2-chloropyridine
para-methylphenylmagnesium bromide
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With C32H41N12Ni2O(3+)*3F6P(1-) In tetrahydrofuran at 25℃; for 5h; Inert atmosphere; Schlenk technique; | 100% |
With N-heterocyclic carbene-based nickel(II) complex In tetrahydrofuran at 20℃; for 12h; Kumada reaction; | 99% |
With chloro(1,3-bis(pyridin-2-ylmethyl)imidazolylidene)nickel(II) hexafluorophosphate In tetrahydrofuran at 20℃; for 12h; Kumada-Corriu coupling reaction; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: para-bromotoluene With lithium Stage #2: With zinc(II) chloride Stage #3: 2-chloropyridine; nickel phosphine amido pincer complex In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70℃; for 12h; Negishi cross-coupling; Further stages.; | 99.5% |
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis; | 80% |
2-[4-(2-pyridinyl)phenyl]methylenehydrazinecarboxylic acid tert-butyl ester
A
2-(4-methylphenyl)pyridine
B
N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine
Conditions | Yield |
---|---|
With hydrogen; triethylamine; 5%-palladium/activated carbon at 40℃; under 760.051 Torr; for 5h; | A 0.69% B 99.17% |
With hydrogen; sodium carbonate; 5%-palladium/activated carbon at 40℃; under 760.051 Torr; for 5h; | A 0.25% B 99.16% |
With hydrogen; 5%-palladium/activated carbon In methanol at 50℃; under 760.051 Torr; for 5h; | A 2.69% B 97.11% |
at 40 - 62℃; under 1520.1 Torr; for 5h; Hydrogen/nitrogen (1/2); | A 0.1% B 97.2% |
With hydrogen; 5%-palladium/activated carbon at 5 - 58℃; under 1520.1 Torr; for 5 - 8h; Nitrogen gas; | A 2.11% B 94.41% |
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate In tetrahydrofuran at 100℃; for 24h; Suzuki-Miyaura coupling; | 99% |
With potassium phosphate monohydrate; 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; palladium diacetate In 1,4-dioxane; 1,3,5-trimethyl-benzene at 135℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere; | 98% |
With 4-di-tert-butylphosphanyl-1-phenyl-5-(2,6-dimethoxyphenyl)-1H-[1,2,3]triazole; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 12h; Suzuki coupling; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With potassium phosphate tribasic heptahydrate; palladium dichloride In ethanol; water at 80℃; for 0.166667h; Suzuki-Miyaura reaction; | 99% |
With potassium phosphate tribasic heptahydrate; palladium diacetate In isopropyl alcohol at 80℃; for 0.133333h; Suzuki coupling; | 98% |
With potassium phosphate tribasic heptahydrate; palladium dichloride In water; N,N-dimethyl-formamide at 20℃; for 12h; Suzuki cross-coupling reaction; | 98% |
Conditions | Yield |
---|---|
With Ni(Cl){2-(Ph2P)C6H4NCH(Ph)P(O)Ph2} In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 25℃; for 24h; Negishi coupling reaction; Inert atmosphere; | 99% |
With C38H34Br2N4Ni2P2 In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 90℃; for 12h; Reagent/catalyst; Negishi Coupling; Inert atmosphere; Schlenk technique; | 99% |
With C27H22Cl2N3NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one for 6h; Inert atmosphere; Schlenk technique; Heating; | 99% |
With C21H18N8Ni2O(2+)*2F6P(1-) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20 - 80℃; Negishi coupling reaction; | 98% |
trimethylpyridin-2-ylammonium iodide
p-tolylzinc(II) chloride
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With C38H34Br2N4Ni2P2; potassium iodide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 65℃; for 12h; Reagent/catalyst; Concentration; Inert atmosphere; Schlenk technique; | 99% |
With C32H26ClN2NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 85℃; for 12h; Inert atmosphere; | 97% |
With bis(tricyclohexylphosphine)nickel(II) dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 90℃; for 8h; Negishi coupling reaction; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With dichlorobis(trimethylphosphine)nickel In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70℃; for 12h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 2-fluoropyridine; p-tolylzinc(II) chloride With bis(tricyclohexylphosphine)nickel(II) dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 25 - 100℃; for 10h; Schlenk technique; Inert atmosphere; Stage #2: p-tolylzinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 10h; Inert atmosphere; Schlenk technique; | 99% |
2-pyridyl dimethylsulfamate
para-methylphenylmagnesium bromide
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With C38H34Br2N4Ni2P2 In tetrahydrofuran at 35℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
With C36H52Br2N4NiSi In tetrahydrofuran at 70℃; for 24h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique; | 99% |
2-(4-methylphenyl)pyridine N-oxide
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With ammonium chloride; zinc In tetrahydrofuran at 22 - 38℃; for 0.583333h; | 98% |
With palladium on activated charcoal; ammonium formate In methanol at 20℃; | 95% |
With methanol; palladium 10% on activated carbon; ammonium formate at 20℃; Inert atmosphere; | 95% |
With tetrahydroxydiboron In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.166667h; | 151 mg |
2-chloropyridine
para-methylphenylmagnesium bromide
A
2-(4-methylphenyl)pyridine
B
(4,4'-dimethyl-1,1'-biphenyl)
Conditions | Yield |
---|---|
With C68H72Cl2N6NiP2 In diethyl ether at 25℃; for 12h; Kumada coupling reaction; Inert atmosphere; | A 98% B n/a |
2-bromo-pyridine
trimethyl((5-methyl-2-(p-tolyl)-1,3,2-dioxaborinan-5-yl)methoxy)silane
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol at 100℃; for 18h; Suzuki Coupling; Inert atmosphere; | 96% |
2-methoxypyridine
para-methylphenylmagnesium bromide
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With (IPr)Ni(π-allyl)Cl In tetrahydrofuran at 60℃; for 12h; Kumada Cross-Coupling; Inert atmosphere; | 95% |
With C68H72Cl2N6NiP2 In tetrahydrofuran at 25℃; for 24h; Inert atmosphere; | 91% |
With bis(1,5-cyclooctadiene)nickel (0); C23H28N4 In tetrahydrofuran; m-xylene at 60℃; for 4h; Kumada Cross-Coupling; Inert atmosphere; Sealed tube; | 54% |
With dichlorobis(trimethylphosphine)nickel In tetrahydrofuran at 23℃; for 15h; |
Conditions | Yield |
---|---|
With N-methyl-2-phenyl-3-(dicyclohexylphosphino)-1H-indole; palladium diacetate; triethylamine; sodium t-butanolate In water at 100℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 95% |
4-methylphenylboronic acid
pyridin-2-yl sulfurofluoridate
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate In ethanol; water at 35℃; for 3h; Suzuki Coupling; chemoselective reaction; | 95% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; Inert atmosphere; Schlenk technique; | 95% |
2-bromo-pyridine
para-methylphenylmagnesium bromide
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With nickel(II) fluoride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 60℃; for 16h; Inert atmosphere; | 93% |
With C16H16Cl2CoN8(1+)*F6P(1-) In tetrahydrofuran at 20℃; for 2h; Kumada-Corriu cross-coupling; | 92% |
With [Ni(1-(1-ethyl-benzimidazol-2-ylmethyl)-3-mesitylimidazolin-2-ylidene)2][Cl]2; sodium acetate In tetrahydrofuran at 20℃; Kumada-Corriu coupling reaction; Inert atmosphere; |
para-bromotoluene
2-(trimethylsilyl)pyridine
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With potassium fluoride; copper(l) iodide; palladium diacetate; catacxium A In N,N-dimethyl-formamide at 90℃; for 12h; Hiyama coupling; Inert atmosphere; | 92% |
2-bromo-pyridine
p-tolylboronic pinacol ester
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With tricyclohexylphosphine-copper chloride; sodium t-butanolate In toluene at 100℃; for 15h; Reagent/catalyst; Inert atmosphere; Sealed tube; | 92% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In neat (no solvent) at 110℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 77% |
Conditions | Yield |
---|---|
Stage #1: para-bromotoluene With iodine; magnesium In tetrahydrofuran at 35℃; for 2h; Stage #2: 2-bromo-pyridine; tetrakis(triphenylphosphine) palladium(0); zinc(II) chloride In tetrahydrofuran; toluene at 50℃; for 2.5h; Conversion of starting material; | 91.7% |
Stage #1: para-bromotoluene With ethylene dibromide; trifluoroacetic acid; cobalt(II) bromide; zinc In acetonitrile at 20℃; for 1h; Inert atmosphere; Sealed tube; Stage #2: 2-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide; acetonitrile at 50℃; for 1h; Inert atmosphere; Sealed tube; | 78% |
Stage #1: para-bromotoluene With iodine; magnesium In tetrahydrofuran at 35℃; for 2h; Stage #2: 2-bromo-pyridine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 50℃; for 2.5h; Conversion of starting material; | 9% |
Conditions | Yield |
---|---|
With PEG 4000; palladium diacetate; potassium carbonate at 120℃; for 15h; | 91% |
2-fluoropyridine
para-methylphenylmagnesium bromide
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With C35H31BrN4NiP In tetrahydrofuran at 25℃; for 12h; Schlenk technique; Inert atmosphere; | 91% |
With C26H24ClN2NiP*0.1C7H8 In diethyl ether at 25℃; for 24h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With palladium diacetate; tris-(o-tolyl)phosphine In toluene at 20℃; for 5h; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With oxygen; palladium diacetate; toluene-4-sulfonic acid In tetrahydrofuran for 9h; Reflux; | 91% |
With hydrogenchloride; iodine; oxygen In dimethyl sulfoxide at 80℃; for 4h; | 85% |
With oxygen In ethanol at 100℃; under 760.051 Torr; for 26h; | 71% |
With oxygen; copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid In hexan-1-ol at 110℃; for 24h; Sealed tube; Schlenk technique; | 67% |
With tris(2,2'-bipyridyl)ruthenium dichloride; oxygen; toluene-4-sulfonic acid In acetonitrile at 82℃; for 48h; Irradiation; | 50% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 65℃; for 24h; Negishi cross-coupling; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling; | 89% |
Conditions | Yield |
---|---|
Stage #1: 2-hydroxypyridin With potassium carbonate; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Stage #2: 4-methylphenylboronic acid With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura coupling; Inert atmosphere; | 88% |
2-pyridyl dimethylsulfamate
p-tolylzinc(II) chloride
2-(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With 1-Methylpyrrolidine; C20H20ClN3Ni In tetrahydrofuran at 50℃; for 12h; Schlenk technique; Inert atmosphere; | 88% |
2-(4-methylphenyl)pyridine
((2,6-iPr2C6H3)NCH2CH2N(2,6-iPr2C6H3))Y(CH2SiMe3)(THF)2
Conditions | Yield |
---|---|
In benzene at 20℃; for 48h; | 100% |
triethylsilane
2-(4-methylphenyl)pyridine
2-(4-methyl-2-(triethylsilyl)phenyl)pyridine
Conditions | Yield |
---|---|
Stage #1: 2-(4-methylphenyl)pyridine With norborn-2-ene; C30H33IrN2O2 In toluene at 115℃; for 3h; Inert atmosphere; Stage #2: triethylsilane In toluene at 115℃; for 24h; Inert atmosphere; | 99% |
Stage #1: 2-(4-methylphenyl)pyridine With C30H34ClIrN2 In o-xylene at 100℃; for 6h; Stage #2: triethylsilane With tert-butylethylene for 18h; | 87% |
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); norbornene; potassium acetate In toluene at 120℃; for 20h; Inert atmosphere; | 84% |
With norborn-2-ene; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); potassium acetate In toluene at 120℃; for 16h; Schlenk technique; Inert atmosphere; | 84% |
With norbornene; [Ir(hydride)2(1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene)(pyridine)3][BF4] In tetrahydrofuran at 110℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique; | 71% |
2-(4-methylphenyl)pyridine
3-(methoxycarbonyl)-υ-triazolo<3,4-a>pyridine
Conditions | Yield |
---|---|
With [Cp*Rh(CH3CN)3](SbF6)2 In 2,2,2-trifluoroethanol at 140℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; acetic acid; silver(I) triflimide In 2,2,2-trifluoroethanol at 120℃; for 24h; Sealed tube; Green chemistry; regioselective reaction; | 99% |
2-(4-methylphenyl)pyridine
bis(pinacol)diborane
Conditions | Yield |
---|---|
With C25H40O2P2Ru In tetrahydrofuran at 120℃; for 20h; Inert atmosphere; Sealed tube; | 99% |
With C25H36O2P2Ru In tetrahydrofuran at 120℃; for 20h; Sealed tube; Glovebox; Schlenk technique; Inert atmosphere; regioselective reaction; | 99% |
2-(4-methylphenyl)pyridine
2-(4-methylphenyl)pyridine N-oxide
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid In water at 73℃; | 97% |
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at 40℃; for 12h; Inert atmosphere; | 81% |
With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice; | 34% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; magnesium oxide; palladium diacetate In 1,2-dichloro-ethane at 80℃; | 97% |
Conditions | Yield |
---|---|
With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate In dichloromethane at 40℃; for 48h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In toluene at 60℃; for 12h; Schlenk technique; Inert atmosphere; | 97% |
2-(4-methylphenyl)pyridine
N-benzoylbenzenesulfenamide
2-(4-methyl-2,6-bis(phenylthio)phenyl)pyridine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; (R)-2,2'-bis[bis(3,5-dimethyl-4-methoxyphenyl)phosphino]-1,1'-binaphthyl In toluene at 60℃; for 48h; Schlenk technique; Inert atmosphere; enantioselective reaction; | 97% |
styrene
2-(4-methylphenyl)pyridine
2-(2,6-divinylphenyl-4-methyl)-phenylpyridine
Conditions | Yield |
---|---|
With 1-pentyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)amide; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper (I) acetate; silver sulfate at 25℃; for 15h; Reagent/catalyst; Sealed tube; Inert atmosphere; | 97% |
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; silver(I) triflimide at 20℃; for 24h; Sealed tube; Inert atmosphere; Green chemistry; | 94% |
2-(4-methylphenyl)pyridine
Benzohydroxamic acid
A
BPA
B
N-(5-methyl-2-(pyridin-2-yl)phenyl)benzamide
Conditions | Yield |
---|---|
Stage #1: Benzohydroxamic acid; Poly(bisphenol A carbonate) With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In 2-methyltetrahydrofuran at 30℃; for 4h; Stage #2: 2-(4-methylphenyl)pyridine With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) triflimide at 60℃; for 15h; | A 97% B 78% |
2-(4-methylphenyl)pyridine
bromobenzene
2-(5'-methyl[1,1':3',1'’-terphenyl]-2'-yl)pyridine
Conditions | Yield |
---|---|
With rhodium(II) acetate dimer; 1,3-bis(mesityl)imidazolium chloride; sodium t-butanolate; tricyclohexylphosphine In toluene at 80℃; | 96% |
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1-Adamantanecarboxylic acid; potassium carbonate In toluene at 120℃; for 18h; Inert atmosphere; |
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver sulfate In 1,2-dichloro-ethane at 80℃; for 12h; Sealed tube; | 96% |
Conditions | Yield |
---|---|
Stage #1: 2-(4-methylphenyl)pyridine With tert-butyl methyl ether; nitric acid In tetrahydrofuran at 0℃; Stage #2: With sulfuric acid In dichloromethane at 0℃; for 1h; Further stages.; | 95% |
With dodecacarbonyl-triangulo-triruthenium; copper(II) nitrate trihydrate; oxone||potassium monopersulfate triple salt; tetrabutylammonium acetate; silver trifluoroacetate In 1,2-dichloro-ethane at 95℃; for 36h; Sealed tube; regioselective reaction; | 76% |
With sulfuric acid; potassium nitrate |
IUPAC Name: 2-(4-Methylphenyl)pyridine
Following is the structure of 2-(4-Tolyl)pyridine (CAS NO.4467-06-5):
Empirical Formula: C12H11N
Molecular Weight: 169.2224 g/mol
EINECS: 224-734-8
Index of Refraction: 1.568
Molar Refractivity: 53.76 cm3
Molar Volume: 164.2 cm3
Density: 1.03 g/cm3
Flash Point: 119.3 °C
Surface Tension: 39.7 dyne/cm
Enthalpy of Vaporization: 52.28 kJ/mol
Boiling Point: 304.2 °C at 760 mmHg
Vapour Pressure of 2-(4-Tolyl)pyridine (CAS NO.4467-06-5): 0.0016 mmHg at 25 °C
Appearance of 2-(4-Tolyl)pyridine (CAS NO.4467-06-5): clear yellow to gold liquid
Canonical SMILES: CC1=CC=C(C=C1)C2=CC=CC=N2
InChI: InChI=1S/C12H11N/c1-10-5-7-11(8-6-10)12-4-2-3-9-13-12/h2-9H,1H3
InChIKey: KJNZQKYSNAQLEO-UHFFFAOYSA-N
2-(4-Tolyl)pyridine (CAS NO.4467-06-5) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
2-(4-Tolyl)pyridine , its cas register number is 4467-06-5. It also can be called 2-(4-Methylphenyl)pyridine ; 2-p-Tolylpyridine ; and pyridine, 2-(4-methylphenyl)- .
2-(4-Tolyl)pyridine (CAS NO.4467-06-5) is not compatible with other strong oxidizing agents. And it aould avoid the condition of incompatible materials. While, also should prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, carbon dioxide. Its hazardous polymerization has not been reported. This chemical should be stored in a cool, dry place, or be stored in a tightly closed container.
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