638-53-9

Usage

Uses

Used in Organic Synthesis:
Tridecanoic acid is used as a metabolite in the aging mouse brain and serves as a key component in organic synthesis, particularly for the synthesis of Testosterone Tridecanoate.
Used in Wastewater Treatment:
Tridecanoic acid is utilized as a glycol ester in wastewater treatment processes, playing a crucial role in reducing the presence of organic molecules such as caproic acid, alkanoic acid, and multivariate logistic regression. This application aids in improving water quality and environmental sustainability.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 2846, 1970 DOI: 10.1021/jo00833a096

Purification Methods

Crystallise the acid from acetone. [Beilstein 2 IV 1117.]

InChI:InChI=1/C13H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13(14)15/h2-12H2,1H3,(H,14,15)

Upstream product

• 114379-24-7 rac-(E)-2-hexadecen-4-ol 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 2507-55-3 2-hydroxytetradecanoic acid 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 3922-24-5 1,1,1-trichloro-tridecane 
• 2345-28-0 pentadecan-2-one 
• 151-50-8 potassium cyanide 
• 112-52-7 1-chlorododecane 
• 112-41-4 1-dodecene 
• 201230-82-2 carbon monoxide 
• 87145-85-5 2,2':5',2-terthiophene-5-carboxylic acid 
• 67-64-1 acetone 
• 124-38-9 carbon dioxide 
• 31805-90-0 dodecyl potassium 

Downstream Products

• 17746-06-4 n-tridecanoyl chloride 
• 80006-41-3 thallium(I) n-tridecanoate 
• 620623-16-7 C₇₃H₈₉F₆N₅O₁₄ 
• 1233091-82-1 5-(4-dodecylphenyl)-1,3,4-thiadiazol-2-amine 
• 1369885-82-4 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-N-(5-(4-dodecylphenyl)-1,3,4-thiadiazol-2-yl)-2,2-dimethylcyclopropanecarboxamide 
• 123-01-3 1-dodecylbenzene 
• 6313-88-8 4-dodecylacetophenone 
• 21021-55-6 4-dodecylbenzoic acid 
• 6005-99-8 1-phenyltridecan-1-one 
• 1620993-10-3 3,5-dihydroxyphenyl tridecanoate 
• 2984-55-6 2-hydroxydodecanoic acid 
• 19790-87-5 2-Hydroxytridecanoic acid 
• 928-17-6 (R)-β-hydroxypalmitic acid 
• 6064-90-0 methyl heneicosanoate 

Relevant academic research and scientific papers

2,2':5',2''-Terthiophene-5-carboxylic Acid and 2,2':5',2''-Terthiophene-5,5''-dicarboxylic Acid

2,2':5',2''-Terthiophene-5-carboxylic acid was obtained in excellent yield by treating 2,2':5',2''-terthiophene with lithium diisopropylamide, followed by carboxylation of the lithium salt with solid carbon dioxide.The 5,5''-dicarboxylic acid was obtained similarly, when 2 equiv of base were used.Attempted syntheses of the monoacid, based on the oxidation of the corresponding aldehyde or the acetyl derivative, were unsuccessful.Both the monoacid and the 5,5'-diacid sensitized the hemolysis of human erythrocytes in the presence of ultraviolet light.

Convenient preparation and use of potassium tetracarbonylferrate, K2[Fe(CO)4], an easy-to-handle analogue of the Collman reagent

A convenient synthesis of K2[Fe(CO)4] from Fe(CO)5, KOH and tri(n-butyl)phosphine is described. This non-pyrophoric dianionic potassium ferrate displays the same reactivity as Na2[Fe(CO)4], provided that the reactions are conducted in DMAC or THF-DMAC solvent mixtures.

Pd-Catalyzed Regioselective Branched Hydrocarboxylation of Terminal Olefins with Formic Acid

A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.

Ruthenium-catalysed hydroxycarbonylation of olefins

State-of-the-art catalyst systems for hydroxy- and alkoxycarbonylations of olefins make use of palladium complexes. In this work, we report a complementary ruthenium-catalysed hydroxycarbonylation of olefins applying an inexpensive Ru-precursor (Ru3(CO)12) and PCy3as a ligand. Crucial for the success of this transformation is the use of hexafluoroisopropanol (HFIP) as the solvent in the presence of an acid co-catalyst (PTSA). Overall, moderate to good yields are obtained using aliphatic olefins including the industrially relevant substrate di-isobutene. This atom-efficient catalytic transformation provides straightforward access to various carboxylic acids from unfunctionalized olefins.

Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation

The synthesis of carboxylic acids is of fundamental importance in the chemical industry and the corresponding products find numerous applications for polymers, cosmetics, pharmaceuticals, agrochemicals, and other manufactured chemicals. Although hydroxycarbonylations of olefins have been known for more than 60 years, currently known catalyst systems for this transformation do not fulfill industrial requirements, for example, stability. Presented herein for the first time is an aqueous-phase protocol that allows conversion of various olefins, including sterically hindered and demanding tetra-, tri-, and 1,1-disubstituted systems, as well as terminal alkenes, into the corresponding carboxylic acids in excellent yields. The outstanding stability of the catalyst system (26 recycling runs in 32 days without measurable loss of activity), is showcased in the preparation of an industrially relevant fatty acid. Key-to-success is the use of a built-in-base ligand under acidic aqueous conditions. This catalytic system is expected to provide a basis for new cost-competitive processes for the industrial production of carboxylic acids.

Pd-Catalyzed Highly Chemo- And Regioselective Hydrocarboxylation of Terminal Alkyl Olefins with Formic Acid

An efficient Pd-catalyzed hydrocarboxylation of alkenes with HCOOH is described. A wide variety of linear carboxylic acids bearing various functional groups can be obtained with excellent chemo- and regioselectivities under mild reaction conditions. The reaction process is operationally simple and requires no handling of toxic CO.

Synthetic method of terminal carboxylic acid

The invention discloses a synthetic method of a terminal carboxylic acid. The synthetic method is characterized by comprising the steps of adding an olefin represented by a formula (3) shown in the description, formic acid, acetic anhydride, Pd(OAc)2 and a monophosphorus ligand TFPP into an organic solvent in a proportion, carrying out hydrogen carbonylation reaction on the olefin represented by the formula (3) shown in the description, formic acid and acetic anhydride at 80-90 DEG C for 48h-72h under the catalysis of the metal palladium salt Pd(OAc)2 and the monophosphorus ligand TFPP so as to obtain the terminal carboxylic acid represented by a formula shown in the description, and separating a target product, namely the terminal carboxylic acid after the reaction is finished, wherein olefin represented by the formula (3) is selected from cycloolefins, or linear olefins of which the R1 is electron donating groups. By virtue of the method disclosed by the invention, corresponding terminal carboxylic acid and a derivative thereof can be prepared through the reaction under mild conditions of low temperature and no high pressure; and the steps of the synthetic method are simple and convenient, the operation is convenient, the yield is high, the energy source can be greatly saved, and the synthetic efficiency can be greatly improved.

Synthetic organic raw materials synthesis method of thirteen acid (by machine translation)

Abstract Raw materials of organic synthesis tridecanoic acid synthesis method, comprises the following steps: 2 mol 2-bromotetradecanol, 4-6 mol dioctyl phthalate solution 5 were added to the reaction vessel, controlled the stirring speed at 150-180 rpm for 70-90 min and controlled solution temperature to 2-5 "C, added 3-4 mol titanium aluminium chloride, continued to react 130-160 min, added 700 ml sodium bromide solution, standing for 20-40 min, separated the oil layer, washed with m-chlorophenol solution, washed with formamide solution, recrystallizated in the methyl sulfide 10 solution, dehydrated with dehydration, got the finished product tridecanoic acid.

α-Oxidative decarboxylation of fatty acids catalysed by cytochrome P450 peroxygenases yielding shorter-alkyl-chain fatty acids

Cytochrome P450 peroxygenases belonging to the CYP152 family catalyse the oxidation of fatty acids using H2O2. CYP152N1 isolated from Exiguobacterium sp. AT1b exclusively catalyses the α-selective hydroxylation of myristic acid at physiological H2O2 concentration. However, a series of shorter-alkyl-chain fatty acids such as tridecanoic acid were produced from myristic acid by increasing the concentration of H2O2 (1-10 mM). The yield of tridecanoic acid from myristic acid reached 17%. An 18O-labeled oxidant study suggested that CYP152N1 catalysed the overoxidation of α-hydroxymyristic acid to form α-ketomyristic acid, which in turn was spontaneously decomposed by H2O2 to yield tridecanoic acid. Crystal structure analysis of CYP152N1 revealed its high similarity to other CYP152 family enzymes, such as CYP152A1 and CYP152B1. MD simulations of α-hydroxymyristic acid accommodated in CYP152N1 proposed a possible pre-oxidation conformation of α-hydroxymyristic acid for the decarboxylation reaction.

Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible-Light–Nickel Catalysis

We report the efficient carboxylation of bromides and triflates with K2CO3 as the source of CO2 in the presence of an organic photocatalyst in combination with a nickel complex under visible light irradiation at room temperature. The reaction is compatible with a variety of functional groups and has been successfully applied to the synthesis and derivatization of biologically active molecules. In particular, the carboxylation of unactivated cyclic alkyl bromides proceeded well with our protocol, thus extending the scope of this transformation. Spectroscopic and spectroelectrochemical investigations indicated the generation of a Ni0 species as a catalytic reactive intermediate.