mass of the PEO block: 10000 g/mol, PFMA content: 11 wt percent, polydispersity index: 1.9

Conditions	Yield
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper(I) bromide In various solvent(s) at 85℃;

6-O-(3-mercaptopropanoyl)-D-mannopyranose + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → 6-O-(3-mercaptopropanoyl)-D-mannopyranose (1337993-91-5) + 6-O-(3-mercaptopropanoyl)-D-mannopyranose

Conditions	Yield
With Dimethyl(phenyl)phosphine In N,N-dimethyl-formamide at 20℃; for 16h; Michael condensation; Inert atmosphere; optical yield given as %de;

6-O-(3-mercaptopropanoyl)-D-mannopyranose + 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl methacrylate (2144-54-9) + 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl methacrylate (1996-88-9) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → 6-O-(3-mercaptopropanoyl)-D-mannopyranose (1337993-91-5) + 6-O-(3-mercaptopropanoyl)-D-mannopyranose + 6-O-(3-mercaptopropanoyl)-D-mannopyranose + 6-O-(3-mercaptopropanoyl)-D-mannopyranose + 6-O-(3-mercaptopropanoyl)-D-mannopyranose + 6-O-(3-mercaptopropanoyl)-D-mannopyranose

Conditions	Yield
With Dimethyl(phenyl)phosphine In N,N-dimethyl-formamide at 20℃; for 16h; Michael Addition; Inert atmosphere; Overall yield = 84 %;	A n/a B n/a C n/a D n/a E n/a F n/a

...Expand

6-O-(3-mercaptopropanoyl)-D-mannopyranose + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8) → C21H25F13O9S

Conditions	Yield
With Dimethyl(phenyl)phosphine Michael Addition;

Upstream product

• 760-93-0 methacryloyl anhydride 
• 647-42-7 1H,1H,2H,2H-tridecafluoro-n-octanol 
• 920-46-7 Methacryloyl chloride 
• 2043-57-4 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane 
• 5536-61-8 sodium methacrylate 
• 75-25-2 Bromoform 
• 67-64-1 acetone 
• 67-66-3 chloroform 
• 6900-35-2 potassium methacrylate 
• 79-41-4 poly(methacrylic acid) 

Relevant articles and documents

Synthesis of fluorinated block copolymers and their application as novel polymerisation surfactants in supercritical carbon dioxide

Screened anionic copolymerisation of methyl methacrylate with the perfluoroalkyl methacrylates 2 affords well-defined AB block copolymers 4-6, which serve as effective surfactants in the dispersion polymerisation of methyl methacrylate in supercritical carbon dioxide.

Cyanide-Free One-Pot Synthesis of Methacrylic Esters from Acetone

Methacrylic esters, represented by methyl methacrylate (MMA), are widely used as commodity chemicals. Here, the one-pot synthesis of methacrylic esters from acetone, a haloform and alcohols in the presence of an organic base is described. Using DBU as the organic base for the reaction of acetone, chloroform and methanol in acetonitrile afforded MMA in 66 % yield. When the solvent was replaced by benzonitrile, the product MMA was successfully purified by distillation. Applicability of this process to various alcohols was also investigated to show ethyl, phenyl, CF3CH2, and n-C6F13CH2CH2 esters were obtained in moderate yields. The use of bromoform instead of chloroform resulted in the improvement of the yield, for example, methyl and n-C6F13CH2CH2 esters up to 81 and 70 %, respectively. The reaction with deuterated starting materials acetone-d6 and MeOH-d4, with DBU in acetonitrile afforded deuterated MMA (MMA-d8) in 70 % yield.

METHOD FOR PRODUCING UNSATURATED ACID AND/OR UNSATURATED ACID ESTER

The present invention relates to a method for producing an unsaturated acid and/or an unsaturated acid ester, containing a process A of reacting a compound (1) represented by the following formula (1) at a temperature of 0° C. to 350° C. in the presence of a Br?nsted acid catalyst and/or a Lewis acid catalyst, to prepare a compound (2) represented by the following formula (2); in which each of R1, R2 and R4 independently represents a hydrogen atom, a deuterium atom or an alkyl group; each of R3 and R5 independently represents a hydrogen atom or a deuterium atom; R6 represents a hydrogen atom, a deuterium atom, or an alkyl group or an aryl group; and X represents a chlorine atom, a fluorine atom, a bromine atom, or an iodine atom.