Conditions | Yield |
---|---|
With trichlorosilane; N,N-dimethyl-formamide In dichloromethane at 0℃; for 6h; | 100% |
Stage #1: 4-methoxy-benzaldehyde With Dimethylphenylsilane; copper(l) chloride In various solvent(s) at 20℃; for 42h; Reduction; Stage #2: With water; toluene-4-sulfonic acid In various solvent(s) at 20℃; Hydrolysis; | 100% |
With tri-n-butyl-tin hydride; phenylboronic acid In dichloromethane at 20℃; for 20h; | 100% |
Conditions | Yield |
---|---|
With pyridine; 3-carboxypyridinium dichromate In dichloromethane for 0.333333h; Product distribution; Ambient temperature; other reagents and ratio of reagents; | 100% |
Conditions | Yield |
---|---|
With methylamine at 60℃; for 10h; | A 100% B n/a |
Conditions | Yield |
---|---|
With methylamine at 60℃; for 10h; | A 100% B n/a |
trimethyl(4-methoxybenzyloxy)silane
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With iodine In methanol microwave irradiation; | 100% |
With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.0166667h; | 98% |
With Nafion-H(R); silica gel In hexane at 20℃; for 0.25h; | 98% |
tert-butyl((4-methoxybenzyl)oxy)dimethylsilane
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With iodine In methanol microwave irradiation; | 100% |
With 2,6-disulphated cellulose In methanol at 25℃; for 0.5h; Catalytic behavior; Solvent; Time; Green chemistry; | 97% |
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 3h; | 97% |
2-(4-methoxy-benzyloxy)-tetrahydro-pyran
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With aluminium trichloride; 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate; (3,4-dimethoxyphenyl)methanol for 0.0333333h; | 100% |
With sulfuric acid; silica gel In methanol at 20℃; for 0.5h; | 98% |
With methanol at 20℃; for 0.5h; | 98% |
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With water | 100% |
Conditions | Yield |
---|---|
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave; | 99.8% |
With 2-pyrrolidinon; samarium diiodide Reagent/catalyst; Glovebox; | 99% |
With dimethylsulfide borane complex In 2-methyltetrahydrofuran at 90℃; under 7500.75 Torr; for 0.333333h; Inert atmosphere; Flow reactor; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With methanol; potassium permanganate at 25℃; chemoselective reaction; | 99% |
With zirconocene dichloride; diisobutylaluminium hydride In tetrahydrofuran at -20℃; Inert atmosphere; regioselective reaction; | 97% |
Stage #1: p-methoxybenzyl acetate With phenylsilane; fac-[Mn-(xantphos)(CO)3Br] at 100℃; for 6h; Inert atmosphere; Stage #2: With water; sodium hydroxide In methanol at 20℃; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With iron(III) sulfate; water In toluene at 110℃; for 0.7h; Ionic liquid; | 99% |
With oxygen; eosin y In dimethyl sulfoxide at 25℃; for 12h; Irradiation; | 81% |
With water; dimethyl sulfoxide at 50℃; for 24h; Schlenk technique; Sealed tube; | 72% |
Conditions | Yield |
---|---|
With iron(III) sulfate; water In toluene at 110℃; for 0.7h; Ionic liquid; | 99% |
With water; silica gel; sodium iodide In acetone at 20℃; for 24h; Irradiation; | 86% |
With water In acetone at 25℃; Rate constant; various ratios of solvents; |
4,4,5,5-tetramethyl-2-((4-methoxylbenzyl)oxy)-1,3,2-dioxaborolane
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With silica gel In ethyl acetate; Petroleum ether | 99% |
With silica gel at 25℃; Inert atmosphere; Glovebox; | 95% |
With silica gel In methanol for 4h; Reflux; | 95% |
Conditions | Yield |
---|---|
With Ximenia american In aq. phosphate buffer; water at 30℃; for 72h; pH=7; Enzymatic reaction; | A n/a B 98% |
Stage #1: 4-methoxy-benzaldehyde With potassium hydroxide for 0.0833333h; Cannizzaro Reaction; Milling; Inert atmosphere; Sealed tube; Green chemistry; Stage #2: With hydrogenchloride In water Green chemistry; | A 95% B 94% |
With sodium hydroxide In water at 15℃; for 2h; Cannizzaro Reaction; | A 91% B n/a |
Conditions | Yield |
---|---|
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.133333h; | 98% |
With sodium tetrahydroborate; lithium perchlorate In acetonitrile for 0.416667h; | 93% |
With zinc(II) tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In diethyl ether at 0℃; for 0.5h; | 89% |
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In tetrahydrofuran for 3.7h; Ambient temperature; | 88% |
With sodium tetrahydroborate; potassium carbonate In dichloromethane; water at 0 - 15℃; chemoselective reaction; |
Conditions | Yield |
---|---|
With diisobutylaluminum borohydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; | 98% |
With chloro-trimethyl-silane; Benzyltriethylammonium borohydride In dichloromethane at 25℃; for 4.5h; | 97% |
With [Zn(BH4)2(py)] In tetrahydrofuran for 6.6h; Heating; | 96% |
(S)-2,3-bis(tert-butyldimethylsilyloxy)propyl 4-methoxybenzoate
A
4-Methoxybenzyl alcohol
B
(S)-2,3-bis(tert-butyldimethylsilyloxy)propan-1-ol
Conditions | Yield |
---|---|
Stage #1: (S)-2,3-bis(tert-butyldimethylsilyloxy)propyl 4-methoxybenzoate With diisobutylaluminium hydride In hexane; dichloromethane for 0.833333h; Stage #2: With methanol In hexane; dichloromethane for 0.0833333h; | A n/a B 98% |
Conditions | Yield |
---|---|
With samarium diiodide; water In tetrahydrofuran at 23℃; for 0.0833333h; Reagent/catalyst; Inert atmosphere; Schlenk technique; chemoselective reaction; | 98% |
With samarium diiodide; water; triethylamine In tetrahydrofuran at 23℃; for 18h; Inert atmosphere; chemoselective reaction; | 92% |
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique; | 82% |
4-methoxy-1-[(ethoxymethoxy)methyl]benzene
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
phosphotungstic acid In ethanol for 4h; Heating; | 97% |
With 1-methylimidazole hydrogen sulfate at 50℃; for 1.25h; chemoselective reaction; | 92% |
Conditions | Yield |
---|---|
With lithium borohydride In diethyl ether; toluene at 100℃; for 2h; | 96% |
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Glovebox; Autoclave; | 94% |
With ethandithiol; sodium tetrahydroborate In tetrahydrofuran for 24h; Heating; | 88% |
diethylzinc
4-methoxy-benzaldehyde
A
(S)-1-(4-methoxyphenyl)propanol
B
(R)-1-(4'-methoxyphenyl)-1-propanol
C
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With (1S)-(+)-3-exo-(dimethylamino)isoborneol In toluene at 0℃; for 12h; Yields of byproduct given. Title compound not separated from byproducts; | A 96% B n/a C 2% |
With (S)-12-(hydroxymethyl)-14-methyl-1(5,8)-quinolina-4(1,4)-benzenacyclohexaphane In toluene at 20℃; for 17h; Title compound not separated from byproducts; | A n/a B n/a C 5% |
With (P,P)-(+)-bis[5]helicene diol In toluene for 48h; Product distribution; Addition; | |
With (-)-8-(9H-fluoren-9-ylidene)-1-(2-hydroxyphenyl)-7-methyl-5,6,7,8-tetrahydronaphthalen-2-ol In hexane; toluene at 0℃; for 168h; Schlenk technique; Inert atmosphere; enantioselective reaction; | A n/a B n/a C n/a |
Conditions | Yield |
---|---|
bis(benzene)chromium(0) In benzene at 70℃; for 3h; Reduction; | A 95% B n/a |
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With cerium(IV) triflate; water In acetonitrile at 25℃; | 95% |
(4-methoxyphenyl)methyl picolinate
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With zinc diacetate In methanol; dichloromethane at 20℃; for 4h; | 95% |
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 30℃; for 1h; | 95% |
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With sodium hydroxide In water Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With sodium hydride; sodium iodide; zinc(II) iodide In tetrahydrofuran; mineral oil at 40℃; for 12h; Sealed tube; | 95% |
With samarium diiodide; water; triethylamine In tetrahydrofuran at 23℃; for 0.0833333h; Reagent/catalyst; Inert atmosphere; Schlenk technique; chemoselective reaction; | 86% |
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With cerium(III) chloride In acetonitrile for 3h; Heating; | 94% |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 24h; | 94% |
2-aminopyridine
4-Methoxybenzyl alcohol
2-(4-methoxybenzylamino)pyridine
Conditions | Yield |
---|---|
With dichloro-[1,3-bis(2,4-dimethylbenzyl)perhydrobenzimidazol-2-ylidene](p-cymene)ruthenium(II); potassium tert-butylate at 120℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube; | 100% |
With iron(II,III) oxide; potassium tert-butylate In 1,4-dioxane at 90℃; for 168h; Inert atmosphere; | 99% |
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With dichloro-[1,3-bis(4-tert-butylbenzyl)perhydrobenzimidazol-2-ylidene](p-cymene)ruthenium(II); potassium tert-butylate at 120℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube; | 100% |
With copper; potassium hydroxide In toluene at 180℃; for 36h; Inert atmosphere; | 99% |
With zinc(II) nitrate hexahydrate; potassium tert-butylate In toluene at 140℃; for 36h; Sealed tube; Inert atmosphere; Schlenk technique; | 98% |
Conditions | Yield |
---|---|
Stage #1: formic acid With silica gel at 20℃; for 0.0166667h; Stage #2: 4-Methoxybenzyl alcohol With silica gel at 110℃; for 0.0166667h; | 100% |
With aminopropylated mesoporous SBA-15 silica at 40℃; for 0.0833333h; Neat (no solvent); chemoselective reaction; | 95% |
With iodine at 20℃; for 0.116667h; neat (no solvent); | 94% |
Conditions | Yield |
---|---|
With hydrogen bromide In benzene at 78℃; for 1h; Bromination; | 100% |
With hydrogen bromide In benzene at 78℃; for 1h; | 100% |
With phosphorus tribromide In diethyl ether at 0℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With 2,2'-bipyridylchromium peroxide In benzene for 0.8h; Heating; | 100% |
With tris(4-methylphenyl)bismuthine oxide In toluene for 2h; Ambient temperature; | 100% |
With 2,2'-bipyridylchromium peroxide In benzene for 0.8h; Product distribution; Heating; effect of various chromium(VI) based oxidants; | 100% |
Conditions | Yield |
---|---|
With Au NCs/TiO2; oxygen; sodium hydroxide In water at 80℃; under 7500.75 Torr; for 6h; Autoclave; Green chemistry; | 100% |
With palladium 10% on activated carbon; water; sodium hydroxide at 80℃; under 600.06 Torr; for 6h; | 100% |
With gold oxide; oxygen; copper(II) oxide; sodium hydroxide; silver(l) oxide In water at 40℃; under 750.075 Torr; for 16h; | 100% |
Conditions | Yield |
---|---|
With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane at 20℃; Substitution; | 100% |
With thionyl chloride; triethylamine In dichloromethane at -10 - 0℃; for 4.25h; Large scale; | 99% |
With oxalyl dichloride; 1-methyl-3-(2-(3-methyl-2-oxoimidazolidin-1-yl)ethyl)-1H-imidazol-3-ium hexafluorophosphate at 20 - 60℃; for 24h; Reagent/catalyst; | 99% |
itaconic acid anhydride
4-Methoxybenzyl alcohol
4-((4-methoxybenzyl)oxy)-2-methylene-4-oxobutanoic acid
Conditions | Yield |
---|---|
In hexane; toluene at 60℃; for 36h; Inert atmosphere; | 100% |
at 55 - 60℃; for 40h; | 90% |
In hexane; toluene at 60℃; for 36h; | 88% |
1,1,1,3,3,3-hexamethyl-disilazane
4-Methoxybenzyl alcohol
trimethyl(4-methoxybenzyloxy)silane
Conditions | Yield |
---|---|
With N,N'-diiodo-N,N'-1,2-ethanediylbis(p-toluenesulphonamide) for 0.0166667h; Microwave irradiation; | 100% |
With asymmetric salen type di-Schiff base-based zinc complex supported on Fe3O4 nanoparticles at 20℃; for 0.133333h; | 100% |
With Nafion SAC-13 at 20℃; for 0.05h; | 99% |
Conditions | Yield |
---|---|
With Amberlyst-15 In dichloromethane for 2.5h; Reflux; | 100% |
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide at 20℃; for 3h; chemoselective reaction; | 91% |
With sulfated tungstate at 80℃; for 2h; Green chemistry; | 80% |
Conditions | Yield |
---|---|
at 20℃; for 0.0833333h; Neat (no solvent); | 100% |
With lanthanum(III) nitrate at 20℃; for 0.166667h; | 90% |
With pyridine In diethyl ether for 2h; Reflux; Inert atmosphere; | 85% |
With pyridine In benzene Ambient temperature; |
trichloroacetonitrile
4-Methoxybenzyl alcohol
O-(4-methoxybenzyl)-trichloroacetimidate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexane at 0℃; for 0.25h; Solvent; | 100% |
Stage #1: 4-Methoxybenzyl alcohol With sodium hydride In diethyl ether at 20℃; for 0.25h; Inert atmosphere; Stage #2: trichloroacetonitrile In diethyl ether at 0℃; | 98% |
Stage #1: 4-Methoxybenzyl alcohol With sodium hydride In diethyl ether at 20℃; for 0.5h; Stage #2: trichloroacetonitrile In diethyl ether at 0 - 20℃; Further stages.; | 96% |
Conditions | Yield |
---|---|
In dichloromethane for 15h; Ambient temperature; | 100% |
(3S,4aR,6R,8aR)-6-Methoxy-8a-methyl-1-oxo-3-pent-4-enyl-decahydro-naphthalene-2-carboxylic acid methyl ester
4-Methoxybenzyl alcohol
(3S,4aR,6R,8aR)-6-Methoxy-8a-methyl-1-oxo-3-pent-4-enyl-decahydro-naphthalene-2-carboxylic acid 4-methoxy-benzyl ester
Conditions | Yield |
---|---|
100% |
4-Methoxybenzyl alcohol
(3-iodo-4-methoxyphenyl)methanol
Conditions | Yield |
---|---|
With tetramethylammonium dibromoiodate(I) at 20℃; for 0.166667h; | 100% |
With N-iodosaccharine In acetonitrile at 20℃; for 12h; Iodination; | 92% |
With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichloroiodate at 20℃; for 0.166667h; | 91% |
With Genapol LRO; iodine; Selectfluor In water at 20℃; for 18h; | 49% |
Conditions | Yield |
---|---|
With 2,3'-bipyridine; ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol at 20℃; for 24h; | 100% |
With ammonium hydroxide; iodine at 60℃; for 2h; | 99% |
With ammonium hydroxide; iodine at 60℃; for 2h; | 99% |
Conditions | Yield |
---|---|
Stage #1: 4-Methoxybenzyl alcohol With n-butyllithium; chloro-diphenylphosphine In tetrahydrofuran Stage #2: With methyl iodide In tetrahydrofuran at 20℃; for 1h; Stage #3: phenylmagnesium chloride In tetrahydrofuran at 20℃; for 1h; | 100% |
4-Methoxybenzyl alcohol
1-(azidomethyl)-4-methoxybenzene
Conditions | Yield |
---|---|
With thionyl chloride; sodium azide In N,N-dimethyl-formamide | 100% |
With tetrabutylammoniun azide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; | 94% |
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 0 - 20℃; Inert atmosphere; | 89% |
2,3,4-tri-O-benzoyl-6-deoxy-α-L-glucopyranosyl bromide
4-Methoxybenzyl alcohol
C35H32O9
Conditions | Yield |
---|---|
With 4 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane at -10℃; | 100% |
2-Mercaptobenzothiazole
4-Methoxybenzyl alcohol
2-<(4-methoxyphenyl)methylthio>benzothiazole
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; | 100% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; | 100% |
With N-cetyl-N-(4-sulfobutyl)pyrrolidinium trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 12h; Schlenk technique; | 94% |
BOC-glycine
4-Methoxybenzyl alcohol
4-methoxybenzyl 2-(tert-butoxycarbonylamino)acetate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; | 100% |
fenclorim
4-Methoxybenzyl alcohol
4-chloro-6-(4-methoxybenzyloxy)-2-phenylpyrimidine
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0℃; for 1.5h; | 100% |
(4-methoxybenzylidene)triphenylphosphorane
4-Methoxybenzyl alcohol
(E)-3,4,4',5-tetramethoxystilbene
Conditions | Yield |
---|---|
With nickel In tetrahydrofuran for 12h; Wittig type olefination; Reflux; | 100% |
Reported in EPA TSCA Inventory.
The CAS registry number of Anisic alcohol is 105-13-5. Its EINECS registry number is 203-273-6. The IUPAC name is (4-methoxyphenyl)methanol. 4-Methoxybenzyl alcohol is also called p-Anise Alcohol; p-Anisyl alcohol; Methoxybenzenemethanol; 4-methoxy-Benzenemethanol; Benzenemethanol,4-methoxy-; p-methoxy-benzyl alcohol; 4-methoxyphenol; 4-methoxy-1,3-benzothiazol-2-amine. In addition, the molecular formula is C8H10O2. What's more, it is a clear colourless to yellowish liquid after melting. It can be used in organic synthesis and used as a solvent and food flavor.
Physical properties about Anisic alcohol are: (1)ACD/LogP: 0.944; (2)ACD/LogD (pH 5.5): 0.94; (3)ACD/LogD (pH 7.4): 0.94; (4)ACD/BCF (pH 5.5): 3.07; (5)ACD/BCF (pH 7.4): 3.07; (6)ACD/KOC (pH 5.5): 77.76; (7)ACD/KOC (pH 7.4): 77.76; (8)#H bond acceptors: 2 ; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.531; (12)Molar Refractivity: 39.383 cm3; (13)Molar Volume: 127.252 cm3; (14)Polarizability: 15.613 10-24cm3; (15)Surface Tension: 38.7470016479492 dyne/cm; (16)Density: 1.086 g/cm3; (17)Flash Point: 110.271 °C; (18)Enthalpy of Vaporization: 52.47 kJ/mol; (19)Boiling Point: 258.999 °C at 760 mmHg; (20)Vapour Pressure: 0.00700000021606684 mmHg at 25°C
Preparation of Anisic alcohol: it can be prepared by anise, methanal and sodium hydroxide in the presence of ethanol through cannizzaro reaction. After the reaction, through a series of extraction by benzene, acidification by acetic acid, neutralization by sodium hydrogen carbonate, washing, distillation and vacuum distillation you can get the desired product.
Uses of Anisic alcohol: it can be used to get 4-methoxy-benzaldehyde and 4-methoxy-benzonitrile. This reaction will need reagents aq. NH3, NiSO4-K2S2O8 and NaOH, and solvent H2O. The reaction time is 1.5 hours with ambient temperature. The yield is about 8%.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In addition, it may has risk of impaired fertility and harm to the unborn child. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).
You can still convert the following datas into molecular structure:
(1)SMILES: COc1ccc(CO)cc1;
(2)InChI: InChI=1/C8H10O2/c1-10-8-4-2-7(6-9)3-5-8/h2-5,9H,6H2,1H3;
(3)InChIKey: MSHFRERJPWKJFX-UHFFFAOYAE;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 1600uL/kg (1.6mL/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 26, 1948. | |
mouse | LD50 | skin | > 10mL/kg (10mL/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 26, 1948. | |
rabbit | LD50 | skin | 3gm/kg (3000mg/kg) | Food and Cosmetics Toxicology. Vol. 12, Pg. 825, 1974. | |
rat | LD50 | oral | 1200uL/kg (1.2mL/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 26, 1948. |
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