(5-methoxy-2-((4-methoxyphenyl)ethynyl)phenyl)(methyl)-sulfane
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With trifluoroacetic acid; silver(l) oxide at 25℃; for 1.5h; Schlenk technique; | 89% |
6-methoxy-benzo[b]thiophene
para-iodoanisole
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With dichloro(2,2'-bipyridine)nickel(II); lithium hexamethyldisilazane In 2-methyltetrahydrofuran at 120℃; for 16h; Schlenk technique; Sealed tube; Inert atmosphere; Glovebox; regiospecific reaction; | 85% |
With palladium diacetate; silver trifluoroacetate; trifluoroacetic acid In water at 20℃; for 48h; Inert atmosphere; | 60% |
para-iodoanisole
6-methoxy-benzo[b]thiophen-2-yl boronic acid
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water at 110℃; for 12h; Suzuki coupling; Ionic liquid; Inert atmosphere; | 81% |
With sodium carbonate; tetrakis(triphenylphosphine)palladium (0) In toluene | 1.25 g (96%) |
6-methoxy-2-iodobenzo[b]thiophene
4-methoxyphenylboronic acid
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
80% |
α-(3-methoxyphenyl-thio)-4-methoxyacetophenone
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Stage #1: α-(3-methoxyphenyl-thio)-4-methoxyacetophenone In toluene under 760.051 Torr; for 2h; Reflux; Inert atmosphere; Dean-Stark; Large scale; Stage #2: With methanesulfonic acid In toluene at 90℃; for 4h; Inert atmosphere; Large scale; Stage #3: In n-heptane; toluene at 80 - 90℃; for 4h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Large scale; | 79.6% |
With PPA at 85 - 95℃; for 1.25h; | |
With polyphosphoric acid at 90℃; for 1h; Inert atmosphere; | |
With PPA |
4-methoxyphenylacetylen
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With eosin y In dimethyl sulfoxide for 14h; Irradiation; | 70% |
With titanium(III) chloride In N,N-dimethyl-formamide at -25 - 20℃; Cycloaddition; | 60% |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With Octanethiol; trifluorormethanesulfonic acid In dichloromethane at 40℃; for 12h; | 70% |
α-(3-methoxyphenyl-thio)-4-methoxyacetophenone
A
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
B
2-(4'-methoxyphenyl)-4-methoxybenzo[b]thiophene
Conditions | Yield |
---|---|
With PPA at 85 - 90℃; for 1h; | A 69% B n/a |
With PPA at 70℃; | A 68% B 23% |
With PPA Heating; Yield given; Yields of byproduct given; | |
With polyphosphoric acid at 65 - 90℃; for 2h; Product distribution / selectivity; |
6-methoxy-benzo[b]thiophene
1-bromo-4-methoxy-benzene
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With potassium acetate; {1,3-bis(2,6-diethylaniline)acenaphthylenyl-4,5-imidazolium-2-ylidene}PdCl2-(pyridine) In N,N-dimethyl acetamide at 130℃; for 12h; Inert atmosphere; Sealed tube; | 67% |
2-fluoro-4-methoxy-benzaldehyde
p-methoxybenzylmercaptan
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60 - 160℃; for 66h; | 55% |
4-Methoxy-2-methylsulfenylaniline
phenylacetylene
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With tert.-butylnitrite In nitromethane at 80℃; for 12h; Schlenk technique; Inert atmosphere; | 50% |
4-methoxyphenylboronic acid
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) at 100℃; for 4h; Yield given; |
1-bromo-4-methoxy-benzene
6-methoxy-benzo[b]thiophen-2-yl boronic acid
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate Suzuki coupling reaction; |
6-methoxy-benzo[b]thiophene
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: BuLi 1.2: B(OiPr)3 1.3: HCl 2.1: Na2CO3; Pd(PPh3)4 View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 2.08 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: N-Bromosuccinimide / tetrahydrofuran; hexane / 3 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere View Scheme |
3-methoxybenzenethiol
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: K2CO3 / acetone 1.2: BF3*Et2O 2.1: BuLi 2.2: B(OiPr)3 2.3: HCl 3.1: Na2CO3; Pd(PPh3)4 View Scheme |
6-methoxybenzothiazol-2-ylamine
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: aq. KOH / 17 h / Heating 1.2: 92 percent / 1 h / 20 °C 2.1: aq. HCl; NaNO2 2.2: 57 percent / aq. HBF4 / 0 - 20 °C 3.1: 60 percent / TiCl3 / dimethylformamide / -25 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium hydroxide / water / 17 h / Reflux 1.2: 1 h / 20 °C 2.1: fluoroboric acid; sodium nitrite / water / 0.67 h / 0 - 5 °C / Enzymatic reaction 3.1: eosin y / dimethyl sulfoxide / 14 h / Irradiation View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide; methyl iodide 2: tert.-butylnitrite / nitromethane / 12 h / 80 °C / Schlenk technique; Inert atmosphere View Scheme |
4-Methoxy-2-methylsulfenylaniline
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: aq. HCl; NaNO2 1.2: 57 percent / aq. HBF4 / 0 - 20 °C 2.1: 60 percent / TiCl3 / dimethylformamide / -25 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: fluoroboric acid; sodium nitrite / water / 0.67 h / 0 - 5 °C / Enzymatic reaction 2: eosin y / dimethyl sulfoxide / 14 h / Irradiation View Scheme |
4-methoxy-aniline
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 62 percent / Br2; AcOH / 0.75 h / 20 °C 2.1: aq. KOH / 17 h / Heating 2.2: 92 percent / 1 h / 20 °C 3.1: aq. HCl; NaNO2 3.2: 57 percent / aq. HBF4 / 0 - 20 °C 4.1: 60 percent / TiCl3 / dimethylformamide / -25 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: 51 percent / CuI / o-xylene / 94 h / 145 °C 2.1: aq. HCl; NaNO2 2.2: 57 percent / aq. HBF4 / 0 - 20 °C 3.1: 60 percent / TiCl3 / dimethylformamide / -25 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: acetic acid; bromine / 3 h / 10 °C 2.1: potassium hydroxide / water / 17 h / Reflux 2.2: 1 h / 20 °C 3.1: fluoroboric acid; sodium nitrite / water / 0.67 h / 0 - 5 °C / Enzymatic reaction 4.1: eosin y / dimethyl sulfoxide / 14 h / Irradiation View Scheme |
1-(1,1-Dichloro-ethyl)-4-methoxy-benzene
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaNH2; NH3 2: 60 percent / TiCl3 / dimethylformamide / -25 - 20 °C View Scheme |
1-(4-methoxyphenyl)ethanone
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: PCl5 / benzene 2: NaNH2; NH3 3: 60 percent / TiCl3 / dimethylformamide / -25 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: bromine / methanol / 2.5 h / 10 °C 1.2: 4 h / 0 - 20 °C 2.1: polyphosphoric acid / 2 h / 65 - 90 °C View Scheme |
3-methoxybenzenethiol
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOH / ethanol 2: polyphosphoric acid / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 80 percent / KOH / aq. ethanol; ethyl acetate / 3 h / Ambient temperature 2: 68 percent / polyphosphoric acid / 70 °C View Scheme | |
Multi-step reaction with 2 steps 1: 80.4 percent / KOH / ethanol; H2O; ethyl acetate / Ambient temperature 2: 69 percent / PPA / 1 h / 85 - 90 °C View Scheme |
2-Bromo-4'-methoxyacetophenone
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOH / ethanol 2: polyphosphoric acid / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 80 percent / KOH / aq. ethanol; ethyl acetate / 3 h / Ambient temperature 2: 68 percent / polyphosphoric acid / 70 °C View Scheme | |
Multi-step reaction with 2 steps 1: 80.4 percent / KOH / ethanol; H2O; ethyl acetate / Ambient temperature 2: 69 percent / PPA / 1 h / 85 - 90 °C View Scheme |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 1.5h; Heating / reflux; | |
With toluene-4-sulfonic acid In toluene for 6h; Heating / reflux; |
3-methoxybenzenethiol
2-Bromo-4'-methoxyacetophenone
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With potassium hydroxide; PPA In ethanol; water; ethyl acetate | |
With potassium hydroxide; PPA In ethanol; water; ethyl acetate |
Lawessons reagent
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With methanesulfonic acid In chlorobenzene | |
With methanesulfonic acid In chlorobenzene |
4-methoxybenzo[b]thiophene
acetophenone
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With PPA; phosphoric acid In water; toluene |
3-methoxybenzenethiol
2-Bromo-4'-methoxyacetophenone
A
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
B
α-(3-methoxyphenyl-thio)-4-methoxyacetophenone
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water; Petroleum ether | A 78.5 g (76%) B n/a |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
1,2-bis(4-methoxyphenyl)ethane
Conditions | Yield |
---|---|
W-2 Raney Ni In ethanol for 0.5h; Heating; | 100% |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene
Conditions | Yield |
---|---|
With bromine In chloroform at 60℃; | 100% |
With bromine In chloroform at 60℃; | 100% |
With N-Bromosuccinimide In tetrahydrofuran at 0 - 20℃; for 3h; | 97% |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
4-chlorobenzoyl chloride
4-Bromophenyl-[6-methoxy-2-(4-methoxy-phenyl)benzo[b]thien-3-yl]methanone
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0 - 25℃; for 3.5h; Friedel-Crafts Acylation; | 96% |
With copper(II) bis(trifluoromethanesulfonate) at 100℃; for 2h; Friedel Crafts acylation; Ionic liquid; Inert atmosphere; | 79% |
With aluminium trichloride In dichloromethane | 65% |
4-(2-chloro-ethoxy)-benzoyl chloride
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 50℃; for 12h; Friedel-Crafts Acylation; Inert atmosphere; | 95% |
acetic anhydride
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
6-acetoxy-2-(4-acetoxyphenyl)benzo[b]thiophene
Conditions | Yield |
---|---|
Stage #1: 2-(4'-methoxyphenyl)-6-methoxybenzothiophene With pyridine; hydrogenchloride; tributyl-amine at 170 - 180℃; Stage #2: With water In ethyl acetate for 0.25h; Stage #3: acetic anhydride With triethylamine In ethyl acetate at 25 - 65℃; for 1h; | 91.1% |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
Stage #1: C15H24N3O2S(1+)*F6Sb(1-); 2-(4'-methoxyphenyl)-6-methoxybenzothiophene In acetonitrile at 70℃; for 16h; Inert atmosphere; Stage #2: sodium hexafluoroantimonate In dichloromethane; water for 0.0833333h; Inert atmosphere; regioselective reaction; | 90% |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
6-hydroxy-2-(4-hydroxyphenyl)benzo[B]-thiophene
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at 0 - 5℃; | 89.3% |
With pyridine hydrochloride at 190℃; for 1h; | 87% |
With pyridine hydrochloride at 180℃; for 1h; | 87% |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
3,4,5-triethoxybenzoyl chloride
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane for 0.5h; | 88% |
AlCl3 In dichloromethane; water | |
aluminum (III) chloride In dichloromethane for 0.75h; |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
dimethyl sulfoxide
Conditions | Yield |
---|---|
Stage #1: 2-(4'-methoxyphenyl)-6-methoxybenzothiophene; dimethyl sulfoxide With trifluoromethylsulfonic anhydride In dichloromethane at -30 - 20℃; for 1.75h; Inert atmosphere; Stage #2: With diethylamine In dichloromethane at 20℃; for 6h; Inert atmosphere; | 88% |
4-fluorobenzoyl chloride
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
6-methoxy-2-(4-methoxyphenyl)-3-(4-fluorobenzoyl)benzo[b]thiophene
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0℃; for 72h; Inert atmosphere; | 87% |
With aluminium trichloride In dichloromethane | 74% |
With aluminum (III) chloride In dichloromethane for 18h; Friedel-Crafts Acylation; Inert atmosphere; | 69% |
4-azidobenzoyl chloride
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
3-(4-Azidobenzoyl)-6-methoxy-2-(4-methoxyphenyl)benzothiophene
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 20℃; for 5.5h; in the dark; | 82% |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
3,4-dimethoxybenzoic acid chloride
Conditions | Yield |
---|---|
aluminum (III) chloride In dichloromethane for 7h; | 76% |
aluminum (III) chloride In dichloromethane for 7h; | 76% |
AlCl3 In dichloromethane; water |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
ethyl 4-(chlorocarbonyl)benzoate
3-<(4'-ethoxycarbonyl)benzoyl>-6-methoxy-2-(4-methoxyphenyl)benzothiophene
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane for 12h; | 73% |
4-fluorobenzoyl chloride
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; for 18h; Friedel-Crafts Acylation; Inert atmosphere; | 70% |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
benzenesulfonic acid-4-[6-methoxy-2-(4-methoxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenyl ester
Conditions | Yield |
---|---|
iron(III) sulfate pentahydrate; iron In toluene at 100 - 111℃; for 5.5h; Product distribution / selectivity; | 66.4% |
Stage #1: 2-(4'-methoxyphenyl)-6-methoxybenzothiophene; p-benzenesulfonyloxybenzoyl chloride; iron(III) sulfate pentahydrate; iron In toluene at 99 - 114℃; Stage #2: With sodium hydroxide In water; toluene at 62 - 66℃; Product distribution / selectivity; Inert atmosphere; | 66.4% |
With iron; iron(III) sulfate pentahydrate In toluene at 98 - 111℃; for 16.5h; Product distribution / selectivity; Inert atmosphere; | 66.4% |
iron(III) chloride In toluene at 23 - 63℃; for 6h; Product distribution / selectivity; Friedel Crafts Acylation; |
3,4,5-Trimethoxybenzoyl chloride
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane for 5h; | 63% |
With aluminium trichloride In dichloromethane | |
AlCl3 In dichloromethane; water | |
aluminum (III) chloride In dichloromethane for 5h; |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
2,6-dimethoxybenzoyl chloride
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane for 6h; | 60% |
With aluminium trichloride In dichloromethane | |
AlCl3 In dichloromethane; water | |
aluminum (III) chloride In dichloromethane for 6h; |
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
4-iodobenzoic acid chloride
(4-iodophenyl)(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)methanone
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; for 24h; Friedel-Crafts Acylation; Inert atmosphere; | 60% |
With aluminum (III) chloride In dichloromethane for 3h; |
4-(toluene-4-sulfonyloxy)-benzoyl chloride
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
toluene-4-sulfonic acid 4-[6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carbonyl]phenyl ester
Conditions | Yield |
---|---|
iron(III) sulfate pentahydrate; iron In toluene for 10.5h; Reflux; | 58.4% |
iron(III) sulfate pentahydrate; iron In toluene for 10.5h; Friedel Crafts Acylation; Reflux; | |
Stage #1: 4-(toluene-4-sulfonyloxy)-benzoyl chloride; 2-(4'-methoxyphenyl)-6-methoxybenzothiophene; iron(III) sulfate pentahydrate; iron In toluene for 10.5h; Reflux; Stage #2: With sodium hydroxide In water; toluene at 60 - 70℃; for 0.75h; Product distribution / selectivity; | |
With iron; iron(III) sulfate pentahydrate In toluene for 10.5h; Reflux; |
6-bromohexanoyl chloride
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
3-(6-bromohexanoyl)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen
Conditions | Yield |
---|---|
With aluminium trichloride In 1,2-dichloro-ethane for 1h; Ambient temperature; | 55% |
AlCl3 In 1,2-dichloro-ethane | 55% |
The 6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene is an organic compound with the formula C16H14O2S. The IUPAC name of this chemical is 6-methoxy-2-(4-methoxyphenyl)-1-benzothiophene. With the CAS registry number 63675-74-1, it is also named as benzo[b]thiophene, 6-methoxy-2-(4-methoxyphenyl)-. The product's categories are Benzothiophenes; Building Blocks; Heterocyclic Building Blocks. It is almost white crystals should be sealed in the container, stored in the cool and dry place and avoided direct sunshine.
The other characteristics of 6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene can be summarized as: (1)ACD/LogP: 5.87; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 2; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 3; (6)Polar Surface Area: 46.7 Å2; (7)Index of Refraction: 1.629; (8)Molar Refractivity: 80.42 cm3; (9)Molar Volume: 226.3 cm3; (10)Polarizability: 31.88×10-24 cm3; (11)Surface Tension: 43.4 dyne/cm; (12)Enthalpy of Vaporization: 66.53 kJ/mol; (13)Vapour Pressure: 2.19E-07 mmHg at 25°C; (14)Rotatable Bond Count: 3; (15)Exact Mass: 270.07145; (16)MonoIsotopic Mass: 270.07145; (17)Topological Polar Surface Area: 46.7; (18)Heavy Atom Count: 19; (19)Complexity: 289.
People can use the following data to convert to the molecule structure.
1. SMILES:O(c3ccc(c2sc1cc(OC)ccc1c2)cc3)C
2. InChI:InChI=1/C16H14O2S/c1-17-13-6-3-11(4-7-13)15-9-12-5-8-14(18-2)10-16(12)19-15/h3-10H,1-2H3
3. InChIKey:HRWAGCVMOGWQJF-UHFFFAOYAU
4. Std. InChI:InChI=1S/C16H14O2S/c1-17-13-6-3-11(4-7-13)15-9-12-5-8-14(18-2)10-16(12)19-15/h3-10H,1-2H3
5. Std. InChIKey:HRWAGCVMOGWQJF-UHFFFAOYSA-N
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