Product Name

  • Name

    11-MERCAPTOUNDECANOIC ACID

  • EINECS
  • CAS No. 71310-21-9
  • Article Data22
  • CAS DataBase
  • Density 0.998 g/cm3
  • Solubility
  • Melting Point 46-50 °C(lit.)
  • Formula C11H22O2S
  • Boiling Point 352.209 °C at 760 mmHg
  • Molecular Weight 218.36
  • Flash Point 166.81 °C
  • Transport Information
  • Appearance solid with an extremely unpleasant odour
  • Safety 26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 71310-21-9 (11-MERCAPTOUNDECANOIC ACID)
  • Hazard Symbols IrritantXi
  • Synonyms 11-Mercaptoundecanoicacid;w-Mercaptoundecanoic acid;11-sulfanylundecanoic acid;11-mercaptoundecanoic acid;Undecanoic acid, 11-mercapto-;
  • PSA 76.10000
  • LogP 3.51170

Synthetic route

11-bromoundecanoic acid
2834-05-1

11-bromoundecanoic acid

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid; thiourea In water94%
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-(acetylthio)undecanoic acid

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
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-ethoxythiocarbonylmercapto-undecanoic acid

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
With ammonia
11,12-dithia-tetracosanedioic acid

11,12-dithia-tetracosanedioic acid

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; zinc
11-bromoundecanoic acid
2834-05-1

11-bromoundecanoic acid

thiourea
17356-08-0

thiourea

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
With ethanol Verseifen mit wss.-alkoh.NaOH;
11-chloroundecanoic acid
1860-44-2

11-chloroundecanoic acid

potassium ethyl xanthogenate
140-89-6

potassium ethyl xanthogenate

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
(i), (ii) (pyrolysis); Multistep reaction;
11-ethoxythiocarbonylmercapto-undecanoic acid
100912-41-2

11-ethoxythiocarbonylmercapto-undecanoic acid

aqueous alcoholic ammonia

aqueous alcoholic ammonia

A

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

B

ethylxanthogenamide

ethylxanthogenamide

1,10-undecadiene
13688-67-0

1,10-undecadiene

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
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

undecane-1,11-diol

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aq. HBr / octane
2: CrO3
4: OH(1-)
View Scheme
1-Bromo-11-hydroxyundecane
1611-56-9

1-Bromo-11-hydroxyundecane

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
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

10-undecenoic acid

aqueous KOH-solution

aqueous KOH-solution

A

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

B

ethylxanthogenamide

ethylxanthogenamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: aq. base
View Scheme
11-iodo-undecanoic acid
63632-65-5

11-iodo-undecanoic acid

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous NaHCO3; Na2S2
2: zinc; glacial acetic acid; HCl
View Scheme
10-undecenoic acid
112-38-9

10-undecenoic acid

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
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

BrH*C12H26N2O2S

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
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-bromo-undecanoic acid methyl ester

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thiourea / ethanol; water
2: sodium hydroxide / water
View Scheme
11-(acetylthio)undecanoic acid
6974-31-8

11-(acetylthio)undecanoic acid

A

ethanol
64-17-5

ethanol

B

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

Conditions
ConditionsYield
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

11-mercaptounadecanoic acid

acetyl chloride
75-36-5

acetyl chloride

11-(acetylthio)undecanoic acid
6974-31-8

11-(acetylthio)undecanoic acid

Conditions
ConditionsYield
With acetic acid; zinc In dichloromethane at 0 - 20℃; for 1h;100%
2-aminoethylimidazolidone
6281-42-1

2-aminoethylimidazolidone

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

11-mercapto-N-[2-(2-oxoimidazolidin-1-yl)ethyl]undecaneamide

11-mercapto-N-[2-(2-oxoimidazolidin-1-yl)ethyl]undecaneamide

Conditions
ConditionsYield
at 160℃; for 6h; Inert atmosphere;100%
1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]dodecane
934499-56-6

1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]dodecane

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

11-(dodec-1-yldisulfanyl)undecanoic acid

11-(dodec-1-yldisulfanyl)undecanoic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.25h;99%
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

11,11'-disulfanediyldiundecanoic acid
29265-73-4

11,11'-disulfanediyldiundecanoic acid

Conditions
ConditionsYield
With sulfuryl dichloride In dichloromethane at 0℃; for 0.1h;99%
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

trityl chloride
76-83-5

trityl chloride

11-[(triphenylmethyl)sulfanyl]undecanoic Acid
202462-83-7

11-[(triphenylmethyl)sulfanyl]undecanoic Acid

Conditions
ConditionsYield
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

11-mercaptounadecanoic acid

3-(3-bromopropyl)-1-methyl-1H-imidazol-3-ium bromide

3-(3-bromopropyl)-1-methyl-1H-imidazol-3-ium bromide

11-((3-(1-methyl-1H-imidazol-3-ium-3-yl)propyl)thio)undecanoate

11-((3-(1-methyl-1H-imidazol-3-ium-3-yl)propyl)thio)undecanoate

Conditions
ConditionsYield
With potassium carbonate In ethanol at 20℃; for 72h; Schlenk technique;98%
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

octavinylsilsesquioxane
69655-76-1

octavinylsilsesquioxane

C104H200O28S8Si8

C104H200O28S8Si8

Conditions
ConditionsYield
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

(5,5-dimethyl-2-thiono-1,3,2-dioxophosphorinanyl) sulfenyl bromide

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

11-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]undecanoic acid
1002347-32-1

11-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]undecanoic acid

Conditions
ConditionsYield
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

11-mercaptounadecanoic acid

undecylenic acid
112-37-8

undecylenic acid

Conditions
ConditionsYield
With di-tert-butyl peroxide; triethyl phosphite In diethyl ether94%
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 25℃; for 6h; Irradiation;85 %Spectr.
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

11-(10'-carboxy-decyldisulfanyl)undecanoic acid
23483-56-9

11-(10'-carboxy-decyldisulfanyl)undecanoic acid

Conditions
ConditionsYield
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

11-mercaptounadecanoic acid

tris(10-carboxydecyl) trithioarsenite

tris(10-carboxydecyl) trithioarsenite

Conditions
ConditionsYield
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

(5,5-dimethyl-2-thiono-1,3,2-dioxophosphorinanyl) sulfenyl bromide

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

C18H35O2PS3

C18H35O2PS3

Conditions
ConditionsYield
In dichloromethane at -30℃;92%
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

2-methylene-2,3-dihydrothieno[3,4-b][1,4]dioxine
1443919-53-6

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
1443919-60-5

11-((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methylthio)undecanoic acid

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In methanol at 90℃; UV-irradiation;92%
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

2-fluoro-6-methylbenzaldehyde
117752-04-2

2-fluoro-6-methylbenzaldehyde

11-((2-formyl-3-methylphenyl)thio)undecanoic acid

11-((2-formyl-3-methylphenyl)thio)undecanoic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; Schlenk technique; Inert atmosphere;91.5%
Diethyl disulfide
110-81-6

Diethyl disulfide

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

11-(11-ethyldithio)undecanoic acid
87050-15-5

11-(11-ethyldithio)undecanoic acid

Conditions
ConditionsYield
With triethylamine at 70℃; for 24h;89%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

11-mercaptoundecanoic acid 2,5-dioxopyrrolidin-1-yl ester
240125-70-6

11-mercaptoundecanoic acid 2,5-dioxopyrrolidin-1-yl ester

Conditions
ConditionsYield
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

11-mercaptounadecanoic acid

4-pyrenylbutanol
67000-89-9

4-pyrenylbutanol

4-(pyren-4-yl) butyl-11-mercaptoundecanoate

4-(pyren-4-yl) butyl-11-mercaptoundecanoate

Conditions
ConditionsYield
With hafnium/THF In toluene for 48h; Reflux; Molecular sieve;89%
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

trityl chloride
76-83-5

trityl chloride

C29H34O2S

C29H34O2S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 20h; Inert atmosphere;89%
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

acetic anhydride
108-24-7

acetic anhydride

11-(acetylthio)undecanoic acid
6974-31-8

11-(acetylthio)undecanoic acid

Conditions
ConditionsYield
In pyridine at 0 - 20℃;89%
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

2-ethoxy-4-bromothiazole

2-ethoxy-4-bromothiazole

C16H27NO3S2

C16H27NO3S2

Conditions
ConditionsYield
With C12H17O2Si(1-)*C31H49O2P*Br(1-)*Pd(2+); triethylamine In tert-butyl alcohol at 20℃; for 3h;88%
carbon disulfide
75-15-0

carbon disulfide

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

benzyl bromide
100-39-0

benzyl bromide

11-(((benzylthio)carbonothioyl)thio)undecanoic acid
939984-30-2

11-(((benzylthio)carbonothioyl)thio)undecanoic acid

Conditions
ConditionsYield
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

1,2,3-Benzotriazole

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

11-(1H-benzotriazole-1-yl)-11-oxoundecane-1-thiol
1311269-55-2

11-(1H-benzotriazole-1-yl)-11-oxoundecane-1-thiol

Conditions
ConditionsYield
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

ethanol

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

ethyl 11-mercaptoundecanoate
1725-06-0

ethyl 11-mercaptoundecanoate

Conditions
ConditionsYield
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

11-mercaptounadecanoic acid

(3R,4R)-3,4-bis(diphenylphosphanyl)pyrrolidine
99135-90-7

(3R,4R)-3,4-bis(diphenylphosphanyl)pyrrolidine

1-((3R,4R)-3,4-Bis-diphenylphosphanyl-pyrrolidin-1-yl)-11-mercapto-undecan-1-one

1-((3R,4R)-3,4-Bis-diphenylphosphanyl-pyrrolidin-1-yl)-11-mercapto-undecan-1-one

Conditions
ConditionsYield
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

11-mercaptounadecanoic acid

1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane
1262447-14-2

1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane

11-(dodec-1-yl-trisulfanyl)undecanoic acid
1262447-17-5

11-(dodec-1-yl-trisulfanyl)undecanoic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.25h; air;86%
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-propionic acid

3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-propionic acid

9H-fluoren-9-ylmethyl N-(4-aminobutyl)carbamate hydrochloride

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

11-mercapto-undecanoic acid [4-(3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-propionylamino)-butyl]-amide

Conditions
ConditionsYield
Multistep reaction;85%
Multistep reaction;
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

diethyl iodomethanephosphonate
10419-77-9

diethyl iodomethanephosphonate

11-[(diethoxyphosphoryl)thiomethyl]undecanoic acid
634158-90-0

11-[(diethoxyphosphoryl)thiomethyl]undecanoic acid

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;85%
1,6,9,12,15,18-hexachloro[C60-Ih]fullerene

1,6,9,12,15,18-hexachloro[C60-Ih]fullerene

11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

C115H106O10S5

C115H106O10S5

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

Undecanoic acid,11-mercapto- Specification

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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