1-(2-Nitrovinyl)benzene supplier

Name
(E)-2-Nitroethenylbenzene
EINECS 203-066-0
CAS No. 5153-67-3
Article Data205
CAS DataBase
Density 1.177 g/cm³
Solubility Insoluble in water.
Melting Point 55-58 °C
Formula C₈H₇NO₂
Boiling Point 255.8 °C at 760 mmHg
Molecular Weight 149.149
Flash Point 117.5 °C
Transport Information UN2811
Appearance yellow crystals.
Safety S26;S36
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Benzene,(2-nitroethenyl)-, (E)-;Styrene, b-nitro-, (E)- (8CI);(E)-(2-Nitroethenyl)benzene;(E)-1-Nitro-2-phenylethene;(E)-1-Nitro-2-phenylethylene;(E)-b-Nitrostyrene;[(1E)-2-Nitroethenyl]benzene;trans-1-Nitro-2-phenylethylene;trans-b-Nitrostyrene;
PSA 45.82000
LogP 2.45720

Synthetic route

: 75-52-5
nitromethane

: 100-52-7
benzaldehyde

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With sulfonic acid amine MCM-41 mesoporous silica nanoparticles at 90℃; for 20h; Temperature;	99%
With m-aminobenzoic acid-(L)-phenylglycinol ammonium at 20℃; for 40h;	99%
With ammonium acetate In toluene at 100℃; for 22h;	99%

: 141377-54-0, 145920-96-3, 149495-00-1, 15990-45-1
2-nitro-1-phenylethan-1-ol

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
Stage #1: 2-nitro-1-phenylethan-1-ol With potassium carbonate In water for 0.25h; Green chemistry; Stage #2: With hydrogenchloride In water pH=6; Green chemistry;	96%
With H-Y zeolite In toluene for 8h; Heating;	93%
With H-Y zeolite In toluene for 8h; Product distribution; Heating; also with other zeolites;	93%

: 292638-84-7
styrene

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With silver(I) nitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In 1,2-dichloro-ethane at 70℃; for 12h; Kinetics; Reagent/catalyst; Solvent; Concentration; Molecular sieve; Inert atmosphere; stereoselective reaction;	95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In 1,4-dioxane at 80℃; for 1h; Reagent/catalyst; Solvent; Green chemistry; stereoselective reaction;	95%
Stage #1: styrene With chloro-trimethyl-silane; copper(ll) sulfate pentahydrate; guanidine nitrate In acetonitrile at 0 - 20℃; Inert atmosphere; Stage #2: With triethylamine In acetonitrile at 20℃; for 0.5h; Inert atmosphere; stereoselective reaction;	92%

: 588-72-7
[(E)-2-bromoethenyl]benzene

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With tetranitromethane In acetonitrile Irradiation;	95%

: 75-52-5
nitromethane

: 100-52-7
benzaldehyde

A: 5153-67-3
nitrostyrene

B: 117538-84-8
(1,3-dinitropropan-2-yl)benzene

Conditions

Conditions	Yield
aminopropyl-functionalized silica at 90℃; for 2h; Product distribution; Further Variations:; Catalysts;	A 95% B 3%
MCM-41-NHMe at 90℃; for 1h;	A 81% B n/a
With azide amine MCM-41 mesoporous silica nanoparticles at 90℃; for 20h;	A 42% B 47%

...Expand

: 140-10-3
(E)-3-phenylacrylic acid

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With copper(II) nitrate In acetonitrile at 110℃; for 8h; Reagent/catalyst; Solvent; Temperature; Sealed tube; Green chemistry; regioselective reaction;	94%
With pyridine; Iron(III) nitrate nonahydrate In toluene at 100℃; for 12h; Reagent/catalyst; Solvent;	90%
With chloro-trimethyl-silane; copper(II) nitrate trihydrate In acetonitrile at 100℃; for 2h; Reagent/catalyst; stereoselective reaction;	89%

: 75-52-5
nitromethane

: 1125-88-8
benzaldehyde dimethyl acetal

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With lepidocricite; water In acetonitrile at 105℃; for 48h; Henry Nitro Aldol Condensation; Inert atmosphere;	93%
With phosphotungstic acid immobilized on amine-grafted mesoporous silica at 50℃; for 12h; Inert atmosphere;	92%
With sulfonic acid and 3-aminopropyltriethoxysilane functionalized at K10-montmorillonite (SO3H-APTES at K10-MMT) at 90℃; for 2h; Reagent/catalyst; Time; Henry Nitro Aldol Condensation;	99.2 %Chromat.
Stage #1: benzaldehyde dimethyl acetal With highly porous and stable acid-base bifunctional metal-organic framework chromium(III) terephthalate containing sulfonic acid and amine groups (MIL-101-NH2-SO3H) In o-xylene at 49.84℃; Stage #2: nitromethane In o-xylene at 49.84℃; Henry Nitro Aldol Condensation;

: 75-52-5
nitromethane

: 1125-88-8
benzaldehyde dimethyl acetal

A: 5153-67-3
nitrostyrene

B: 100-52-7
benzaldehyde

Conditions

Conditions	Yield
With FeO2H; water In acetonitrile at 105℃; for 48h; Reagent/catalyst; Henry Nitro Aldol Condensation; Inert atmosphere;	A 93% B 6%
With lepidocricite; water In acetonitrile at 80℃; for 12h; Reagent/catalyst; Henry Nitro Aldol Condensation; Inert atmosphere;	A 41.6% B 57%

...Expand

: C8H7NO3

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With sodium iodide; tin(ll) chloride In ethanol for 0.116667h; Reflux; Green chemistry;	92%

: 31771-33-2
2-phenyl-4,4,6-trimethyltetrahydro-(2H)-1,3-oxazine

: 75-52-5
nitromethane

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With acetic acid In acetonitrile for 5h; Heating;	90%

: 3425-99-8, 37887-94-8
(1R*,2R*)-1,2-dibromo-2-phenyl-1-nitroethane

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 130 - 135℃; for 0.05h; microwave irradiation;	89%
With dimethyl sulfoxide at 25℃; for 18h;	51%

: 92550-70-4
4-methylphenylstyryl sulfide

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With tert.-butylnitrite In water at 100℃; for 12h;	87%

: 292638-84-7
styrene

A: 5153-67-3
nitrostyrene

B: 100-52-7
benzaldehyde

C: 100-47-0
benzonitrile

D: 98-86-2
acetophenone

E: 65-85-0
benzoic acid

Conditions

Conditions	Yield
With formic acid; sodium nitrite In acetonitrile at 70℃; for 4h; Mechanism; Reagent/catalyst; Solvent; Temperature; Schlenk technique;	A n/a B n/a C 84% D n/a E n/a

...Expand

: 75-52-5
nitromethane

: 100-52-7
benzaldehyde

A: 5153-67-3
nitrostyrene

B: 141377-54-0, 145920-96-3, 149495-00-1, 15990-45-1
2-nitro-1-phenylethan-1-ol

Conditions

Conditions	Yield
With CaO modified benzyl bromide at 102℃; for 5h; Reagent/catalyst; Temperature; Henry Nitro Aldol Condensation;	A 15.6% B 82.9%
aminopropyltriethoxysilane on silica-alumina at 100℃; for 6h; Product distribution; Kinetics; Further Variations:; Catalysts;	A 99 % Chromat. B n/a

...Expand

: 3425-99-8, 37887-94-8
C8H7Br2NO2

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; sodium carbonate In dimethyl sulfoxide at 20℃; for 1.5h; Inert atmosphere; Irradiation;	81%

: 3-nitro-2-phenylpropane-1,1-dicarbonitrile

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With dmap; di-tert-butyl dicarbonate In toluene at 45 - 50℃;	80%

: 292638-84-7
styrene

A: 5153-67-3
nitrostyrene

B: 21205-24-3
2-isonitroso-1-nitro-2-phenylethane

Conditions

Conditions	Yield
With tert.-butylnitrite In dimethyl sulfoxide at 32 - 35℃; for 0.5h; Green chemistry;	A 7% B 73%

: 7422-28-8, 17421-57-7, 50849-52-0
(Z)-1-Phenyl-2-(trimethylstannyl)aethen

A: 5153-67-3
nitrostyrene

B: 15241-23-3
(Z)-nitrostyrene

Conditions

Conditions	Yield
With tetranitromethane In dimethyl sulfoxide for 3h; Ambient temperature;	A n/a B 65%

: rac-(5S,6R,7S)-5-(4-chlorophenyl)-6-nitro-7-phenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one

A: 5153-67-3
nitrostyrene

: rac-(5R,6R,7S)-5-(4-chlorophenyl)-6-nitro-7-phenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one

Conditions

Conditions	Yield
In dimethyl sulfoxide at 110℃; for 48h;	A 15% B 61%

: 75-52-5
nitromethane

: 100-46-9
benzylamine

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With copper(II) choride dihydrate; 3-chloro-benzenecarboperoxoic acid at 0 - 60℃; for 10h; Henry Nitro Aldol Condensation; Inert atmosphere;	61%

: 621-82-9
Cinnamic acid

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate; sodium nitrite for 0.133333h; Microwave irradiation;	57%

: 75-52-5
nitromethane

: 100-52-7
benzaldehyde

: 590-86-3
isovaleraldehyde

A: 5153-67-3
nitrostyrene

B: (2S,3R)-2-(prop-2-yl)-3-phenylbutanal

C: 1000072-29-6
2-(prop-2-yl)-3-phenylbutanal

Conditions

Conditions	Yield
Stage #1: nitromethane; benzaldehyde With O-(tert-butyldiphenylsilyl)-L-tyrosine lithium salt; magnesium sulfate In dichloromethane at 25℃; for 48h; Stage #2: isovaleraldehyde In dichloromethane at 25℃; for 72h; Michael addition; optical yield given as %ee; enantioselective reaction;	A 50% B n/a C n/a

...Expand

: 79-24-3
Nitroethane

: 71-43-2
benzene

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With palladium(II) trifluoroacetate; silver(I) acetate In 1,2-dimethoxyethane; dimethyl sulfoxide at 100℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere; regioselective reaction;	50%

: 292638-84-7
styrene

A: 5153-67-3
nitrostyrene

B: 7064-02-0
phenyl (5-phenyl-4,5-dihydroisoxazol-3-yl)methanone

Conditions

Conditions	Yield
With tert.-butylnitrite; manganese(III) triacetate dihydrate In acetonitrile at 20℃; for 5h; Schlenk technique; Inert atmosphere;	A 50% B 5%

: 6783-05-7
trans-2-phenylvinylboronic acid

: 5153-67-3
nitrostyrene

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; bismuth (III) nitrate pentahydrate In benzene at 70℃; for 12h; Inert atmosphere;	48%

: 75-52-5
nitromethane

: 100-52-7
benzaldehyde

A: 5153-67-3
nitrostyrene

B: 149495-00-1
(S)-1-phenyl-2-nitroethanol

Conditions

Conditions	Yield
With bis(α-ethylphenylamine) cupric chloride In methanol at 20℃; for 72h; Henry reaction; optical yield given as %ee; enantioselective reaction;	A 46% B n/a

...Expand

: 292638-84-7
styrene

A: 5153-67-3
nitrostyrene

B: 2-nitro-1-phenylethyl nitrate

Conditions

Conditions	Yield
With peroxynitrous acid In acetonitrile at 5 - 10℃; for 1h;	A 45% B n/a

: 104-53-0
3-phenyl-propionaldehyde

: 75-52-5
nitromethane

: 100-52-7
benzaldehyde

A: 5153-67-3
nitrostyrene

B: 1089665-81-5
2-benzyl-2-(2-nitro-1-phenylethyl)ethanal

C: 1021394-80-8
(2S,3R)-4-nitro-2-(1-phenylmethyl)-3-phenylbutanal

D: 1235612-22-2
2-benzyl-2-(2-nitro-1-phenylethyl)ethanal

Conditions

Conditions	Yield
Stage #1: nitromethane; benzaldehyde With O-(tert-butyldiphenylsilyl)-L-tyrosine lithium salt; magnesium sulfate In dichloromethane at 25℃; for 48h; Stage #2: 3-phenyl-propionaldehyde In dichloromethane at 25℃; for 72h; Michael addition; enantioselective reaction;	A 43% B n/a C n/a D n/a

...Expand

: 141377-54-0, 145920-96-3, 149495-00-1, 15990-45-1
2-nitro-1-phenylethan-1-ol

A: 5153-67-3
nitrostyrene

B: 149495-00-1
(S)-1-phenyl-2-nitroethanol

C: 145920-96-3
(R)-2-nitro-1-phenylethanol

Conditions

Conditions	Yield
With vinyl acetate; Pseudomonas fluorescens amino lipase In hexane; toluene at 30℃; for 48h; Title compound not separated from byproducts;	A 40% B n/a C n/a

...Expand

: 75-52-5
nitromethane

: 100-52-7
benzaldehyde

A: 5153-67-3
nitrostyrene

B: 149495-00-1
(S)-1-phenyl-2-nitroethanol

C: 145920-96-3
(R)-2-nitro-1-phenylethanol

Conditions

Conditions	Yield
With bis(α-ethylphenylamine) copper acetate In methanol at 20℃; for 72h; Henry reaction; optical yield given as %ee; enantioselective reaction;	A 40% B n/a C n/a
With bis(α-ethylphenylamine) zinc acetate In methanol at 20℃; for 72h; Henry reaction; optical yield given as %ee; enantioselective reaction;	A 32% B n/a C n/a

...Expand

: 5153-67-3
nitrostyrene

: 6125-24-2
2-Phenylnitroethane

Conditions

Conditions	Yield
With magnesium(II) perchlorate; model of NADH grafted on silica matrix In acetonitrile at 65℃; for 120h;	100%
With sodium tetrahydroborate; silica gel In chloroform; isopropyl alcohol at 0 - 23℃; for 1.33333h; Inert atmosphere;	99%
With hydrogen; tris(triphenylphosphine)rhodium(l) chloride In benzene at 50℃; under 2585.81 Torr; for 14h;	98%

: 5153-67-3
nitrostyrene

: 117390-40-6
5-carbamoyl thieno<2,3-b>pyridine

: 125056-17-9
bromo-8 octyl dimethylchlorosilane

: 6125-24-2
2-Phenylnitroethane

Conditions

Conditions	Yield
With magnesium(II) perchlorate; silice (Merck Kieselgel Art.:7734) Product distribution; multistep reaction; 1.) grafting on a silica matrix, reflux, in toluene, 12 h, 2.) reflux, toluene, 5 days. 3.) acetonitrile, 65 deg C, 5 days; reagent quqntity, reaction time varied;	100%

...Expand

: 5153-67-3
nitrostyrene

: 60947-52-6
(1,4-dinitrobutane-2,3-diyl)dibenzene

Conditions

Conditions	Yield
With samarium diiodide; isopropylamine In water	100%
With tetraethylammonium tosylate In water; N,N-dimethyl-formamide at 0℃; Electrolysis;	71%
With titanium(III) chloride; ammonium acetate In tetrahydrofuran; water at 0℃; for 0.5h;	6%

: 5153-67-3
nitrostyrene

: 557-20-0
diethylzinc

: 119880-63-6, 7796-78-3
(1-nitromethyl-propyl)-benzene

Conditions

Conditions	Yield
With chiral (OCHPhCHMeN(i-Pr))PNMe2; copper(I) triflate In hexane; toluene at -30℃; for 3h; Addition;	100%
copper(I) 2-(Me2NCH2)-3-(Me3Si)-naphthalene-1-thiolate In diethyl ether; hexane at -20℃; for 4h; Michael addition;	98%
With magnesium bromide In diethyl ether for 1h; Ambient temperature;	92%

: 120-72-9
indole

: 5153-67-3
nitrostyrene

: 51626-47-2
3-(2-nitro-1-phenylethyl)-1H-indole

Conditions

Conditions	Yield
Stage #1: nitrostyrene With 2-[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-N-[2-(-4-phenyl-4,5-dihydrothiazol-2-yl)phenyl]benzenamine; zinc trifluoromethanesulfonate In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: indole In toluene at -20℃; for 15h; Friedel Crafts alkylation; Inert atmosphere;	100%
With Zn(2+)*2C6H6NO2S2(1-) In ethanol at 20℃; for 24h; Solvent; Reagent/catalyst;	100%
Stage #1: nitrostyrene With (S)-10,10'-bis[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-9,9'-biphenanthrene; samarium trifluoromethanesulfonate In chloroform at 20℃; for 0.25h; Inert atmosphere; Stage #2: indole In chloroform at 20℃; for 18h; Friedel-Crafts alkylation; Inert atmosphere;	99%

: 603-76-9
1-methylindole

: 5153-67-3
nitrostyrene

: 109811-96-3
1-methyl-3-(2-nitro-1-phenylethyl)-1H-indole

Conditions

Conditions	Yield
With Zn(2+)*2C6H6NO2S2(1-) In ethanol at 20℃; for 24h;	100%
With 1H-pyrrolo[2,3-b]pyridinium substituted-borate salt In toluene at 0 - 20℃; for 24h;	99%
Stage #1: nitrostyrene With (S)-10,10'-bis[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-9,9'-biphenanthrene; zinc(II) trifluoroacetate In diethyl ether at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1-methylindole In diethyl ether at 20℃; Friedel-Crafts alkylation; Inert atmosphere;	99%

: 5153-67-3
nitrostyrene

: 291-64-5
cycloheptane

: (E)-(2-cycloheptylethenyl)benzene

Conditions

Conditions	Yield
With dibenzoyl peroxide In benzene for 6h; Heating;	100%

: 5153-67-3
nitrostyrene

: 292-64-8
Cyclooctan

: (E)-β-cyclooctylstyrene

Conditions

Conditions	Yield
With dibenzoyl peroxide In benzene for 12h; Heating;	100%
With di-tert-butyl peroxide; copper diacetate In 1,2-dichloro-ethane at 100℃; Schlenk technique; Inert atmosphere;	86%
With di-tert-butyl peroxide; copper In 1,2-dichloro-ethane at 110℃; for 8h; Sealed tube; Inert atmosphere; Schlenk technique;	85%

: 5153-67-3
nitrostyrene

: 108-94-1
cyclohexanone

: 4591-64-4, 51262-17-0, 51262-18-1, 84025-84-3, 84025-87-6, 84025-83-2
(S)-2-[(R)-2-nitro-1-phenylethyl]cyclohexanone

Conditions

Conditions	Yield
With 1-[(S)-2'-methylpyrrolidine]-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate at 20℃; for 22h; Michael addition; Ionic liquid; optical yield given as %ee; enantioselective reaction;	100%
With (S)-6-phenyl-3-[(S)-pyrrolidin-2-ylmethyl]-2-thioxotetrahydropyrimidin-4(1H)-one; water; 4-nitro-benzoic acid In tetrahydrofuran for 18h; Michael reaction; optical yield given as %ee; enantioselective reaction;	100%
With 4-nitro-benzoic acid; (S)-6-phenyl-3-[(S)-pyrrolidin-2-ylmethyl]-2-thioxotetrahydropyrimidin-4(1H)-one In tetrahydrofuran; water Product distribution / selectivity; Michael Reaction;	100%

: 5153-67-3
nitrostyrene

: 108-59-8
malonic acid dimethyl ester

: dimethyl [(1S)-2-nitro-1-phenylethyl]malonate

Conditions

Conditions	Yield
With calcium p-methoxyphenolate; anti-5,4-diphenyl pyridinebisoxazoline In toluene at -20℃; for 432h; Michael condensation; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	100%
With C34H46N4Ni(2+)2Br(1-) In dichloromethane at 4℃; for 16h; Catalytic behavior; Solvent; Michael Addition; enantioselective reaction;	99%
With (5,7-bis(trifluoromethyl)-1H-benzoimidazol-2-yl)-9-epiquinine amine In dichloromethane at -20℃; for 40h; asymmetric Michael addition; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	98%

: 29943-42-8
Tetrahydro-4H-pyran-4-one

: 5153-67-3
nitrostyrene

: (R)-tetrahydro-3-((R)-2-nitro-1-phenylethyl)pyran-4-one

Conditions

Conditions	Yield
With 1-[(S)-2'-methylpyrrolidine]-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate at 20℃; for 17h; Michael addition; Ionic liquid; optical yield given as %ee; enantioselective reaction;	100%
With bis(((S)-pyrrolidin-2-yl)methyl) phosphonate dihydrochloride; sodium hydrogencarbonate at 20℃; for 17h; Michael condensation; Ionic liquid; optical yield given as %ee; enantioselective reaction;	98%
Stage #1: Tetrahydro-4H-pyran-4-one With N-((S)-1-phenylethyl)-5-((S)-pyrrolidin-2-yl)oxazole-4-carboxamide; acetic acid In neat (no solvent) at 20℃; for 0.0833333h; Michael Addition; Stage #2: nitrostyrene In neat (no solvent) at 20℃; for 30h; Reagent/catalyst; Michael Addition; stereoselective reaction;	95%

: 5153-67-3
nitrostyrene

: 18854-66-5
tris(allyl)aluminum

: 1-nitro-2-phenylpent-4-ene

Conditions

Conditions	Yield
Stage #1: nitrostyrene; tris(allyl)aluminum In diethyl ether at 0℃; for 0.0333333h; Stage #2: With hydrogen bromide In diethyl ether at 0℃; Further stages.;	100%

: 5153-67-3
nitrostyrene

: 513-53-1
1-methyl-1-propanethiol

: 1012859-62-9
C12H17NO2S

Conditions

Conditions	Yield
In water at 20℃; for 4h; Michael-type addition;	100%

: 5153-67-3
nitrostyrene

: 75-08-1
ethanethiol

: 25408-68-8
(1-Ethylsulfanyl-2-nitro-ethyl)-benzene

Conditions

Conditions	Yield
In water at 20℃; for 4h; Michael-type addition;	100%

: 5153-67-3
nitrostyrene

: 53933-47-4
N-((1S)-1-phenylethyl)hydroxylamine

: C16H18N2O3

Conditions

Conditions	Yield
In tetrahydrofuran	100%

: 5153-67-3
nitrostyrene

: 67-64-1
acetone

: (R)-5-nitro-4-phenylpentan-2-one

Conditions

Conditions	Yield
With (S)-di-tert-butyl 2-{3-[(1S,2S)-2-amino-1,2-diphenylethyl]thioureido}succinate; acetic acid In water; toluene at 20℃; for 48h; Michael reaction; optical yield given as %ee; enantioselective reaction;	100%
Stage #1: acetone With ((S)-pyrrolidin-2-yl)methyl phenylcarbamate In toluene at 20℃; for 0.5h; Michael Addition; Stage #2: nitrostyrene In toluene at 20℃; for 24h; Michael Addition; stereoselective reaction;	93%
With water; O,O-diethyl [(1S,2S)-2-amino-1,2-diphenylethyl]phosphoramidothioate; acetic acid In toluene at 70℃; for 24h; Reagent/catalyst; Solvent; Temperature; Michael Addition; enantioselective reaction;	90%

: 5153-67-3
nitrostyrene

: 590-86-3
isovaleraldehyde

: (2S,3R)-2-isopropyl-4-nitro-3-phenylbutanal

Conditions

Conditions	Yield
With : H-D-Pro-Pro-Glu supported on polyethyleneglycol-polystyrene (TentaGel resin) In chloroform; isopropyl alcohol at -15℃; for 72h; optical yield given as %ee; enantioselective reaction;	100%
With 4-methyl-morpholine; C16H26N4O5 In neat (no solvent) at 20℃; for 72h; stereoselective reaction;	96%
With 4-methyl-morpholine; H-D-Pro-L-Pro-L-Glu-NH2*TFA In chloroform; isopropyl alcohol at 20℃; for 48h; optical yield given as %ee; stereoselective reaction;	93%

: 104-53-0
3-phenyl-propionaldehyde

: 5153-67-3
nitrostyrene

: 1021394-80-8
(2S,3R)-4-nitro-2-(1-phenylmethyl)-3-phenylbutanal

Conditions

Conditions	Yield
With 4-methyl-morpholine; C16H26N4O5 In neat (no solvent) at 20℃; for 24h; stereoselective reaction;	100%
With 4-methyl-morpholine; (R)-2-(((2S,3S,4R)-2-((2-carboxyethoxy)methyl)-4-methoxytetrahydro-2H-pyran-3-yl)carbamoyl)pyrrolidin-1-ium 2,2,2-trifluoroacetate In dichloromethane at 20℃; for 22h; Michael Addition; Inert atmosphere; stereoselective reaction;	97%
With 4-methyl-morpholine; H-D-Pro-L-Pro-L-Glu-NH2*TFA In chloroform; isopropyl alcohol at 20℃; optical yield given as %ee; enantioselective reaction;	94%

: 5153-67-3
nitrostyrene

: 123-38-6
propionaldehyde

: 475294-87-2
(2S,3R)-2-methyl-4-nitro-3-phenylbutanal

Conditions

Conditions	Yield
With : H-D-Pro-Pro-Glu supported on polyethyleneglycol-polystyrene (TentaGel resin) In chloroform; isopropyl alcohol at -15℃; for 17h; optical yield given as %ee; enantioselective reaction;	100%
With (S)-2-(triphenylsilyl)pyrrolidine In hexane at -20℃; for 48h; Michael reaction; optical yield given as %de; diastereoselective reaction;	97%
With 4-methyl-morpholine; C16H26N4O5 In neat (no solvent) at 20℃; for 24h; stereoselective reaction;	96%

: 5153-67-3
nitrostyrene

: 123-72-8
butyraldehyde

: (2S,3R)-2-ethyl-4-nitro-3-phenylbutanal

Conditions

Conditions	Yield
With : H-D-Pro-Pro-Glu supported on polyethyleneglycol-polystyrene (TentaGel resin) In chloroform; isopropyl alcohol at -15℃; for 20h; optical yield given as %ee; enantioselective reaction;	100%
With 4-methyl-morpholine; (R)-2-(((2S,3S,4R)-2-((2-carboxyethoxy)methyl)-4-methoxytetrahydro-2H-pyran-3-yl)carbamoyl)pyrrolidin-1-ium 2,2,2-trifluoroacetate In dichloromethane at 20℃; for 22h; Michael Addition; Inert atmosphere; stereoselective reaction;	97%
With 4-methyl-morpholine; H-D-Pro-L-Pro-L-Glu-NH2*TFA In chloroform; isopropyl alcohol at 20℃; optical yield given as %ee; enantioselective reaction;	96%

: 5153-67-3
nitrostyrene

: 66-25-1
hexanal

: (+)-(2S)-2-[(R)-2-nitro-1-phenyl-ethyl]-hexanal

Conditions

Conditions	Yield
With : H-D-Pro-Pro-Glu supported on polyethyleneglycol-polystyrene (TentaGel resin) In chloroform; isopropyl alcohol at -15℃; for 19h; optical yield given as %ee; enantioselective reaction;	100%
With 4-methyl-morpholine; C16H26N4O5 In neat (no solvent) at 20℃; for 24h; stereoselective reaction;	100%
With 4-methyl-morpholine; H-D-Pro-L-Pro-L-Glu-NH2*TFA In chloroform; isopropyl alcohol at 20℃; optical yield given as %ee; enantioselective reaction;	98%

: 5153-67-3
nitrostyrene

: 3156-41-0
1-nitro-4-(2-nitrovinyl)benzene

: (S)-2-((R)-2-nitro-1-(4-nitrophenyl)ethyl)cyclohexanone

Conditions

Conditions	Yield
With (S)-6-phenyl-3-[(S)-pyrrolidin-2-ylmethyl]-2-thioxotetrahydropyrimidin-4(1H)-one; water; 4-nitro-benzoic acid In tetrahydrofuran for 18h; Michael reaction; optical yield given as %ee; enantioselective reaction;	100%

: 5153-67-3
nitrostyrene

: 769-42-6
1,3-dimethylbarbituric acid

: 1,3-dimethyl-5-(2-nitro-1-phenylethyl)pyrimidine-2,4,6(1H,3H,5H)-trione

Conditions

Conditions	Yield
With 2Zn(2+)2NO3(1-)2C3H7NO2Y(3+)4C14H11NO3(2-) In ethanol; water at 20℃; for 0.25h; Reagent/catalyst; Michael Addition;	100%
With water; diethylamine at 20℃; for 1h; Reagent/catalyst; Time; Michael Addition; Green chemistry;	99%

: 5153-67-3
nitrostyrene

: 104497-09-8
6-amino-1,3-dimethylbarbituric acid

: 95834-23-4
6-amino-1,3-dimethyl-5-(2-nitro-1-phenylethyl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With 2Zn(2+)2NO3(1-)2C3H7NO2Y(3+)4C14H11NO3(2-) In ethanol; water at 20℃; for 0.25h; Michael Addition;	100%

: 104-53-0
3-phenyl-propionaldehyde

: 5153-67-3
nitrostyrene

: 1089665-81-5
2-benzyl-2-(2-nitro-1-phenylethyl)ethanal

Conditions

Conditions	Yield
With 4-methyl-morpholine; (S)-2-(((2S,3R)-2-((2-carboxyethoxy)methyl)tetrahydro-2H-pyran-3-yl)carbamoyl)pyrrolidin-1-ium 2,2,2-trifluoroacetate In dichloromethane at 20℃; for 19h; Michael Addition; Inert atmosphere; stereoselective reaction;	100%

: 95-20-5
2-methyl-1H-indole

: 5153-67-3
nitrostyrene

: 109809-52-1
2-methyl-3-(2-nitro-1-phenylethyl)-1H-indole

Conditions

Conditions	Yield
With aminosulfonic acid at 60℃; for 0.5h; Michael addition;	99%
Stage #1: nitrostyrene With (S)-10,10'-bis[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-9,9'-biphenanthrene; zinc(II) trifluoroacetate In diethyl ether at 20℃; for 0.25h; Inert atmosphere; Stage #2: 2-methyl-1H-indole In diethyl ether at 20℃; Friedel-Crafts alkylation; Inert atmosphere;	99%
With pyrrolidinium 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonate at 50℃; for 12h; Friedel Crafts alkylation;	99%

: 5153-67-3
nitrostyrene

: 141-97-9
ethyl acetoacetate

: 72709-62-7
ethyl 2-acetyl-4-nitro-3-phenylbutyrate

Conditions

Conditions	Yield
With lithium phenolate; (S)-3,3′-bis[hydroxy(diphenyl)methyl]-1,1′-binaphthalene-2,2′-diol In dichloromethane at 20℃; for 48h; Michael reaction; Inert atmosphere;	99%
With triethylamine at 20℃; Michael Addition; Green chemistry;	99%
bis(acetylacetonate)nickel(II) In 1,4-dioxane at 90℃; for 17h;	98%

: 5153-67-3
nitrostyrene

: 123-54-6
acetylacetone

: 72709-61-6
(+/-)-3-(2-nitro-1-phenylethyl)pentane-2,4-dione

Conditions

Conditions	Yield
With triethylamine at 20℃; Michael Addition; Green chemistry;	99%
With N21,N23-bis(4-bromobenzyl)-2-(((2-(pyridin-3-yl)ethyl)amino)methyl)-5,10,15,20-tetrakis(3,5-ditert-butyl-4-oxo-cyclohexa-2,5-dienylidene)porphyrinogen In ethanol at 20℃; for 16h; Catalytic behavior; Kinetics; Reagent/catalyst; Solvent; Michael Addition; Inert atmosphere;	99%
With 1-methyl-3-(2-(piperidin-1-yl)ethyl)-1H-imidazol-3-ium-chloride In neat (no solvent) at 20℃; for 0.5h; Reagent/catalyst; Time; Michael Addition; Sonication;	98%

: 5153-67-3
nitrostyrene

: 105-53-3
diethyl malonate

: 71639-13-9
diethyl 2-(3-nitrophenylethyl)malonate

Conditions

Conditions	Yield
With lithium phenolate; (S)-3,3′-bis[hydroxy(diphenyl)methyl]-1,1′-binaphthalene-2,2′-diol In dichloromethane at 20℃; for 48h; Michael reaction; Inert atmosphere;	99%
With triethylamine at 20℃; Michael Addition; Green chemistry;	99%
With C16H25N5S In tetrahydrofuran at 25℃; for 2h; Michael Addition;	96%

1-(2-Nitrovinyl)benzene Specification

The 1-(2-Nitrovinyl)benzene with the cas number 5153-67-3, is also called trans-beta-Nitrostyrene. The systematic name is Benzene, (2-nitroethenyl)-, (E)- (9CI) and IUPAC name is [(E)-2-nitroethenyl]benzene. This chemical is Yellow crystals. Its product categories is Ethanes/ethenes.

Properties Computed from Structure: (1)Molecular Weight: 149.14668 [g/mol]; (2)Molecular Formula: C₈H₇NO₂; (3)XLogP3 2.1 ; (4)H-Bond Donor: 0; (5)H-Bond Acceptor: 2; (6)Rotatable Bond Count: 1; (7)Tautomer Count: 2; (8)Exact Mass: 149.047678; (9)MonoIsotopic Mass: 149.047678; (10)Topological Polar Surface Area: 45.8; (11)Heavy Atom Count: 11; (12)Formal Charge: 0; (13)Complexity: 154; (14)Isotope Atom Count: 0; (15)Defined Atom StereoCenter Count: 0; (16)Undefined Atom StereoCenter Count: 0; (17)Defined Bond StereoCenter Count: 1; (18)Undefined Bond StereoCenter Count: 0; (19)Covalently-Bonded Unit Count: 1.

Uses: This chemical can react with benzene-1,2-diamine, to product 2-phenyl-1H-benzoimidazole. This reaction needs solvent ethanol at heating condition. The reaction time is 3.0 hours. The yield is 40%.

When you are using this chemical, please be cautious about it as the following: (1)Irritating to eyes, respiratory system and skin; (2)In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; (3)Wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: [N+](\C=C\c1ccccc1)([O-])=O
(2)InChI: InChI=1/C8H7NO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H/b7-6+
(3)InChIKey: PIAOLBVUVDXHHL-VOTSOKGWSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	intraperitoneal	33mg/kg (33mg/kg)		Chimica Therapeutica. Vol. 6, Pg. 186, 1971.

Product Name

(E)-2-Nitroethenylbenzene

Synthetic route

1-(2-Nitrovinyl)benzene Specification

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