(E)-3-(Trifluoromethyl)crotonic acid

Base Information

• Chemical Name: (E)-3-(Trifluoromethyl)crotonic acid
• CAS No.: 400-28-2
• Molecular Formula: C5H5F3O2
• Molecular Weight: 154.08700
• Mol file: 400-28-2.mol

Synonyms:(E)-4,4,4-trifluoro-3-methylbut-2-enoic acid;(E)-3-(trifluoromethyl)-2-butenoic acid;E-4,4,4-Trifluoro-3-methyl-2-butenoic acid;trifluoromethylcrotonic acid;

Chemical Property of (E)-3-(Trifluoromethyl)crotonic acid

Chemical Property:

• Boiling Point: 80-84℃
• PKA: 3.59±0.33(Predicted)
• PSA: 37.30000
• Density: 1.334±0.06 g/cm3(Predicted)
• LogP: 1.57960

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (E)-3-(Trifluoromethyl)crotonic acid

There total 2 articles about (E)-3-(Trifluoromethyl)crotonic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(E)-3-trifluoromethyl-2-butenoic acid ethyl ester (691-77-0) → (2E)-4,4,4-Trifluoro-3-methylbut-2-enoic acid (400-28-2,93404-33-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; for 7h; Yield given; Ambient temperature;

DOI:10.1021/jo00108a022

Reference yield:

2,3-dihydroxy-3-methyl-4,4,4-trifluorobutanoic acid (119620-23-4) → 3-trifluoromethyl-2-butenoic acid (93404-33-2) + (2E)-4,4,4-Trifluoro-3-methylbut-2-enoic acid (400-28-2,93404-33-2)

Guidance literature:

With sulfuric acid; In water; at 200 ℃; for 16h; Overall yield = 8.78 g; Optical yield = 86.667 percent de;

DOI:10.1016/j.tet.2020.131758

Reference yield: 56.0%

o-aminobenzaldehyde (529-23-7) + (2E)-4,4,4-Trifluoro-3-methylbut-2-enoic acid (400-28-2,93404-33-2) → (E)-4,4,4-Trifluoro-3-methyl-but-2-enoic acid (2-formyl-phenyl)-amide

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; for 42h; Ambient temperature;

upstream raw materials:

(E)-3-trifluoromethyl-2-butenoic acid ethyl ester

2,3-dihydroxy-3-methyl-4,4,4-trifluorobutanoic acid

Downstream raw materials:

(E)-N-[2-amino-6-(benzyloxy)-5-nitrosopyrimidin-4-yl]-4,4,4-trifluoro-3-methylbut-2-enamide

(2'E,4R,5S)-4-Methyl-5-phenyl-3-(4',4',4'-trifluoro-3'-methylbut-2-enoyl)oxazolidin-2-one

(4S)-4-Benzyl-3-(4,4,4-trifluoro-3-methylbut-2-enoyl)oxazolidin-2-one

(-)-3-trifluoromethylbutanoic acid

Refernces

• 1、 Smith, Andrew D.,Wu, Jiufeng,Young, Claire M.. "Isothiourea-catalysed transfer hydrogenation of α,β-unsaturated para-nitrophenyl esters". supporting information. . Retrieved 2020/12/21.
• 2、 Nemoto,Satoh,Fukumoto,Kabuto. "A rapid access to both enantiomers of 1,2,3,4-tetranor B-trienic 18,18,18-trifluorosteroids. The first enantiocontrolled total synthesis of 18,18,18-trifluorosteroids". . p. 594 - 600. Retrieved 2007/10/02.