17696-11-6

Basic information

• Product Name: 8-Bromooctanoic acid
• Synonyms: 8-bromooctanoic;8-BROMO-N-OCTANOIC ACID;8-BROMOOCTANOIC ACID;8-BROMOCAPRYLIC ACID;i-bromocaprylic acid;8-BROMOOCTANOIC ACID 97%;8-Bromooctanoic acid,95%;8-broMo bitterness
• CAS NO: 17696-11-6
• Molecular Formula: C₈H₁₅BrO₂
• Molecular Weight: 223.11
• EINECS: 1533716-785-6
• Product Categories: Miscellaneous;Organic acids;All Aliphatics;omega-Bromocarboxylic Acids;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Aliphatics
• Mol File: 17696-11-6.mol

Chemical Properties

• Melting Point: 35-37 °C(lit.)
• Boiling Point: 147-150 °C2 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: White to cream/Crystalline Powder
• Density: 1.3542 (rough estimate)
• Vapor Pressure: 0.0032mmHg at 25°C
• Refractive Index: 1.4613 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.77±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
• BRN: 1756103
• CAS DataBase Reference: 8-Bromooctanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Bromooctanoic acid(17696-11-6)
• EPA Substance Registry System: 8-Bromooctanoic acid(17696-11-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 17696-11-6(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
8-Bromooctanoic acid is used as a synthetic intermediate for the production of 8-(N-Methyl-4,4'-bipyridinyl)-octanoic acid, which is an important compound in the field of organic chemistry.
2. Used in the Preparation of Other Compounds:
8-Bromooctanoic acid is also utilized in the preparation of 8-Mercaptooctanoic acid, another significant organic compound with various applications.
3. Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 8-Bromooctanoic acid, due to its synthetic utility, may also find applications in the pharmaceutical industry for the development of new drugs or drug candidates.
4. Used in Research and Development:
8-Bromooctanoic acid can be employed in research and development laboratories for the synthesis of novel compounds and the study of their properties and potential applications in various fields, including pharmaceuticals, materials science, and chemical engineering.

InChI:InChI=1/C4H10O2.C4H6O/c5-3-1-2-4-6;1-3-5-4-2/h5-6H,1-4H2;3-4H,1-2H2

Upstream product

• 6557-85-3 6-bromohexyl malonic acid diethyl ester 
• 4286-55-9 1-bromo-6-hexanol 
• 996-82-7 sodium diethylmalonate 
• 629-41-4 1,8-Octanediol 
• 18719-24-9 oct-7-enoic acid 
• 50816-19-8 8-bromooctanol 
• 54863-44-4 8-bromooctanenitrile 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 502-49-8 cycloactanone 
• 629-03-8 1 ,6-dibromohexane 
• 123-99-9 azelaic acid 
• 624-17-9 diethyl azelate 
• 1593-55-1 azelaic acid monoethyl ester 
• 29823-21-0 Ethyl 8-bromooctanoate 

Downstream Products

• 506-24-1 Stearolic acid 
• 37688-96-3 1,14-dibromotetradecane 
• 106-79-6 dimethyl sebacate 
• 26825-89-8 methyl 16-bromohexadecanoate 
• 1472-93-1 dimethyl 1,18-octadecanedioate 
• 22686-32-4 di-(1-carboxylheptyl) diselenide 
• 52956-93-1 (7-carboxyheptyl)triphenylphosphonium bromide 
• 55182-92-8 9-tetradecynoic acid 
• 26825-92-3 methyl 8-bromooctanoate 
• 106689-24-1 9-thiaoctadecanoic acid 
• 764-89-6 8-hydroxycaprylic acid 
• 1642-49-5 dec-9-ynoic acid 
• 50816-19-8 8-bromooctanol 
• 136451-84-8 2-oxo-1,2-diphenylethyl 8-bromooctanoate 

Relevant articles and documents

Base- A nd Catalyst-Induced Orthogonal Site Selectivities in Acylation of Amphiphilic Diols

Seeking to selectively functionalize natural and synthetic amphiphiles, we explored acylation of model amphiphilic diols. The use of a nucleophilic catalyst enabled a remarkable shift of the site selectivity from the polar site, preferred in background noncatalyzed or base-promoted reactions, to the apolar site. This tendency was significantly enhanced for organocatalysts comprising an imidazole active site surrounded by long/branched tails. An explanation of these orthogonal modes of selectivity is supported by competitive experiments with monoalcohol substrates.

Preparation method of halogenated acid compounds

The present invention discloses a method for preparing halogenated acid compounds. Specifically, the present invention provides a method for preparing halogenated acid compounds as shown in formula I, which takes the halogen alcohol compounds shown in formula II as raw materials, reacts with TEMPO, sodium hypochlorite and sodium chlorite, adjusts the reaction pH with inexpensive carbon dioxide, and finally prepares halogenated acid compounds. The preparation method has high yield, relatively little toxicity and environmental protection, which is suitable for industrial production.

Synthesis method of ethyl 8-bromocaprylate

The invention provides a synthesis method of ethyl 8-bromocaprylate, which comprises the following steps: S1, carrying out substitution reaction on 1,6-dibromohexane and diethyl malonate to obtain a compound 2-(6-bromohexyl)-diethyl malonate; S2, enabling the 2-(6-bromohexyl)-diethyl malonate to carry out ester hydrolysis and a decarboxylation reaction so as to obtain 8-bromocaprylic acid; and S3, carrying out an esterification reaction on the 8-bromocaprylic acid and absolute ethyl alcohol to obtain ethyl 8-bromocaprylate. According to the synthesis method of ethyl 8-bromocaprylate, disclosed by the embodiment of the invention, firstly, 1,6-dibromohexane initial raw material and diethyl malonate are subjected to substitution reaction to generate 2-(6-bromohexyl) diethyl malonate, and then ester hydrolysis and decarboxylation reaction are carried out to obtain 8-bromocaprylic acid; and finally,esterification reaction is carried out to generate ethyl 8-bromocaprylate. The raw materials are easy to obtain, side reactions in the reaction are few, the process is simple, and the method is suitable for industrial production, and has a very wide application prospect.

Design, synthesis, and biological evaluation of potent photoaffinity probes of oleanolic acid

To study the target proteins of oleanolic acid, a series of novel photoaffinity probes were designed and synthesized. Their affinity for the target proteins was evaluated in an enzyme inhibition assay against glycogen phosphorylase, a known target protein of oleanolic acid. Among these compounds, probe 2 exhibited the most potent activity with an IC50value of 5.98 μM, which was about 2.5-fold more potent than its parent compound oleanolic acid. The results showed that the synthesized photoaffinity probes retained the binding affinity for their target proteins, and might be used as powerful tools to fish out the target proteins of oleanolic acid.

Synthesis, antiproliferation, and docking studies of N-phenyl-lipoamide and 8-mercapto-N-phenyloctanamide derivatives: Effects of C6 position thiol moiety

Some N-phenyl lipoamide and 8-mercapto- N-phenyloctanamide derivatives were synthesized and their in vitro antiproliferative activity was evaluated. The experimental results indicated that 8-mercapto-N-phenyloctanamides might be good histone deacetylase inhibitors rather than N-phenyl lipoamides, who had thiol moiety at C6 position. To verify the antiproliferation data on structural basis, in silico docking studies of the representative compounds into the crystal structure of histone deacetylase- like protein using AutoDock 4.0 program were performed. Furthermore, sulfur acetylated 8-mercapto-Nphenyloctanamide improved its in vitro antiproliferative activity, probably due to the increasing of its cell membrane permeability. While the identification of enzymatic target of N-phenyl lipoamides with dithiolane is still ongoing. Springer Science+Business Media, LLC 2011.

Carbon-carbon bond fission on oxidation of primary alcohols to carboxylic acids

α-Carbon-carbon bond cleavage is shown to be a general side reaction accompanying the oxidation of unbranched primary alcohols to the corresponding carboxylic acids using HNO3, CrO3/H2SO 4/H2O/acetone, CrO3/CH3COOH, PDC/DMF, H5IO6/CrO3, KMnO4/H +, KMnO4/HO-, NiCl2/NaClO, TEMPO/PhI(OAc)2. Therefore, the product formed is always contaminated with a carboxylic acid containing one carbon atom less. Systems such as PhI(OAc)2/TEMPO or H5IO6/CrO 3/CH3CN reduce to a minimum the content of this impurity. Temperature, the order of reagent addition, and additives such as oxalic acid or cerium salts produce a profound effect on the formation of the undesirable impurity during the Jones oxidation of primary alcohols.

A simple and cost effective synthesis of 3,11-dimethylnonacosan-2-one, a female sex pheromone of the German cockroach

A convenient synthesis of 3,11-dimethylnonacosan-2-one (1) is described. Our strategy involves the use of well known C-alkylation and ethyl acetoacetate synthesis reactions as key steps. We expect that this method will prove to be useful for large scale preparation of 1 and modification of dimethylnonacosanones.

Influence of terminal branching on the transdermal permeation-enhancing activity in fatty alcohols and acids

In order to investigate the effect of terminal chain branching in the skin permeation enhancers, seven alcohols and seven acids with the chain length of 8-12 carbons and terminal methyl or ethyl branching were prepared. Their transdermal permeation-enhancing activities were evaluated in vitro using theophylline as a model permeant and porcine skin, and compared to those of the linear standards. Terminal methyl branching increased the enhancing activity only in 12C acid, no effect was seen in the shorter ones. Terminal ethyl however produced a significant increase in activity. In the alcohols, the branching was likely to change the mode of action, due to a different relationship between the activity and the chain length.

Process for the monoalkylation of C-H acid methylene groups

The ratio of the alkali(ne earth) carbonate to the methylene group-containing substrate is above 0.6 : 1 in the monoalkylation of C-H acid methylene groups by reaction of the substrate in a polar aprotic solvent with a dihalogen compound having its halogens separated by a chain of at least3C and with reaction being in presence of the alkali(ne earth) carbonates and a phase transfer catalyst and being accompanied by continuous removal of the water formed. An Independent claim is also included for production of omega-haloalkyl-nitriles or -carboxylic acids by reacting a malonic acid diester or cyanoacetic ester with an alpha,omega-dihaloalkane as above and then saponifying and decarboxylating the product.

Asymmetric synthesis of unnatural (Z,Z,E)-octadecatrienoid and eicosatrienoid by lipoxygenase-catalyzed oxygenation

The asymmetric synthesis of unnatural 13-hydroxy-(6Z,9Z,11E,13S)-octadecatrienoid and 15-hydroxy-(8Z,11Z,13E,15S)-eicosatrienoid is described using a biomimetic oxidation route. The main highlights of this synthesis are the asymmetric hydroxylation of the substrate with soybean lipoxygenase and cis selective Wittig olefination.