Conditions | Yield |
---|---|
With cobalt(II) nitrate hexahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; manganese (II) nitrate tetrahydrate; oxygen; acetic acid at 40℃; under 760.051 Torr; for 0.75h; | 100% |
With N,N,N',N'-tetramethylguanidine In dichloromethane at 20℃; for 1h; | 99% |
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium nitrite In dichloromethane; water at 20℃; under 760.051 Torr; for 11h; in air; | 99% |
p-methylsulfinylbenzaldehyde
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With indium; tungsten(VI) chloride In tetrahydrofuran at 20℃; for 0.0833333h; | 95% |
With niobium pentachloride; sodium iodide In acetonitrile at 20℃; for 0.0833333h; | 95% |
With iododioxobis(triphenylphosphine)rhenium(V); phenylsilane In tetrahydrofuran at 20℃; for 2.25h; chemoselective reaction; | 92% |
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With H6P2W18O62 In toluene at 100℃; for 0.0833333h; | 95% |
4-(methylthio)benzoic acid
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In toluene for 24h; Irradiation; | 94% |
With 2,6-dimethylpyridine; nickel(II) bromide trihydrate; phenylsilane; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc; dimethyl dicarbonate In ethyl acetate at 60℃; for 24h; Schlenk technique; Inert atmosphere; | 72 %Chromat. |
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide In dichloromethane at 20℃; for 1h; | 93% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide at 130℃; for 12h; Sealed tube; Inert atmosphere; | 92% |
With copper(l) iodide; zinc(II) fluoride at 150℃; for 36h; Sealed tube; Under air; | 85% |
With copper(l) iodide; zinc diacetate at 135℃; for 36h; regioselective reaction; | 70% |
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With iodosylbenzene In dichloromethane at 20℃; for 0.333333h; | 90% |
methyl-phenyl-thioether
N,N-dimethyl-formamide
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate at -5 - 45℃; for 7h; | 89.2% |
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With 1,2,3-trimethoxybenzene; oxalyl dichloride In dichloromethane at 0℃; for 0.00166667h; Inert atmosphere; chemoselective reaction; | 89% |
carbon monoxide
(4-bromophenyl)thioanisole
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite In toluene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere; | 88% |
4-(methylthio)benzyl bromide
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With benzo[c]cinnoline In N,N-dimethyl-formamide at 80℃; Kornblum Aldehyd Synthesis; | 87% |
Conditions | Yield |
---|---|
With copper(l) iodide; oxygen In dimethyl sulfoxide at 120℃; for 25h; chemoselective reaction; | 85% |
Conditions | Yield |
---|---|
With [Rh(1,3,4,5-tetramethylimidazole-2-ylidene)(trop2NH)][trifluoromethanesulfonate]; potassium tert-butylate; dinitrogen monoxide In tetrahydrofuran; water; toluene at 50℃; under 750.075 Torr; Schlenk technique; Molecular sieve; Overall yield = 88 %; Overall yield = 165 mg; | A 3% B 85% |
4-(Methylthio)-N-methylbenzenemethanamine
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry; | 85% |
4-(methylthio)benzyl alcohol
A
(4-(methylsulfinyl)phenyl)methanol
B
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In neat (no solvent) at 70℃; for 6h; Irradiation; Green chemistry; | A 15% B 85% |
(4-thiomethoxyphenyl)boronic acid
Glyoxilic acid
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With 1,2,3,4-tetrahydroisoquinoline In acetonitrile at 20℃; Green chemistry; | 77% |
1-(azidomethyl)-4-methylsulfanylbenzene
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: 1-(azidomethyl)-4-methylsulfanylbenzene With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 4h; Inert atmosphere; Stage #2: With water In dimethyl sulfoxide; mineral oil for 0.25h; Inert atmosphere; | 75% |
3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide
4-(methylthio)phenyl trifluoromethanesulfonate
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With triethylsilane; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate In acetonitrile at 80℃; for 16h; Inert atmosphere; Sealed tube; | 73% |
Conditions | Yield |
---|---|
With triethylsilane; dichloro bis(acetonitrile) palladium(II); sodium carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 20 - 100℃; under 15001.5 Torr; for 20h; Inert atmosphere; Autoclave; | 69% |
Conditions | Yield |
---|---|
With iron(III) chloride hexahydrate In 1,4-dioxane; water at 80 - 100℃; for 18h; | 66% |
(E)-4-(methylthio)benzaldehyde oxime
B
p-methylsulfinylbenzaldehyde
C
4-(methylsulfonyl)benzaldehyde oxime
D
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With dihydrogen peroxide; bis(acetylacetonato)dioxidomolybdenum(VI) In acetone at 20℃; Product distribution; Further Variations:; Catalysts; Solvents; | A 5% B 3% C 3% D 60% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In water at 189℃; for 48h; | 60% |
4-(methylthio)benzyl alcohol
A
p-methylsulfinylbenzaldehyde
B
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In n-heptane at 80℃; under 760.051 Torr; for 24h; | A 21% B 59% |
With polystyrene-supported hypervalent iodine(V) reagent In 1,2-dichloro-ethane at 85℃; for 1h; | |
With N-(2-iodylphenyl)glutarylamide supported on amonomethylpolystyrene resin In 1,2-dichloro-ethane at 85℃; for 1h; | A 7 %Spectr. B 85 %Spectr. |
2-nitropropane
4-(methylthio)benzyl bromide
B
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran Hass-Bender/Henry reaction; | A 57% B n/a |
4-(methylthio)benzyl bromide
A
4-(methylthio)benzyl alcohol
B
1-bromomethyl-4-methanesulfinylbenzene
C
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With dihydrogen peroxide at 70℃; for 1h; | A n/a B 52% C n/a |
Conditions | Yield |
---|---|
With 9-(benzoyl(cyclohexyl)carbamoyl)-10-phenylacridinium perchlorate In water; acetonitrile at 20℃; for 18h; Irradiation; Green chemistry; chemoselective reaction; | 49% |
4-(methylthio)benzyl alcohol
A
p-methylsulfinylbenzaldehyde
B
(4-(methylsulfinyl)phenyl)methanol
C
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With 1-iodyl-2-butoxybenzene In acetonitrile for 15h; Heating; | A 16% B 46% C 32% |
With 4-(2-iodylphenoxy)butanoylaminomethylated polystyrene In 1,2-dichloro-ethane for 3h; Heating; |
p-methylsulfinylbenzaldehyde
B
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With DL-dithiothreitol; methionine sulfoxide reductase A from Pseudomonas alcaliphila In aq. phosphate buffer at 30℃; for 1h; pH=8; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A 43% B n/a |
With recombinant methionine sulfoxide reductase A from Pseudomonas monteilii; diothiothreitol In aq. phosphate buffer at 30℃; for 4h; pH=8; Sealed tube; Resolution of racemate; Green chemistry; Enzymatic reaction; enantioselective reaction; | A n/a B n/a |
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide; trichlorophosphate | |
Multi-step reaction with 2 steps 1: acetic acid 2: hexamethylenetetramine; acetic acid / Erhitzen des Reaktionsprodukts mit H2O View Scheme |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; sodium hydroxide at 70℃; for 2h; | 100% |
With oxone In tetrahydrofuran; water at 20℃; for 24h; | 94% |
With sodium perborate In acetic acid at 45 - 50℃; | 90% |
With oxygen at 100℃; for 20h; Reagent/catalyst; Schlenk technique; chemoselective reaction; | 87% |
4-(Methylthio)benzaldehyde
4-(methylthio)benzamide
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; sodium hydroxide; (CTA)2SO4 at 50℃; for 2h; | 100% |
With nitromethane; trifluoromethylsulfonic anhydride; acetic acid In formic acid at 80 - 120℃; | 57% |
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; pyridine / methanol / 24 h / 20 °C 2: [RuCl2(η2-C6H6){P(NMe2)3}]; water / 3 h / 100 °C / Inert atmosphere; Sealed tube View Scheme |
4-(Methylthio)benzaldehyde
trimethyl orthoformate
1-(1,1-dimethoxy-methyl)-4-methylsulfanyl-benzene
Conditions | Yield |
---|---|
With potassium tert-butylate; toluene-4-sulfonic acid In methanol at 20℃; for 1.5h; Inert atmosphere; | 100% |
With toluene-4-sulfonic acid In methanol for 1.5h; Ambient temperature; | 83% |
With toluene-4-sulfonic acid In methanol at 20℃; for 1h; |
Conditions | Yield |
---|---|
With hydrogen; phosphotungstic acid 44-hydrate; [Fe(C5H4P(i-Pr)2)2Rh(C8H12)]BF4 In water; isopropyl alcohol at 20℃; under 5171.62 Torr; for 16h; | 100% |
With isopropyl alcohol; hydrotalcite at 81.84℃; for 3h; Kinetics; Further Variations:; Temperatures; Reagents; | 100% |
Stage #1: 4-(Methylthio)benzaldehyde With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); phenylsilane at 80℃; for 0.666667h; Stage #2: With tetrabutyl ammonium fluoride at 20℃; for 0.5h; Reagent/catalyst; Temperature; Time; Solvent; chemoselective reaction; | 98% |
ethyl acetoacetate
urea
4-(Methylthio)benzaldehyde
ethyl 6-methyl-4-[4-(methylsulfanyl)phenyl]-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate
Conditions | Yield |
---|---|
With copper(II) bis(trifluoromethanesulfonate) In ethanol at 100℃; for 1h; Biginelli reaction; Microwave irradiation; Inert atmosphere; | 100% |
Wells-Dawson heteropolyacid catalyst at 80℃; for 1.5h; Biginelli reaction; | 92% |
With 25,26,27,28-terahydroxycalix[4]arene-5,11,7,23-tetrasulfonic acid In ethanol for 8h; Biginelli reaction; Reflux; | 92% |
4-(Methylthio)benzaldehyde
1-t-Butoxycarbonylpiperazine
Conditions | Yield |
---|---|
Stage #1: 4-(Methylthio)benzaldehyde; 1-t-Butoxycarbonylpiperazine In methanol for 0.5h; Stage #2: With borohydride; polymer-supported In methanol for 24h; | 100% |
Conditions | Yield |
---|---|
With sodium hydroxide In water; isopropyl alcohol at 0 - 20℃; for 5h; | 100% |
With sodium hydroxide In water; isopropyl alcohol at 0 - 20℃; | 100% |
1,1′-(9-ethyl-9H-carbazole-3,6-diyl)diethanone
4-(Methylthio)benzaldehyde
C34H29NO2S2
Conditions | Yield |
---|---|
With sodium hydroxide In water; tert-butyl alcohol at 0 - 20℃; for 5h; | 100% |
With sodium hydroxide In water; tert-butyl alcohol at 0 - 20℃; | 100% |
ethyl acetoacetate
1,3-cylohexanedione
4-(Methylthio)benzaldehyde
2-Methyl-4-(4-methylsulfanyl-phenyl)-5-oxo-1,4, 5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With Cu(OTf)2; ammonium acetate In ethanol at 100℃; for 0.25h; Hantzsch reaction; Microwave irradiation; | 100% |
Conditions | Yield |
---|---|
With copper(II) choride dihydrate; ammonium acetate In ethanol for 4h; Reflux; | 100% |
With 1,1,1,3',3',3'-hexafluoro-propanol; ammonium acetate at 55℃; for 1.5h; | 84% |
Conditions | Yield |
---|---|
With sodium acetate In ethanol; water at 20℃; | 100% |
4-(Methylthio)benzaldehyde
p-methylsulfinylbenzaldehyde
Conditions | Yield |
---|---|
With phthaloyl peroxide In dichloromethane at 25℃; for 8h; Schlenk technique; chemoselective reaction; | 99% |
Stage #1: 4-(Methylthio)benzaldehyde With aluminum (III) chloride In methanol; dichloromethane at 20℃; for 0.0166667h; Stage #2: With [bis(acetoxy)iodo]benzene In methanol; dichloromethane at 20℃; for 12h; | 99% |
With nitric acid; phosphorus pentoxide; silica gel In water for 0.0833333h; | 97% |
4-(Methylthio)benzaldehyde
γ-aminopropyl-2-methyl-6-phenyl-1,3-dioxa-6-aza-2-silacyclooctane
Conditions | Yield |
---|---|
With potassium carbonate In benzene at 20℃; for 6h; | 99% |
Methyltriphenylphosphonium bromide
4-(Methylthio)benzaldehyde
4-methythiostyrene
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; Wittig reaction; | 99% |
With sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 99% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 2h; Wittig Olefination; Inert atmosphere; Stage #2: 4-(Methylthio)benzaldehyde In tetrahydrofuran; hexane at 0 - 20℃; for 16h; Wittig Olefination; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With sodium metabisulfite In N,N-dimethyl-formamide at 80℃; for 0.1h; Microwave irradiation; | 99% |
Stage #1: 4-(Methylthio)benzaldehyde In N,N-dimethyl-formamide at 240℃; under 7500.75 Torr; for 0.0833333h; Microwave irradiation; Stage #2: 1,2-diamino-benzene In N,N-dimethyl-formamide at 240℃; under 7500.75 Torr; for 0.0833333h; Microwave irradiation; |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; Aldol Condensation; | 99% |
4-methoxy-aniline
phosphonic acid diethyl ester
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) In neat (no solvent) at 80℃; for 0.166667h; chemoselective reaction; | 99% |
4-(Methylthio)benzaldehyde
4-(methylthio)benzoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; sodium hydroxide; (CTA)2SO4 at 20℃; for 20h; | 98% |
With sodium hydroxide In water at 20 - 75℃; for 20h; | 85% |
With perchloric acid; mercury(II) diacetate; N-bromoacetamide In acetic acid at 24.9℃; Kinetics; Mechanism; Thermodynamic data; other temperatures, ΔG(excit.), ΔH(excit.), ΔS(excit.); |
Conditions | Yield |
---|---|
With sodium hydroxide; 3-chloro-benzenecarboperoxoic acid at 1 - 3℃; for 2h; | 98% |
With Oxone In neat (no solvent) for 1.5h; Milling; Green chemistry; chemoselective reaction; | 97% |
With C2MoO9(2-)*H2O*2C19H42N(1+); dihydrogen peroxide In water at 20℃; for 0.0166667h; chemoselective reaction; | 97% |
Bromoform
4-(Methylthio)benzaldehyde
2-hydroxy-2-(4-methylthiophenyl)ethanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; lithium bromide In 1,4-dioxane | 98% |
With potassium hydroxide; lithium bromide In 1,4-dioxane; water 1.) 0 deg C, 18 h, 2.) 23 deg C, 24 h; | 7.6 g |
4-(Methylthio)benzaldehyde
4-(methylthio)benzaldehyde oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium hydroxide In ethanol at 80℃; for 4h; Inert atmosphere; | 98% |
With sodium hydroxide; hydroxylamine hydrochloride In ethanol; water at 0℃; | 46% |
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water for 24h; |
N-methylhydroxyamine hydrochloride
4-(Methylthio)benzaldehyde
N-[4-(methylthio)benzylidene]methylamine N-oxide
Conditions | Yield |
---|---|
With sodium sulfate; sodium carbonate at 20℃; for 0.0833333h; Neat (no solvent); | 98% |
With sodium hydrogencarbonate In dichloromethane at 20℃; | 82% |
With sodium acetate In ethanol at 50 - 60℃; for 3h; | 78% |
piperidine
(4-methoxyphenyl)zinc(II) bromide
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With copper(l) iodide In acetonitrile at 20℃; for 3h; | 98% |
Conditions | Yield |
---|---|
With triethylamine In chloroform at 20℃; for 16h; | 98% |
hydrogen cyanide
4-(Methylthio)benzaldehyde
2-hydroxy-2-(4-(methylthio)phenyl)acetonitrile
Conditions | Yield |
---|---|
With Prunus communis L. (R)-hydroxynitrile lyase In various solvent(s) at 20℃; for 12h; | 98% |
With hydroxynitrile lyase isozyme 5 from Prunus communis In tert-butyl methyl ether at 25℃; for 4h; pH=5; pH-value; Temperature; Reagent/catalyst; Solvent; Enzymatic reaction; | 94% |
With hydroxynitrile lyase PcHNL5, L343F mutant at 10℃; for 12h; pH=2.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | n/a |
4-chloro-aniline
4-(Methylthio)benzaldehyde
4-chloro-N-[4-methylsulfanylbenzylidene]aniline
Conditions | Yield |
---|---|
98% | |
In methanol for 4h; Reflux; | 88% |
With acetic acid In ethanol at 78℃; for 10h; |
2-hydroxy-2-phenylacetophenone
4-(Methylthio)benzaldehyde
2-(4-(methylthio)phenyl)-4,5-diphenyl-1H-imidazole
Conditions | Yield |
---|---|
With P2O5/SiO2; ammonium acetate at 100℃; for 2h; | 98% |
With triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate; ammonium acetate at 100℃; for 2h; neat (no solvent); | 98% |
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate at 100℃; for 2.5h; Neat (no solvent); | 95% |
With ammonium acetate at 130℃; for 1.33333h; Neat (no solvent); | 90% |
4-(Methylthio)benzaldehyde
N-phenyl-1,2-benzenediamine
2-[4-(methylthio)phenyl]-1-phenyl-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With sodium metabisulfite In N,N-dimethyl-formamide at 100℃; for 0.1h; Microwave irradiation; | 98% |
1,3-cylohexanedione
2,4-diamino-6-hydroxypyrimidine
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With zirconium(IV) oxide In ethylene glycol at 120℃; for 0.133333h; Green chemistry; | 98% |
Molecular Structure of 4-(methylthio)benzaldehyde (CAS NO.3446-89-7):
IUPAC Name: 4-methylsulfanylbenzaldehyde
CAS No: 3446-89-7
EINECS: 222-365-7
Molecular Formula: C8H8OS
Molecular Weight: 152.21 g/mol
Melting Point: 6 °C
Density: 1.13 g/cm3
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: 42.37 Å2
Index of Refraction: 1.577
Molar Refractivity: 44.36 cm3
Molar Volume: 133.7 cm3
Surface Tension: 43.3 dyne/cm
Flash Point: 133.3 °C
Enthalpy of Vaporization: 50.5 kJ/mol
Boiling Point: 267 °C at 760 mmHg
Vapour Pressure: 0.00836 mmHg at 25°C
Product Categories: Aromatic Aldehydes & Derivatives (substituted)
InChI
InChI=1/C8H8OS/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
Smiles
O=Cc1ccc(SC)cc1
Product Categories about 4-(methylthio)benzaldehyde (3446-89-7) are Aromatic Aldehydes & Derivatives (substituted)
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 23-24/25-36-26-7/9
S23:Do not breathe vapour.
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S7:Keep container tightly closed.
S9:Keep container in a well-ventilated place.
WGK Germany: 3
F: 13
Hazard Note: Irritant/Stench
HS Code: 29309070
4-(methylthio)benzaldehyde , with CAS number of 3446-89-7, can be called p-(Methylthio)benzaldehyde ; benzaldehyde, 4-(methylthio)- ; 4-(Methylsulfanyl)benzaldehyd . 4-(methylthio)benzaldehyde (CAS NO.3446-89-7) is stable under normaltemperatures and pressures.but incompatible with strong oxidizingagents. It is a clear yellow liquid.
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