372-29-2

Basic information

• Product Name: Ethyl 3-amino-4,4,4-trifluorocrotonate
• Synonyms: ETHYL 3-AMINO-4,4,4-TRIFLUORO-2-BUTENOATE;ETHYL 3-AMINO-4,4,4-TRIFLUOROBUT-2-ENOATE;ETHYL 3-AMINO-4,4,4-TRIFLUOROCROTONATE;3-AMINO-4,4,4-TRIFLUOROCROTONIC ACID ETHYL ESTER;3-AMINO-4,4,4-TRIFLUOROCROTONIC ETHYL ESTER;2-BUTENOIC ACID, 3-AMINO-4,4,4-TRIFLUORO, ETHYL ESTER;Ethyl 3-Amino-4,4,4-Trifluorocrotonate Ethyl 3-Amino-4,4,4-Trifluoro-2-Butenoate;Ethyl 3-amino-4,4,4-trifluorocrotonate 97%
• CAS NO: 372-29-2
• Molecular Formula: C₆H₈F₃NO₂
• Molecular Weight: 183.13
• EINECS: 1312995-182-4
• Product Categories: Fluorinated ketene derivatives;Ketene derivatives
• Mol File: 372-29-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 26°C
• Boiling Point: 83 °C15 mm Hg(lit.)
• Flash Point: 149 °F
• Appearance: Colourless liquid or white solid
• Density: 1.245 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.16mmHg at 25°C
• Refractive Index: n20/D 1.424(lit.)
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 0.76±0.70(Predicted)
• Sensitive: Air Sensitive
• BRN: 4397839
• CAS DataBase Reference: Ethyl 3-amino-4,4,4-trifluorocrotonate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3-amino-4,4,4-trifluorocrotonate(372-29-2)
• EPA Substance Registry System: Ethyl 3-amino-4,4,4-trifluorocrotonate(372-29-2)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-36/37
• Safety Statements: 26-36-36/37
• RIDADR: 3259
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 372-29-2(Hazardous Substances Data)

Usage

Chemical Properties

Colourless liquid or white solid

Uses

Ethyl 3-amino-4,4,4-trifluorocrotonate is used as building block in chemical synthesis. Attributes Development Product Contact

InChI:InChI=1/C6H8F3NO2/c1-2-12-5(11)3-4(10)6(7,8)9/h10H,2-3H2,1H3/b10-4+

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 141-78-6 ethyl acetate 
• 631-61-8 ammonium acetate 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 

Downstream Products

• 453-32-7 3-Amino-4,4,4-trifluorbutyramid 
• 854122-75-1 2-chloro-5-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-{[methyl(1-methylethyl)amino]sulfonyl}-benzamide 
• 939377-15-8 ethyl 2-phenyl-4-(trifluoromethyl)oxazole-5-carboxylate 
• 499766-87-9 ethyl 2-methyl-4-(trifluoromethyl)oxazole-5-carboxylate 
• 119022-51-4 5-trifluoromethyl-3-hydroxy-1-methylpyrazole 
• 141860-79-9 2-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazine-6-one 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF 6-(HALOALKYL)-2-HALO-5-ACYLPYRIDINES AND INTERMEDIATES FOR THIS PROCESS

The present invention relates to a process for preparing compounds of formula (I) (I), wherein R represents C1-C2-alkyl or C1-C2-haloalkyl, R1 represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, phenyl-C2-C4- alkenyl or phenyl-C2-C4-alkynyl, and X represents chlorine or bromine, by reacting a compound of formula (II) (II), wherein RA represents -CN or –COOH and R is defined as in formula (I), in a first step A) with a dehydroxyhalogenation agent selected from COCl2, diphosgene, triphosgene, cyanuric chloride, SOCl2, SO2Cl2, PCl3, PCl5, POCl3, PBr3, SOBr2 and SO2Br2, to arrive at a compound of formula (III) (III), wherein RB represents -CN or –COX, and X and R are defined as in formula (I), and the compound of formula (III) is reacted in step B) with a compound of formula (IV) R1M1(lV), - 41 - wherein M1 represents Li or MgY, wherein Y represents chlorine or bromine, and R1 is defined as in formula (I), and optionally further reacting the compound of formula (I) to a triazole derivative of formula (VIII) (VIII). It further relates to a process for preparing the compound of formula (II) and to particular compounds of formula (II) and (III).

PREPARATION OF 6-HALO-2-(HALOALKYL)-3-ACYLPYRIDINES AND INTERMEDIATES THEREFOR

The present invention relates to a process for preparing compounds of formula (I) wherein R represents C1-C2-alkyl and X represents chlorine or bromine, by reacting a compound of formula (II) wherein R is defined as in formula (I), in a first step A) with a dehydroxyhalogenation agent selected from COCl2, diphosgene, triphosgene, cyanuric chloride, SOCI2, SO2CI2, PCI3, PCI5, POCI3, PBr3, SOBr2 and SO2Br2 to arrive at a compound of formula (III) wherein X and R are defined as in formula (I), and the compound of formula (III) is reacted in step B) with a malonate of formula (IV) wherein R1 represents C1-C6-alkyl, C2-C6, -alkenyl. C2-C6-alkynyl, C3-C8-cycloalkyl or benzyl; in presence of a base and a magnesium compound to arrive at a compound of formula (V) wherein X and R are defined as in formula (I); and R1 is defined as in formula (IV); and decarboxylating the compound of formula (V). Optionally the resulting compound of formula (I) is further reacted to a triazole derivative of formula (VIII). It further relates to the compounds of formula (V).

Method for preparing 3-amino-4,4,4-trifluorocrotonate

The invention discloses a method for preparing 3-amino-4,4,4-trifluorocrotonate with high raw material utilization rate. According to the invention, 4,4,4-trifluoroacetyl ethyl acetate and excessive ammonium acetate are subjected to an amination reaction to obtain a reaction solution, then the reaction solution is separated to an organic phase and an aqueous phase, ammoniacal liquor is added in the aqueous phase to obtain ammonium acetate, and finally ammonium acetate is cycled to continuous reaction.