methanol
3-methoxy-4-hydroxybenzoic acid
4-hydroxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride for 12h; Reflux; | 100% |
With hydrogenchloride In diethyl ether Fischer-Speier Esterification; Reflux; | 100% |
With thionyl chloride at 0 - 20℃; Inert atmosphere; | 100% |
methyl 4-(benzyloxy)-3-methoxybenzoate
4-hydroxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In various solvent(s) at 20℃; under 760 Torr; for 6h; | 95% |
Conditions | Yield |
---|---|
With perchloric acid; sodium percarbonate; vanadia for 2h; Cooling; | 94% |
With 2,2':6,2''-terpyridine; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate; sodium hydroxide at 90℃; for 24h; Green chemistry; chemoselective reaction; | 83% |
With 1-(ferrocenylbutyl)-4-(3-methylimidazolium) tetrafluoroborate; iodine; potassium carbonate at 50 - 60℃; for 22h; Inert atmosphere; | 40% |
With oxygen; methylene blue at 10 - 15℃; for 144h; Mechanism; Irradiation; also with EtOH; also without irradiation in the presence of p-toluenesulfonic acid; | |
With perchloric acid; dihydrogen peroxide; vanadia In water at 5℃; for 6h; oxidative esterification; | 83 % Chromat. |
Trimethyl orthoacetate
3-methoxy-4-hydroxybenzoic acid
4-hydroxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
microwave irradiation; | 90% |
Conditions | Yield |
---|---|
With sulfuric acid; sodium hydrogencarbonate; mercury In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate | 82% |
methanol
carbon monoxide
2-methoxy-phenol
4-hydroxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; oxygen; potassium carbonate; potassium iodide at 100℃; under 6000.6 Torr; for 18h; | 76% |
Conditions | Yield |
---|---|
With sodium hydroxide at 25℃; for 6h; | A 64% B n/a |
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
A
4-hydroxy-3-methoxybenzoic acid methyl ester
B
vanillin
C
4-hydroxy-3-methoxybenzoylacetic acid
D
1-(3-methoxy-4-hydroxyphenyl)ethanone
Conditions | Yield |
---|---|
With salcomine; oxygen In methanol at 25℃; under 7600 Torr; for 72h; | A 20% B 16% C n/a D n/a |
With salcomine; oxygen In methanol at 25℃; under 7600 Torr; for 72h; Product distribution; also with following CH2N2/ether action, other products; | A 20% B 16% C n/a D n/a |
methyl 3-methoxybenzoate
A
4-hydroxy-3-methoxybenzoic acid methyl ester
B
3-methoxymethylsalicylate
C
methyl 5-methoxy-2-hydroxybenzoate
Conditions | Yield |
---|---|
Stage #1: methyl 3-methoxybenzoate With 6,7-dichlorobenzo[d][1,2]dioxine-1,4-dione In chloroform at 50℃; for 24h; Stage #2: With water; sodium hydrogencarbonate In methanol at 50℃; for 1h; Inert atmosphere; Overall yield = 55 %; regioselective reaction; | A 20% B 18% C 17% |
diazomethane
3-methoxy-4-hydroxybenzoic acid
4-hydroxy-3-methoxybenzoic acid methyl ester
methanol
2-methoxy-4-propenylphenol
acetic anhydride
A
4-hydroxy-3-methoxybenzoic acid methyl ester
B
Acetic acid 2-methoxy-4-[1-methoxy-2-(2-methoxy-4-propyl-phenoxy)-propyl]-phenyl ester
(E)-1-<(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-1-benzofuran-5-yl>-1-propene
D
vanillin
Acetic acid 4-(2-hydroperoxy-1-methoxy-propyl)-2-methoxy-phenyl ester
Acetic acid 4-(2-acetylperoxy-1-methoxy-propyl)-2-methoxy-phenyl ester
Conditions | Yield |
---|---|
With pyridine; oxygen Mechanism; Product distribution; 1.) 10 -15 deg C, 5 d, methylene blue, irradiation, 2.) r.t., overnight; also with ethanol; |
methyl 1-(3-bromopropyl)-3-methoxy-4-ketocyclohexa-2,5-diene-1-carboxylate
A
4-hydroxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride In benzene Heating; Yields of byproduct given; | |
With tri-n-butyl-tin hydride In benzene Heating; Yield given; |
Methyl ferulate
A
4-hydroxy-3-methoxybenzoic acid methyl ester
B
vanillin
Conditions | Yield |
---|---|
With oxygen; salcomine In chloroform at 25℃; under 7500.6 Torr; for 48h; Product distribution; Mechanism; different phenols, solvents and reaction times; | A 61 % Chromat. B 39 % Chromat. |
With oxygen; [N,N'-bis(salicylidene)ethane-1,2-diaminato]cobalt(II) In chloroform at 24.84℃; under 7500.75 Torr; for 48h; Product distribution; |
hydrogenchloride
methanol
3-methoxy-4-hydroxybenzoic acid
4-hydroxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With oxygen; [N,N'-bis(salicylidene)ethane-1,2-diaminato]cobalt(II) In chloroform at 24.84℃; under 7500.75 Torr; for 48h; Product distribution; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: diluted NaOH-solution 2: diluted hydrochloric acid / 160 - 170 °C / im geschlossenen Rohr 3: HCl View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diluted hydrochloric acid / 160 - 170 °C / im geschlossenen Rohr 2: HCl View Scheme |
methanol
2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetonitrile
A
4-hydroxy-3-methoxybenzoic acid methyl ester
B
C11H13NO4
Conditions | Yield |
---|---|
With manganese(IV) oxide; water for 24h; Title compound not separated from byproducts.; |
2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetonitrile
4-hydroxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With manganese(IV) oxide; acetic acid In methanol; water for 24h; |
methanol
A
4-hydroxy-3-methoxybenzoic acid methyl ester
B
methyl syringate
C
vanillin
D
syringic aldehyde
Conditions | Yield |
---|---|
With oxygen; phosphomolybdic acid In water at 170℃; under 3825.38 Torr; |
Conditions | Yield |
---|---|
With oxygen; phosphomolybdic acid In water at 170℃; under 3825.38 Torr; |
methanol
A
4-hydroxy-3-methoxybenzoic acid methyl ester
B
2,4'-dihydroxy-3'-methoxyacetophenone
C
vanillin
Conditions | Yield |
---|---|
phosphomolybdic acid In water at 170℃; under 7500.75 Torr; Inert atmosphere; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: silver(l) oxide; sodium hydroxide / water / 3 h / 80 °C 2: sulfuric acid / 2.5 h / 100 °C / Autoclave View Scheme | |
Multi-step reaction with 2 steps 1: recombinant aldehyde dehydrogenase from bovine lens; 1,4-dithio-D,L-threitol; water‐forming NADH oxidase from Streptococcus mutans; NAD / aq. phosphate buffer / 24 h / 40 °C / pH 8.5 / Green chemistry; Enzymatic reaction 2: methanol; ethyl acetate / 1 h / 30 °C View Scheme |
3-methoxy-4-hydroxybenzoic acid
diazomethyl-trimethyl-silane
4-hydroxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
In methanol; ethyl acetate at 30℃; for 1h; |
methanol
guaiacylglycerol-β-guaiacyl ether
A
4-hydroxy-3-methoxybenzoic acid methyl ester
B
2-methoxy-phenol
Conditions | Yield |
---|---|
With oxygen; sodium hydroxide at 200℃; under 7500.75 Torr; for 10h; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave; | A 23 %Chromat. B 31 %Chromat. |
4-hydroxy-3-methoxybenzoic acid methyl ester
allyl bromide
methyl 3-methoxy-4-(2-propenoxy)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 40℃; for 16h; Inert atmosphere; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 2h; | 95% |
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Metallation; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 18h; Alkylation; | 92% |
With sodium hydride 1.) DMF, r.t., 2 h; 2.) r.t., 24 h; Multistep reaction; |
4-hydroxy-3-methoxybenzoic acid methyl ester
trifluoromethylsulfonic anhydride
3-methoxy-4-trifluoromethane-sulfonyloxy-benzoic acid methyl ester
Conditions | Yield |
---|---|
With 2,4,6-trimethyl-pyridine In dichloromethane at -78 - 20℃; for 4h; | 100% |
With pyridine In dichloromethane at 0℃; for 0.333333h; | 100% |
With pyridine In dichloromethane at 0℃; for 4h; | 99% |
4-hydroxy-3-methoxybenzoic acid methyl ester
benzyl bromide
methyl 4-(benzyloxy)-3-methoxybenzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; | 100% |
1,5-dibromo-pentane
4-hydroxy-3-methoxybenzoic acid methyl ester
1',5'-bis<2-methoxy-(4-methoxycarbonyl)phenoxy>pentane
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 3h; Inert atmosphere; | 100% |
With potassium carbonate In N,N-dimethyl-formamide for 3h; Inert atmosphere; | 7.92 g |
2-(prop-2-yn-1-yl)propane-1,3-diol
4-hydroxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 0.583333h; Inert atmosphere; Stage #2: 2-(prop-2-yn-1-yl)propane-1,3-diol In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; | 100% |
4-hydroxy-3-methoxybenzoic acid methyl ester
1,3-chlorobromopropane
methyl 4-(3-chloropropoxy)-3-methoxybenzoate
Conditions | Yield |
---|---|
With potassium carbonate; sodium chloride In acetone at 55 - 60℃; for 5h; Heating / reflux; | 99.5% |
With potassium carbonate In acetone; acetonitrile at 75 - 79℃; for 5h; Heating / reflux; | 99.3% |
With potassium chloride; potassium carbonate In acetone at 55 - 60℃; for 10h; Heating / reflux; | 98.2% |
4-hydroxy-3-methoxybenzoic acid methyl ester
2,3,4,6-tetra-O-acetyl-D-allopyranosyl N-phenyltrifluoroacetimidate
methyl 3-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-allopyranosyloxy)benzoate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 2h; Molecular sieve; | 99% |
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With potassium carbonate at 80℃; for 0.5h; Stage #2: 1-Bromodocosane at 70℃; for 15h; | 99% |
4-hydroxy-3-methoxybenzoic acid methyl ester
4-bromobutyric acid allyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 1.5h; | 99% |
4-hydroxy-3-methoxybenzoic acid methyl ester
benzyl chloride
methyl 4-(benzyloxy)-3-methoxybenzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h; | 98% |
With potassium carbonate In acetonitrile at 90℃; for 2h; Inert atmosphere; | 97% |
With potassium carbonate In acetonitrile at 20℃; for 8h; Inert atmosphere; | 81% |
With potassium carbonate; potassium iodide In acetone Inert atmosphere; Reflux; | 57% |
With potassium hydroxide |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 3h; Ambient temperature; | 98% |
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 25℃; for 2h; | 95% |
With potassium carbonate In N,N-dimethyl-formamide | 93% |
2,3-dihydro-2H-furan
methanol
4-hydroxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene at 50℃; for 1h; Diels-Alder reaction; | 98% |
With [bis(acetoxy)iodo]benzene at 50℃; for 1h; Oxidation; Diels-Alder cycloaddition; | 88% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene at 0℃; for 1h; Product distribution; Further Variations:; Temperatures; Diels-Alder reaction; | 98% |
With [bis(acetoxy)iodo]benzene at 50℃; for 1h; Diels-Alder reaction; | 98% |
4-hydroxy-3-methoxybenzoic acid methyl ester
ethyl iodide
4-ethoxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; | 98% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; Alkylation; | 82% |
With potassium carbonate In N,N-dimethyl-formamide |
4-hydroxy-3-methoxybenzoic acid methyl ester
1-iodo-propane
methyl 3-methoxy-4-propoxybenzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; | 98% |
4-hydroxy-3-methoxybenzoic acid methyl ester
Dibenzyl N,N-diisopropylphosphoramidite
Conditions | Yield |
---|---|
With 1H-tetrazole; dihydrogen peroxide In dichloromethane; water at 0 - 20℃; for 1h; | 98% |
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In dichloromethane; acetonitrile at 20℃; for 8h; Stage #2: With dihydrogen peroxide In dichloromethane; acetonitrile at 20℃; for 2h; | 97% |
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In dichloromethane; acetonitrile at 20℃; for 8h; Stage #2: With dihydrogen peroxide In dichloromethane; acetonitrile at 0 - 20℃; for 2h; | 97% |
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In dichloromethane; acetonitrile at 20℃; for 8h; Stage #2: With dihydrogen peroxide In dichloromethane; acetonitrile at 0 - 20℃; for 2h; |
4-hydroxy-3-methoxybenzoic acid methyl ester
1-Bromo-2-chloroethane
4-(2-Chloro-ethoxy)-5-methoxy-benzoic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80 - 85℃; for 8h; Heating / reflux; | 97.8% |
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 3h; | 97% |
ethyl bromide
4-hydroxy-3-methoxybenzoic acid methyl ester
4-ethoxy-3-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 2h; | 97% |
4-hydroxy-3-methoxybenzoic acid methyl ester
4-bromo-2-fluorobenzyl bromide
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 4-bromo-2-fluorobenzyl bromide In N,N-dimethyl-formamide at 20℃; | 96% |
4-hydroxy-3-methoxybenzoic acid methyl ester
1-chloro-2-(2-methoxyethoxy)ethane
3-methoxy-4-[2-(2-methoxyethoxy)ethoxy]benzoic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 24h; | 96% |
Conditions | Yield |
---|---|
With potassium phosphate; trifluoromethylsulfonic anhydride; methanesulfonato(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II) In water; toluene at 120℃; Flow reactor; | 96% |
Conditions | Yield |
---|---|
Stage #1: methanol; 4-hydroxy-3-methoxybenzoic acid methyl ester With iodobenzene; 3-chloro-benzenecarboperoxoic acid Stage #2: methyl vinyl ketone In methanol at 20℃; for 0.5h; Diels-Alder Cycloaddition; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; | 96% |
4-hydroxy-3-methoxybenzoic acid methyl ester
tert-butyl N-(2-chloroethyl)carbamate
methyl 4-{2-[(tert-butoxycarbonyl)amino]ethoxy}-3-methoxybenzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; | 96% |
4-hydroxy-3-methoxybenzoic acid methyl ester
methyl 4-(cyclopropylmethoxy)-3-methoxybenzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 170℃; for 1h; Microwave irradiation; Sealed tube; | 96% |
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-bromomethyl-4-bromobenzene In N,N-dimethyl-formamide at 20℃; | 95% |
4-hydroxy-3-methoxybenzoic acid methyl ester
1-chloro-3,6,9-trioxadecane
3-methoxy-4-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}benzoic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 24h; | 95% |
4-hydroxy-3-methoxybenzoic acid methyl ester
2-(trifluoromethoxy)ethyl trifluoromethanesulphonate
methyl 3-methoxy-4-(2-(trifluoromethoxy)ethoxy)benzoate
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.666667h; Inert atmosphere; Stage #2: 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate In N,N-dimethyl-formamide; mineral oil at 0 - 40℃; for 0.666667h; | 95% |
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With sodium hydride In N,N-dimethyl-formamide Inert atmosphere; Stage #2: 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate In N,N-dimethyl-formamide at 20 - 50℃; for 4h; |
Molecular Formula: C9H10O4
Formula Weight: 182.17
EINECS: 223-525-9
Index of Refraction: 1.534
Molar Refractivity: 46.58 cm3
Molar Volume: 149.7 cm3
Surface Tension: 43.1 dyne/cm
Density: 1.216 g/cm3
Flash Point: 120.2 °C
Enthalpy of Vaporization: 54.61 kJ/mol
Boiling Point: 286 °C at 760 mmHg
Vapour Pressure: 0.00157 mmHg at 25 °C
Melting point: 64-67 °C(lit.)
Appearance: Pale yellow to beige powder and granules
Structure of Methyl vanillate (CAS NO.3943-74-6):
IUPAC Name: Methyl 4-hydroxy-3-methoxybenzoate
Canonical SMILES: COC1=C(C=CC(=C1)C(=O)OC)O
InChI: InChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3
InChIKey: BVWTXUYLKBHMOX-UHFFFAOYSA-N
Product Category of Methyl vanillate (CAS NO.3943-74-6): Fine Chemical & intermediates;Aromatic Esters
1. | ivn-mus LD50:180 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#06782 . |
Methyl vanillate (CAS NO.3943-74-6) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65. You can see actual entry in RTECS for complete information.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S24/25:Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
Methyl vanillate , its cas register number is 3943-74-6. It also can be called Methyl 4-hydroxy-3-methoxybenzoate ; 4-Hydroxy-3-methoxybenzoic acid methyl ester ; and Vanillic acid, methyl ester . It should be stored in a cool, dry, well-ventilated area away from incompatible substances. It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately.
In addition, Methyl vanillate (CAS NO.3943-74-6) could be stable under normal temperatures and pressures. You must not take it with strong oxidants. And also prevent it to broken down into hazardous decomposition products: irritating and toxic fumes and gases.
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