73768-94-2

Basic information

• Product Name: 11-Mercapto-1-undecanol
• Synonyms: NANOTHINKS(R) ALCO11;11-MERCAPTO-1-UNDECANOL;0677NANOTHINKS ALCO11;11-Hydroxy-1-Undecanethiol;11-Mercaptoundecanol;11-mercapto-1-undecanol solution;nanothinks tm alco11;11-Hydroxy-1-undecanethiol, 11-Hydroxy-1-undecanthiol, 11-Hydroxyundecane-1-thiol
• CAS NO: 73768-94-2
• Molecular Formula: C₁₁H₂₄OS
• Molecular Weight: 204.37
• Product Categories: fatty alcohol series
• Mol File: 73768-94-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 33-37 °C(lit.)
• Boiling Point: 303.979 °C at 760 mmHg
• Flash Point: 54 °F
• Appearance: /
• Density: 0.790 g/mL at 25 °C
• Vapor Pressure: 8.59E-05mmHg at 25°C
• Refractive Index: n20/D 1.359
• Storage Temp.: 2-8°C
• Solubility: Chloroform, DMSO (Sparingly), Methanol (Slightly)
• PKA: 10.49±0.10(Predicted)
• CAS DataBase Reference: 11-Mercapto-1-undecanol(CAS DataBase Reference)
• NIST Chemistry Reference: 11-Mercapto-1-undecanol(73768-94-2)
• EPA Substance Registry System: 11-Mercapto-1-undecanol(73768-94-2)

Safety Data

• Hazard Codes: F,Xi
• Statements: 36/37/38
• Safety Statements: 7-16-36-26
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 73768-94-2(Hazardous Substances Data)

Usage

Description

11-Mercapto-1-undecanol is an organic compound characterized by the presence of a thiol (-SH) group and a hydroxyl (-OH) group. It is a versatile building block for the synthesis of various organic compounds and materials, particularly in the field of surface science and nanotechnology.

Uses

Used in Surface Science:
11-Mercapto-1-undecanol is used as a precursor for the formation of self-assembled monolayers (SAMs) on gold surfaces. The hydrophilic nature of the molecule allows for the creation of stable and well-ordered monolayers, which can be further functionalized with various groups.
Used in Nanotechnology:
11-Mercapto-1-undecanol is used as a stabilizing agent and functionalizing agent for gold nanoparticles. The thiol group can bind to the gold surface, providing stability and allowing for the attachment of additional functional groups to the nanoparticles.
Used in Organic Synthesis:
11-Mercapto-1-undecanol can be oxidized to its corresponding disulfide using N-phenyltriazolinedione, which is useful for the synthesis of various organic compounds and materials. The ability to form disulfide bonds can be exploited in the creation of novel structures and materials with unique properties.
Overall, 11-Mercapto-1-undecanol is a valuable compound in various fields, including surface science, nanotechnology, and organic synthesis, due to its unique chemical properties and reactivity.

InChI:InChI=1/C11H24OS/c12-10-8-6-4-2-1-3-5-7-9-11-13/h12-13H,1-11H2

Synthetic route

2-(11-Hydroxy-undecyl)-isothiourea; hydrobromide → 11-mercapto-1-undecanol (73768-94-2)

Conditions	Yield
With sodium hydroxide Yield given;

thioacetic acid S-(11-hydroxy-undecyl) ester (73768-96-4) → 11-mercapto-1-undecanol (73768-94-2) + 11-hydroxyundecyldisulfide (119438-02-7)

Conditions	Yield
With sodium methylate Yield given;

1-Bromo-11-hydroxyundecane (1611-56-9) → 11-mercapto-1-undecanol (73768-94-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na / methanol / 6 h / Heating 2: CH3ONa View Scheme
Multi-step reaction with 2 steps 1: ethanol 2: 10percent aq. NaOH View Scheme
Stage #1: 1-Bromo-11-hydroxyundecane With thiourea In dimethyl sulfoxide at 20℃; for 21h; Stage #2: With potassium hydroxide In water; dimethyl sulfoxide at 80℃; for 0.0833333h;	7.2 g
Stage #1: 1-Bromo-11-hydroxyundecane With thiourea In ethanol Heating; Inert atmosphere; Stage #2: With sodium hydroxide In water Inert atmosphere;

Undecenole + azobisisobutyronitrile (34241-39-9) + thioacetic acid (507-09-5) → 11-mercapto-1-undecanol (73768-94-2)

Conditions	Yield
With sodium hydroxide; Hg In ethanol; water

11-mercapto-1-undecanol (73768-94-2) → 11-hydroxyundecyldisulfide (119438-02-7)

Conditions	Yield
With iodine In ethanol for 1h; Ambient temperature;	100%
With iodine In dichloromethane	100%
With N-chloro-succinimide In dichloromethane for 0.166667h; Inert atmosphere;	98%

1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]dodecane (934499-56-6) + 11-mercapto-1-undecanol (73768-94-2) → 11-(dodec-1-yldisulfanyl)undecan-1-ol

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

1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane (1262447-14-2) + 11-mercapto-1-undecanol (73768-94-2) → 11-(dodec-1-yl-trisulfanyl)undecan-1-ol (1262447-16-4)

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

(5,5-dimethyl-2-thiono-1,3,2-dioxophosphorinanyl) sulfenyl bromide (934751-37-8) + 11-mercapto-1-undecanol (73768-94-2) → 11-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)di-sulfanyl]undecan-1-ol (1170712-93-2)

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	95%
In dichloromethane at -30 - 20℃; for 0.5h; Inert atmosphere;	4.42 g
In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	4.42 g

bis-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinan-2-yl)disulfide (4073-59-0) + 11-mercapto-1-undecanol (73768-94-2) → 11-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)di-sulfanyl]undecan-1-ol (1170712-93-2)

Conditions	Yield
Stage #1: bis-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinan-2-yl)disulfide With bromine In dichloromethane at -30℃; for 0.25h; Inert atmosphere; Stage #2: 11-mercapto-1-undecanol In dichloromethane at 20℃; for 0.5h;	95%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 0℃; for 0.0833333h; Solvent;	89%
Stage #1: bis-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinan-2-yl)disulfide With bromine Stage #2: 11-mercapto-1-undecanol

11-mercapto-1-undecanol (73768-94-2) + 1-(4'-methoxyphenyl)-2-<4'-(benzyloxy)phenyl>ethanol (155142-78-2) → 14-<4'-(benzyloxy)phenyl>-13-(4'-methoxyphenyl)-12-thiatetradecanol

Conditions	Yield
With zinc(II) iodide In 1,2-dichloro-ethane for 1.5h; Ambient temperature;	93%

5,5-dimethyl-2-thiolo-2-thiono-1,3,2-dioxaphosphorinane (697-45-0) + 11-mercapto-1-undecanol (73768-94-2) → 11-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)di-sulfanyl]undecan-1-ol (1170712-93-2)

Conditions	Yield
Stage #1: 5,5-dimethyl-2-thiolo-2-thiono-1,3,2-dioxaphosphorinane With bromine In dichloromethane at -30℃; for 0.25h; Inert atmosphere; Stage #2: 11-mercapto-1-undecanol In dichloromethane at 20℃; for 0.5h;	93%
Stage #1: 5,5-dimethyl-2-thiolo-2-thiono-1,3,2-dioxaphosphorinane With bromine Stage #2: 11-mercapto-1-undecanol

dichloromethane (75-09-2) + 11-mercapto-1-undecanol (73768-94-2) → 11-(11-hydroxyundecylsulfanylmethylsulfanyl)undecan-1-ol

Conditions	Yield
With triethylamine at 30℃; for 24h; Inert atmosphere;	67%
With triethylamine; RhCl(PPh3)3 at 20℃; for 24h;	63%

ethanol (64-17-5) + chloranil (118-75-2) + 11-mercapto-1-undecanol (73768-94-2) → 2,3,6-tris((11-undecanol)sulphanyl)-5-ethoxy-1,4-benzoquinone (1393725-45-5) + 2,3,5,6-tetrakis((11-undecanol)sulphanyl)-1,4-benzoquinone (1393725-46-6)

Conditions	Yield
With sodium carbonate for 24h;	A 27% B 63%

2-chloro-3-[4-(3,4-methylenedioxybenzyl)piperazino]-1,4-naphthoquinone + 11-mercapto-1-undecanol (73768-94-2) → 2-(1-piperonylpiperazin-4-yl)-3-(11-hydroxyundecylthio)-1,4-naphthoquinone

Conditions	Yield
With sodium carbonate In ethanol at 20℃; for 24h;	57%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + ethanol (64-17-5) + 11-mercapto-1-undecanol (73768-94-2) → 2-((11-undecanol)sulphanyl)-3-ethoxy-1,4-naphthoquinone (1393725-36-4) + 2,3-bis((11-undecanol)sulphanyl)-1,4-naphthoquinone (1393725-37-5)

Conditions	Yield
With sodium carbonate for 24h;	A 34% B 53%

11-mercapto-1-undecanol (73768-94-2) → sodium 11-mercaptoundecyl sulfate

Conditions	Yield
Stage #1: 11-mercapto-1-undecanol With sulfur trioxide-N,N-dimethylformamide complex In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: With sodium hydroxide In ethanol Inert atmosphere;	53%

11-mercapto-1-undecanol (73768-94-2) + 1,2-bis<4'-(tetrahydro-2''H-pyran-2''-yloxy)phenyl>ethanol (155142-80-6) → 13,14-bis(4'-hydroxyphenyl)-12-thiatetradecanol + 11-{1,2-Bis-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-ethylsulfanyl}-undecan-1-ol

Conditions	Yield
With zinc(II) iodide In 1,2-dichloro-ethane for 4h; Ambient temperature;	A 11% B 52%

2-(6-aminohexyl-1-ol)-3-chloro-1,4-naphthoquinone + 11-mercapto-1-undecanol (73768-94-2) → 2-(6-aminohexyl-1-ol)-3-(11-hydroxyundecylthio)-1,4-naphthoquinone

Conditions	Yield
With sodium carbonate In ethanol at 20℃; for 24h;	51%

5-bromovaleric acid methyl ester (5454-83-1) + 11-mercapto-1-undecanol (73768-94-2) → methyl 17-hydroxy-6-thia-heptadecanoate

Conditions	Yield
	48%

11-mercapto-1-undecanol (73768-94-2) + 1-(4'-methoxyphenyl)-2-<4'-(tetrahydro-2''H-pyran-2''-yloxy)phenyl>ethanol (155142-79-3) → 14-(4'-hydroxyphenyl)-13-(4'-methoxyphenyl)-12-thiatetradecanol + 11-{1-(4-Methoxy-phenyl)-2-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-ethylsulfanyl}-undecan-1-ol

Conditions	Yield
With zinc(II) iodide In 1,2-dichloro-ethane for 1.5h; Ambient temperature;	A 40% B 46%

poly(methacrylic acid) (79-41-4) + 11-mercapto-1-undecanol (73768-94-2) → 11-mercaptoundecyl methacrylate (1107606-86-9)

Conditions	Yield
With dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate In dichloromethane at 20℃; for 24h; Inert atmosphere;	45%
With dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate In dichloromethane at 20℃; for 24h; Inert atmosphere;	45%

5,5',6,6'-tetraphenyl-bis(1,2,4-triazine)-3,3'-disulfide (106510-63-8) + 11-mercapto-1-undecanol (73768-94-2) → 5,6-diphenyl-1,2,4-triazine-3-yl 11-hydroxyundecyl disulfide

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 1h;	23%

decacarbonyl-1κ(4)C,2κ(3)C,3κ(3)C-μ-hydrido-2:3κ(2)H-μ-hydroxy-2:3κ(2)O-trisosmium-(3 Os-Os) + 11-mercapto-1-undecanol (73768-94-2) → [Os3(CO)10(μ-H)(μ-O(CH2)11SH)] (1024616-80-5) + [Os3(CO)10(μ-H)(μ-S(CH2)11OH)] (1024616-78-1) + [Os3(CO)10(μ-H)(μ,μ-O(CH2)11S)Os3(CO)10(μ-H)] (1024616-96-3)

Conditions	Yield
With HBF4 In diethyl ether; toluene (Ar or N2); using Schlenk techniques; addn. of excess of HS(CH2)11OH andHBF4/ether (one drop) to soln. of Os3(CO)10(μ-H)(μ-OH) in toluene ; reflux for 5 h; removal of solvent in vac., chromy. using hexane/CH2Cl2 as eluent; elem.anal.;	A 8% B 10% C 1%

menadione (58-27-5) + 11-mercapto-1-undecanol (73768-94-2) → 2-(11-hydroxy-undecylsulfanyl)-3-methyl-[1,4]naphthoquinone

Conditions	Yield
In methanol; isopropyl alcohol at 20℃; for 24h;	8%

11-mercapto-1-undecanol (73768-94-2) + trifluoroacetic anhydride (407-25-0) → 11-mercaptoundecyl trifluoroacetate (138524-05-7)

Conditions	Yield
In hexane for 0.00833333h;

11-mercapto-1-undecanol (73768-94-2) + 1,10-iododecanethiol (187339-30-6) → 11-(10-Iodo-decyldisulfanyl)-undecan-1-ol (187339-34-0)

Conditions	Yield
With iodine In ethanol

11-mercapto-1-undecanol (73768-94-2) + 12-Iodo-dodecane-1-thiol (187339-32-8) → 11-(12-Iodo-dodecyldisulfanyl)-undecan-1-ol (187339-36-2)

Conditions	Yield
With iodine In ethanol

11-mercapto-1-undecanol (73768-94-2) + 9-(2-carboxyethyl)adenine p-nitrophenyl ester (70138-80-6) → 11-[2-(9-adeninyl)propionylthio]-1-undecanol + 11-[2-(9-adeninyl)propionyloxy]undecyl disulfide

Conditions	Yield
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 25℃; for 48h; Substitution; oxidation; Title compound not separated from byproducts.;

11-mercapto-1-undecanol (73768-94-2) + α-bromopropionyl bromide (563-76-8) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate), surface-initiated atom transfer radical polymerization, Mn 33100-68900, Mw/Mn 1.29-1.45; monomer(s): methyl methacrylate;

Conditions	Yield
Stage #1: 11-mercapto-1-undecanol With Si and Au implanted silicon for 24h; Solid phase reaction; Stage #2: α-bromopropionyl bromide With triethylamine Condensation; solid phase reaction; Stage #3: methacrylic acid methyl ester Polymerization; solid phase reaction; Further stages.;

11-mercapto-1-undecanol (73768-94-2) + α-bromopropionyl bromide (563-76-8) + acrylic acid methyl ester (292638-85-8) → poly(methyl acrylate), prepared by three-stage surface-initiated atom transfer radical polymerization, thick film 389 Angstroem, Mn = 41600, PDI = 1.32; monomer(s): 2-bromo-propionic acid, 11-mercapto-1-undecanol; methyl acrylate

Conditions	Yield
Multistep reaction.;

11-mercapto-1-undecanol (73768-94-2) + α-bromopropionyl bromide (563-76-8) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate), prepared by three-stage surface-initiated atom transfer radical polymerization, thick film 381 Angstroem, Mn = 37400, PDI = 1.48; monomer(s): 2-bromo-propionic acid, 11-mercapto-1-undecanol; methyl methacrylate

Conditions	Yield
Multistep reaction.;

11-mercapto-1-undecanol (73768-94-2) + α-bromopropionyl bromide (563-76-8) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate), prepared by single step surface-initiated atom transfer radical polymerization, thick film 370 Angstroem; monomer(s): 2-bromo-propionic acid, 11-mercapto-1-undecanol; methyl methacrylate

Conditions	Yield
Multistep reaction.;

Upstream product

• 34241-39-9 azobisisobutyronitrile 
• 507-09-5 tiolacetic acid 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 73768-96-4 thioacetic acid S-(11-hydroxy-undecyl) ester 

Downstream Products

• 875609-48-6 11-triphenylmethylthio-1-undecanol 
• 1255381-70-4 C₃₃H₄₁NOS 
• 1526990-55-5 S,S′-{disulfanediylbis[undecane-11,1-diyloxy-4,1-phenylenediazene-2,1-diyl-3,1-phenylene]}diethanethioate 
• 1346654-86-1 6-((11-hydroxyundecyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide 
• 1346654-83-8 6-((11-hydroxyundecyl)thio)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide 
• 1393725-45-5 2,3,6-tris((11-undecanol)sulphanyl)-5-ethoxy-1,4-benzoquinone 
• 1393725-46-6 2,3,5,6-tetrakis((11-undecanol)sulphanyl)-1,4-benzoquinone 
• 186541-67-3 C₃₆H₅₈O₆S₄ 
• 402828-41-5 11,11'-dithiobis[1-(2-bromo-2-methylpropionyloxy)undecane] 
• 119438-02-7 11-hydroxyundecyldisulfide 
• 138524-05-7 11-sulfanylundecanyltrifluoroethanoate 

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