71090-35-2

Basic information

• Product Name: 2-nitroethene-1,1-diamine
• Synonyms: 2-nitroethene-1,1-diamine;1,1-DIAMINO-2-NITROETHENE;2,2-Diaminonitroethene;2-nitroethylene-1,1-diamine
• CAS NO: 71090-35-2
• Molecular Formula: C₂H₅N₃O₂
• Molecular Weight: 103.08
• Mol File: 71090-35-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 203-205 °C(Solv: ethanol (64-17-5))
• Boiling Point: 212.4°C at 760 mmHg
• Flash Point: 82.2°C
• Appearance: /
• Density: 1.372g/cm³
• Vapor Pressure: 0.174mmHg at 25°C
• Refractive Index: 1.56
• PKA: 2.80±0.70(Predicted)
• CAS DataBase Reference: 2-nitroethene-1,1-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-nitroethene-1,1-diamine(71090-35-2)
• EPA Substance Registry System: 2-nitroethene-1,1-diamine(71090-35-2)

Safety Data

• Hazardous Substances Data: 71090-35-2(Hazardous Substances Data)

Usage

General Description

2-Nitroethene-1,1-diamine, also known as NEN, is a chemical compound with the molecular formula C2H6N4O2. It is a nitroamine compound, which means it contains both a nitro group and an amine group. NEN is used primarily as a precursor in the production of energetic materials, such as explosives and propellants. It is also used in the synthesis of pharmaceuticals and other organic compounds. The material is highly reactive and must be handled with care due to its explosive nature. NEN is considered to be a hazardous compound and is subject to strict regulations and safety protocols.

InChI:InChI=1/C2H5N3O2/c3-2(4)1-5(6)7/h1H,3-4H2

Synthetic route

1,1-di(methylsulfanyl)-2-nitroethylene (13623-94-4) → 1,1-diamino-2-nitroethene (71090-35-2)

Conditions	Yield
With ammonia In methanol at 50℃; for 18h;	100%
With ammonia	77%
With ammonia In methanol at 50℃; for 18h;	76.9%

(E)-1-Methoxy-2-nitro-1-ethenamin (102729-23-7) → 1,1-diamino-2-nitroethene (71090-35-2)

Conditions	Yield
With ammonia In ethanol for 1h; Heating;	91.4%

ethyl nitroacetimidate (90993-43-4) → nitroacetamidine (13514-88-0) + 1,1-diamino-2-nitroethene (71090-35-2)

Conditions	Yield
With amino-crotonic acid ethyl ester In water at 65 - 70℃; for 7h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1,1-diamino-2-nitroethene (71090-35-2) + acetylacetone (123-54-6) → 2-amino-4,6-dimethyl-3-nitropyridine (22934-23-2)

Conditions	Yield
In 2-methoxy-ethanol	93%
With acetic acid In ethanol for 4h; Heating;	52%
In 2-methoxy-ethanol; water

N-(4-fluorophenyl)maleimide (6633-22-3) + 1,1-diamino-2-nitroethene (71090-35-2) → 2-(5-amino-4-nitro-2-oxo-2,3-dihydro-1H-pyrrol-3-yl)-N-(4-fluorophenyl)acetamide

Conditions	Yield
In ethanol at 40℃; for 6h;	92%

N-p-tolylphenylmaleimide (1631-28-3) + 1,1-diamino-2-nitroethene (71090-35-2) → (5-amino-4-nitro-2-oxo-2,3-dihydro-1H-pyrrol-3-yl)-N-(p-tolyl)acetamide

Conditions	Yield
In ethanol at 40℃; for 6h;	87%

indole-2,3-dione (91-56-5) + 1,1-diamino-2-nitroethene (71090-35-2) + dimedone (126-81-8) → 2'-amino-7',7'-dimethyl-3'-nitro-7',8'-dihydro-1'H-spiro[indoline-3,4'-quinoline]-2,5'(6'H)-dione (1384517-72-9)

Conditions	Yield
With toluene-4-sulfonic acid In water Reflux;	85%

1-(p-Chlorphenyl)-3-dimethylamino-2-propen-1-on (28587-05-5, 67382-35-8) + 1,1-diamino-2-nitroethene (71090-35-2) → 2-Amino-6-(4-chlorphenyl)-3-nitropyridin (102291-55-4)

Conditions	Yield
With acetic acid In ethanol for 4h; Heating;	82%

1,1-diamino-2-nitroethene (71090-35-2) + (E)-3-(2-(4-chlorophenyl)-2-oxoethylidene)indolin-2-one (183947-04-8) → 3-(5-amino-2-(4-chlorophenyl)-4-nitro-1H-pyrrol-3-yl)indolin-2-one

Conditions	Yield
In ethanol for 12h; Reflux; Green chemistry;	82%

1,1-diamino-2-nitroethene (71090-35-2) + 3-Dimethylamino-1-phenyl-2-propen-1-on (31919-75-2) → 2-amino-3-nitro-6-phenylpyridine (102266-15-9)

Conditions	Yield
With acetic acid In ethanol for 4h; Heating;	80%

1,3-dimethylbarbituric acid (769-42-6) + indole-2,3-dione (91-56-5) + 1,1-diamino-2-nitroethene (71090-35-2) → 7'-amino-1',3'-dimethyl-6'-nitro-1'H-spiro[indoline-3,5'pyrido[2,3-d]pyrimidine]-2,2',4'(3'H,8'H)-trione (1384517-73-0)

Conditions	Yield
With toluene-4-sulfonic acid In water Reflux;	80%

1,3-dimethylbarbituric acid (769-42-6) + 1,1-diamino-2-nitroethene (71090-35-2) + 1-benzyl-5-bromoisatin (79183-44-1) → 7'-amino-1-benzyl-5-bromo-1',3'-dimethyl-6'-nitro-1'H-spiro[indoline-3,5'-pyrido[2,3-d]pyrimidine]-2,2',4'(3'H,8'H)-trione (1384517-74-1)

Conditions	Yield
With toluene-4-sulfonic acid In water Reflux;	80%

indole-2,3-dione (91-56-5) + 1,3-cylohexanedione (504-02-9) + 1,1-diamino-2-nitroethene (71090-35-2) → 2'-amino-3'-nitro-7',8'-dihydro-1'H-spiro[indoline-3,4'-quinoline]-2,5'(6'H)-dione (1384517-68-3)

Conditions	Yield
With toluene-4-sulfonic acid In water Reflux;	80%

cis-1-amino-1-buten-3-one (2802-09-7) + 1,1-diamino-2-nitroethene (71090-35-2) → 6-amino-5-nitro-2-picoline (21901-29-1)

Conditions	Yield
With acetic acid In ethanol for 4h; Heating;	78%

5-nitroisatin (611-09-6) + 1,3-cylohexanedione (504-02-9) + 1,1-diamino-2-nitroethene (71090-35-2) → 2'-amino-3',5-dinitro-7',8'-dihydro-1'H-spiro[indoline-3,4'-quinoline]-2,5'(6'H)-dione (1384517-70-7)

Conditions	Yield
With toluene-4-sulfonic acid In water Reflux;	77%

(E)-3-(2-oxo-2-phenylethylidene)indolin-2-one (31541-36-3, 34880-79-0, 56680-29-6) + 1,1-diamino-2-nitroethene (71090-35-2) → 3-(5-amino-4-nitro-2-phenyl-1H-pyrrol-3-yl)indolin-2-one

Conditions	Yield
In ethanol for 12h; Reflux; Green chemistry;	76%

1,1-diamino-2-nitroethene (71090-35-2) + (Z)-3-Dimethylamino-1-phenyl-propenone; hydrochloride (91131-98-5) → 2-Amino-1,4-dihydro-3-nitro-6-phenylpyridin (102266-10-4)

Conditions	Yield
In methanol for 1h; Heating;	75%

5-bromo-1-methyl-1H-indole-2,3-dione (2058-72-2) + 1,3-cylohexanedione (504-02-9) + 1,1-diamino-2-nitroethene (71090-35-2) → 2'-amino-5-bromo-1-methyl-3'-nitro-7',8'-dihydro1'H-spiro[indoline-3,4'-quinoline]-2,5'(6'H)-dione (1384517-71-8)

Conditions	Yield
With toluene-4-sulfonic acid In water Reflux;	75%

5-Bromo-1H-indole-2,3-dione (87-48-9) + 1,3-cylohexanedione (504-02-9) + 1,1-diamino-2-nitroethene (71090-35-2) → 2'-amino-5-bromo-3'-nitro-7',8'-dihydro-1'H-spiro[indoline-3,4'-quinoline]-2,5'(6'H)-dione (1384517-69-4)

Conditions	Yield
With toluene-4-sulfonic acid In water Reflux;	75%

ethanol (64-17-5) + 1,1-diamino-2-nitroethene (71090-35-2) + 3-Formylchromone (17422-74-1) → 5-ethoxy-3-nitro-5H-chromeno[4,3-b]pyridin-2-amine

Conditions	Yield
With perchloric acid at 50℃;	74%

1,1-diamino-2-nitroethene (71090-35-2) + 3-Diethylaminoacrolein (13070-22-9, 34899-98-4) → 2-amino-3-nitropyridine (4214-75-9)

Conditions	Yield
With acetic acid In ethanol for 4h; Heating;	72%

1,1-diamino-2-nitroethene (71090-35-2) + 4-((E)-5-Dimethylamino-3-oxo-pent-4-enyl)-benzoic acid methyl ester (187242-84-8) → 4-[2-(6-Amino-5-nitro-pyridin-2-yl)-ethyl]-benzoic acid methyl ester (187242-87-1)

Conditions	Yield
With acetic acid In ethanol for 5h; Heating;	72%

1,1-diamino-2-nitroethene (71090-35-2) + (Z)-1-(4-Chloro-phenyl)-3-dimethylamino-propenone; hydrochloride (102266-13-7) → 2-Amino-6-(4-chlorphenyl)-1,4-dihydro-3-nitropyridin (102266-11-5)

Conditions	Yield
In methanol for 1h; Heating;	71%

1,1-diamino-2-nitroethene (71090-35-2) + cyanoacetic acid (372-09-8) → 5,5-Diamino-4-nitro-3-oxo-4-butensaeurenitril

Conditions	Yield
In acetic anhydride for 8h; Ambient temperature;	70.6%

1,1-diamino-2-nitroethene (71090-35-2) + (Z)-3-Dimethylamino-1-thiophen-2-yl-propenone; hydrochloride (102266-14-8) → 2-Amino-1,4-dihydro-3-nitro-6-(2-thienyl)pyridin (102266-12-6)

Conditions	Yield
In methanol for 1h; Heating;	70%

1,1-diamino-2-nitroethene (71090-35-2) + benzaldehyde (100-52-7) → 2,6-Diamino-1,4-dihydro-3,5-dinitro-4-phenylpyridin (146580-39-4)

Conditions	Yield
With acetic acid In ethanol for 3h; Heating;	67%

1,1-diamino-2-nitroethene (71090-35-2) + ethyl 4-(5-ethoxycarbonyl-3,5-dioxopentyl)benzoate (528596-98-7) → ethyl 2-amino-6-[2-(4-ethoxycarbonylphenyl)ethyl]-3-nitroisonicotinate (528597-01-5)

Conditions	Yield
In methanol for 0.75h; Heating;	65%

methyl (Z)-2-(3-nitrobenzylidene)-3-oxobutanoate (119128-13-1) + 1,1-diamino-2-nitroethene (71090-35-2) → 6-Amino-2-methyl-5-nitro-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester (133488-57-0)

Conditions	Yield
In ethanol for 5h; Heating; other enones, other keteneaminales;	64.3%
With piperidine In ethanol for 5h; Heating;	64.3%

(Z)-3-(dimethylamino)-1-(thiophen-2-yl)prop-2-en-1-one (34772-98-0) + 1,1-diamino-2-nitroethene (71090-35-2) → 3-nitro-6-(thiophen-2-yl)pyridin-2-amine (102266-16-0)

Conditions	Yield
With acetic acid In ethanol for 4h; Heating;	63%

2-dimethylaminomethylcyclohexanone hydrochloride (42036-65-7, 151777-85-4, 151777-88-7) + 1,1-diamino-2-nitroethene (71090-35-2) → 3-Nitro-1,4,5,6,7,8-hexahydro-quinolin-2-ylamine (187242-98-4)

Conditions	Yield
In ethanol for 13h; Heating;	61%

1,5-diphenyl-1,4-pentadien-3-one (538-58-9, 35225-79-7, 58321-78-1, 115587-57-0, 131348-67-9, 79616-73-2) + 1,1-diamino-2-nitroethene (71090-35-2) → 2-Amino-1,4-dihydro-3-nitro-4-phenyl-6-styrylpyridin (146580-33-8)

Conditions	Yield
With acetic acid In ethanol for 0.25h; Heating;	59%

Upstream product

• 13623-94-4 1,1-di(methylsulfanyl)-2-nitroethylene 
• 102729-23-7 (E)-1-Methoxy-2-nitro-1-ethenamin 
• 90993-43-4 ethyl nitroacetimidate 

Downstream Products

• 21901-29-1 6-amino-5-nitro-2-picoline 
• 3346-63-2 2,6-diamino-3-nitro-pyridine 
• 146580-31-6 2-Amino-1,4-dihydro-4-methyl-3-nitro-6-phenylpyridin 
• 7598-26-7 5-Methyl-3-nitro-2-aminopyridine 
• 102291-55-4 2-Amino-6-(4-chlorphenyl)-3-nitropyridin 
• 146580-36-1 2-amino-3-nitro-4-methyl-6-phenylpyridine 
• 133488-55-8 6-Amino-1,4-dihydro-2-methyl-5-nitro-4-phenyl-nicotinsaeuremethylester 
• 133488-57-0 6-Amino-2-methyl-5-nitro-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester 
• 133488-62-7 2-Amino-1,4,5,6,7,8-hexahydro-3-nitro-4-phenyl-chinolin-5-on 
• 133494-84-5 6-Amino-2-methyl-5-nitro-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester 
• 146580-33-8 2-Amino-1,4-dihydro-3-nitro-4-phenyl-6-styrylpyridin 
• 102266-15-9 2-amino-3-nitro-6-phenylpyridine 
• 146580-39-4 2,6-Diamino-1,4-dihydro-3,5-dinitro-4-phenylpyridin 
• 102266-10-4 2-Amino-1,4-dihydro-3-nitro-6-phenylpyridin 

Relevant articles and documents

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