14112-98-2

Basic information

• Product Name: 7-OXOOCTANOIC ACID
• Synonyms: 7-OXOOCTANOIC ACID;7-ketooctanoic acid;7-Ketocaprylic acid;7-Oxooctanoic acid 98%
• CAS NO: 14112-98-2
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19
• EINECS: 237-967-5
• Product Categories: C8;Carbonyl Compounds;Carboxylic Acids
• Mol File: 14112-98-2.mol

Chemical Properties

• Melting Point: 27-29 °C(lit.)
• Boiling Point: 160-162 °C4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.0543 (rough estimate)
• Vapor Pressure: 0.000127mmHg at 25°C
• Refractive Index: 1.4310 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.75±0.10(Predicted)
• CAS DataBase Reference: 7-OXOOCTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 7-OXOOCTANOIC ACID(14112-98-2)
• EPA Substance Registry System: 7-OXOOCTANOIC ACID(14112-98-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 14112-98-2(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
7-Oxooctanoic acid is used as a test compound for high-resolution electrospray ionization mass spectrometry. It aids in investigating the applicability of this technique to measure the average oxygen to carbon ratio (O/C) in secondary organic aerosols, which is crucial for understanding atmospheric chemistry and air quality.
Used in Synthesis of Haptens:
In the field of chemistry, 7-Oxooctanoic acid is utilized in the synthesis of haptens. These haptens are essential for obtaining antibodies that can detect triacetone triperoxide, an improvised explosive. This application is vital for enhancing safety measures and detection capabilities in security and defense sectors.
Used in Synthesis of "Queen Substance":
7-Oxooctanoic acid also plays a role in the synthesis of the "queen substance" of the honey bee. This pheromone is crucial for the regulation of social behavior and reproduction within honey bee colonies. The compound's involvement in this process highlights its significance in the field of entomology and apiculture.

InChI:InChI=1/C8H14O3/c1-7(9)5-3-2-4-6-8(10)11/h2-6H2,1H3,(H,10,11)

Upstream product

• 874-23-7 2-acetylcyclohexanone 
• 29291-86-9 2-(5-chloro-pentyl)-2-methyl-[1,3]dioxolane 
• 124-38-9 carbon dioxide 
• 13885-60-4 7-Oxo-octansaeure-<6-oxo-heptylester> 
• 1453-25-4 1-methylcycloheptene 
• 5454-83-1 5-bromovaleric acid methyl ester 
• 141-97-9 ethyl acetoacetate 
• 20449-21-2 2-(but-3-en-1-yl)-2-methyl-1,3-dioxolane 
• 122-59-8 2-phenoxyacetic acid 
• 67-56-1 methanol 
• 4952-03-8 1-methylcyclohexane hydroperoxide 
• 141-82-2 malonic acid 
• 36219-80-4 7-oxo-octanal 
• 30460-73-2 (E)-1-acetoxy-2,7-octadiene 

Downstream Products

• 36651-36-2 ethyl 7-oxaoctanoate 
• 30414-67-6 3,5-Dihydroxy-4-(7-oxooctanoyl)-toluol 
• 65690-30-4 7-Oxo-octansaeure-(2-trimethylsilyl-ethylester) 
• 17173-22-7 2-(7-Oxo-octanoyl)-4,5-dimethoxy-phenylessigsaeure-methylester 
• 58134-62-6 3,5-Dimethoxy-2-<7-oxo-octanoyl>-phenylessigsaeure-methylester 
• 16209-12-4 3,5-Dimethoxy-2-(7-oxo-octanoyl)-phenylessigsaeure-benzylester 
• 17173-14-7 <+/->-7-hydroxyoctanoic acid 
• 77128-20-2 benzyl 7-oxooctanoate 
• 111-16-0 heptanedioic acid 
• 75-25-2 Bromoform 
• 13159-14-3 (E)-7-phenyl-6-heptenoic acid 
• 64-19-7 acetic acid 
• 66432-71-1 Toluene-4-sulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-hexyl ester 
• 32862-82-1 2-(8-hydroxynonyl)-4,6-dimethoxybenzoic acid 

Relevant articles and documents

A Microbial Synthesis of R and S-9-Hydroxy-(E)-2-Decenoic Acid(9-HDA), A Queen Honeybee Pheromone

(R,E)-9-hydroxy-2-decenoic acid (9-HDA) and its (S,E)-isomer have been prepared by using an organic-microbial approach.

Ultrasound-assisted synthesis and in vitro antimicrobial activity of novel 5-oxo-2-pyrrolidinecarboxamides and 7-oxo-2-azepanecarboxamides

A facile one-pot reaction has been set up for the synthesis of novel 5-oxo-2-pyrrolidinecarboxamides and 7-oxo-2-azepanecarboxamides 4a-j from three-component reaction of keto carboxylic acids 1a-d, various primary amines 2a-b and isocyanides 3a-b under ultrasound irradiation. The present protocol offers attractive characteristics such as easy handling methodology, good-to-excellent yields, environmental friendliness, clean reaction, higher atom economy, convenient operation, and shorter reaction time. The newly synthesized 5-oxo-2-pyrrolidinecarboxamides and 7-oxo-2-azepanecarboxamides 4a-j have been screened for their antimicrobial activity and the majority of these cyclic amides exhibited weak antimicrobial activity.

Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.

Synthesis of α-Tertiary Amine Derivatives by Intermolecular Hydroamination of Unfunctionalized Alkenes with Sulfamates under Trifluoromethanesulfonic Acid Catalysis

An efficient and mild trifluoromethanesulfonic acid-catalyzed hydroamination of unfunctionalized alkenes to afford α-tertiary amine derivatives at temperatures as low as room temperature is reported. 2,2,2-Trifluoroethyl sulfamate was found to be the optimal nitrogen source because its good solubility in both organic solvents and water facilitated both conversion and purification. The reaction conditions were compatible with a variety of substrate functional groups and afforded moderate to good yields. The desired amine compounds could be obtained easily by means of a mild, one-pot, redox-neutral deprotection procedure. Caryolane amine was synthesized with excellent chemo- and regioselectivities by means of a cascade hydroamination reaction of β-caryophyllene.

Controlling the photochemical reactions of alkenes by light-path length effects of a microchannel reactor

Photoirradiation of Me2CO-H2O solution of pent-4-en-1-ol (1a) with a high-pressure mercury lamp in a test tube gave 8-hydroxyoctan-2-one (3a) in 66 % yield along with oxetane (4a) and the isomer (4a') in 10 % yield. Irradiation of the running Me2CO-H2O solution of 1a in the flow system of a microchannel reactor (MCR) gave mainly 4a. The photoreaction of 1,1-diphenylethene (2a) with triethylamine gave a Markovnikov-type adduct (5a) and an anti-Markovnikov-type adduct (6a). The use of the MCR enhanced the production of 5a. These phenomena were explained by the light-path length effects of the MCR.

Analytical methodology for determination of organic aerosol functional group distributions

Secondary organic aerosol (SOA) particles result from the condensation of oxidized volatile organic compounds (VOC) and consist of a complex mixture that is not conducive to complete compositional analysis. We present a simple methodology for determining the quantities of aldehydes and ketones, alcohols, and carboxylic acids in such samples via derivatization and high-performance liquid chromatography (HPLC) with ultraviolet-visible absorption detection and tandem mass spectrometry (MS/MS). Useful concentration ranges are presented with an examination of the specificity of these compounds in multiply substituted systems. Such data are valuable in modeling the formation of laboratory-generated aerosols and in identifying point sources of field-collected aerosol samples. Calibration curves on standard samples, MS/MS transitions, including collisionally induced dissociation (CID) products, and a quantitative examination of the specificity of the derivatization reagents toward multiple functional groups are presented for a series of aliphatic standard samples. These methods are then applied to filter extracts from SOA derived from 1-iodooctane photolysis at 254 nm to demonstrate the methodology on a complex system. Ultimately, this methodology enables the measurement of variations in the chemical nature of the oxygen within an SOA particle, providing a distribution of functional group concentrations. This article not subject to U.S. Copyright. Published 2013 by the American Chemical Society.

An efficient iron-catalyzed carbon-carbon single-bond cleavage via retro-claisen condensation: A mild and convenient approach to synthesize a variety of esters or ketones

An efficient iron-salt-catalyzed carbon-carbon bond cleavage occurring through a retro-Claisen condensation reaction has been developed. The reaction is useful for the synthesis of a variety of esters or ketones under mild conditions. This method works under solvent-free conditions without the need of an inert atmosphere. This protocol is also applicable for the one-pot syntheses of ketones through tandem carbon-carbon bond formation (substitution or Michael) followed by a retro-Claisen reaction. However, for Michael adducts, ring annulation takes place subsequently. Notably, this method is very simple, convenient, high yielding, and only a catalytic (5 to 1.0 mol-%) amount of Fe(OTf)3 is needed.

Indium-catalyzed retro-claisen condensation

(Chemical Equation Presented) Retro-aldol reaction: Indium-catalyzed reaction of a 1,3-diketone with an alcohol proceeds under solvent-free conditions by nucleophilic attack of the alcohol on a carbonyl group of the 1,3-diketone and carbon-carbon bond cleavage by a retro-Claisen condensation to give an ester in high yield (see scheme). Using water and an amine as nucleophiles instead of an alcohol gave the corresponding carboxylic acid and amide.

Synthesis of a multifunctional pheromone of the honeybee Apis mellifera via condensation of 7-oxooctanal with malonic acid

Condensation of 7-oxooctanal with malonic acid in a Doebner reaction produces 9-oxo-2E-decenoic acid (42% yield) and a comparable amount of products from Tishchenko disproportionation of the starting aldehyde (7-oxooctyl-7- oxooctanoate) and re-esterification by acetic acid (7-oxooct-1-ylacetate and 7-oxooctanoic acid).

Arylmethyl esters as protecting groups for carboxylic, carbonic and carbamic acids: Deprotection via homogeneous palladium-catalyzed hydrogenolysis

4-Quinolylmethyl (4-QUI) esters of carboxylic acids and 1-naphthylmethyl (1-NAP) esters of carbonic and carbamic acids are reduced by palladium-catalyzed hydrogenolysis by formate anion. The reaction conditions are compatible with the presence of a benzyl ester and of an alkene double bond.