4-Trifluoromethylsalicylic acid

Base Information

• Chemical Name: 4-Trifluoromethylsalicylic acid
• CAS No.: 328-90-5
• Molecular Formula: C8H5F3O3
• Molecular Weight: 206.121
• Hs Code.: 29189900
• European Community (EC) Number: 700-368-9,608-795-1
• UNII: UKY7YRE9E9
• DSSTox Substance ID: DTXSID00186474
• Nikkaji Number: J460.699J
• Wikidata: Q72512906
• ChEMBL ID: CHEMBL3244577
• Mol file: 328-90-5.mol

Synonyms:2-hydroxy-4-trifluoromethylbenzoic acid;4-TFMSA;4-trifluoromethylsalicylic acid;HTB

Chemical Property of 4-Trifluoromethylsalicylic acid

Chemical Property:

• Vapor Pressure: 0.00124mmHg at 25°C
• Melting Point: 178 °C
• Refractive Index: 1.509
• Boiling Point: 286.4 °C at 760 mmHg
• PKA: 2.45±0.10(Predicted)
• Flash Point: 127 °C
• PSA: 57.53000
• Density: 1.539 g/cm³
• LogP: 2.10920
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 206.01907850
• Heavy Atom Count: 14
• Complexity: 226

Purity/Quality:

99% ^*data from raw suppliers

DesacetylTriflusal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(F)(F)F)O)C(=O)O
• General Description: 4-Trifluoromethylsalicylic acid is a derivative of salicylic acid featuring a trifluoromethyl group at the 4-position, which is synthesized through carboxylation reactions of trifluoromethylphenol derivatives under anhydrous conditions. It serves as a key intermediate in the formation of dyes, such as when coupled with diazotized m-nitroaniline, and can be further reduced to yield 5-amino-4-trifluoromethylsalicylic acid. 4-Trifluoromethylsalicylic acid's reactivity and structural features make it useful in organic synthesis and potential applications in medicinal or materials chemistry.

Technology Process of 4-Trifluoromethylsalicylic acid

There total 15 articles about 4-Trifluoromethylsalicylic 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: 94.0%

2-methoxymethoxy-4-(trifluoromethyl)benzene (368422-29-1) → 4-trifluoromethylsalicylic acid (328-90-5)

Guidance literature:

With boron trifluoride diethyl etherate; In methanol; at 25 ℃; for 15h;

DOI:10.1002/1099-0690(200108)2001:15<2911::AID-EJOC2911>3.0.CO;2-W

Reference yield: 86.0%

4-trifluoromethylbenzoic acid (455-24-3) → 4-trifluoromethylsalicylic acid (328-90-5)

Guidance literature:

With oxygen; potassium acetate; palladium diacetate; p-benzoquinone; In N,N-dimethyl acetamide; at 115 ℃; for 15h; under 3800.26 Torr;

DOI:10.1021/ja907198n

Reference yield:

triflusal (322-79-2) → acetate (71-50-1) + 4-trifluoromethylsalicylic acid (328-90-5)

Guidance literature:

With cetyltrimethylammonim bromide; sodium hydroxide; In acetonitrile; at 25 ℃; Reagent/catalyst; Kinetics;

DOI:10.1016/j.molliq.2015.03.006

upstream raw materials:

2,5-bis-(trifluoromethyl)phenol

carbon dioxide

3-Trifluoromethylphenol

2-methoxymethoxy-4-(trifluoromethyl)benzene

Downstream raw materials:

2-hydroxy-5-(3-nitro-phenylazo)-4-trifluoromethyl-benzoic acid

triflusal

2-hydroxy-4-trifluoromethyl-benzoic acid-(2-hydroxy-ethyl ester)

2-hydroxy-4-trifluoromethyl-benzoic acid anilide

Refernces

Trifluoromethylaminosalicylic Acids and Related Reactions

10.1021/ja01613a076

The study explores the carboxylation of various trifluoromethylphenol derivatives and related compounds under anhydrous conditions, focusing on the conversion of CF3 groups to COOH groups. Key chemicals involved include m-trifluoromethylphenol, 5-trifluoromethylresorcinol, 5-amino-3-trifluoromethylphenol, and carbon dioxide, with potassium carbonate acting as a base to facilitate the carboxylation reactions. The study reports the formation of specific isomers such as 4-trifluoromethylsalicylic acid and 6-amino-4-trifluoromethylsalicylic acid, and investigates the carboxylation of 5-amino-3-methylphenol, revealing that the product is 6-amino-4-methylsalicylic acid, contrary to previous assumptions. Additionally, the study examines the coupling of 4-trifluoromethylsalicylic acid with diazotized m-nitroaniline to form a dye, which upon reduction yields 5-amino-4-trifluoromethylsalicylic acid. The study also delves into the oxidation of ketones to esters using peroxytrifluoroacetic acid, highlighting its efficiency in converting ketones to esters with high yields, particularly noting the successful oxidation of methyl cyclopropyl ketone to cyclopropyl acetate.

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