Methyl 2-hydroxy-2-(trifluoromethyl)pent-4-enoate

Base Information

• Chemical Name: Methyl 2-hydroxy-2-(trifluoromethyl)pent-4-enoate
• CAS No.: 117015-45-9
• Molecular Formula: C₇H₉F₃O₃
• Molecular Weight: 198.142
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID301232396
• Mol file: 117015-45-9.mol

Synonyms:117015-45-9;Methyl 2-hydroxy-2-(trifluoromethyl)pent-4-enoate;methyl 2-hydroxy-2-(trifluoromethyl)-4-pentenoate;114645-32-8;2-HYDROXY-2-TRIFLUOROMETHYL-PENT-4-ENOIC ACID METHYL ESTER;SCHEMBL5704826;Methyl 2-hydroxy-2-(trifluoromethyl)-3-vinylpropanoate;KLIFMERYWGSJJF-UHFFFAOYSA-N;DTXSID301232396;MFCD00236694;AKOS006346708;SB85106;CS-0339134;Methyl2-hydroxy-2-(trifluoromethyl)pent-4-enoate;4-Pentenoic acid, 2-hydroxy-2-(trifluoromethyl)-, methyl ester

Chemical Property of Methyl 2-hydroxy-2-(trifluoromethyl)pent-4-enoate

Chemical Property:

• Boiling Point: 81 °C(Press: 60 Torr)
• PKA: 10.16±0.29(Predicted)
• PSA: 46.53000
• Density: 1.265±0.06 g/cm3(Predicted)
• LogP: 1.02890
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 198.05037863
• Heavy Atom Count: 13
• Complexity: 212

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 2-hydroxy-2-(trifluoromethyl)-4-pentenoate 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC=C)(C(F)(F)F)O

Technology Process of Methyl 2-hydroxy-2-(trifluoromethyl)pent-4-enoate

There total 3 articles about Methyl 2-hydroxy-2-(trifluoromethyl)pent-4-enoate 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: 80.0%

propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + methyl 3,3,3-trifluoropyruvate (13089-11-7) → methyl ester of 2-hydroxy-2-trifluoromethyl-4-pentenoic acid (117015-45-9)

Guidance literature:

With tin(IV) chloride; In hexane; 1.) -70 deg C, -50 deg C, -10 deg C (2 h);

DOI:10.1007/BF00962669

Reference yield: 54.0%

methyl 3,3,3-trifluoropyruvate (13089-11-7) + allylmagnesium bromide (1730-25-2) → methyl ester of 2-hydroxy-2-trifluoromethyl-4-pentenoic acid (117015-45-9)

Guidance literature:

In diethyl ether; at -50 - 20 ℃;

DOI:10.1016/0040-4020(95)00888-F

Reference yield: 39.0%

allyl iodid (556-56-9) + methyl 3,3,3-trifluoropyruvate (13089-11-7) → methyl ester of 2-hydroxy-2-trifluoromethyl-4-pentenoic acid (117015-45-9) + dimethyl bis(trifluoromethyl)tartarate, meso form (114645-33-9) + dimethyl bis(trifluoromethyl)tartarate, racemate (19607-29-5,114645-33-9,114645-41-9)

Guidance literature:

With zinc; In ethanol; Yields of byproduct given; 1) kept 1 h after exothermic start, 2) reflux 0.5 h;

upstream raw materials:

propene

methyl 3,3,3-trifluoropyruvate

allyl iodid

allylmagnesium bromide

Downstream raw materials:

(+/-)-methyl 2-benzyloxy-2-trifluoromethyl-4-pentenoate