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TRANS-BETA-NITROSTYRENE is a yellow crystalline solid that exists in the form of yellow prisms when obtained from ethanol. It is a chemical compound with unique properties that make it suitable for various applications across different industries.

102-96-5

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102-96-5 Usage

Uses

Used in Chemical Industry:
TRANS-BETA-NITROSTYRENE is used as an intermediate in the synthesis of various organic compounds for the chemical industry. Its chemical properties allow it to be a versatile building block in the creation of a wide range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, TRANS-BETA-NITROSTYRENE is used as a key component in the development of new drugs. Its unique chemical structure contributes to the design and synthesis of novel therapeutic agents.
Used in Dye and Pigment Industry:
TRANS-BETA-NITROSTYRENE is utilized as a starting material for the production of dyes and pigments. Its yellow crystalline nature makes it a valuable component in the formulation of colorants for various applications.
Used in Research and Development:
TRANS-BETA-NITROSTYRENE serves as a valuable research compound for scientists and researchers working on the development of new materials and chemical processes. Its unique properties make it an interesting subject for study and potential applications in various fields.

Air & Water Reactions

TRANS-BETA-NITROSTYRENE may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

TRANS-BETA-NITROSTYRENE is incompatible with strong oxidizing agents and strong bases. .

Fire Hazard

Flash point data for TRANS-BETA-NITROSTYRENE are not available. TRANS-BETA-NITROSTYRENE is probably combustible.

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 102-96-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 2 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 102-96:
(5*1)+(4*0)+(3*2)+(2*9)+(1*6)=35
35 % 10 = 5
So 102-96-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H7NO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H/b7-6-

102-96-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (2-Nitrovinyl)benzene

1.2 Other means of identification

Product number -
Other names OMEGA-NITROSTYRENE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:102-96-5 SDS

102-96-5Synthetic route

nitromethane
75-52-5

nitromethane

benzaldehyde
100-52-7

benzaldehyde

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With 3-(diethylamino)propyltrimethoxysilane supported on silica-alumina at 100℃; for 6h;99%
With mesoporous hybrid catalyst HYB-75P-25B at 373℃; for 14h; Henry reaction; Inert atmosphere;98%
With basic groups-derivatized mesoporous silica-enveloped Fe3O4 nanoparticles Henry Nitro Aldol Condensation;98%
nitromethane
75-52-5

nitromethane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With benzenesulfonic acid and amine group containing periodic mesoporous organosilica at 90℃; for 20h;A 97.5%
B 2.5%
With DMAN-SO3H-SiO2-5-5 In water at 89.84℃; for 24h; Catalytic behavior; Time; Henry Nitro Aldol Condensation;A 92%
B 8%
With grDMAN-SO3H-SiO2-5 In water at 89.84℃; for 15h; Catalytic behavior; Time; Henry Nitro Aldol Condensation;A 15%
B 85%
nitromethane
75-52-5

nitromethane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With porous aromatic framework PAF-1-NHCH2CH2NH2-SO3H at 90℃; for 24h; Inert atmosphere;97.2%
With acidic-basic groups-derivatized mesoporous silica-enveloped Fe3O4 nanoparticles In water at 90℃; for 5h;96%
With water at 90℃; for 5h; Inert atmosphere;95 %Chromat.
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With copper(II) nitrate In acetonitrile at 85℃; for 5h; Inert atmosphere;97%
With diethyl ether; mixture of gaseous nitrogen oxides
With sodium nitrite
potassium styryltrifluoroborate

potassium styryltrifluoroborate

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With sodium dihydrogen phosphate monohydrate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium nitrite In toluene at 120℃; for 0.5h; Temperature; Reagent/catalyst; Solvent; Microwave irradiation; Inert atmosphere;92%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With N-heterocyclic carbenes modified magnesium nanoparticles In tetrahydrofuran at 60℃; for 20h; Reagent/catalyst; Temperature; Molecular sieve;85%
Cinnamic acid
621-82-9

Cinnamic acid

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With tert.-butylnitrite; silica gel In acetonitrile at 100℃; under 2250.23 Torr; Time; Temperature; Pressure; Solvent; Microwave irradiation;85%
With Vilsmeier reagent; potassium nitrate In acetonitrile at 20℃; Reagent/catalyst; Temperature; Sonication;82%
With nitric acid In acetonitrile for 0.025h; Solvent; Microwave irradiation;78%
With trichloroisocyanuric acid; N,N-dimethyl-formamide; sodium nitrite for 8h; Reflux;72%
Multi-step reaction with 2 steps
1: lime/chalk/
2: nitric acid
View Scheme
styrene
292638-84-7

styrene

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With iodine; sodium nitrite In water; ethylene glycol; ethyl acetate for 48h; Ambient temperature;81%
With silver nitrate; acetyl chloride In acetonitrile at 0 - 65℃; for 1h;55%
With tert.-butylnitrite In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;26%
thiourea
17356-08-0

thiourea

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

bis(formamidine)disulphide dihydrobromide
1071-86-9, 19040-64-3, 50606-57-0

bis(formamidine)disulphide dihydrobromide

Conditions
ConditionsYield
With (1,2-dibromo-2-nitroethyl)benzene In acetoneA n/a
B 81%
styrene
292638-84-7

styrene

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

2-nitro-1-phenylethan-1-one oxime
21205-24-3

2-nitro-1-phenylethan-1-one oxime

Conditions
ConditionsYield
With tert.-butylnitrite; water In dimethyl sulfoxide at 50℃; for 1.5h;A 6%
B 81%
nitromethane
75-52-5

nitromethane

benzaldehyde
100-52-7

benzaldehyde

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

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

(1,3-dinitropropan-2-yl)benzene

Conditions
ConditionsYield
With hexan-1-amine; silica gel In toluene at 90℃; for 1.5h;A 80%
B 14%
With cinchona alkaloid and aminopropyl group-based hybrid organic-inorganic catalyst In toluene at 70℃; for 5h; Henry Nitro Aldol Condensation;A 51%
B 18%
With ethylenediamine In water; toluene at 70℃; for 10h; Reagent/catalyst; Henry Nitro Aldol Condensation;A 40%
B 40%
With silica-alumina-supported amine catalyst at 100℃; for 8h;A 71 %Spectr.
B 29 %Spectr.
nitromethane
75-52-5

nitromethane

benzaldehyde
100-52-7

benzaldehyde

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With ammonium acetate at 90℃; for 0.416667h; Henry reaction; Microwave irradiation;A 71%
B 12%
With ammonium acetate at 60℃; for 0.75h; Henry reaction; Ultrasound irradiation;A 21%
B 57%
With amino-functionalized MIL-101 catalyst In butan-1-ol at 80℃; for 8h;
2-(2-nitro-1-phenylethoxy)-5-phenyltetrahydro-1,2-oxazole-3,3-dicarbonitrile
1345735-45-6

2-(2-nitro-1-phenylethoxy)-5-phenyltetrahydro-1,2-oxazole-3,3-dicarbonitrile

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

5-phenyl-4,5-dihydro-1,2-oxazole-3-carbonitrile 2-oxide
61207-10-1

5-phenyl-4,5-dihydro-1,2-oxazole-3-carbonitrile 2-oxide

Conditions
ConditionsYield
With water; acetic acid for 1h; Reflux;A 52%
B 70%
nitromethane
75-52-5

nitromethane

benzylamine
100-46-9

benzylamine

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With 4-(4-fluorophenyl)naphthalene-1,2-dione; oxygen at 80℃; for 12h;67%
(1,2-dibromo-2-nitroethyl)benzene
3425-99-8

(1,2-dibromo-2-nitroethyl)benzene

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

bis(formamidine)disulphide dihydrobromide
1071-86-9, 19040-64-3, 50606-57-0

bis(formamidine)disulphide dihydrobromide

Conditions
ConditionsYield
With thiourea In ethanol at 20 - 25℃; for 24h;A n/a
B 62.5%
styrene
292638-84-7

styrene

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

2-nitro-1-phenylethyl nitrate

2-nitro-1-phenylethyl nitrate

C

(1-Nitro-2-nitrooxy-ethyl)-benzene

(1-Nitro-2-nitrooxy-ethyl)-benzene

Conditions
ConditionsYield
With Nitrogen dioxide; ozone In dichloromethane at -20℃; Product distribution; multistep reaction;A 58%
B n/a
C n/a
nitromethane
75-52-5

nitromethane

benzaldehyde
100-52-7

benzaldehyde

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

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

(R)-2-nitro-1-phenylethanol

Conditions
ConditionsYield
With copper(II) acetate monohydrate; (3aR,3a'R,8aS,8a'S)-2,2'-(propane-2,2-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole) In ethanol at 20℃; for 24h; Henry reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;A 10%
B 58%
styrene
292638-84-7

styrene

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With tert.-butylnitrite; oxygen In water; dimethyl sulfoxide at 50℃; for 1.5h;A 38%
B 32%
styrene
292638-84-7

styrene

Nitrogen dioxide
10102-44-0

Nitrogen dioxide

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

C

benzaldehyde
100-52-7

benzaldehyde

D

benzoic acid
65-85-0

benzoic acid

E

2-nitroacetophenone
614-21-1

2-nitroacetophenone

Conditions
ConditionsYield
In tetrachloromethane react. at 25°C under N2 (anaerobic), further products; products identified by g.c./m.s.;A 1%
B 33%
C 7%
D 5%
E 31%
In tetrachloromethane react. at 25°C, further products; products identified by g.c./m.s.;A 12%
B 24%
C 9%
D 1%
E 29%
nitromethane
75-52-5

nitromethane

benzaldehyde
100-52-7

benzaldehyde

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

C

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

(1,3-dinitropropan-2-yl)benzene

Conditions
ConditionsYield
With N,N-dimethylethylenediamine In toluene at 50℃; for 1h; Henry Nitro Aldol Condensation;A 32%
B 18%
C 18%
With 1,8-bis(tetramethylguanidino)naphthalene In neat (no solvent) at 129.84℃; Reagent/catalyst; Time; Henry Nitro Aldol Condensation; Inert atmosphere;A 7%
B 13%
C 16%
With silica-alumina-supported double-amine catalyst at 100℃; for 8h;A 3 %Spectr.
B 4 %Spectr.
C 93 %Spectr.
With silica-alumina-supported amine catalyst at 100℃; for 8h;A 68 %Spectr.
B 7 %Spectr.
C 8 %Spectr.
With silica-alumina(500)-NEt2 at 100℃; for 20h;
dimethyl 2-phenylethenylphosphonate
1707-07-9

dimethyl 2-phenylethenylphosphonate

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

dimethyl 2-hydroxy-1-nitro-2-phenylethylphosphonate
78728-63-9

dimethyl 2-hydroxy-1-nitro-2-phenylethylphosphonate

C

2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

Conditions
ConditionsYield
With dinitrogen tetraoxide at 0 - 20℃; for 3h; Nitration;A n/a
B 30%
C n/a
4,5-dinitro-1,5-diphenyl-pent-1-en-3-one

4,5-dinitro-1,5-diphenyl-pent-1-en-3-one

A

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

(E)-3-phenylacrylic acid

B

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With potassium hydroxide
nitromethane
75-52-5

nitromethane

2-Methylbutylamine
96-15-1

2-Methylbutylamine

benzaldehyde
100-52-7

benzaldehyde

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

nitromethane
75-52-5

nitromethane

sodium ethanolate
141-52-6

sodium ethanolate

benzaldehyde
100-52-7

benzaldehyde

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
Zerlegen des Produktes mit verd.Schwefelsaeure;
nitromethane
75-52-5

nitromethane

benzaldehyde
100-52-7

benzaldehyde

(E)-3-Ureido-but-2-enoic acid ethyl ester
5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
at 160℃; im geschlossenen Rohr;
NSC 4573
21080-09-1

NSC 4573

benzaldehyde
100-52-7

benzaldehyde

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

benzylidene phenylamine
538-51-2

benzylidene phenylamine

nitromethane
75-52-5

nitromethane

ethanol
64-17-5

ethanol

benzil
134-81-6

benzil

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
Natriumverbindung reagiert, Einw. von Mineralsaeuren;
nitromethane
75-52-5

nitromethane

benzil
134-81-6

benzil

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Conditions
ConditionsYield
With pyridine; sodium ethanolate Behandlung des Reaktionsgemisches mit wss. HCl;
1-Phenyl-2-nitroethyl-p-chlorphenylsulfon
42604-93-3

1-Phenyl-2-nitroethyl-p-chlorphenylsulfon

A

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

B

4-chlorobenzenesulfinic acid
100-03-8

4-chlorobenzenesulfinic acid

Conditions
ConditionsYield
With sodium hydroxide In acetone at 20℃; Rate constant; Equilibrium constant;
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

2-Phenylnitroethane
6125-24-2

2-Phenylnitroethane

Conditions
ConditionsYield
With polymer-bound NADH (2a)100%
With magnesium(II) perchlorate; "grafted NADH model" reagent In acetonitrile; benzene at 80℃; for 120h;100%
With tri(1-naphthyl)phosphonium tris(pentafluorophenyl)borohydride In dichloromethane-d2 for 12h; Reagent/catalyst; Glovebox; Sealed tube;100%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

ethyl acetoacetate
141-97-9

ethyl acetoacetate

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

ethyl 2-acetyl-4-nitro-3-phenylbutyrate

Conditions
ConditionsYield
With nickel polymer catalyst In chloroform for 48h; Reflux;100%
With C23H37N3O9S In dichloromethane at 20℃; for 16h; asymmetric Michael addition; enantioselective reaction;99%
With C31H36N6OS3 In toluene at 25℃; for 48h; Michael Addition; enantioselective reaction;99%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

acetylacetone
123-54-6

acetylacetone

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

(+/-)-3-(2-nitro-1-phenylethyl)pentane-2,4-dione

Conditions
ConditionsYield
With N,N-dimethyl-3-trimethoxysilylpropanamine:N-(3,5-bistrifluoromethylphenyl)-N'-(3-trimethoxysilyl-1-propyl)thiourea (1:1) mesoporous silica nanoparticles at 20℃; for 3h;100%
With squaramide-containing Dawson organo-polyoxotungstates In dichloromethane for 13h; Reagent/catalyst; Heating;99%
With C27H18F15N7O3 In dimethyl sulfoxide at 20℃; for 3h; Michael Addition;98%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

phenylmethanethiol
100-53-8

phenylmethanethiol

benzyl (2-nitro-1-phenylethyl) sulfide
34980-76-2, 63509-10-4, 63509-11-5

benzyl (2-nitro-1-phenylethyl) sulfide

Conditions
ConditionsYield
at 20℃; for 0.1h; Michael addition; neat (no solvent);100%
at 20℃; for 2h; Michael addition; Neat (no solvent); regioselective reaction;92%
In water at 20℃; for 1h; thia-Michael addition;91%
With 2,2'-azobis(isobutyronitrile); quinoclamine; N,N-dimethyl-formamide; Quinine In toluene
morpholine
110-91-8

morpholine

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

4-(2-nitro-1-phenylethyl)morpholine

4-(2-nitro-1-phenylethyl)morpholine

Conditions
ConditionsYield
at 20℃; for 0.0166667h; Michael addition; neat (no solvent);100%
With MCM-41 immobilized phenanthrolinium dibromide In water at 20℃; for 0.5h; Catalytic behavior; Michael Addition;95%
With samarium(III) trifluoromethanesulfonate In dichloromethane at 20℃; for 24h; Reagent/catalyst; Inert atmosphere;94%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

methyl-4-phenylmethylamino-2-butene-1-carboxylate
85669-65-4

methyl-4-phenylmethylamino-2-butene-1-carboxylate

(2RS,3SR,4SR)-1N-phenylmethyl-2-phenyl-3-nitro-4-carbomethoxymethylpyrrolidine

(2RS,3SR,4SR)-1N-phenylmethyl-2-phenyl-3-nitro-4-carbomethoxymethylpyrrolidine

Conditions
ConditionsYield
In methanol for 16h; Ambient temperature;100%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-methoxy-N-(2-nitro-1-phenylethyl)benzenamine

4-methoxy-N-(2-nitro-1-phenylethyl)benzenamine

Conditions
ConditionsYield
at 20℃; for 0.0166667h; Michael addition; Grinding; neat (no solvent);100%
With magnesia at 25℃; for 0.3h; Green chemistry;98%
With MCM-41 immobilized phenanthrolinium dibromide In water at 20℃; for 1.5h; Catalytic behavior; Michael Addition;93%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

cyclohexanone
108-94-1

cyclohexanone

(S)-2-[(R)-2-nitro-1-phenylethyl]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
ConditionsYield
With 2,6-bis(1-((S)-pyrrolidin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)pyridine at 20℃; for 16h; Michael addition; optical yield given as %de;100%
With C2HF3O2*C25H23N2O2PS; triethylamine; benzoic acid at -30℃; for 22h; Michael addition; stereoselective reaction;99%
Stage #1: cyclohexanone With 3-butyl-1-(butyl-4-sulfobutyl)imidazolium trifluoromethanesulfonate; C13H28N2 In water at 20℃; for 0.333333h; Michael Addition; Green chemistry;
Stage #2: (2-nitroethenyl)benzene In water at 20℃; for 10h; Green chemistry; enantioselective reaction;
99%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

para-thiocresol
106-45-6

para-thiocresol

(2-nitro-1-phenylethyl)(p-tolyl)sulfane
92851-02-0

(2-nitro-1-phenylethyl)(p-tolyl)sulfane

Conditions
ConditionsYield
at 20℃; for 0.1h; Michael addition; Grinding; neat (no solvent);100%
In water at 20℃; for 0.166667h; thia-Michael addition;94%
With squaric acid In water at 20℃; for 1.33333h; Michael addition;85%
pyrrole
109-97-7

pyrrole

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

2-(2-nitro-1-phenylethan-1-yl)pyrrole
112616-92-9

2-(2-nitro-1-phenylethan-1-yl)pyrrole

Conditions
ConditionsYield
With [tetrapropylammonium]2[Zn2(1,4-benzenedicarboxylate)3(dimethylamine)2] In neat (no solvent) at 70℃; for 4h; Temperature; Reagent/catalyst; Michael Addition; Green chemistry;100%
In water at 150℃; for 0.1h; Michael addition; Microwave irradiation;99%
With UiO-66(Ce) metal-organic framework In 1,2-dichloro-ethane at 80℃; for 24h; Catalytic behavior; Friedel-Crafts Alkylation; Schlenk technique;97%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

(R)-1-chloro-4-(2-nitro-1-phenylethyl)benzene
1245819-33-3

(R)-1-chloro-4-(2-nitro-1-phenylethyl)benzene

Conditions
ConditionsYield
With heterogeneous Rh/Ag bimetallic nanoparticle catalyst immobilized on chiral polymer In water; toluene at 100℃; for 24h; Inert atmosphere; enantioselective reaction;100%
With potassium hydrogen difluoride; C60H52Cl2Rh2 In water; toluene at 50℃; for 51h; Inert atmosphere; enantioselective reaction;94%
With chlorobis(ethylene)rhodium(I) dimer; potassium hydrogen bifluoride; C28H22 In water; toluene at 100℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;92%
With chlorobis(ethylene)rhodium(I) dimer; C17H27NO In water; toluene at 100℃; for 16h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;87 %Chromat.
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

C16H18N2O2
1266995-18-9

C16H18N2O2

Conditions
ConditionsYield
at 20℃; for 0.1h; Michael addition; neat (no solvent);100%
(2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine
848821-58-9

(2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

isovaleraldehyde
590-86-3

isovaleraldehyde

C31H38N2O3Si

C31H38N2O3Si

Conditions
ConditionsYield
With acetic acid In toluene at 25℃;100%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

5-ethyl-2-(m-tolyl)oxazol-4(5H)-one
1393357-24-8

5-ethyl-2-(m-tolyl)oxazol-4(5H)-one

(5R)-5-ethyl-5-((R)-2-nitro-1-phenylethyl)-2-(m-tolyl)oxazol-4(5H)-one
1393357-08-8

(5R)-5-ethyl-5-((R)-2-nitro-1-phenylethyl)-2-(m-tolyl)oxazol-4(5H)-one

Conditions
ConditionsYield
With 2,6-bis((2S-((2-naphthyl)2(HO)C)pyrrolidino)CH2)-4-Me-phenol; diethylzinc In tetrahydrofuran; hexane; propiononitrile at 20℃; for 16h; Michael reaction; Inert atmosphere; optical yield given as %ee; stereoselective reaction;100%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

5-isobutyl-2-(m-tolyl)oxazol-4(5H)-one
1393357-25-9

5-isobutyl-2-(m-tolyl)oxazol-4(5H)-one

(5R)-5-isobutyl-5-((R)-2-nitro-1-phenylethyl)-2-(m-tolyl)oxazol-4(5H)-one

(5R)-5-isobutyl-5-((R)-2-nitro-1-phenylethyl)-2-(m-tolyl)oxazol-4(5H)-one

Conditions
ConditionsYield
With 2,6-bis((2S-((2-naphthyl)2(HO)C)pyrrolidino)CH2)-4-Me-phenol; diethylzinc In tetrahydrofuran; hexane; propiononitrile at 20℃; for 16h; Michael reaction; Inert atmosphere; optical yield given as %ee; stereoselective reaction;100%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

5-allyl-2-(m-tolyl)oxazol-4(5H)-one
1393357-27-1

5-allyl-2-(m-tolyl)oxazol-4(5H)-one

(5R)-5-allyl-5-((R)-2-nitro-1-phenylethyl)-2-(m-tolyl)oxazol-4(5H)-one
1393357-11-3

(5R)-5-allyl-5-((R)-2-nitro-1-phenylethyl)-2-(m-tolyl)oxazol-4(5H)-one

Conditions
ConditionsYield
With 2,6-bis((2S-((2-naphthyl)2(HO)C)pyrrolidino)CH2)-4-Me-phenol; diethylzinc In tetrahydrofuran; hexane; propiononitrile at 20℃; for 16h; Michael reaction; Inert atmosphere; optical yield given as %ee; stereoselective reaction;100%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

5-(2-(methylthio)ethyl)-2-(m-tolyl)oxazol-4(5H)-one
1393357-29-3

5-(2-(methylthio)ethyl)-2-(m-tolyl)oxazol-4(5H)-one

(5R)-5-(2-(methylthio)ethyl)-5-((R)-2-nitro-1-phenylethyl)-2-(m-tolyl)oxazol-4(5H)-one
1393357-13-5

(5R)-5-(2-(methylthio)ethyl)-5-((R)-2-nitro-1-phenylethyl)-2-(m-tolyl)oxazol-4(5H)-one

Conditions
ConditionsYield
With 2,6-bis((2S-((2-naphthyl)2(HO)C)pyrrolidino)CH2)-4-Me-phenol; diethylzinc In tetrahydrofuran; hexane; propiononitrile at 20℃; for 16h; Michael reaction; Inert atmosphere; optical yield given as %ee; stereoselective reaction;100%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

6-[1-aza-2-(dimethylamino)prop-1-enyl]-1,3-dimethyl uracil

6-[1-aza-2-(dimethylamino)prop-1-enyl]-1,3-dimethyl uracil

C18H21N5O4

C18H21N5O4

Conditions
ConditionsYield
In water at 20℃; for 8h; Solvent; regioselective reaction;100%
2-chlorobenzylthiol
39718-00-8

2-chlorobenzylthiol

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

(S)-2-chlorobenzyl (2-nitro-1-phenylethyl) sulfide

(S)-2-chlorobenzyl (2-nitro-1-phenylethyl) sulfide

Conditions
ConditionsYield
Stage #1: (2-nitroethenyl)benzene With 1-[(3R,4S)-1-benzyl-4-phenylpyrrolidin-3-yl]-3-[3,5-bis(trifluoromethyl)phenyl]urea In dichloromethane at 20℃; for 0.333333h; Molecular sieve;
Stage #2: 2-chlorobenzylthiol In dichloromethane at -80℃; for 48h; Michael Addition; Molecular sieve; enantioselective reaction;
100%
indole
120-72-9

indole

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

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

3-(2-nitro-1-phenylethyl)-1H-indole

Conditions
ConditionsYield
With 2,2,2-trifluoroethanol; 1-(3,5-bis(trifluoromethyl)phenyl)-3-(2-(difluoroboryl)phenyl)urea In dichloromethane at 23℃; for 24h; Kinetics; Reagent/catalyst; Inert atmosphere;99%
Stage #1: (2-nitroethenyl)benzene With C24H12F8N2O7Si2 In 1,2-dichloro-benzene for 0.0833333h; Inert atmosphere;
Stage #2: indole In 1,2-dichloro-benzene at 23℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere;
99%
With zinc diacetate In ethanol at 20℃; for 0.333333h; Michael addition;98%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

aniline
62-53-3

aniline

NSC 4573
21080-09-1

NSC 4573

Conditions
ConditionsYield
at 20℃; for 0.116667h; Michael addition; neat (no solvent);99%
With magnesia at 25℃; for 0.4h; Green chemistry;95%
With iranian dolomite In water at 20℃; for 0.5h; Michael Addition;93%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

2-Naphthalenethiol
91-60-1

2-Naphthalenethiol

[2]naphthyl-(2-nitro-1-phenyl-ethyl)-sulfide
110130-43-3

[2]naphthyl-(2-nitro-1-phenyl-ethyl)-sulfide

Conditions
ConditionsYield
at 20℃; for 0.116667h; Michael addition; Grinding; neat (no solvent);99%
With diethyl ether; triethylamine
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

thioacetic acid
507-09-5

thioacetic acid

S-2-nitro-1-phenylethyl thiolacetate
29651-81-8

S-2-nitro-1-phenylethyl thiolacetate

Conditions
ConditionsYield
With tributyl-amine In diethyl ether for 1h; Michael addition; Cooling with ice;99%
at 20℃; for 0.0833333h; Michael condensation; neat (no solvent);98%
With piperidine
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

1-phenylbutan-1,3-dione
93-91-4

1-phenylbutan-1,3-dione

2-(2-nitro-1-phenylethyl)-1-phenylbutane-1,3-dione
82947-13-5

2-(2-nitro-1-phenylethyl)-1-phenylbutane-1,3-dione

Conditions
ConditionsYield
With squaramide-containing Dawson organo-polyoxotungstates In dichloromethane for 13h; Reagent/catalyst; Heating;99%
at 20℃; Michael addition; Neat (no solvent); Grinding; optical yield given as %de;70%
bis(acetylacetonate)nickel(II) In 1,4-dioxane for 46h; Heating;60%
With triethylamine In dichloromethane at 20℃; for 24h; Michael Addition;
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

Methyl thioglycolate
2365-48-2

Methyl thioglycolate

methyl {[alpha-(nitromethyl)benzyl]thio}acetate
76665-83-3, 91134-32-6

methyl {[alpha-(nitromethyl)benzyl]thio}acetate

Conditions
ConditionsYield
With C37H56N4O4; lanthanum(lll) triflate In 1,2-dichloro-ethane at 0℃; for 1h; Sulfa-Michael addition;99%
With triethylamine In tetrahydrofuran at 20℃; for 2h; Michael addition;97%
In benzene Heating;
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

toluene
108-88-3

toluene

N-hydroxy-2-phenyl-2-p-tolylacetimidoyl chloride
4099-50-7

N-hydroxy-2-phenyl-2-p-tolylacetimidoyl chloride

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel-Crafts alkylation; Inert atmosphere;99%
With aluminium trichloride
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

4-Nitro-3-phenyl-2-(triphenyl-λ5-phosphanylidene)-butyric acid ethyl ester
37709-90-3

4-Nitro-3-phenyl-2-(triphenyl-λ5-phosphanylidene)-butyric acid ethyl ester

Conditions
ConditionsYield
In chloroform at 20℃; for 3h; Michael condensation;99%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

thiophenol
108-98-5

thiophenol

(2-nitro-1-phenylethyl) phenyl sulfide
4231-84-9

(2-nitro-1-phenylethyl) phenyl sulfide

Conditions
ConditionsYield
With C23H32F6N4O2S2 In dichloromethane at -40℃; for 1h; Michael Addition;99%
at 20℃; for 0.116667h; Michael addition; neat (no solvent);98%
With triethylamine In ethanol at 20℃; for 0.0833333h; Inert atmosphere;97%
5-methoxylindole
1006-94-6

5-methoxylindole

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

5-methoxy-3-(2-nitro-1-phenylethyl)-1H-indole

5-methoxy-3-(2-nitro-1-phenylethyl)-1H-indole

Conditions
ConditionsYield
With di(naphthalen-1-yl)silanediol In dichloromethane at 23℃; for 48h; Inert atmosphere;99%
With 2,6-bis(2,2-dimethylpropionylamino)benzoic acid In chloroform at 40℃; for 24h; Friedel-Crafts Alkylation;99%
With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 2h; Friedel-Crafts Alkylation;96%

102-96-5Relevant academic research and scientific papers

Humic substances as catalysts m condensation reactions

Klavins, Maris,Dipane, Judite,Babre, Kristine

, p. 737 - 742 (2001)

Humic substances (HS) demonstrate appreciable impact on the rate of the condensation reactions as shown in the example of the reaction between hydrazine and 4-(dimethylamino)-benzaldhyde in an aquatic environment. The catalytic activity of HS has also been demonstrated in Knoevenagel and Claisen-Schmidt reactions for condensation of carbonyl compounds with CH acids. The aquatic fulvic acids are the most active in these reactions. The velocity of the studied reactions also depends on pH, temperature, the concentration and origin of HS used. A possible micellar and acid-base catalysis mechanism in aquatic media has been suggested.

Porous Boron Nitride as a Weak Solid Base Catalyst

Nakamura, Shohei,Takagaki, Atsushi,Watanabe, Motonori,Yamada, Kanta,Yoshida, Masaaki,Ishihara, Tatsumi

, p. 6033 - 6039 (2020)

Porous boron nitride was synthesized by pyrolysis from boric acid and urea mixed in varying molar ratios. The boron nitride prepared had high surface areas ranging from 376 to 647 m2 g?1 with both microporous and mesoporous structures. The sample prepared with a urea-to-boric acid molar ratio of 5 exhibited the highest pore volume with the highest surface area of mesopores. Boron-K edge X-ray absorption fine structure spectroscopy revealed that the surface structure consisted of BN3 sites along with BN2O, BNO2, and BO3 sites. Fourier transform infrared (FTIR) spectroscopy indicated the formation of amino and hydroxyl groups on the surface. Analysis using color indicator reagents and deuterated chloroform-adsorbed FTIR results indicated that the porous boron nitride had very weak base sites of strength +7.2>H?≥+6.3. Porous boron nitride exhibited a high activity for the nitroaldol reaction with a high selectivity for nitroalkene (>97 %). A good correlation was observed between the catalytic activity of the boron nitride catalysts and their porous structures.

Water-controlled nitro-oximation of alkenes under catalyst-free conditions

Tang, Lin,Yang, Zhen,Chang, Xueping,Zou, Guodong,Zhou, Yuqiang,Rao, Weihao,Ma, Xiantao,Zhao, Geng

, p. 4272 - 4275 (2018)

A convenient and precise nitration and oximation of alkenes with tert-butyl nitrite has been reported, yielding α-nitro ketoximes in satisfactory yields with broad substrate generality and excellent stereoselectivity under mild conditions. Experiments indicate that tert-butyl nitrite serves as both NO and NO2 sources and water plays a key role in this difunctionalization reaction.

Cu(II) homogeneous and heterogeneous catalysts for the asymmetric Henry reaction

Jones, Matthew D.,Cooper, Christine J.,Mahon, Mary F.,Raithby, Paul. R.,Apperley, David,Wolowska, Joanna,Collison, David

, p. 8 - 14 (2010)

New homogeneous Cu(II) complexes have been prepared, fully characterised and tested for the asymmetric Henry reaction. Heterogeneous Cu(II) catalysts have been synthesised for comparison purposes.

Diastereoselective synthesis of polysubstituted cyclopentanols and cyclopentenes containing stereogenic centers via domino Michael/cyclization reaction

Ahadi,Naghdiani,Balalaie,Rominger

, p. 6860 - 6866 (2015)

A highly efficient domino Michael/cyclization reaction was developed for the synthesis of cyclopentanols and cyclopentenes with four and three stereogenic centers that were generated in one-pot reaction conditions with high diastereoselectivity. The reactions proceeded through a one-pot three-component reaction of β-nitrostyrenes, malononitrile and phenacyl bromide derivatives in basic media at room temperature.

A simple O-sulfated thiohydroximate molecule to be the first micromolar range myrosinase inhibitor

Cerniauskaite, Deimante,Gallienne, Estelle,Karciauskaite, Henreta,Farinha, Andrea S.F.,Rousseau, Jolanta,Armand, Sylvie,Tatibou?t, Arnaud,Sackus, Algirdas,Rollin, Patrick

, p. 3302 - 3305 (2009)

New non-hydrolyzable analogues of glucosinolates have been prepared. Myrosinase inhibition was observed with modified aglycon moieties, even bulky phenothiazine analogue 6 gave reasonable inhibition. The simplest structure 8 derived from dimethylaminoethanethiol has shown to be the most potent inhibitor with an IC50 of 3.32 μM.

Direct synthesis and application of bridged diamino-functionalized periodic mesoporous organosilicas with high nitrogen contents

Zhu, Feng-Xia,Zhao, Pu-Su,Sun, Xiao-Jun,An, Li-Tao,Deng, Yong,Wu, Jia-Min

, p. 70 - 75 (2017)

Bridged diamino-functionalized periodic mesoporous organosilicas [BD-PMO(Et), Et = ethyl] materials were synthesized directly by co-condensation of 2-bis (triethoxysilyl)ethane (BTEE) and 1,4-bis[3-(tirmethoxysilyl)-propyl]ethylenediamino (BTMSEN) under acidic conditions with pluronic triblock copolymer P123 as a template. The nitrogen content in BD-PMO(Et) could be adjusted up to 40% without disturbing the ordered mesoporous structure. These materials were proved to be effective heterogeneous catalysts for the liquid-phase reactions such as Knoevenagel and Henry condensations as well as in the intermolecular cross-double-Michael addition reaction between α-methyl-β-nitrostyrene and α, β-unsaturated ketone. They exhibited comparable catalytic activities with homogeneous catalyst piperazine and can be reused for several times without any negative environmental impact.

Mild and Regioselective Three-component Heteroarylation-Nitration of Alkenes with Imidazo[1,2-a]pyridines and tert-Butyl Nitrite

Liu, Ping,Sun, Peipei,Xie, Shentong,Zhang, Jie

, (2020)

An efficient and regioselective three-component heteroarylation-nitration of alkenes with imidazo[1,2-a]pyridines and tert-butyl nitrite has been developed. The process tolerants a variety of functional groups under mild conditions in the absence of catalysts and additives to give nitro functionalized imidazo[1,2-a]pyridine derivatives in moderate to good yields. The reaction is also applicable for some other aza-heterocycles. (Figure presented.).

Preparation and synergetic catalytic effects of amino-functionalized MCM-41 catalysts

Lang, Wanzhong,Su, Bo,Guo, Yajun,Chu, Lianfeng

, p. 1167 - 1174 (2012)

Four amine functionalized mesoporous catalysts were synthesized by grafting primary, dualistic and two secondary amines onto the channel walls of mesoporous silica, MCM-41. We examined the effects of organoamine loading amount on the acid-base synergism of the catalysts in the self-condensation reaction of n-butanal, a Knoevenagel condensation and a Henry reaction. We observed the balance of the amine and residual silanol amounts is crucial to the catalytic performances of the functionalized mesoporous catalysts. An optimum organoamine loading amount exists, which is dependent on the organoamine type. There is little difference in the optimum organoamine loading amount between different reactions. The secondary organoamine functionalized MCM-41 exhibits the best catalytic performance in the experimental range.

Facile and efficient michael addition of indole to nitroolefins catalyzed by zn(OAc)22H2O

Ji, Xiang,Tong, Haibo,Yuan, Yu

, p. 372 - 379 (2011)

The Zn(OAc)22H2O-catalyed Michael addition reaction of indole to electron-deficient nitroolefins to afford the corresponding adducts in good to excellent yields with high selectivity is reported.

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