71310-21-9

Basic information

• Product Name: 11-MERCAPTOUNDECANOIC ACID
• Synonyms: MUNDA;NANOTHINKS(R) ACID11;11-MERCAPTOUNDECANOIC ACID;NANOTHINKS ACID11;10-Carboxy-1-Decanethiol;11-mercaptoundecanoic acid solution;nanothinkstm acid11;10-Caroboxy-1-decanethiol
• CAS NO: 71310-21-9
• Molecular Formula: C₁₁H₂₂O₂S
• Molecular Weight: 218.36
• Product Categories: Thiols/Mercaptans;ThiolsOrganic Building Blocks;Self Assembly&Contact Printing;Self-Assembly Materials;Sulfur Compounds;Thiols
• Mol File: 71310-21-9.mol
• Article Data: 15

Chemical Properties

• Melting Point: 46-50 °C(lit.)
• Boiling Point: 352.209 °C at 760 mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 0.998 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.483
• Storage Temp.: 2-8°C
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: 11-MERCAPTOUNDECANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 11-MERCAPTOUNDECANOIC ACID(71310-21-9)
• EPA Substance Registry System: 11-MERCAPTOUNDECANOIC ACID(71310-21-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 71310-21-9(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow solid

Uses

Different sources of media describe the Uses of 71310-21-9 differently. You can refer to the following data:
1. 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.
2. 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.

General Description

11-mercaptoundecanoic acid (MUA) has long alkane chains and carboxyl containing thiols that are highly packed and form a self-assembled monolayer (SAM). It modifies the surface of nanoparticles to facilitate their dispersion into water and solvent based mediums.

InChI:InChI=1/C11H22O2S/c12-11(13)9-7-5-3-1-2-4-6-8-10-14/h14H,1-10H2,(H,12,13)

Synthetic route

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

Conditions	Yield
With sodium hydroxide; sulfuric acid; thiourea In water	94%
Stage #1: 11-bromoundecanoic acid With thiourea In ethanol for 20h; Reflux; Schlenk technique; Stage #2: With sodium hydroxide In water at 90℃; for 20h; Inert atmosphere; Schlenk technique; Stage #3: With sulfuric acid In water Cooling with ice; Inert atmosphere; Schlenk technique;	92%
Stage #1: 11-bromoundecanoic acid With thiourea In water for 2.5h; Heating; Stage #2: With sodium hydroxide for 2h; Heating;	90%

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

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 4h; chemoselective reaction;	90%
With potassium hydroxide
With aq. base
With hydroxide

11-ethoxythiocarbonylmercapto-undecanoic acid (100912-41-2) → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
With ammonia

11,12-dithia-tetracosanedioic acid → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
With hydrogenchloride; acetic acid; zinc

11-bromoundecanoic acid (2834-05-1) + thiourea (17356-08-0) → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
With ethanol Verseifen mit wss.-alkoh.NaOH;

11-chloroundecanoic acid (1860-44-2) + potassium ethyl xanthogenate (140-89-6) → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
(i), (ii) (pyrolysis); Multistep reaction;

11-ethoxythiocarbonylmercapto-undecanoic acid (100912-41-2) + aqueous alcoholic ammonia → 11-mercaptounadecanoic acid (71310-21-9) + ethylxanthogenamide

1,10-undecadiene (13688-67-0) → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) B2H6, 2.) H2O2 2: aq. HBr / octane 3: CrO3 5: OH(1-) View Scheme

undecane-1,11-diol (765-04-8) → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. HBr / octane 2: CrO3 4: OH(1-) View Scheme

1-Bromo-11-hydroxyundecane (1611-56-9) → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: CrO3 3: OH(1-) View Scheme
Multi-step reaction with 2 steps 1.1: Jones reagent / acetone / 5 h / 0 - 20 °C 2.1: thiourea / ethanol / 20 h / Reflux; Schlenk technique 2.2: 20 h / 90 °C / Inert atmosphere; Schlenk technique 2.3: Cooling with ice; Inert atmosphere; Schlenk technique View Scheme

10-undecenoic acid (112-38-9) + aqueous KOH-solution → 11-mercaptounadecanoic acid (71310-21-9) + ethylxanthogenamide

Conditions	Yield
Multi-step reaction with 2 steps 2: aq. base View Scheme

11-iodo-undecanoic acid (63632-65-5) → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous NaHCO3; Na2S2 2: zinc; glacial acetic acid; HCl View Scheme

10-undecenoic acid (112-38-9) → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: petroleum ether; 10.11-epoxy-undecanoic acid (1); HBr / bei Anwesenheit von Luftsauerstoff 2: ethanol / Verseifen mit wss.-alkoh.NaOH View Scheme

BrH*C12H26N2O2S (1337529-72-2) → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
Stage #1: BrH*C12H26N2O2S With sodium hydroxide In water Stage #2: With sulfuric acid In water

11-bromo-undecanoic acid methyl ester (6287-90-7) → 11-mercaptounadecanoic acid (71310-21-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: thiourea / ethanol; water 2: sodium hydroxide / water View Scheme

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

Conditions	Yield
With C28H41NOP2Ru; hydrogen In 1,4-dioxane at 150℃; under 30003 Torr; for 36h; Autoclave;	A 78 %Spectr. B 92 %Spectr.

11-mercaptounadecanoic acid (71310-21-9) + acetyl chloride (75-36-5) → 11-(acetylthio)undecanoic acid (6974-31-8)

Conditions	Yield
With acetic acid; zinc In dichloromethane at 0 - 20℃; for 1h;	100%

2-aminoethylimidazolidone (6281-42-1) + 11-mercaptounadecanoic acid (71310-21-9) → 11-mercapto-N-[2-(2-oxoimidazolidin-1-yl)ethyl]undecaneamide

Conditions	Yield
at 160℃; for 6h; Inert atmosphere;	100%

1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]dodecane (934499-56-6) + 11-mercaptounadecanoic acid (71310-21-9) → 11-(dodec-1-yldisulfanyl)undecanoic acid

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.25h;	99%

11-mercaptounadecanoic acid (71310-21-9) → 11,11'-disulfanediyldiundecanoic acid (29265-73-4)

Conditions	Yield
With sulfuryl dichloride In dichloromethane at 0℃; for 0.1h;	99%

11-mercaptounadecanoic acid (71310-21-9) + trityl chloride (76-83-5) → 11-[(triphenylmethyl)sulfanyl]undecanoic Acid (202462-83-7)

Conditions	Yield
In dichloromethane at 20℃; for 2.5h;	98%
With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 5h; Inert atmosphere;	92%
With N-ethyl-N,N-diisopropylamine In toluene for 24h;	90%

11-mercaptounadecanoic acid (71310-21-9) + 3-(3-bromopropyl)-1-methyl-1H-imidazol-3-ium bromide → 11-((3-(1-methyl-1H-imidazol-3-ium-3-yl)propyl)thio)undecanoate

Conditions	Yield
With potassium carbonate In ethanol at 20℃; for 72h; Schlenk technique;	98%

11-mercaptounadecanoic acid (71310-21-9) + octavinylsilsesquioxane (69655-76-1) → C104H200O28S8Si8

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran for 1.5h; Irradiation;	97.1%

(5,5-dimethyl-2-thiono-1,3,2-dioxophosphorinanyl) sulfenyl bromide (934751-37-8) + 11-mercaptounadecanoic acid (71310-21-9) → 11-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]undecanoic acid (1002347-32-1)

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere;	94%
In dichloromethane at 20℃;
In dichloromethane at -30 - 20℃; for 0.5h; Inert atmosphere;

11-mercaptounadecanoic acid (71310-21-9) → undecylenic acid (112-37-8)

Conditions	Yield
With di-tert-butyl peroxide; triethyl phosphite In diethyl ether	94%
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 25℃; for 6h; Irradiation;	85 %Spectr.

11-mercaptounadecanoic acid (71310-21-9) → 11-(10'-carboxy-decyldisulfanyl)undecanoic acid (23483-56-9)

Conditions	Yield
With sulfuryl dichloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	93%
With iodine In tetrahydrofuran; dimethyl sulfoxide at 45℃;	91%
With dihydrogen peroxide; sodium hydroxide In water at 20℃; for 1.5h;	87%

11-mercaptounadecanoic acid (71310-21-9) → tris(10-carboxydecyl) trithioarsenite

Conditions	Yield
With arsenic(III) trioxide In methanol at 20℃; for 48h;	92%

(5,5-dimethyl-2-thiono-1,3,2-dioxophosphorinanyl) sulfenyl bromide (934751-37-8) + 11-mercaptounadecanoic acid (71310-21-9) → C18H35O2PS3

Conditions	Yield
In dichloromethane at -30℃;	92%

11-mercaptounadecanoic acid (71310-21-9) + 2-methylene-2,3-dihydrothieno[3,4-b][1,4]dioxine (1443919-53-6) → 11-((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methylthio)undecanoic acid (1443919-60-5)

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In methanol at 90℃; UV-irradiation;	92%

11-mercaptounadecanoic acid (71310-21-9) + 2-fluoro-6-methylbenzaldehyde (117752-04-2) → 11-((2-formyl-3-methylphenyl)thio)undecanoic acid

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; Schlenk technique; Inert atmosphere;	91.5%

Diethyl disulfide (110-81-6) + 11-mercaptounadecanoic acid (71310-21-9) → 11-(11-ethyldithio)undecanoic acid (87050-15-5)

Conditions	Yield
With triethylamine at 70℃; for 24h;	89%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 11-mercaptounadecanoic acid (71310-21-9) → 11-mercaptoundecanoic acid 2,5-dioxopyrrolidin-1-yl ester (240125-70-6)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;	89%
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;	60%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	38%
Stage #1: 11-mercaptounadecanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride Stage #2: 1-hydroxy-pyrrolidine-2,5-dione Further stages.;
Stage #1: 1-hydroxy-pyrrolidine-2,5-dione; 11-mercaptounadecanoic acid In tetrahydrofuran at -5℃; for 0.25h; Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran for 24.75h;

11-mercaptounadecanoic acid (71310-21-9) + 4-pyrenylbutanol (67000-89-9) → 4-(pyren-4-yl) butyl-11-mercaptoundecanoate

Conditions	Yield
With hafnium/THF In toluene for 48h; Reflux; Molecular sieve;	89%

11-mercaptounadecanoic acid (71310-21-9) + trityl chloride (76-83-5) → C29H34O2S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 20h; Inert atmosphere;	89%

11-mercaptounadecanoic acid (71310-21-9) + acetic anhydride (108-24-7) → 11-(acetylthio)undecanoic acid (6974-31-8)

Conditions	Yield
In pyridine at 0 - 20℃;	89%

11-mercaptounadecanoic acid (71310-21-9) + 2-ethoxy-4-bromothiazole → C16H27NO3S2

Conditions	Yield
With C12H17O2Si(1-)*C31H49O2P*Br(1-)*Pd(2+); triethylamine In tert-butyl alcohol at 20℃; for 3h;	88%

carbon disulfide (75-15-0) + 11-mercaptounadecanoic acid (71310-21-9) + benzyl bromide (100-39-0) → 11-(((benzylthio)carbonothioyl)thio)undecanoic acid (939984-30-2)

Conditions	Yield
Stage #1: carbon disulfide; 11-mercaptounadecanoic acid With sodium hydroxide In water at 20℃; for 0.5h; Stage #2: benzyl bromide In water at 20℃; for 24h; Further stages.;	87.51%

1,2,3-Benzotriazole (95-14-7) + 11-mercaptounadecanoic acid (71310-21-9) → 11-(1H-benzotriazole-1-yl)-11-oxoundecane-1-thiol (1311269-55-2)

Conditions	Yield
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 11-mercaptounadecanoic acid In dichloromethane for 3h;	87%

ethanol (64-17-5) + 11-mercaptounadecanoic acid (71310-21-9) → ethyl 11-mercaptoundecanoate (1725-06-0)

Conditions	Yield
With sulfuric acid for 2h; Reflux;	87%
With Amberlyst-15 at 70℃; under 5171.62 Torr; for 24h; Molecular sieve; Inert atmosphere;	80.6%

11-mercaptounadecanoic acid (71310-21-9) + (3R,4R)-3,4-bis(diphenylphosphanyl)pyrrolidine (99135-90-7) → 1-((3R,4R)-3,4-Bis-diphenylphosphanyl-pyrrolidin-1-yl)-11-mercapto-undecan-1-one

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 23℃; for 6h;	86%

11-mercaptounadecanoic acid (71310-21-9) + 1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane (1262447-14-2) → 11-(dodec-1-yl-trisulfanyl)undecanoic acid (1262447-17-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.25h; air;	86%

11-mercaptounadecanoic acid (71310-21-9) + 3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-propionic acid + 9H-fluoren-9-ylmethyl N-(4-aminobutyl)carbamate hydrochloride → 11-mercapto-undecanoic acid [4-(3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-propionylamino)-butyl]-amide

Conditions	Yield
Multistep reaction;	85%
Multistep reaction;

11-mercaptounadecanoic acid (71310-21-9) + diethyl iodomethanephosphonate (10419-77-9) → 11-[(diethoxyphosphoryl)thiomethyl]undecanoic acid (634158-90-0)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	85%

1,6,9,12,15,18-hexachloro[C60-Ih]fullerene + 11-mercaptounadecanoic acid (71310-21-9) → C115H106O10S5

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene at 20℃;	84%

Upstream product

• 2834-05-1 11-bromoundecanoic acid 
• 17356-08-0 thiourea 
• 100912-41-2 11-ethoxythiocarbonylmercapto-undecanoic acid 
• 6974-31-8 11-(acetylthio)undecanoic acid 
• 6287-90-7 11-bromo-undecanoic acid methyl ester 
• 1337529-72-2 BrH*C₁₂H₂₆N₂O₂S 
• 112-38-9 10-undecenoic acid 
• 63632-65-5 11-iodo-undecanoic acid 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 765-04-8 undecane-1,11-diol 
• 13688-67-0 1,10-undecadiene 
• 1860-44-2 11-chloroundecanoic acid 
• 140-89-6 potassium ethyl xanthogenate 

Downstream Products

• 80683-81-4 11-(methylthio)undecanoic acid 
• 138153-91-0 11-Mercapto-undecanoic acid benzylamide 
• 6974-31-8 11-(acetylthio)undecanoic acid 
• 23483-56-9 11-(10'-carboxy-decyldisulfanyl)undecanoic acid 
• 939984-30-2 11-(((benzylthio)carbonothioyl)thio)undecanoic acid 
• 1129546-14-0 bis[10-(4-{[(4'-cyanobiphenyl-4-yl)oxy]carbonyl}phenoxy)decyl] 5-[(11-sulfanylundecanoyl)oxy]benzene-1,3-dicarboxylate 
• 1129546-19-5 3,5-bis[(3,4,5-tris{[4-(dodecyloxy)benzyl]oxy}benzyl)oxy]benzyl 11-sulfanylundecanoate 
• 792921-26-7 11-tritylsulfanyl-undecanoic acid {2-[2-(2-amino-ethoxy)-ethoxy]-ethyl}-amide 
• 916980-32-0 C₃₄H₃₉NO₄S 
• 1174631-46-9 11-tritylsulfanyl-undecanoic acid 2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl ester 
• 1309603-39-1 C₅₇H₆₈N₄O₇S 
• 1333432-10-2 N-(4-ethynylphenyl)-11,11'-disulfanediyldiundecanoic amide 

Relevant articles and documents

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Use of Self-Assembeld Monolayers of Alkyl Mercaptans To Investigate the Chemisorption and Photochemistry of p-Nitrobenzoic Acid on Silver Islands

Surface-enhanced Raman spectra were obtained from p-nitrobenzoic acid (PNBA) adsorbed onto silver island films that had previously been coated with self-assembled monolayers of alkyl mercaptans.PNBA adsorbed onto silver as a p-nitrobenzoate ion, penetrating through the hydrocarbon layer.However, the alkyl coating hindered the chemisorption and revealed the existence and location of two types of adsorption sites.The photo-induced reduction of PNBA1,2 was not observable when the molecule was adsorbed on silver previously coated with hexadecyl mercaptan.In general, the reaction was much slower when silver was coated with hydrophobic layers than when it was bare or coated with hydrophilic layers.These results are discussed and interpreted in favor of a polymolecular mechanism for the photoinduced reaction.

Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides

Direct hydrogenation of thioesters with H2 provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds.

BORATE MOIETY-CONTAINED LINKER AND BIO-SENSING ELEMENT CONTAINING THE SAME

A borate moiety-contained linker and a bio-sensing element containing the same are disclosed. The borate moiety-contained linker can be used to modify a sensing molecule and connect the sensing molecule to a substrate to form the bio-sensing element.

Sodium borohydride-mediated transesterification

In the presence of sodium borohydride, esters react with alcohols with formation of the corresponding esters. The reaction is sensitive to the solvent, structure of the ester, and is often concurrent with reduction. Thioesters containing an ester group can be selectively cleaved by the reagent. Both esters and thioesters attached to solid support are resistant toward sodium borohydride. The in situ prepared sodium tetraalkoxyborate is introduced as an efficient reagent and catalyst for transesterification.