Conditions | Yield |
---|---|
With sodium acetate; methylamine In methanol; ethanol for 2h; Henry Nitro Aldol Condensation; | 91% |
With aluminum oxide; potassium carbonate for 0.0666667h; microwave irradiation; | 90% |
With ethylenediamine functionalized magnetic Fe3O4 supported on SiO2 nanoparticles; air at 80℃; for 4h; | 89% |
1,3-benzodioxol-5-ylmethyl amine
nitromethane
5-(2-nitrovinyl)benzo[1,3]dioxole
Conditions | Yield |
---|---|
With 4-(4-fluorophenyl)naphthalene-1,2-dione; oxygen at 80℃; for 12h; | 53% |
5-(2-nitrovinyl)benzo[1,3]dioxole
Conditions | Yield |
---|---|
With acetic acid; zinc(II) chloride |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / dimethyl sulfoxide / 95 - 120 °C 2: trichlorophosphate 3: sodium acetate; methylamine / ethanol; methanol / 2 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate 2: sodium acetate; methylamine / ethanol; methanol / 2 h View Scheme |
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid at 100℃; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 70℃; for 4h; | 100% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4h; | 95% |
With diisobutylaluminium hydride In 1,4-dioxane at 60℃; for 3h; | 82% |
Conditions | Yield |
---|---|
Stage #1: cyclohexanone With (S)-1-(2,3,4,6-tetra-O-acetyl)glucosyl-3-(pyrrolidin-2-ylmethyl)-thiourea trifluoroacetate; triethylamine at 20℃; for 0.333333h; Stage #2: 5-(2-nitrovinyl)benzo[1,3]dioxole With butyric acid at -15℃; for 52h; Michael condensation; | 99% |
Stage #1: cyclohexanone With C2HF3O2*C17H19N2O2PS; triethylamine at 25℃; for 0.5h; Stage #2: With benzoic acid for 0.25h; Stage #3: 5-(2-nitrovinyl)benzo[1,3]dioxole at -30℃; for 40h; Michael addition; optical yield given as %ee; enantioselective reaction; | 95% |
With C12H21N4O2(1+)*Cl(1-); triethylamine In methanol at 20℃; for 36h; Michael Addition; enantioselective reaction; | 95% |
Conditions | Yield |
---|---|
With 1-((1S,2S)-2-aminocyclohexyl)-3-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)thiourea; zinc trifluoromethanesulfonate In toluene at 35℃; for 3h; Friedel-Crafts Alkylation; Inert atmosphere; enantioselective reaction; | A 99% B n/a |
5-(2-nitrovinyl)benzo[1,3]dioxole
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.2h; Sealed tube; | 98% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; C41H50N4O2P2 In toluene at 40℃; for 24h; stereoselective reaction; | 98% |
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With 4-methyl-morpholine; C25H31F6N5O2S*C2HF3O2; benzoic acid In dichloromethane at -10℃; for 0.166667h; Michael Addition; Inert atmosphere; Stage #2: butyraldehyde In dichloromethane at -10 - 20℃; Inert atmosphere; enantioselective reaction; | 97% |
5-(2-nitrovinyl)benzo[1,3]dioxole
3-(3-chlorophenyl)propanal
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With 4-methyl-morpholine; C25H31F6N5O2S*C2HF3O2; benzoic acid In dichloromethane at -10℃; for 0.166667h; Michael Addition; Inert atmosphere; Stage #2: 3-(3-chlorophenyl)propanal In dichloromethane at -10 - 20℃; Inert atmosphere; enantioselective reaction; | 97% |
5-(2-nitrovinyl)benzo[1,3]dioxole
3-(4-methoxyphenyl)propional
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With 4-methyl-morpholine; C25H31F6N5O2S*C2HF3O2; benzoic acid In dichloromethane at -10℃; for 0.166667h; Michael Addition; Inert atmosphere; Stage #2: 3-(4-methoxyphenyl)propional In dichloromethane at -10 - 20℃; Inert atmosphere; enantioselective reaction; | 97% |
prop-2-ene-1-thiol
5-(2-nitrovinyl)benzo[1,3]dioxole
2-(allylthio)-2-(3,4-(methylenedioxy)phenyl)-1-nitroethane
Conditions | Yield |
---|---|
With piperidine In diethyl ether | 96% |
5-(2-nitrovinyl)benzo[1,3]dioxole
butyraldehyde
(2R,3S)-3-(benzo[d][1,3]dioxol-5-yl)-2-ethyl-4-nitrobutyraldehyde
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With benzoic acid; <(S)-2'-hydroxymethylpyrrolidinyl-N'-carboxy>-(S)-proline In dichloromethane at -20℃; for 0.333333h; Michael addition; Stage #2: butyraldehyde In dichloromethane at -20℃; for 60h; Michael addition; optical yield given as %ee; enantioselective reaction; | 96% |
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With 4-methyl-morpholine; C25H31F6N5O2S*C2HF3O2; benzoic acid In dichloromethane at -10℃; for 0.166667h; Michael Addition; Inert atmosphere; Stage #2: isovaleraldehyde In dichloromethane at -10 - 20℃; Inert atmosphere; enantioselective reaction; | A 96% B n/a |
5-(2-nitrovinyl)benzo[1,3]dioxole
4-Methoxycarbonyl-buten-(3)-yl-(1)-malonsaeurediaethylester
B
(2R,3R,4S)-diethyl 2-(benzo[d][1,3]dioxol-5-yl)-4-(2-methoxy-2-oxoethyl)-3-nitrocyclohexane-1,1-dicarboxylate
Conditions | Yield |
---|---|
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea In toluene at 20℃; for 360h; Overall yield = 95 %; Overall yield = 88.4 mg; stereoselective reaction; | A n/a B 95% |
5-(2-nitrovinyl)benzo[1,3]dioxole
methyl 1-acetyl-3-oxoindoline-2-carboxylate
(S)-methyl 1-acetyl-2-((S)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-3-oxoindoline-2-carboxylate
Conditions | Yield |
---|---|
With C30H29F6N3OS In dichloromethane at 0℃; for 24h; Reagent/catalyst; Solvent; Time; Michael Addition; enantioselective reaction; | 95% |
5-(2-nitrovinyl)benzo[1,3]dioxole
dimethyl (prop-2-yn-1-yl)malonate
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -78℃; for 4h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With C34H34FeN4O3 In dichloromethane for 0.0833333h; Michael Addition; Inert atmosphere; Stage #2: C8H12O3 In dichloromethane at 20℃; for 4h; Michael Addition; Inert atmosphere; | 94% |
5-(2-nitrovinyl)benzo[1,3]dioxole
Benzimidazol-2-thiol
Conditions | Yield |
---|---|
With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 80℃; for 8h; | 94% |
5-(2-nitrovinyl)benzo[1,3]dioxole
4-(benzo[d][1,3]dioxol-5-yl)-1H-1,2,3-triazole
Conditions | Yield |
---|---|
With sodium azide In water Heating; Green chemistry; regioselective reaction; | 94% |
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With C50H43CuF3N4O5S In tetrahydrofuran at -20℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-ethoxycarbonyl-1-cyclopentanone In tetrahydrofuran at -20℃; for 72h; Inert atmosphere; stereoselective reaction; | 94% |
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With 4-methyl-morpholine; C25H31F6N5O2S*C2HF3O2; benzoic acid In dichloromethane at -10℃; for 0.166667h; Michael Addition; Inert atmosphere; Stage #2: 3-phenyl-propionaldehyde In dichloromethane at -10 - 20℃; Inert atmosphere; enantioselective reaction; | 94% |
5-(2-nitrovinyl)benzo[1,3]dioxole
acetone
(S)-4-(benzo[d][1,3]dioxol-5-yl)-5-nitropentan-2-one
Conditions | Yield |
---|---|
With (1R,2R)-(-)-N-diphenylthiophosphorylcyclohexane-1,2-diamine; phenol In toluene at 0℃; for 108h; Michael addition; optical yield given as %ee; enantioselective reaction; | 93% |
With N-((1R,2R)-2-amino-1,2-diphenylethyl)-P,P-diphenylphosphinothioic amide In toluene at 20℃; for 36h; asymmetric Michael addition; optical yield given as %ee; enantioselective reaction; | 90% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile at 20℃; for 2h; Michael Addition; Inert atmosphere; | 93% |
5-(2-nitrovinyl)benzo[1,3]dioxole
1-methyl-5-nitro-1H-indole-2,3-dione
L-proline
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole; 1-methyl-5-nitro-1H-indole-2,3-dione With 1,2-propylene cyclic carbonate In water at 90℃; for 0.25h; Stage #2: L-proline With carbon dioxide In water at 90℃; for 1h; regioselective reaction; | 92% |
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With C34H34FeN4O3 In dichloromethane for 0.0833333h; Michael Addition; Inert atmosphere; Stage #2: acetylacetone In dichloromethane at 20℃; for 5h; Michael Addition; Inert atmosphere; | 91% |
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((1S)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In dichloromethane at 20℃; for 24h; Michael Addition; |
5-(2-nitrovinyl)benzo[1,3]dioxole
1-methyl-5-nitro-1H-indole-2,3-dione
L-proline
Conditions | Yield |
---|---|
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole; 1-methyl-5-nitro-1H-indole-2,3-dione With 1,2-propylene cyclic carbonate In water at 90℃; for 0.25h; Stage #2: L-proline With carbon dioxide In water at 90℃; for 1h; regioselective reaction; | 91% |
Conditions | Yield |
---|---|
With iron(III) chloride hexahydrate In neat (no solvent) at 80℃; for 24h; Michael Addition; Green chemistry; | 90% |
With zinc(II) acetate dihydrate In cyclohexane at 80℃; for 18h; Michael addition; | 83% |
With silica gel at 20℃; for 2.5h; Michael addition; Neat (no solvent); | 82% |
With water at 100℃; for 10h; Un-catalyzed Friedel-Crafts alkylation; | 64% |
at 100℃; for 9h; Friedel Crafts alkylation; Neat (no solvent); | 63% |
indole
5-(2-nitrovinyl)benzo[1,3]dioxole
(S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-1H-indole
Conditions | Yield |
---|---|
With 2‐(((1S,2R)‐2‐hydroxy‐2,3‐dihydro‐1H‐inden‐1‐yl)carbamothioyl)quinolin‐1‐ium tetrakis[3,5‐bis(trifluoromethyl)phenyl]borate In chloroform at 0℃; for 19h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 90% |
5-(2-nitrovinyl)benzo[1,3]dioxole
malonic acid dimethyl ester
C14H15NO8
Conditions | Yield |
---|---|
With Cl(1-)*C32H12BF24(1-)*C6H5N2O2(1-)*C42H48CoN6(3+) In [(2)H6]acetone at 0℃; for 24h; | 90% |
5-(2-nitrovinyl)benzo[1,3]dioxole
5-(2-nitroethyl)benzo[1,3]dioxole
Conditions | Yield |
---|---|
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane at 0 - 5℃; for 6h; | 88% |
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane at 0℃; for 6h; | 88% |
With magnesium(II) perchlorate; "grafted NADH model" reagent In acetonitrile; benzene at 80℃; for 120h; | 72% |
5-(2-nitrovinyl)benzo[1,3]dioxole
(E)-4-methyl-N-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide
2-((2S,3R,4S)-2-(benzo[d][1,3]dioxol-5-yl)-1,2,3,4-tetrahydro-3-nitro-1-tosylquinolin-4-yl)-1-phenylethanone
Conditions | Yield |
---|---|
Stage #1: 4-methyl-N-(2-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide With 1-(3,5-Bis-trifluoromethyl-phenyl)-3-[(R)-quinolin-4-yl-((2R,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-thiourea In toluene at 0℃; for 0.0833333h; Stage #2: 5-(2-nitrovinyl)benzo[1,3]dioxole In toluene at 0℃; for 36h; Michael Addition; stereoselective reaction; | 88% |
Stage #1: 4-methyl-N-(2-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide With C28H26F6N4S In toluene at 0℃; for 0.0833333h; Stage #2: 5-(2-nitrovinyl)benzo[1,3]dioxole In toluene at 0℃; for 36h; stereoselective reaction; | 88% |
IUPAC Name: 3,4-Methylenedioxy-beta-nitrostyrene
The MF of 3,4-Methylenedioxy-beta-nitrostyrene (1485-00-3) is C9H7NO4.
The MW of 3,4-Methylenedioxy-beta-nitrostyrene (1485-00-3) is 193.16.
Synonyms of 3,4-Methylenedioxy-beta-nitrostyrene (1485-00-3): 1,3-Benzodioxole, 5- (2-nitroethenyl)- ; 3,4-Methylenedioxy-.beta.-nitrostyrene ; 5-(2-Nitrovinyl)-1,3-benzodioxole ; 5-[(E)-2-Nitrovinyl]-1,3-benzodioxole ; Styrene, 3,4-methylenedioxy-.beta.-nitro- ; 1,3-Benzodioxole, 5-[(E)-2-nitroethenyl]-
Product Categories: Ethanes/ethenes
Index of Refraction: 1.64
Form: yellow powder
Density: 1.401 g/ml
Flash Point: 168.8 °C
Boiling Point: 334.9 °C
Melting Point: 162 °C
Sensitive: Light Sensitive
BRN: 192350
3,4-Methylenedioxy-beta-nitrostyrene (1485-00-3) is used as pharmaceutical intermediates, organic synthesis.
1. | ipr-mus LD :>500 mg/kg | CBCCT* “Summary Tables of Biological Tests” National Research Council Chemical-Biological Coordination Center. 6 (1954),375. | ||
2. | ivn-mus LD50:32 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#00689 . |
A poison by intravenous route. Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.Safety information of 3,4-Methylenedioxy-beta-nitrostyrene (1485-00-3):
Hazard Codes Xn,Xi,T
Risk Statements
36/37/38 Irritating to eyes, respiratory system and skin
22 Harmful if swallowed
25 Toxic if swallowed
Safety Statements
36/37/39 Wear suitable protective clothing, gloves and eye/face protection
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
45 In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR UN 2811 6.1/PG 3
RTECS WL5270000
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