4749-28-4

Basic information

• Product Name: 2-NITROPROPENE
• Synonyms: 2-NITROPROPENE;2-Nitro-1-propene;TL-1147;2-nitroprop-1-ene
• CAS NO: 4749-28-4
• Molecular Formula: C₃H₅NO₂
• Molecular Weight: 87.08
• Mol File: 4749-28-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 65-67 °C
• Boiling Point: 130.87°C (rough estimate)
• Flash Point: 31.9°C
• Appearance: /
• Density: 1.0559
• Vapor Pressure: 19.1mmHg at 25°C
• Refractive Index: 1.4358
• CAS DataBase Reference: 2-NITROPROPENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROPROPENE(4749-28-4)
• EPA Substance Registry System: 2-NITROPROPENE(4749-28-4)

Safety Data

• Hazardous Substances Data: 4749-28-4(Hazardous Substances Data)

Usage

Safety Profile

Potentially dangerouspolymerization reaction on contact with alkalies. Whenheated to decomposition it emits toxic fumes of NOx. Seealso NITROALKANES.

InChI:InChI=1/C3H5NO2/c1-3(2)4(5)6/h1H2,2H3

Synthetic route

2-NITROPROPANOL (2902-96-7) → 2-nitropropene (4749-28-4)

Conditions	Yield
With phthalic anhydride Heating;	94%
With phthalic anhydride at 150 - 185℃; for 1.5h;	72%
With triethylamine; trifluoroacetic anhydride Inert atmosphere;	56%

2-nitro-1-butanol (609-31-4) → 2-nitropropene (4749-28-4)

Conditions	Yield
With phthalic anhydride at 150 - 200℃;	52%

1-(2-nitro-propyl)-piperidine (3275-15-8) → 2-nitropropene (4749-28-4)

Conditions	Yield
With diethyl ether; Di(2-ethylhexyl)phthalate; boron trifluoride anschliessendes Erhitzen unter 1 Torr auf 105grad;

1-chloro-2-nitro-propane (2425-66-3) → 2-nitropropene (4749-28-4)

Conditions	Yield
With silica gel at 325℃;

2-nitroacetoxypropane (3750-82-1) → 2-nitropropene (4749-28-4)

Conditions	Yield
With sodium carbonate; benzene

benzoic acid-(2-nitro-propyl ester) (5437-73-0) → 2-nitropropene (4749-28-4) + benzoic acid (65-85-0)

Conditions	Yield
auch unter vermindertem Druck;

N-<2-nitro-propyl>-piperidine hydrochloride → 2-nitropropene (4749-28-4)

Conditions	Yield
at 105 - 160℃; under 70 Torr;

2-nitroacetoxypropane (3750-82-1) + calcium magnesium phosphate → 2-nitropropene (4749-28-4) + acetic acid (64-19-7)

Conditions	Yield
at 285℃;

propene (187737-37-7) → 2-nitropropene (4749-28-4) + propionaldehyde (123-38-6) + acetone (67-64-1)

Conditions	Yield
With bis(acetonitrile)chloronitropalladium(II) In chloroform at 25℃; under 0.1 Torr; for 6h; Product distribution; Further Variations:; Reagents;	A 6 % Chromat. B 1 % Chromat. C 93 % Chromat.

N,N-bis(trimethylsilyloxy)-1-propen-2-amine (102588-22-7) → 2-nitropropene (4749-28-4)

Conditions	Yield
With bromine; tetrabutylammonium acetate In dichloromethane at -78 - 20℃;	95 % Spectr.

2-nitropropane (79-46-9) + 1-Nitropropane (108-03-2) → 2-nitropropene (4749-28-4) + 1-Nitropropen (3156-70-5)

Conditions	Yield
With nitric acid at 200℃; under 16274.9 Torr; Product distribution / selectivity;

2-nitropropyl phtalate → 2-nitropropene (4749-28-4)

Conditions	Yield
Pyrolysis;

2-nitropropene (4749-28-4) + N-(3α-acetoxy-11-oxonorcholan-23-ylcarbonyloxy)pyridine-2-thione (89025-69-4) → 3α-acetoxy, 25-nitro-25-(pyridine-2-thiyl)-11-oxo,27-nor-5β-cholestane (104543-15-9)

Conditions	Yield
With camphor-10-sulfonic acid In benzene at -20 - -10℃; for 0.5h; Irradiation;	100%

2-nitropropene (4749-28-4) + Phenylselenyl chloride (5707-04-0) + silver trifluoroacetate (2966-50-9) → 2-nitro-2-phenylseleno-propyl-trifluoroacetate (104313-35-1)

Conditions	Yield
In dichloromethane Ambient temperature;	97%

2-nitropropene (4749-28-4) + 2-methylcyclohexane-1,3-dione (1193-55-1) → 2-Methyl-2-(2-oxopropyl)-1,3-cyclohexanedione (32561-57-2)

Conditions	Yield
potassium fluoride In xylene at 120℃; for 19h;	96%

2-nitropropene (4749-28-4) + 4-benzyloxy-1H-indole (20289-26-3) → 1-<4-(benzyloxy)indol-3-yl>-2-nitropropane (2873-49-6)

Conditions	Yield
In benzene Heating;	96%
In benzene Heating;	59%

2-nitropropene (4749-28-4) + cyclohexanone (108-94-1) + acetic anhydride (108-24-7) → 2-(2-acetyl-aci-nitropropyl)cyclohexanone (125405-73-4, 125405-74-5, 132336-66-4)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran 1.) -78 deg C, 2 h; 2.) -78 to 20 deg C over 2 h;	96%
Yield given. Multistep reaction;

2-nitropropene (4749-28-4) + α-(2-ethyl acetate) Meldrum's acid (1374824-30-2) → (S)-2-(2,2-dimethyl-5-(2-nitropropyl)-4,6-dioxo-1,3-dioxan-5-yl)ethyl acetate (1374824-20-0)

Conditions	Yield
With (R)-2,4,6-triisopropyl-N-((2-methyl-2-morpholinopropyl)carbamoyl)benzenesulfinamide In cyclopentyl methyl ether at -30℃; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	95%

2-nitropropene (4749-28-4) + thioacetic acid (507-09-5) → S-2-nitropropyl thiolacetate (1365479-49-7)

Conditions	Yield
With tributyl-amine In diethyl ether for 1h; Michael addition; Cooling with ice;	94%

2-nitropropene (4749-28-4) + 5-ethyl-2,2-dimethyl-[1,3]dioxane-4,6-dione (17216-65-8) → (S)-5-ethyl-2,2-dimethyl-5-(2-nitropropyl)-1,3-dioxane-4,6-dione (1374824-13-1)

Conditions	Yield
With (R)-2,4,6-triisopropyl-N-((2-methyl-2-morpholinopropyl)carbamoyl)benzenesulfinamide In cyclopentyl methyl ether at -30℃; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	94%

2-nitropropene (4749-28-4) + 2,2,5-trimethyl-1,3-dioxane-4,6-dione (3709-18-0) → (S)-2,2,5-trimethyl-5-(2-nitropropyl)-1,3-dioxane-4,6-dione (1374824-11-9)

Conditions	Yield
With (R)-2,4,6-triisopropyl-N-((2-methyl-2-morpholinopropyl)carbamoyl)benzenesulfinamide In cyclopentyl methyl ether at -30℃; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	93%

2-nitropropene (4749-28-4) + 2,2-dimethyl-5-phenethyl-[1,3]dioxane-4,6-dione (3709-38-4) → (S)-2,2-dimethyl-5-(2-nitropropyl)-5-phenethyl-1,3-dioxane-4,6-dione (1374824-15-3)

Conditions	Yield
With (R)-2,4,6-triisopropyl-N-((2-methyl-2-morpholinopropyl)carbamoyl)benzenesulfinamide In cyclopentyl methyl ether at -30℃; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	93%

2-nitropropene (4749-28-4) + 2-morpholinopent-1-en-3-one (136368-54-2) → 1-ethyl-5-methyl-2-morpholino-5-nitrocyclopent-2-enol (136368-57-5)

Conditions	Yield
at -20℃; for 2h;	92%

2-nitropropene (4749-28-4) + 2-morpholin-4-yl-1,3-diphenyl-propenone (57310-73-3) → 5-methyl-2-morpholino-5-nitro-1,3-diphenyl-cyclopent-2-enol (136368-82-6)

Conditions	Yield
for 2h;	92%

2-nitropropene (4749-28-4) + 3-(n-butylimino)-butan-2-one (140405-47-6) → 5-(n-butylimino)-1,2-dimethyl-2-nitrocyclopentan-1-ol (140405-49-8)

Conditions	Yield
for 0.5h;	90%

2-nitropropene (4749-28-4) + 2,2-dimethyl-5-(2-(methylthio)ethyl)-1,3-dioxane-4,6-dione (1094204-79-1) → (S)-2,2-dimethyl-5-(2-(methylthio)ethyl)-5-(2-nitropropyl)-1,3-dioxane-4,6-dione (1374824-19-7)

Conditions	Yield
With (R)-2,4,6-triisopropyl-N-((2-methyl-2-morpholinopropyl)carbamoyl)benzenesulfinamide In cyclopentyl methyl ether at -30℃; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	90%

2-nitropropene (4749-28-4) + 5-Acetoxy-2,2-dimethyl-1,3-dioxan-4,6-dion (75307-63-0) → (S)-2,2-dimethyl-5-(2-nitropropyl)-4,6-dioxo-1,3-dioxan-5-yl acetate (1374824-22-2)

Conditions	Yield
With (R)-2,4,6-triisopropyl-N-((2-methyl-2-morpholinopropyl)carbamoyl)benzenesulfinamide In cyclopentyl methyl ether at -30℃; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	90%

5-methoxylindole (1006-94-6) + 2-nitropropene (4749-28-4) → 1-(5-methoxyindol-3-yl)-2-nitropropane (113997-50-5)

Conditions	Yield
In benzene Heating;	89%

2-nitropropene (4749-28-4) + C13H12O3 → C15H17NO3

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (S,Rp)-FeUrPhos In 1,4-dioxane at 25℃; for 72h; Inert atmosphere; Glovebox; stereoselective reaction;	89%

formaldehyd (50-00-0) + 2-nitropropene (4749-28-4) + thiophenol (108-98-5) → 2-Methyl-2-nitro-3-phenylsulfanyl-propan-1-ol (94421-42-8)

Conditions	Yield
With 1,1,3,3-tetramethylguanidine for 5h; Ambient temperature;	88%

2-nitropropene (4749-28-4) + α-(4-(trifluoromethoxy)phenethyl) Meldrum's acid (1374824-28-8) → (S)-2,2-dimethyl-5-(2-nitropropyl)-5-(4-(trifluoromethoxy)phenethyl)-1,3-dioxane-4,6-dione (1374824-17-5)

Conditions	Yield
With (R)-2,4,6-triisopropyl-N-((2-methyl-2-morpholinopropyl)carbamoyl)benzenesulfinamide In cyclopentyl methyl ether at -30℃; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	88%

2-nitropropene (4749-28-4) + acetic anhydride (108-24-7) + pentan-3-one (96-22-0) → C10H17NO4 (125405-68-7, 125405-69-8, 132336-65-3)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran 1.) -78 deg C, 2 h; 2.) -78 to 20 deg C over 2 h;	87%
Yield given. Multistep reaction;

2-nitropropene (4749-28-4) + benzene (71-43-2) → 1-phenyl-acetone (103-79-7)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at -40℃; for 0.0166667h;	85%

2-nitropropene (4749-28-4) + 2,2-Dimethyl-5-(2-methylpropyl)-1,3-dioxane-4,6-dione (74965-92-7) → (S)-5-isobutyl-2,2-dimethyl-5-(2-nitropropyl)-1,3-dioxane-4,6-dione (1374824-14-2)

Conditions	Yield
With (R)-2,4,6-triisopropyl-N-((2-methyl-2-morpholinopropyl)carbamoyl)benzenesulfinamide In cyclopentyl methyl ether at -30℃; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	85%

2-nitropropene (4749-28-4) + C14H14O3 → C16H19NO3

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (S,Rp)-FeUrPhos In 1,4-dioxane at 25℃; for 72h; Inert atmosphere; Glovebox; stereoselective reaction;	85%

2-nitropropene (4749-28-4) + C10H14O3 → C12H19NO3

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (S,Rp)-FeUrPhos In 1,4-dioxane at 25℃; for 60h; Inert atmosphere; Glovebox; stereoselective reaction;	85%

2-nitropropene (4749-28-4) + C11H14O3 → C13H19NO3

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (S,Rp)-FeUrPhos In 1,4-dioxane at 25℃; for 60h; Inert atmosphere; Glovebox; stereoselective reaction;	84%

2-nitropropene (4749-28-4) + piperonal (120-57-0) + methyl (2S)-pyrrolidine carboxylate (2577-48-2) → methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2-nitrohexahydro-1H-pyrrolizine-7a-carboxylate

Conditions	Yield
Stage #1: 2-nitropropene; piperonal; methyl (2S)-pyrrolidine carboxylate With sodium sulfate; triethylamine In acetonitrile at 80℃; for 0.333333h; Stage #2: In acetonitrile at 80℃; for 0.75h; Stage #3: In acetonitrile	83%

indole (120-72-9) + 2-nitropropene (4749-28-4) → α-methyl-β-(3-indolyl)-1-nitroethane (4771-72-6)

Conditions	Yield
In benzene Heating;	81%
In benzene Heating;

2-nitropropene (4749-28-4) + n-hexan-2-one (591-78-6) + acetic anhydride (108-24-7) → C11H19NO4 (125405-62-1, 125405-63-2, 132336-62-0)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran 1.) -78 deg C, 2 h; 2.) -78 to 20 deg C over 2 h;	81%
multistep reaction, other nitroalkenes, other ketones, synthesis of acetic nitronic anhydrides;
Yield given. Multistep reaction;

2-nitropropene (4749-28-4) + α-(3-methoxyphenethyl) Meldrum's acid (1374824-27-7) → (S)-5-(3-methoxyphenethyl)-2,2-dimethyl-5-(2-nitropropyl)-1,3-dioxane-4,6-dione (1374824-16-4)

Conditions	Yield
With (R)-2,4,6-triisopropyl-N-((2-methyl-2-morpholinopropyl)carbamoyl)benzenesulfinamide In cyclopentyl methyl ether at -30℃; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	81%

Upstream product

• 50-00-0 formaldehyd 
• 79-24-3 Nitroethane 
• 79-46-9 2-nitropropane 
• 3750-82-1 2-nitropropyl acetate 
• 108-03-2 1-Nitropropane 
• 609-31-4 2-nitro-1-butanol 
• 102588-22-7 N,N-bis(trimethylsilyloxy)-1-propen-2-amine 
• 187737-37-7 propene 
• 16767-70-7 acetimidic acid 2-nitro-propyl ester; hydrochloride 
• 5437-73-0 benzoic acid-(2-nitro-propyl ester) 
• 2902-96-7 2-NITROPROPANOL 
• 2425-66-3 1-chloro-2-nitro-propane 
• 3275-15-8 1-(2-nitro-propyl)-piperidine 
• 27675-36-1 1-nitropropene 

Downstream Products

• 54210-62-7 3-Hydroxy-3,4-dimethyl-4-nitrocyclohexanon 
• 75436-61-2 1-(2-Oxo-propyl)-cyclohexanecarboxylic acid methyl ester 
• 74457-44-6 methyl 4-keto-2-phenylpentanoate 
• 76532-89-3 1-benzoyl-4-(2-oxopropyl)-2,2a,3,4-tetrahydrobenzindol-5(1H)-one 
• 125405-73-4 2-(2-acetyl-aci-nitropropyl)cyclohexanone 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 5211-62-1 1-(2-methoxyphenyl)propan-2-one 
• 2096-86-8 p-Tolylaceton 
• 51052-00-7 1-(2-methylphenyl)acetone 
• 30213-79-7 3-(4-nitro-phenyl)-5-methylisoxazole 
• 24731-07-5 2-oxo-1-(2-oxo-propyl)-cyclohexanecarboxylic acid ethyl ester 
• 343220-77-9 1-(2-Nitro-propyl)-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 17515-66-1 ethyl 4-oxo-2-(2,2,2-trifluoroacetyl)pentanoate 
• 1008-74-8 5-methyl-3-phenylisoxazole 

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