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inquiry1-Naphthalenemethanol,1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-, (1S,4aS,8aS)- cas 468-68-8Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air,
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inquiryfactory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyl acetate
(-)-drimenol
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 0 - 20℃; for 0.416667h; Inert atmosphere; | 100% |
With potassium hydroxide In methanol at 18℃; for 1h; | 86% |
With potassium hydroxide In methanol | 86% |
(+)-drimane-8,11-diol
(-)-drimenol
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In benzene at 20℃; for 1h; | 92% |
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 6h; regioselective reaction; | 79% |
With toluene-4-sulfonic acid In dichloromethane at 0 - 17℃; Reagent/catalyst; regioselective reaction; | 58% |
(1S,4aS,8aS)-1-(tert-butyldimethylsilyloxymethyl)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetrmethylnaphthalene
(-)-drimenol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 36h; | 92% |
(4aS,8aS)-2,5,5,8a-Tetramethyl-4a,5,6,7,8,8a-hexahydronaphthalene-1-carbaldehyde
(-)-drimenol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at -8 - 20℃; for 2.25h; Reduction; | 89% |
drim-7-en-11-yl (1R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate
(-)-drimenol
Conditions | Yield |
---|---|
With barium dihydroxide In methanol at 20℃; for 2.5h; | 88% |
drimendiol
(-)-drimenol
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; hydrogen In ethanol for 1.25h; | 64% |
((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl acetate
(-)-drimenol
Conditions | Yield |
---|---|
Stage #1: ((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl acetate With sulfuric acid In ethanol for 0.00333333h; Stage #2: With potassium hydroxide In methanol for 0.005h; | 57% |
With sulfuric acid In ethanol | 53% |
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol / 0.25 h / 0 - 20 °C / Inert atmosphere 2: potassium hydroxide / methanol / 0.42 h / 0 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / 1 h / 20 °C 2: toluene-4-sulfonic acid / dichloromethane / 0 - 17 °C View Scheme |
((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl acetate
A
(-)-drimenol
B
((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyl acetate
Conditions | Yield |
---|---|
With sulfuric acid In ethanol at 0 - 20℃; for 0.25h; Inert atmosphere; | A 20% B 56% |
((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl acetate
A
albicanol
B
(-)-drimenol
Conditions | Yield |
---|---|
With sulfuric acid In ethanol at 20℃; for 18h; | A n/a B 52.8% |
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate at 60℃; Temperature; Inert atmosphere; regioselective reaction; | A 52% B 44% |
With triphenylphosphine; diethylazodicarboxylate at 20℃; Reagent/catalyst; Inert atmosphere; regioselective reaction; | A 19% B 23% |
(4aS,8aS)-2,5,5,8a-Tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2,3-dihydroxy-propyl ester
(-)-drimenol
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In toluene for 8h; Ambient temperature; | 50% |
sesquiterpenoic acid glyceride
(-)-drimenol
Conditions | Yield |
---|---|
With diisobutylaluminium hydride |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h; | A n/a B 3 mg |
(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester
(-)-drimenol
Conditions | Yield |
---|---|
With barium dihydroxide In methanol; dichloromethane for 2h; Ambient temperature; |
A
(-)-drimenol
B
((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyl acetate
C
(5R,9R,10R)-(+)-drim-7-en-11-ol
Conditions | Yield |
---|---|
With hog pancreas lipase In phosphate buffer at 20℃; for 22h; pH=6.5; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With Alicyclobacillus acidocaldarius squalene-hopene cyclase; Triton X-100 at 60℃; for 16h; pH=6.0; | A 8.7 mg B 6.3 mg C 4.7 mg D 2.0 mg |
((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl acetate
A
albicanol
B
(-)-drimenol
C
(+)-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol
Conditions | Yield |
---|---|
Stage #1: ((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl acetate With pyridine; trichlorophosphate at 20℃; for 2h; Stage #2: With potassium hydroxide In methanol at 20℃; for 0.333333h; Title compound not separated from byproducts; |
(1S,3aR,5aS,9aS,9bR)-1-hydroxy-dodecahydro-3a,6,6,9a,-tetramethylnaphtho-[2,1-b]furan-2-one
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 30 percent / LiAlH4 / tetrahydrofuran / 4 h / 25 °C 2: 91 percent / LiAlH4 / tetrahydrofuran / 3 h 3: 90 percent / lead tetraacetate / benzene / 4 h / 25 °C 4: 97 percent / LiALH4 / diethyl ether / 1 h / 20 °C 5: 98 percent / imidazole / dimethylformamide / 2 h / 25 °C 6: 45 percent / triethylamine; methanesulfonyl chloride / tetrahydrofuran / 4 h / 25 °C 7: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h / 25 °C View Scheme | |
Multi-step reaction with 6 steps 1: 70 percent / LiAlH4 / tetrahydrofuran / 4 h / 25 °C 2: 90 percent / lead tetraacetate / benzene / 4 h / 25 °C 3: 97 percent / LiALH4 / diethyl ether / 1 h / 20 °C 4: 98 percent / imidazole / dimethylformamide / 2 h / 25 °C 5: 45 percent / triethylamine; methanesulfonyl chloride / tetrahydrofuran / 4 h / 25 °C 6: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h / 25 °C View Scheme |
(3aR,5aS,9aS,9bR)-dodecahydro-3a,6,6,9a,-tetramethylnaphtho-[2,1-b]furan-1,2-diol
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 91 percent / LiAlH4 / tetrahydrofuran / 3 h 2: 90 percent / lead tetraacetate / benzene / 4 h / 25 °C 3: 97 percent / LiALH4 / diethyl ether / 1 h / 20 °C 4: 98 percent / imidazole / dimethylformamide / 2 h / 25 °C 5: 45 percent / triethylamine; methanesulfonyl chloride / tetrahydrofuran / 4 h / 25 °C 6: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h / 25 °C View Scheme |
(1R,2R,4aS,8aS)-(+)-2-hydroxy-1,2,3,4,4a,5,6,7,8,8a-decahydro-2,5,5,8a-tetramethyl-naphthalen-1-aldehyde
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 97 percent / LiALH4 / diethyl ether / 1 h / 20 °C 2: 98 percent / imidazole / dimethylformamide / 2 h / 25 °C 3: 45 percent / triethylamine; methanesulfonyl chloride / tetrahydrofuran / 4 h / 25 °C 4: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h / 25 °C View Scheme | |
Multi-step reaction with 2 steps 1: tin(IV) chloride / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2: sodium tetrahydroborate; methanol / 72 h / 0 - 20 °C / Inert atmosphere View Scheme |
(1S,2R,4aS,8aS)-1-(tert-butyldimethylsilyloxymethyl)-decahydro-2,5,5,8a-tetramethylnaphthalen-2-ol
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 45 percent / triethylamine; methanesulfonyl chloride / tetrahydrofuran / 4 h / 25 °C 2: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h / 25 °C View Scheme |
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / lead tetraacetate / benzene / 4 h / 25 °C 2: 97 percent / LiALH4 / diethyl ether / 1 h / 20 °C 3: 98 percent / imidazole / dimethylformamide / 2 h / 25 °C 4: 45 percent / triethylamine; methanesulfonyl chloride / tetrahydrofuran / 4 h / 25 °C 5: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h / 25 °C View Scheme |
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: LDA / tetrahydrofuran / 1 h / -78 °C 1.2: 65.6 percent / MoO5*pyridine*HMPA / tetrahydrofuran / 0.5 h / -78 °C 2.1: 30 percent / LiAlH4 / tetrahydrofuran / 4 h / 25 °C 3.1: 91 percent / LiAlH4 / tetrahydrofuran / 3 h 4.1: 90 percent / lead tetraacetate / benzene / 4 h / 25 °C 5.1: 97 percent / LiALH4 / diethyl ether / 1 h / 20 °C 6.1: 98 percent / imidazole / dimethylformamide / 2 h / 25 °C 7.1: 45 percent / triethylamine; methanesulfonyl chloride / tetrahydrofuran / 4 h / 25 °C 8.1: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h / 25 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: LDA / tetrahydrofuran / 1 h / -78 °C 1.2: 65.6 percent / MoO5*pyridine*HMPA / tetrahydrofuran / 0.5 h / -78 °C 2.1: 70 percent / LiAlH4 / tetrahydrofuran / 4 h / 25 °C 3.1: 90 percent / lead tetraacetate / benzene / 4 h / 25 °C 4.1: 97 percent / LiALH4 / diethyl ether / 1 h / 20 °C 5.1: 98 percent / imidazole / dimethylformamide / 2 h / 25 °C 6.1: 45 percent / triethylamine; methanesulfonyl chloride / tetrahydrofuran / 4 h / 25 °C 7.1: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h / 25 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: diethyl ether / -78 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.24 h / Reflux 2.2: 20 °C 3.1: toluene-4-sulfonic acid / dichloromethane / 0 - 17 °C View Scheme |
(+)-drim-9(11)-en-8α-ol
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: BH3*THF complex / tetrahydrofuran / 12 h / 20 °C 1.2: 94 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran; ethanol / 12 h / 20 °C 2.1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 1 h / 20 °C View Scheme |
Acetic acid (1R,2R,4aS,8aS)-1-iodomethyl-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-yl ester
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: t-BuOK; t-butyl methyl ether / dimethylsulfoxide / 1 h / 20 °C 1.2: 85 percent / H2O / dimethylsulfoxide / 5 h / 20 °C 2.1: BH3*THF complex / tetrahydrofuran / 12 h / 20 °C 2.2: 94 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran; ethanol / 12 h / 20 °C 3.1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 1 h / 20 °C View Scheme |
(1S,3R,4R,4aS,8aS)-3-(Acetyloxy)-4-formyl-3,4a,8,8-tetramethyldecahydronaphthalen-1-yl acetate
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 77 percent / 2,4,6-collidine / 1.5 h / 200 °C 2: 89 percent / NaBH4 / ethanol / 2.25 h / -8 - 20 °C View Scheme |
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: O3; O2 / CH2Cl2; methanol / 0.17 h / -78 °C 1.2: 78 percent / Me2S / CH2Cl2; methanol / 20 °C 2.1: 77 percent / 2,4,6-collidine / 1.5 h / 200 °C 3.1: 89 percent / NaBH4 / ethanol / 2.25 h / -8 - 20 °C View Scheme |
(+/-)-drim-7-en-11-ol
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / 1 h / Ambient temperature 2: Ba(OH)2 / methanol; CH2Cl2 / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: 43 percent / pyridine / 3 h / 20 °C 2: 88 percent / barium hydroxide / methanol / 2.5 h / 20 °C View Scheme |
(E,E)-3,11-dimethylundeca-2,6,10-trien-1-ol
(-)-drimenol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 56 percent / fluorosulfonic acid / various solvent(s) / 1 h / -78 °C 2: pyridine / CH2Cl2 / 1 h / Ambient temperature 3: Ba(OH)2 / methanol; CH2Cl2 / 2 h / Ambient temperature View Scheme |
(-)-drimenol
(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde
Conditions | Yield |
---|---|
Stage #1: (-)-drimenol With phosphorus pentoxide; dimethyl sulfoxide In dichloromethane at 20℃; for 0.666667h; Cooling with ice; Stage #2: With triethylamine In dichloromethane at 20℃; for 0.666667h; | 99% |
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Dess-Martin Oxidation; | 98% |
With phosphorus pentoxide; dimethyl sulfoxide at 20℃; | 95% |
(-)-drimenol
acetic anhydride
((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyl acetate
Conditions | Yield |
---|---|
In pyridine | 98% |
With pyridine | 97% |
95% | |
With dmap In dichloromethane at 20℃; for 2h; | 95% |
(-)-drimenol
((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyl acetate
Conditions | Yield |
---|---|
97% |
(-)-drimenol
(-)-7α,8α,11-trihydroxydrimane
Conditions | Yield |
---|---|
With methanesulfonamide; AD-mix-β In water; tert-butyl alcohol at 20℃; | 94% |
Multi-step reaction with 3 steps 1: 97 percent / pyridine 2: 57.2 percent / N-methylmorpholine-N-oxide, OsO4 / H2O; acetone; 2-methyl-propan-2-ol / 192 h 3: 99 percent / KOH / methanol / Ambient temperature View Scheme |
(-)-drimenol
Conditions | Yield |
---|---|
With methanesulfonamide; AD-mix-α In water; tert-butyl alcohol at 20℃; | 92% |
(-)-drimenol
methanesulfonyl chloride
((1S,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyl methanesulfonate
Conditions | Yield |
---|---|
With pyridine for 40h; Ambient temperature; | 90% |
With N,N,N,N,-tetramethylethylenediamine In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; |
(-)-drimenol
A
(+)-[(1S,2S,8aS)-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl]methanol
B
[(1S,2R,4aS,8aS)-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl]methanol
Conditions | Yield |
---|---|
With platinum(IV) oxide; hydrogen In ethyl acetate at 0℃; for 0.5h; | A 90% B 8% |
With Crabtree's catalyst; hydrogen In dichloromethane at 0 - 20℃; under 760.051 Torr; for 2h; stereoselective reaction; | A 9% B 89% |
With Crabtree's catalyst; hydrogen In dichloromethane at 0℃; under 760.051 Torr; for 2h; | A 9% B 89% |
With palladium on activated charcoal; hydrogen Overall yield = 85 %; | A n/a B n/a |
(-)-drimenol
(+)-[(1S,2S,8aS)-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl]methanol
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In dichloromethane for 4h; | 75% |
With palladium on activated charcoal; hydrogen at 20℃; for 12h; Inert atmosphere; | 75% |
(-)-drimenol
(-)-(8aS)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane | 60% |
With potassium dichromate; sulfuric acid | |
Multi-step reaction with 2 steps 1: (i) H2, PtO2, AcOEt, (ii) CrO3, aq. AcOH, KHSO4, (iii) Pb(OAc)4, Cu(OAc)2, Py, benzene 2: CrO3, AcOH View Scheme | |
Multi-step reaction with 2 steps 1: hydrogen; palladium on activated charcoal / 12 h / 20 °C / Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C / Inert atmosphere View Scheme |
(-)-drimenol
3β,11-dihydroxydrimene
Conditions | Yield |
---|---|
for 29h; Rhizopus arrhizus; | 60% |
With Rhizopus arrhizus for 29h; | 60% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; potassium osmate(VI) dihydrate; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0 - 20℃; | A 24% B 58% |
(-)-drimenol
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine In toluene at 0 - 20℃; for 3h; Mitsunobu Displacement; Inert atmosphere; | 58% |
(-)-drimenol
(-)-(4aS,8aS)-2,5,5,8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-naphthalen-1-one
Conditions | Yield |
---|---|
With Jones reagent at 0℃; for 1h; | 55% |
(-)-drimenol
A
3β,11-dihydroxydrimene
B
[(1aS,2S,2aS,6aS,7aR)-1a,2a,6,6-tetramethyldecahydronaphtho[2,3-b]oxiren-2-yl]methanol
Conditions | Yield |
---|---|
for 28h; Mucor plumbeus; | A 7% B 3% C 50% |
(-)-drimenol
A
1,1,5,6-tetramethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With iodine In toluene for 5h; Concentration; Solvent; Reagent/catalyst; Reflux; | A 25% B 46% C 24% |
With iodine In 5,5-dimethyl-1,3-cyclohexadiene for 0.7h; Reagent/catalyst; Concentration; Solvent; Reflux; | A 43% B 28% C 29% |
Conditions | Yield |
---|---|
With selenium(IV) oxide for 5h; Heating; | A 8% B 35% C 44% |
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