11-bromoundecanoic acid
11-mercaptounadecanoic acid
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
11-mercaptounadecanoic acid
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
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
With ammonia |
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid; zinc |
Conditions | Yield |
---|---|
With ethanol Verseifen mit wss.-alkoh.NaOH; |
11-chloroundecanoic acid
potassium ethyl xanthogenate
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
(i), (ii) (pyrolysis); Multistep reaction; |
11-ethoxythiocarbonylmercapto-undecanoic acid
A
11-mercaptounadecanoic acid
1,10-undecadiene
11-mercaptounadecanoic acid
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
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: aq. HBr / octane 2: CrO3 4: OH(1-) View Scheme |
1-Bromo-11-hydroxyundecane
11-mercaptounadecanoic acid
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
A
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: aq. base View Scheme |
11-iodo-undecanoic acid
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous NaHCO3; Na2S2 2: zinc; glacial acetic acid; HCl View Scheme |
10-undecenoic acid
11-mercaptounadecanoic acid
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
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
Stage #1: BrH*C12H26N2O2S With sodium hydroxide In water Stage #2: With sulfuric acid In water |
11-bromo-undecanoic acid methyl ester
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thiourea / ethanol; water 2: sodium hydroxide / water View Scheme |
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
acetyl chloride
11-(acetylthio)undecanoic acid
Conditions | Yield |
---|---|
With acetic acid; zinc In dichloromethane at 0 - 20℃; for 1h; | 100% |
2-aminoethylimidazolidone
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
at 160℃; for 6h; Inert atmosphere; | 100% |
1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]dodecane
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 0.25h; | 99% |
11-mercaptounadecanoic acid
11,11'-disulfanediyldiundecanoic acid
Conditions | Yield |
---|---|
With sulfuryl dichloride In dichloromethane at 0℃; for 0.1h; | 99% |
11-mercaptounadecanoic acid
trityl chloride
11-[(triphenylmethyl)sulfanyl]undecanoic Acid
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
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 20℃; for 72h; Schlenk technique; | 98% |
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
11-mercaptounadecanoic acid
11-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]undecanoic acid
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
undecylenic acid
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
11-(10'-carboxy-decyldisulfanyl)undecanoic acid
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
Conditions | Yield |
---|---|
With arsenic(III) trioxide In methanol at 20℃; for 48h; | 92% |
(5,5-dimethyl-2-thiono-1,3,2-dioxophosphorinanyl) sulfenyl bromide
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
In dichloromethane at -30℃; | 92% |
11-mercaptounadecanoic acid
2-methylene-2,3-dihydrothieno[3,4-b][1,4]dioxine
11-((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methylthio)undecanoic acid
Conditions | Yield |
---|---|
With 2,2-dimethoxy-2-phenylacetophenone In methanol at 90℃; UV-irradiation; | 92% |
11-mercaptounadecanoic acid
2-fluoro-6-methylbenzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 85℃; Schlenk technique; Inert atmosphere; | 91.5% |
Diethyl disulfide
11-mercaptounadecanoic acid
11-(11-ethyldithio)undecanoic acid
Conditions | Yield |
---|---|
With triethylamine at 70℃; for 24h; | 89% |
1-hydroxy-pyrrolidine-2,5-dione
11-mercaptounadecanoic acid
11-mercaptoundecanoic acid 2,5-dioxopyrrolidin-1-yl ester
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
4-pyrenylbutanol
Conditions | Yield |
---|---|
With hafnium/THF In toluene for 48h; Reflux; Molecular sieve; | 89% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 20h; Inert atmosphere; | 89% |
11-mercaptounadecanoic acid
acetic anhydride
11-(acetylthio)undecanoic acid
Conditions | Yield |
---|---|
In pyridine at 0 - 20℃; | 89% |
Conditions | Yield |
---|---|
With C12H17O2Si(1-)*C31H49O2P*Br(1-)*Pd(2+); triethylamine In tert-butyl alcohol at 20℃; for 3h; | 88% |
carbon disulfide
11-mercaptounadecanoic acid
benzyl bromide
11-(((benzylthio)carbonothioyl)thio)undecanoic acid
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
11-mercaptounadecanoic acid
11-(1H-benzotriazole-1-yl)-11-oxoundecane-1-thiol
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% |
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
(3R,4R)-3,4-bis(diphenylphosphanyl)pyrrolidine
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
1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane
11-(dodec-1-yl-trisulfanyl)undecanoic acid
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 0.25h; air; | 86% |
11-mercaptounadecanoic acid
Conditions | Yield |
---|---|
Multistep reaction; | 85% |
Multistep reaction; |
11-mercaptounadecanoic acid
diethyl iodomethanephosphonate
11-[(diethoxyphosphoryl)thiomethyl]undecanoic acid
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; | 85% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In toluene at 20℃; | 84% |
The Undecanoic acid,11-mercapto-, with the CAS registry number 71310-21-9, has the systematic name of 11-sulfanylundecanoic acid. It belongs to the following product categories: Thiols/Mercaptans; Thiols Organic Building Blocks; Self Assembly & Contact Printing; Self-Assembly Materials; Sulfur Compounds; Thiols. And the molecular formula of the chemical is C11H22O2S.
The characteristics of Undecanoic acid,11-mercapto- are as followings: (1)ACD/LogP: 3.98; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.182; (4)ACD/LogD (pH 7.4): 1.387; (5)ACD/BCF (pH 5.5): 99.424; (6)ACD/BCF (pH 7.4): 1.594; (7)ACD/KOC (pH 5.5): 555.963; (8)ACD/KOC (pH 7.4): 8.911; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 11; (12)Polar Surface Area: 76.1 Å2; (13)Index of Refraction: 1.483; (14)Molar Refractivity: 62.471 cm3; (15)Molar Volume: 218.783 cm3; (16)Polarizability: 24.766×10-24cm3; (17)Surface Tension: 38.066 dyne/cm; (18)Density: 0.998 g/cm3; (19)Flash Point: 166.81 °C; (20)Enthalpy of Vaporization: 65.591 kJ/mol; (21)Boiling Point: 352.209 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Uses of Undecanoic acid,11-mercapto-: It can react with acetylamino-methanol to produce 11-(acetylamino-methylsulfanyl)-undecanoic acid. This reaction will need reagent trifluoroacetic acid. The reaction time is 0.5 hours with ambient temperature, and the yield is about 72%.
You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: C(CCCCCS)CCCCC(=O)O
(2)InChI: InChI=1/C11H22O2S/c12-11(13)9-7-5-3-1-2-4-6-8-10-14/h14H,1-10H2,(H,12,13)
(3)InChIKey: GWOLZNVIRIHJHB-UHFFFAOYAQ
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