11-Mercaptoundecanoic acid

Base Information

• Chemical Name: 11-Mercaptoundecanoic acid
• CAS No.: 71310-21-9
• Molecular Formula: C11H22O2S
• Molecular Weight: 218.36
• Hs Code.: 29309090
• European Community (EC) Number: 615-278-4
• DSSTox Substance ID: DTXSID00337585
• Nikkaji Number: J524.170G
• Wikidata: Q27097399
• Metabolomics Workbench ID: 151319
• Mol file: 71310-21-9.mol

Synonyms:11-mercaptoundecanoic acid

Chemical Property of 11-Mercaptoundecanoic acid

Chemical Property:

• Appearance/Colour: solid with an extremely unpleasant odour
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 46-50 °C(lit.)
• Refractive Index: 1.483
• Boiling Point: 352.209 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 166.81 °C
• PSA: 76.10000
• Density: 0.998 g/cm³
• LogP: 3.51170
• Storage Temp.: 2-8°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 218.13405111
• Heavy Atom Count: 14
• Complexity: 137

Purity/Quality:

98%,99%, ^*data from raw suppliers

11-Mercaptoundecanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCCCCS)CCCCC(=O)O
• Uses: MUA is used for the carboxylic acid functionalization of 1-dodecanethiol-protected gold nanoparticles (AuNPs) by Murray place-displacement reaction generally utilized in biomedical applications. It can also be used to modify the surface of platinum nanoparticles (PtNPs) by creating a ligand nano-assembly with a high surface coverage for use in surface-enhanced Raman spectroscopy (SERS). A single cell biochip platform can be developed utilizing a cell attachment technique with MUA forming a SAM that was attached to single cells. MUA may be used to prepare a tetrafluorophenyl-activated ester self-assembled monolayer to immobilize amine-modified oligonucleotides and DNA. It is also used to create 3D-assembled gold nanostructures for plasmonic biosensors. MUA as a self-assembled monolayer (SAM) is used as a microfluidic integrated surface plasmon resonance (SPR) for detection and quantification of bacteria in medical diagnostics. It is also used to bio-functionalize the screen printed gold electrodes (SPGEs) that are used for the detection and quantification of dengue. It also forms monolayers on gold nanoparticles (AuNPs) attached via thiol groups. MUA incorporated AuNPs exhibit excellent fluorescence properties which may be used for metal ion detection in serum samples.

Technology Process of 11-Mercaptoundecanoic acid

There total 17 articles about 11-Mercaptoundecanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

11-bromoundecanoic acid (2834-05-1) → 11-mercaptounadecanoic acid (71310-21-9)

Guidance literature:

With sodium hydroxide; sulfuric acid; thiourea; In water;

Reference yield: 90.0%

11-(acetylthio)undecanoic acid (6974-31-8) → 11-mercaptounadecanoic acid (71310-21-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 4h; chemoselective reaction;

DOI:10.1080/00397910903072438

Reference yield:

11-(acetylthio)undecanoic acid (6974-31-8) → ethanol (64-17-5) + 11-mercaptounadecanoic acid (71310-21-9)

Guidance literature:

With C₂₈H₄₁NOP₂Ru; hydrogen; In 1,4-dioxane; at 150 ℃; for 36h; under 30003 Torr; Autoclave;

DOI:10.1021/jacs.0c10884

upstream raw materials:

11-ethoxythiocarbonylmercapto-undecanoic acid

11-(acetylthio)undecanoic acid

11-bromoundecanoic acid

thiourea

Downstream raw materials:

2-nitrobenzyl-11-mercaptoundecanoate

undecylenic acid

11-(methylthio)undecanoic acid

11-(benzoylthio)undecanoic acid

Refernces

• 1、 Su, Chia-Hao,Wu, Pei-Lin,Yeh, Chen-Sheng. "pH Dependence of Interparticle Coupling for Gold Nanoparticle Assemblies Formation: Electrostatic Attraction and Hydrogen Bonding". . p. 189 - 193. Retrieved 2004.
• 2、 Cavalleri,Natale,Stroppolo,Relini,Cosulich,Thea,Novi,Gliozzi. "Azurin immobilisation on thiol covered Au(111)". . p. 4630 - 4635. Retrieved 2000.
• 3、 Rühling, Andreas,Schaepe, Kira,Rakers, Lena,Vonh?ren, Benjamin,Tegeder, Patricia,Ravoo, Bart Jan,Glorius, Frank. "Modular Bidentate Hybrid NHC-Thioether Ligands for the Stabilization of Palladium Nanoparticles in Various Solvents". supporting information. p. 5856 - 5860. Retrieved 2016/05/09.
• 4、 Elmes, Robert B. P.,Orange, Kim N.,Cloonan, Suzanne M.,Williams, D. Clive,Gunnlaugsson, Thorfinnur. "Luminescent ruthenium(II) polypyridyl functionalized gold nanoparticles; Their DNA binding abilities and application as cellular imaging agents". supporting information; scheme or table. p. 15862 - 15865. Retrieved 2012/01/04.