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
• Article Data: 20

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

Chemical Properties

off-white powder

Uses

8-Bromooctanoic acid is used in the synthesis of 8-(N-Methyl-4,4'-bipyridinyl)- octanoic acid. 8-Mercaptooctanoic acid was prepared from 8-bromooctanoic acid.

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

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

Downstream Products

• 55182-92-8 9-tetradecynoic acid 
• 106689-24-1 9-thiaoctadecanoic acid 
• 1642-49-5 dec-9-ynoic acid 
• 26825-92-3 methyl 8-bromooctanoate 
• 77383-17-6 8-bromo-octanoic acid tert-butyl ester 
• 117412-57-4 4-(7-carboxyheptyloxy)benzoic acid 
• 918902-99-5 8-bromooctanoyl-L-Trp(Boc)-L-Tyr-OBn 
• 918903-02-3 C₃₂H₃₃N₃O₆(COC₇H₁₄) 
• 92518-41-7 8-(4-acetyl-3-hydroxy-2-propylphenoxy)octanoic acid 
• 106650-71-9 8-(4-Acetyl-3-hydroxy-2-propyl-phenoxy)-octanoic acid benzhydryl ester 
• 95998-63-3 (E)-19-iodo-3(RS)-methyl-18-nonadecenoic acid 
• 62509-45-9 (Z)-12-Benzyloxy-8-dodecenoic-acid 
• 132210-09-4 4,8-dimethyl-7-(omega-carboxyheptyloxy)coumarin 
• 1002-57-9 8-Aminooctanoic acid 

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.

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.

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.