trifluoromethylsulfonic anhydride
prasterone acetate
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Stage #1: prasterone acetate With potassium carbonate In toluene; benzene at 25℃; for 0.5h; Stage #2: trifluoromethylsulfonic anhydride In toluene; benzene at -18 - -15℃; for 20.33h; Reagent/catalyst; Solvent; Temperature; | 96% |
Stage #1: prasterone acetate With potassium carbonate In toluene; benzene at 25℃; for 0.5h; Stage #2: trifluoromethylsulfonic anhydride In toluene; benzene at -18 - -15℃; for 20.33h; | 96% |
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In dichloromethane at 20℃; for 0.0833333h; Stage #2: With 2-methoxypyridine In dichloromethane at 20 - 30℃; for 2.5h; Reagent/catalyst; | 93% |
N,N-phenylbistrifluoromethane-sulfonimide
prasterone acetate
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Stage #1: prasterone acetate With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃; for 2h; | 85% |
Stage #1: prasterone acetate With potassium hexamethylsilazane In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran for 8h; Inert atmosphere; | 70% |
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -80 - 0℃; for 4h; | 850 mg |
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -80 - 5℃; for 2.5h; | 64.8 g |
trifluoromethylsulfonic anhydride
prasterone acetate
A
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
B
androsta-3,5,16-trien-17-yl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane for 12h; | A 58% B 10% |
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane for 3 - 16h; Product distribution / selectivity; | |
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate With 2,6-dimethylpyridine In ethyl acetate for 0.25h; Stage #2: With 2,6-dimethylpyridine In ethyl acetate for 2h; Product distribution / selectivity; |
trifluoromethylsulfonic anhydride
prasterone acetate
A
dehydroepiandrosterone
B
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In 2-Methylpentane for 0.25h; Stage #2: With triethylamine In 2-Methylpentane for 2h; Product distribution / selectivity; | |
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In ethyl acetate for 0.25h; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate for 2h; Product distribution / selectivity; | |
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In 1,2-dichloro-ethane for 0.25h; Stage #2: With sodium hydride In 1,2-dichloro-ethane for 2h; Product distribution / selectivity; | |
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate for 0.25h; Stage #2: With triethylamine for 2h; Product distribution / selectivity; |
trifluoromethylsulfonic anhydride
prasterone acetate
A
dehydroepiandrosterone
B
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
C
androsta-3,5,16-trien-17-yl trifluoromethanesulfonate
Conditions | Yield |
---|---|
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In dichloromethane for 0.25h; Stage #2: With pyridine In dichloromethane for 2h; Product distribution / selectivity; | |
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In ethyl acetate for 0.25h; Stage #2: With pyridine In ethyl acetate for 2h; Product distribution / selectivity; |
dehydroepiandrosterone
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 2 h / 105 - 110 °C / Inert atmosphere 2.1: potassium carbonate / toluene; benzene / 0.5 h / 25 °C 2.2: 20.33 h / -18 - -15 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: pyridine; dmap / 0.25 h / 20 °C 1.2: 6 h / 20 °C 2.1: triethylamine / dichloromethane / 2 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: pyridine / 20 °C 2.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 2.2: 2 h / -78 °C View Scheme |
prasterone acetate
1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)-sulfonyl)methanesulfonamide
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -80 - -70℃; for 2h; Reagent/catalyst; Large scale; | 112 kg |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
3-Diethylboranylpyridine
abiraterone acetate
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran at 65℃; for 4h; Reflux; | 95% |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 1h; Reflux; | 95% |
With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In tetrahydrofuran; water at 60℃; for 1h; | 94% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
phenylboronic acid
17-phenylandrosta-5,6-dien-3β-ol 3-acetate
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry; Stage #2: phenylboronic acid With sodium carbonate In water at 75℃; Catalytic behavior; Reagent/catalyst; Time; Suzuki Coupling; Inert atmosphere; Green chemistry; | 92% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 100℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Suzuki Coupling; Inert atmosphere; | 85% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.08333h; Inert atmosphere; | 85% |
With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In tetrahydrofuran; water at 60℃; for 23h; Suzuki Coupling; Inert atmosphere; | 70% |
5-methoxy-3-pyridinylboronic acid
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry; Stage #2: 5-methoxy-3-pyridinylboronic acid With sodium carbonate In water at 75℃; Suzuki Coupling; Inert atmosphere; Green chemistry; | 88% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
3-Diethylboranylpyridine
abiraterone acetate
Conditions | Yield |
---|---|
With sodium carbonate In tetrahydrofuran; bis(triphenylphosphine)palladium(II)-chloride | 84% |
3-fluorophenylboronic acid
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry; Stage #2: 3-fluorophenylboronic acid With sodium carbonate In water at 75℃; Suzuki Coupling; Inert atmosphere; Green chemistry; | 83% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 100℃; for 6h; Suzuki Coupling; Inert atmosphere; | 52% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.08333h; Inert atmosphere; | 52% |
5-fluoropyridine-3-boronic acid
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry; Stage #2: 5-fluoropyridine-3-boronic acid With sodium carbonate In water at 75℃; Suzuki Coupling; Inert atmosphere; Green chemistry; | 83% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
pyrimidine 5-boronic acid
3β-acetoxy-17-(pyrimidin-5-yl)androsta-5,16-diene
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry; Stage #2: pyrimidine 5-boronic acid With sodium carbonate In water at 75℃; Suzuki Coupling; Inert atmosphere; Green chemistry; | 83% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
ethyl vinyl ether
A
(Z/E)-3β-Acetoxypregna-5,17(20)-dien-21-al
B
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); triethylamine In dimethyl sulfoxide at 60℃; for 4h; | A 8% B 82% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
5-methylpyridine-3-boronic acid
C27H35NO2
Conditions | Yield |
---|---|
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 80℃; for 1h; Suzuki Coupling; Inert atmosphere; | 82% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
(6-fluoropyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry; Stage #2: (6-fluoropyridin-3-yl)boronic acid With sodium carbonate In water at 75℃; Suzuki Coupling; Inert atmosphere; Green chemistry; | 81% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
3-pyridylboronic acid
abiraterone acetate
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry; Stage #2: 3-pyridylboronic acid With sodium carbonate In water at 75℃; Suzuki Coupling; Inert atmosphere; Green chemistry; | 79% |
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 80℃; for 1h; Suzuki Coupling; Inert atmosphere; | 73% |
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water at -5 - 5℃; Inert atmosphere; Reflux; | 4.5 g |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
(meta-(trifluoromethyl)phenyl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry; Stage #2: [3-(trifluoromethyl) phenyl] boronic acid With sodium carbonate In water at 75℃; Suzuki Coupling; Inert atmosphere; Green chemistry; | 79% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 100℃; for 6h; Suzuki Coupling; Inert atmosphere; | 61% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.08333h; Inert atmosphere; | 61% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.25h; Inert atmosphere; | 61% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
(2-tert-butoxy-2-oxoethyl)zinc(II) bromide
((3S,8R,9S,10R,13S,14S)-3-Acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-acetic acid tert-butyl ester
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; diisobutylaluminium hydride In tetrahydrofuran; toluene 1.) 0 deg C, 5 min, 2.) room temperature, overnight; | 77% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With borane-THF In tetrahydrofuran at -10 - 20℃; for 8h; Inert atmosphere; Stage #2: With sodium perborate In tetrahydrofuran; water at 0 - 20℃; | 76% |
o-fluorophenylboronic acid
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry; Stage #2: o-fluorophenylboronic acid With sodium carbonate In water at 75℃; Suzuki Coupling; Inert atmosphere; Green chemistry; | 75% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 100℃; for 6h; Suzuki Coupling; Inert atmosphere; | 68% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.08333h; Inert atmosphere; | 68% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 100℃; for 6h; Suzuki Coupling; Inert atmosphere; | 65% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.08333h; Inert atmosphere; | 65% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.25h; Inert atmosphere; | 65% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
ethyl vinyl ether
A
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); triethylamine In dimethyl sulfoxide at 60℃; for 4h; | A 62% B 11% |
4-methylphenylboronic acid
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 100℃; for 6h; Suzuki Coupling; Inert atmosphere; | 58% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.08333h; Inert atmosphere; | 58% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.25h; Inert atmosphere; | 58% |
4-Bromophenylboronic acid
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.25h; Inert atmosphere; | 58% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 100℃; for 6h; Suzuki Coupling; Inert atmosphere; | 53% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.08333h; Inert atmosphere; | 53% |
4-fluoroboronic acid
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 100℃; for 6h; Suzuki Coupling; Inert atmosphere; | 57% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.08333h; Inert atmosphere; | 57% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.25h; Inert atmosphere; | 57% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
A
3β-acetoxyandrost-5,16-diene
Conditions | Yield |
---|---|
With [(Pd(PPh3)2)n]; diisobutylaluminium hydride; tert-butyl 2-bromozincpropionate In tetrahydrofuran; toluene 1.) 0 deg C, 5 min, 2.) room temperature, overnight; | A 54% B 9% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With pyridine; ozone In methanol; dichloromethane at -78 - 20℃; Stage #2: With dimethylsulfide In methanol; dichloromethane at -78℃; for 0.5h; | 53% |
4-carboxyphenylboronic acid
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 80 - 85℃; Inert atmosphere; | 53% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With borane-THF In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: With sodium perborate tetrahydrate; water In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; | 28% |
vinyl acetate
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
A
Acetic acid (Z)-2-((3S,8R,9S,10R,13S,14S)-3-acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-vinyl ester
B
Acetic acid (E)-2-((3S,8R,9S,10R,13S,14S)-3-acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-vinyl ester
Conditions | Yield |
---|---|
With triethylamine; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 60℃; for 9h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
α-picoline
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
Conditions | Yield |
---|---|
With n-butyllithium; bis(triphenylphosphine)palladium(II)-chloride; zinc(II) chloride Multistep reaction; |
The Androsta-5,16-diene-3,17-diol, 3-acetate 17-(trifluoromethanesulfonate), (3β)-, with the CAS registry number 115375-60-5, is also known as (3β)-Androsta-5,16-diene-3,17-diol 3-Acetate 17-(trifluoromethanesulfonate). This chemical's molecular formula is C22H29F3O5S and molecular weight is 462.52. What's more, its systematic name is [(3S,10R,13S)-10,13-dimethyl-17-(trifluoromethylsulfonyloxy)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate.
Physical properties of Androsta-5,16-diene-3,17-diol, 3-acetate 17-(trifluoromethanesulfonate), (3β)- are: (1)ACD/LogP: 1.77; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.57; (4)ACD/LogD (pH 7.4): -1.86; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.01; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 57.65 Å2; (13)Index of Refraction: 1.574; (14)Molar Refractivity: 73.14 cm3; (15)Molar Volume: 221.4 cm3; (16)Polarizability: 28.99×10-24cm3; (17)Surface Tension: 50.7 dyne/cm; (18)Density: 1.407 g/cm3; (19)Flash Point: 201.9 °C; (20)Enthalpy of Vaporization: 69.85 kJ/mol; (21)Boiling Point: 410.2 °C at 760 mmHg; (22)Vapour Pressure: 1.83E-07 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)O[C@H]1CC[C@@]2(C3CC[C@]4(C(C3CC=C2C1)CC=C4OS(=O)(=O)C(F)(F)F)C)C
(2)InChI: InChI=1S/C22H29F3O5S/c1-13(26)29-15-8-10-20(2)14(12-15)4-5-16-17-6-7-19(21(17,3)11-9-18(16)20)30-31(27,28)22(23,24)25/h4,7,15-18H,5-6,8-12H2,1-3H3/t15-,16?,17?,18?,20-,21-/m0/s1
(3)InChIKey: MCIVSCZCJRGEJR-KJBVPOJVSA-N
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