3638-64-0

Basic information

• Product Name: Nitroethylene
• Synonyms: NITROETHYLENE;1-Nitroethene;NITROBENZENDICARBOXYLATE,DIMETHYL;nitroethene (2.0M in toluene);1-nitroethylene;Nitroethylene(Nitroethene);1-Nitroethene (~ 1 mole/L in Toluene);Ethene, nitro- (9CI)
• CAS NO: 3638-64-0
• Molecular Formula: C₂H₃NO₂
• Molecular Weight: 73.05
• Mol File: 3638-64-0.mol
• Article Data: 31

Chemical Properties

• Melting Point: -55.5°C
• Boiling Point: 98.55°C
• Flash Point: 23.2 °C
• Appearance: /
• Density: 1.2212
• Vapor Pressure: 45.8mmHg at 25°C
• Refractive Index: 1.4282
• CAS DataBase Reference: Nitroethylene(CAS DataBase Reference)
• NIST Chemistry Reference: Nitroethylene(3638-64-0)
• EPA Substance Registry System: Nitroethylene(3638-64-0)

Safety Data

• Hazardous Substances Data: 3638-64-0(Hazardous Substances Data)

Usage

Uses

Nitroethylene is the simplest ntiroalkene and serves as a useful intermediate for the production of various chemicals and pharmaceutical goods.

Definition

ChEBI: A nitroalkene having ethenyl as the alkene portion.

InChI:InChI=1/C2H3NO2/c1-2-3(4)5/h2H,1H2

Synthetic route

2-nitro-1-ethanol (625-48-9) → 1-nitroethylene (3638-64-0)

Conditions	Yield
With phthalic anhydride at 150 - 180℃; under 80 Torr;	89%
With phthalic anhydride at 180℃; for 3h; Cooling with acetone-dry ice;	69%
With phthalic anhydride at 150 - 180℃; for 23h; Inert atmosphere; Cooling with ice;	55%

phthalic anhydride (85-44-9) + 2-nitro-1-ethanol (625-48-9) → 1-nitroethylene (3638-64-0)

Conditions	Yield
at 140 - 180℃; under 80 Torr; Heating;	80%
at 175 - 180℃; under 80 Torr;

acrylic acid (79-10-7) → 1-nitroethylene (3638-64-0)

Conditions	Yield
With tert.-butylnitrite; silica gel In acetonitrile at 100℃; under 2250.23 Torr; Time; Temperature; Pressure; Microwave irradiation;	80%
With ferric nitrate for 0.5h; Milling;	80%
With Vilsmeier reagent; potassium nitrate In acetonitrile at 20℃; Reagent/catalyst; Temperature; Sonication;	75%

1-nitroethanol (39221-06-2) → 1-nitroethylene (3638-64-0)

Conditions	Yield
With phthalic anhydride In tetrahydrofuran at 130 - 180℃; for 3h;	69%
With phthalic anhydride at 140℃; under 80 Torr;

formaldehyd (50-00-0) + nitromethane (75-52-5) → 1-nitroethylene (3638-64-0)

Conditions	Yield
Leiten ueber mit Bleisalzen aktiviertes Silicagel;
With lead(IV) tetraacetate; silica gel at 250 - 300℃;
With silica gel; lead(II) oxide at 250 - 300℃;
With lead(II) chromate; silica gel at 250 - 300℃;
beim Leiten ueber einen bleisalzhaltigen Silicagel- oder Aluminiumoxydgel Katalysator;

diethyl ether (60-29-7) + 1-chloro-2-nitroethane (625-47-8) + sodium acetate (127-09-3) → 1-nitroethylene (3638-64-0)

2-nitroethanol nitrate (4528-34-1) + ethanol (64-17-5) → 1-nitroethylene (3638-64-0)

Conditions	Yield
at 100℃;

2-nitroethanol nitrate (4528-34-1) → 1-nitroethylene (3638-64-0)

Conditions	Yield
With ethanol at 100℃;

ethanol (64-17-5) + 1,2-dinitroethane (7570-26-5) → 1-nitroethylene (3638-64-0)

Conditions	Yield
at 100℃; unter Ausschluss von Alkali;

1-chloro-2-nitroethane (625-47-8) → 1-nitroethylene (3638-64-0)

Conditions	Yield
With calcium chloride at 250℃;
With calcium carbonate at 300 - 400℃;
With diethyl ether; sodium acetate

1,2-dinitroethane (7570-26-5) → 1-nitroethylene (3638-64-0)

Conditions	Yield
With ethanol at 100℃;

2-nitro-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene (421551-02-2) → 1-nitroethylene (3638-64-0) + 1,3-diphenylisobenzofuran (5471-63-6)

Conditions	Yield
Erhitzen;

2-nitro-1-ethanol (625-48-9) → 1-nitroethylene (3638-64-0) + Nitroethane (79-24-3)

Conditions	Yield
With phthalic anhydride

11-Nitro-9,10-aethanoanthracen (92855-58-8) → 1-nitroethylene (3638-64-0) + anthracene (120-12-7)

Conditions	Yield
In diphenylether at 250℃; Rate constant;

isobutyric acid-(2-nitro-ethyl ester) → 1-nitroethylene (3638-64-0) + isobutyric Acid (79-31-2)

Conditions	Yield
at 225℃; Rate constant; activation energy E, logA, ΔS(excit.); other temp.;

2-nitroethyl acetate (18942-89-7) → 1-nitroethylene (3638-64-0) + acetic acid (64-19-7)

Conditions	Yield
at 225℃; Rate constant; various initial vapour pressures and surface-to-volume ratios; activation energy E, logA, ΔS(excit.); other temp.;

butyric acid-(2-nitro-ethyl ester) → 1-nitroethylene (3638-64-0) + butyric acid (107-92-6)

Conditions	Yield
at 225℃; Rate constant; various initial vapour pressures and surface-to-volume ratios; activation energy E, logA, ΔS(excit.); other temp.;

Trichloressigsaeure-β-nitroaethylester (13005-97-5) → 1-nitroethylene (3638-64-0) + trichloroacetic acid (76-03-9)

Conditions	Yield
at 225℃; Rate constant; various initial vapour pressures and surface-to-volume ratios; activation energy E, logA, ΔS(excit.); other temp.;

Chloro-acetic acid 2-nitro-ethyl ester → 1-nitroethylene (3638-64-0) + chloroacetic acid (79-11-8)

Conditions	Yield
at 225℃; Rate constant; activation energy E, logA, ΔS(excit.); other temp.;

2-nitroethyl acetate → 1-nitroethylene (3638-64-0)

Conditions	Yield
With glass beads at 350℃;
With aluminum(III) sulfate at 240℃;

2-nitro-1-ethanol (625-48-9) + NaHSO4 → 1-nitroethylene (3638-64-0)

Conditions	Yield
bei der Destillation;

methanol (67-56-1) + 1,2-dinitroethane (7570-26-5) + NH4HCO3 → 1-nitroethylene (3638-64-0)

ethene (74-85-1) + nitrogen dioxide → 1-nitroethylene (3638-64-0)

Conditions	Yield
at 25℃;

2-nitroethanol nitrate (4528-34-1) + phosphorus pentoxide → 1-nitroethylene (3638-64-0)

1-chloro-2-nitroethane (625-47-8) + CaCl2 → hydrogenchloride (7647-01-0) + 1-nitroethylene (3638-64-0)

Conditions	Yield
at 275 - 450℃;

1-chloro-2-nitroethane (625-47-8) + CaCO3 → hydrogenchloride (7647-01-0) + 1-nitroethylene (3638-64-0)

Conditions	Yield
at 275 - 450℃;

2-nitroethyl acetate (18942-89-7) + Al2(SO4)3 → 1-nitroethylene (3638-64-0) + acetic acid (64-19-7)

Conditions	Yield
at 250 - 350℃;

2-nitroethyl acetate (18942-89-7) + AlPO4 → 1-nitroethylene (3638-64-0) + acetic acid (64-19-7)

Conditions	Yield
at 250 - 350℃;

2-nitroethyl acetate (18942-89-7) + CaSO4 → 1-nitroethylene (3638-64-0) + acetic acid (64-19-7)

Conditions	Yield
at 250 - 350℃;

1-nitroethylene (3638-64-0) + N-methyl-diphenyl-nitrone (7500-79-0) → 2-Methyl-4-nitro-3,3-diphenyl-isoxazolidine (126399-44-8)

Conditions	Yield
In benzene at 20℃; for 240h;	100%

1-nitroethylene (3638-64-0) + N-diphenylmethylene-N-pheylnitrone (4504-13-6) → 4-nitro-2,3,3-triphenylisoxazolidine (126399-36-8)

Conditions	Yield
In benzene for 1h; Ambient temperature;	100%
at 20℃; regioselective reaction;

1-nitroethylene (3638-64-0) + cyclopenta-1,3-diene (542-92-7) → 5-endo-nitrobicyclo<2.2.1>hept-2-ene (874-44-2)

Conditions	Yield
In diethyl ether at -15℃;	99.6%
With diethyl ether at 105 - 110℃;
With benzene
With diethyl ether

1-nitroethylene (3638-64-0) + N-tert-Butylhydroxylamine (16649-50-6) → N-tert-Butyl-N-(2-nitroethyl)hydroxylamin

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	99%

1-nitroethylene (3638-64-0) + N-demethyl-N-formylthebaibe (99307-35-4) → 4,5α-epoxy-17-formyl-3,6-dimethoxy-7α-nitro-6α,14α-ethenoisomorphinan (101077-43-4)

Conditions	Yield
In benzene for 19h; Heating;	99%

1-nitroethylene (3638-64-0) + benzeneacetic acid methyl ester (101-41-7) → 4-Nitro-2-phenyl-butyric acid methyl ester

Conditions	Yield
With diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane -78 deg C, 1 h; -78 deg C to room temp., 35 min;	99%

methanol (67-56-1) + 1-nitroethylene (3638-64-0) + 4-bromo-2-methoxy-5-methylphenol (40992-09-4) → endo-5-bromo-3,3-dimethoxy-6-methyl-7-nitrobicyclo[2.2.2]oct-5-en-2-one

Conditions	Yield
Stage #1: methanol; 4-bromo-2-methoxy-5-methylphenol With [bis(acetoxy)iodo]benzene at 0℃; Inert atmosphere; Stage #2: 1-nitroethylene In toluene at 20℃; Diels-Alder reaction; Inert atmosphere; regioselective reaction;	99%

3,4,5-Trimethylpyrazole (5519-42-6) + 1-nitroethylene (3638-64-0) → 3,4,5-Trimethyl-1-(2-nitro-ethyl)-1H-pyrazole (83600-05-9)

Conditions	Yield
In benzene for 12h; Ambient temperature;	98%

1-nitroethylene (3638-64-0) + C24H26IN3O2 (1227090-19-8) → C26H29IN4O4 (1227090-20-1)

Conditions	Yield
With indium tribromide In dichloromethane; benzene at 0 - 20℃; Inert atmosphere;	98%

1-nitroethylene (3638-64-0) + tert-butyl 2-oxocyclohexanecarboxylate (137334-09-9, 55623-56-8) → (S)-tert-butyl 1-(2-nitroethyl)-2-oxocyclohexanecarboxylate (1262669-60-2)

Conditions	Yield
With C34H22N2Ni2O4 In ethyl acetate; toluene at 40℃; for 18h; optical yield given as %ee; enantioselective reaction;	98%

1-nitroethylene (3638-64-0) + C18H15NO → 2-((4R,5R)-4-nitro-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)-1-(p-tolyl)ethanone

Conditions	Yield
Stage #1: C18H15NO With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; magnesium sulfate In dichloromethane at 0℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: 1-nitroethylene In dichloromethane; toluene at 0℃; for 60h; Inert atmosphere; Schlenk technique; enantioselective reaction;	98%

1-nitroethylene (3638-64-0) + C21H15NO → 1-(naphthalen-2-yl)-2-((4R,5R)-4-nitro-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)ethanone

Conditions	Yield
Stage #1: C21H15NO With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; magnesium sulfate In dichloromethane; toluene at 0℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: 1-nitroethylene In dichloromethane; toluene at 0℃; for 60h; Schlenk technique; Inert atmosphere; enantioselective reaction;	98%

1-nitroethylene (3638-64-0) + 1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione (91233-19-1) → 2-(1-adamantyl)-1-nitro-1-(pyridine-thiyl)ethane (104543-11-5)

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane; toluene at -20 - -10℃; for 0.5h; Irradiation;	97%

1-nitroethylene (3638-64-0) + 4-fluoroaniline (371-40-4) → (4-Fluoro-phenyl)-(2-nitro-ethyl)-amine (83600-17-3)

Conditions	Yield
In benzene for 12h; Ambient temperature;	97%

1-nitroethylene (3638-64-0) + 9-diazofluorenone (832-80-4) → 2-Nitrospiro (34163-56-9)

Conditions	Yield
In benzene	97%

1-nitroethylene (3638-64-0) + N-methylaniline (100-61-8) → N-methyl-N-(2-nitroethyl)benzenamine (83600-08-2)

Conditions	Yield
In benzene for 12h; Ambient temperature;	96%

3,5-dimethyl-1H-pyrazole (67-51-6) + 1-nitroethylene (3638-64-0) → 3,5-Dimethyl-1-(2-nitro-ethyl)-1H-pyrazole (83600-04-8)

Conditions	Yield
In benzene for 12h; Ambient temperature;	96%

1-nitroethylene (3638-64-0) + DL-leucine methyl ester (18869-43-7) → N-(2-Nitroethyl)-DL-leucine methyl ester (76919-69-2)

Conditions	Yield
In benzene for 12h; Ambient temperature;	96%

1-nitroethylene (3638-64-0) + leucine methyl ester hydrochloride (6322-53-8, 5845-53-4, 7517-19-3) → N-(2-Nitroethyl)-DL-leucine methyl ester (76919-69-2)

Conditions	Yield
With triethylamine In diethyl ether; benzene at 10℃; for 96h;	96%

1-nitroethylene (3638-64-0) + benzene (71-43-2) → deoxybenzoin oxime (952-06-7)

Conditions	Yield
trifluorormethanesulfonic acid at 0 - 5℃; for 0.25h;	96%

1-nitroethylene (3638-64-0) + pentanal (110-62-3) → C7H13NO3 (1022985-53-0)

Conditions	Yield
3-nitrobenzoic acid In toluene at 20℃; for 24h; Michael reaction;	96%

1-nitroethylene (3638-64-0) + 4-quinazolinol (491-36-1) → 3-(2'-nitroethyl)-quinazolin-4-one (83600-06-0)

Conditions	Yield
In benzene for 12h; Ambient temperature;	95%

1-nitroethylene (3638-64-0) → poly(nitroethylene), Mw=7.12E4; monomer(s): nitroethene

Conditions	Yield
With sodium ethanolate In ethanol at 20℃; for 14h; multiple Michael reaction;	95%

1-nitroethylene (3638-64-0) + propionaldehyde (123-38-6) → (R)-2-methyl-4-nitrobutan-1-ol (1022985-41-6)

Conditions	Yield
Stage #1: 1-nitroethylene; propionaldehyde; (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 3-nitrobenzoic acid In toluene at 3℃; Michael addition; Cooling with ice; Stage #2: With sodium tetrahydroborate In methanol; toluene at 0℃; Stage #3: With ammonium chloride In methanol; toluene at 0℃;	95%

1-nitroethylene (3638-64-0) + tert-butyl 2-oxocyclopentanecarboxylate (84109-76-2) → (S)-tert-butyl 1-(2-nitroethyl)-2-oxocyclopentanecarboxylate (1232542-30-1)

Conditions	Yield
With C34H22N2Ni2O4 In ethyl acetate; toluene at 40℃; for 5h; optical yield given as %ee; enantioselective reaction;	95%

1-nitroethylene (3638-64-0) + tert-butyl 3-(1-methyl-1H-indol-3-yl)-2-oxoindoline-1-carboxylate (1610698-76-4) → tert-butyl (S)-3-(1-methyl-1H-indol-3-yl)-3-(2-nitroethyl)-2-oxoindoline-1-carboxylate

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; [Ni(IAP1)2] In o-xylene at -20℃; for 25h; Reagent/catalyst; Concentration; Time; Temperature; Inert atmosphere; enantioselective reaction;	95%

1-nitroethylene (3638-64-0) + C22H21BrN2O3 (1610698-77-5) → tert-butyl (S)-5-bromo-3-(1-methyl-1H-indol-3-yl)-3-(2-nitroethyl)-2-oxoindoline-1-carboxylate

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; [Ni(IAP1)2] In o-xylene at -20℃; for 20h; Inert atmosphere; enantioselective reaction;	95%

Upstream product

• 85-44-9 phthalic anhydride 
• 625-48-9 2-nitro-1-ethanol 
• 50-00-0 formaldehyd 
• 75-52-5 nitromethane 
• 64-17-5 ethanol 
• 7570-26-5 1,2-dinitroethane 
• 18942-89-7 2-nitroethyl acetate 
• 67-56-1 methanol 
• 74-85-1 ethene 
• 4528-34-1 2-nitroethanol nitrate 
• 625-47-8 1-chloro-2-nitroethane 
• 79-10-7 acrylic acid 
• 143781-71-9 Pd(NO₃)(Cl)(C⁽²⁾H₃CN)2 
• 112907-30-9 bis(acetonitrile)chloronitropalladium(II) 

Downstream Products

• 31731-23-4 3-(2-nitroethyl)indole 
• 80242-09-7 decan-5-one oxime 
• 646-14-0 1-nitrohexane 
• 93331-75-0 5-benzyloxy-3-(2-nitro-ethyl)-indole 
• 421551-02-2 2-nitro-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene 
• 874-44-2 5-endo-nitrobicyclo<2.2.1>hept-2-ene 
• 100317-69-9 5,5-dimethyl-2,2-bis-(2-nitro-ethyl)-cyclohexane-1,3-dione 
• 83600-07-1 1-nitro-2-phenylaminoethane 
• 4591-86-0 2-(2-Nitroethyl)cyclohexanone 
• 4883-68-5 4-nitro-Δ'-cyclohexene 
• 54210-59-2 3-Hydroxy-3-methyl-4-nitrocyclohexanon 
• 99362-33-1 benzyl-(2-nitro-ethyl)-amine 
• 99987-95-8 N,N-Bis-<2-nitro-aethyl>-benzylamin 
• 7041-68-1 3-Phenyl-5-nitro-Δ²-isoxazoline 

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HERBICIDAL COMPOUNDS

The present invention relates to a compound of formula (I) wherein: wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and G are as defined herein; and wherein the compound of formula (I) is optionally present as an agrochemically acceptable salt thereof. These compounds are thought to be suitable for use as herbicides. The invention therefore also relates to a method of controlling weeds, especially grassy monocotyledonous weeds, in crops of useful plants, comprising applying a compound of formula (I), or a herbicidal composition comprising such a compound, to the plants or to the locus thereof.