111-56-8

Usage

Uses

Used in Surfactant Synthesis:
2-BROMODODECANOIC ACID is used as a key intermediate in the synthesis of carboxylic amphoteric surfactants containing ether tertiary amino and carboxylic groups. These surfactants are essential in various industries, such as cosmetics, pharmaceuticals, and cleaning products, due to their unique properties like foaming, wetting, and emulsifying capabilities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-BROMODODECANOIC ACID is used as a building block in the synthesis of C12-lipoamino acid. 2-BROMODODECANOIC ACID has potential applications in drug development, particularly in the design of novel therapeutic agents that can target specific biological processes or pathways.
Used in Chemical Research:
2-BROMODODECANOIC ACID is also utilized in chemical research for the development of new compounds and materials. Its unique structure allows for further functionalization and modification, making it a valuable starting material for the creation of new molecules with specific properties and applications.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 398, 1963The Journal of Organic Chemistry, 18, p. 850, 1953 DOI: 10.1021/jo50013a012

InChI:InChI=1/C12H23BrO2/c1-2-3-4-5-6-7-8-9-10-11(13)12(14)15/h11H,2-10H2,1H3,(H,14,15)

Upstream product

• 143-07-7 lauric acid 
• 59117-75-8 2-bromododecanoyl chloride 
• 112-16-3 n-dodecanoyl chloride 

Downstream Products

• 617-60-7 methyl 2-bromododecanoate 
• 32466-54-9 (E)-2-dodecenoic acid 
• 2984-55-6 2-hydroxydodecanoic acid 
• 35237-37-7 2-amino-dodecanoic acid 
• 3054-88-4 α-sulfolauric acid 
• 67491-92-3 2-(2-Hydroxyethylamino)dodecanoic acid 
• 214778-76-4 2-(2,6,13,16,19-Pentaoxa-tricyclo[18.4.0.0^7,12]tetracosa-1⁽²⁴⁾,7⁽¹²⁾,8,10,20,22-hexaen-4-yloxy)-dodecanoic acid benzyloxy-amide 
• 107917-70-4 (+/-)-2-Acetamino-dodecansaeure-(1) 
• 63645-55-6 2-phenoxy-dodecanoic acid 
• 1632280-48-8 diphenylmethyl 2-bromododecanoate 
• 1569315-10-1 (4-methoxyphenyl)methyl 2-bromododecanoate 
• 2387-23-7 1,3-Dicyclohexylurea 
• 66398-13-8 (+/-)-p-nitrophenyl N-(benzyloxycarbonyl)-α-aminododecanoic acid 
• 66398-12-7 (+/-)-(benzyloxycarbonyl)-α-aminododecanoic acid 

Relevant academic research and scientific papers

Adsorption of Metal Ions to Surface-Template Resins Prepared with Amphiphilic Styrene Monomers Bearing Amino Carboxylic Acid

Monomer-type functional surfactants, 2-(p-vinylbenzylamino)alkanoic acid (RnAc) and N,N-dialkyl derivatives (RRnNAc), have been used as both a ligand and an emulsifier for the preparation of surface-template resins. The surfactants adsorbed at the toluene-water interface and emulsified divinylbenzene-styrene in a Cu2+ or Zn2+ solution. Emulsion polymerization using a K2S2O8 initiator (80 °C) or by irradiation with γ-rays gave fine particles of 200-800 nm in diameter. Metal-imprinted resins prepared with RnNAc and RRnNAc showed a high adsorptive capacity for the metal ion (surface-template effect). Cu-imprinted resins prepared with R8NAc were 2.69-times as effective for Cu2+ in competitive sorption from a Cu2+-Zn2+ mixture and Zn-imprinted resins were 1.84-times as effective for Zn2+, compared with unimprinted resins. Because of the great emulsifying power, metal-imprinted resins prepared with R8NAc showed the most metal-selective adsorption and the largest capacity among resins prepared with RnNAc and RRnNAc.

Synthesis and Surface-Active Properties of a Homologous Series of Star-Like Triple-Chain Anionic Surfactants Derived from 1,1,1-Tris(hydroxymethyl)ethane

A novel homologous series of trimeric anionic surfactants, 3C n TE3CNa (where n is a fatty acid chain length of 7, 10, or 12), with three hydrocarbon chains and three carboxylate heads connected via tri-etheric bonds were synthesized from long-chain α-bromo fatty acids and a triol, 1,1,1-tris(hydroxymethyl)ethane. The obtained trimeric carboxylic acids were esterified and purified by silica gel column chromatography, then hydrolyzed with dilute sodium hydroxide solution to form a series of trimeric carboxylate surfactant products. All prepared compounds were analyzed by IR, 1H NMR, and 13C NMR spectroscopy to confirm their chemical structures. Their surface-active properties were investigated. The critical micelle concentrations (cmc) of 3C n TE3CNa were in the range of 0.12-0.71 mmol/L, and the surface tensions at the cmc (γ cmc) were 29.3-34.8 mN/m.

Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators

Novel N-α-haloacylated homoserine lactones, in which a halogen atom was introduced at the α-position of the carbonyl function of the N - acyl chain, have been studied as quorum sensing (QS) modulators and compared with a library of natural N - acylated homoserine lactones (AHLs). The series of novel analogues consists of α-chloro, α-bromo and α-iodo AHL analogues. Furthermore, the biological QS activity of the synthetic AHL analogues compared to the natural AHLs was evaluated. Halogenated analogues demonstrated a reduced activity in the Escherichia coli JB523 bioassay, with the α-iodo lactones being the less active ones and the α-chloro AHLs the most potent QS agonists. Most of the α-haloacylated analogues did not exhibit a significant reduction when tested in the QS inhibition test. Therefore, these novel analogues could be utilized as chemical probes for QS structure-activity studies.

Long-chain acyl-homoserine lactones from Methylobacterium mesophilicum: Synthesis and absolute configuration

The acyl-homoserine lactones (acyl-HSLs) produced by Methylobacterium mesophilicum isolated from orange trees infected with the citrus variegated chlorosis (CVC) disease have been studied, revealing the occurrence of six long-chain acyl-HSLs, i.e., the saturated homologues (S)-N-dodecanoyl (1) and (S)-N-tetradecanoyl-HSL (5), the uncommon odd-chain N-tridecanoyl-HSL (3), the new natural product (S)-N-(2E)-dodecenoyl-HSL (2), and the rare unsaturated homologues (S)-N-(7Z)-tetradecenoyl (4) and (S)-N-(2E,7Z)-tetradecadienyl-HSL (6). The absolute configurations of all HSLs were determined as 3S. Compounds 2 and 6 were synthesized for the first time. Antimicrobial assays with synthetic acyl-HSLs against Gram-positive bacterial endophytes co-isolated with M. mesophilicum from CVC-infected trees revealed low or no antibacterial activity.

Mesoionic 5-alkyl-1,3-dithiolium-4-thiolates: Synthesis and brine shrimp toxicity

A series of twelve 1,3-dithiolium-4-thiolate mesoionic compounds were synthesized and characterized. The synthetical approach starting from α-bromoalkanoic acids to obtain the corresponding 2-N-morpholino-dithiocarbamoyl-carboxylic acids that by on-pot reaction with carbon disulfide and acetic anhydride in triethylamine formed not isolate intermediates, 1,3-dithiolium-4-olates. After, the 2-N-morpholino-5-alkyl-1,3-dithiolium-4-thiolates were obtained by retro 1,3-dipolar addition reactions. The alkyl moiety linked to C-5 of heterocyclic ring permitted the increase of the hydrophobic character and this effect was evaluated on Artemia salina lethality. The results indicated a bell-shaped relationship between the number of carbon of side chain in mesoionic derivatives and LD50 in brine shrimp toxicity assays.

Synthesis and Application of Long-Chain Carboxylate Crown-Ether Ionophores for Transport of Metal Cations

Alkyl-substituted sym-dibenzo-16-crown-5-oxyacetic acid and sym-dibenzo-16-crown-5-oxydodecanic acid were synthesized and applied as ion transport carriers in liquid and film membranes.Increasing crown-ether lipophilicity decreased acid dissociation constants and solubilities of crown-ether carboxylic acids in water but enhanced the solubility and transport ability of the carboxylic anion-K+ complex through a liquid organic (CH2Cl2) membrane.Transport phenomena of the cations alkali-metal ions, alkaline-earth metal ions and transition-metal ions through liquid membranes based on these crown-ether carriers were investigated.Effects of anions, crown-ethers and pH on ion transport are discussed.A mechanism of ion transport through a crown-ether membrane is proposed to include -> and +> in both source and target layers.Ion transport through a polymer/crown-ether film membrane was more efficient than through a liquid membrane. - Key Words: Crown ethers; Ion Transport; Metal Ion; Liquid Membrane; Carrier; Polymer film membrane; Ionophore.

Syntheses of 2-(2-Hydroxyethylamino) Fatty Acids

Eight 2-(2-hydroxyethylamino) fatty acids, 2-(2-hydroxyethylamino)decanoic, -undecanoic, -dodecanoic, -tetradecanoic, -hexadecanoic, -octadecanoic, -nonadecanoic, and docosanoic acid, were synthesized by reacting 2-bromo fatty acids with more than 3 mol of 2-aminoethanol.The surface tension and the critical micelle concentration were determined for these compounds.