1874-22-2

Basic information

• Product Name: 5-Nitrofuran-2-acrylaldehyde
• Synonyms: 5-NITRO-2-FURANACROLEIN;4-NITRO-5-HYDRAZINOBENZOFURAZAN;3-(5-NITRO-2-FURYL)ACROLEIN;2-Furanacrolein, 5-nitro-;2-Propenal, 3-(5-nitro-2-furanyl)-;3-(5-nitro-2-furanyl)-2-propena;3-(Nitro-2-furanyl)-2-propenal;5-nitro-2-furanacrolei
• CAS NO: 1874-22-2
• Molecular Formula: C₇H₅NO₄
• Molecular Weight: 167.12
• EINECS: 217-499-8
• Product Categories: Miscellaneous
• Mol File: 1874-22-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 117°C
• Boiling Point: 295.67°C (rough estimate)
• Flash Point: 141.7 °C
• Appearance: orange-brown crystalline powder
• Density: 1.5216 (rough estimate)
• Vapor Pressure: 0.000591mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• CAS DataBase Reference: 5-Nitrofuran-2-acrylaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitrofuran-2-acrylaldehyde(1874-22-2)
• EPA Substance Registry System: 5-Nitrofuran-2-acrylaldehyde(1874-22-2)

Safety Data

• Statements: 20/21-22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 1874-22-2(Hazardous Substances Data)

Usage

Chemical Properties

orange-brown crystalline powder

InChI:InChI=1/C7H5NO4/c9-5-1-2-6-3-4-7(12-6)8(10)11/h1-5H/b2-1+

Synthetic route

5-nitrofurane-2-carboxaldehyde (698-63-5) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2)

Conditions	Yield
In toluene for 6h; Reflux; Inert atmosphere;	93%
In dichloromethane at 20℃; Wittig Olefination;	30%

5-nitrofurane-2-carboxaldehyde (698-63-5) + aqueous dimethylamine + acetaldehyde (75-07-0) → 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2)

Conditions	Yield
In acetic acid	53%

5-nitrofurane-2-carboxaldehyde (698-63-5) + acetaldehyde (75-07-0) → 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2)

Conditions	Yield
With piperidine; acetic acid In benzene at 0 - 74℃; for 17h;	9%
With piperidine
With piperidine; benzene
With piperidine; acetic acid; benzene
With potassium hydroxide Erhitzen des Reaktionsgemisches mit Acetanhydrid;

3-hydroxy-2-naphthohydrazide (5341-58-2) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → (E)-3-hydroxy-N'-((E)-3-(5-nitrofuran-2-yl)allylidene)-2-naphthohydrazide (1310099-61-6)

Conditions	Yield
With acetic acid for 2h;	99%

4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-3-thiosemicarbazide (63128-98-3) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → C22H26N4O12S (86154-76-9)

Conditions	Yield
With acetic acid In methanol for 0.5h; Heating;	96%

3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → (E)-β-(5-Nitro-fur-2-yl)-acrylonitril (18873-36-4)

Conditions	Yield
With perchloric acid; magnesium(II) perchlorate; tris-(2-chloro-ethyl)-amine In 1,4-dioxane; benzene at 35℃; for 1.5h;	95%
With hydrogen azide; magnesium(II) perchlorate In chloroform at 30 - 50℃; for 1.16667h; Schmidt reaction;	95%
Multi-step reaction with 3 steps 1: aqueous ethanol; hydroxylamine 3: pyridine View Scheme
Multi-step reaction with 4 steps 1: aqueous ethanol; hydroxylamine 2: ethanol; hydrogen chloride 4: pyridine View Scheme

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane (7381-30-8) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → 5-nitro-2-furanacrolein 1,3-dioxolane (105562-29-6)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane 1.) -78 deg C, 3 h, 2.) RT, 14 h;	93%

3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) + toluene-4-sulfonic acid hydrazide (1576-35-8) → C14H13N3O5S

Conditions	Yield
In methanol for 3h; Heating;	90%

3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) + 4-amino-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione → 5-Furan-2-yl-4-[(E)-3-(5-nitro-furan-2-yl)-prop-2-en-(E)-ylideneamino]-2,4-dihydro-[1,2,4]triazole-3-thione

Conditions	Yield
In ethanol for 3h; Heating;	87%

3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) + 4-acetamidobenzenesulfonylhydrazine (3989-50-2) → C15H14N4O6S

Conditions	Yield
In methanol for 3h; Heating;	86%

4-(2-naphthyl)semicarbazide (99844-04-9) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → C18H14N4O4

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	80%

3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) + 4-(2-methoxyethyl)semicarbazide (208396-71-8) → C11H14N4O5

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	80%

p-chlorophenylsulfonyl hydrazide (2751-25-9) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → C13H10ClN3O5S

Conditions	Yield
In methanol for 3h; Heating;	79%

N-ethylthiosemicarbazide (13431-34-0) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → (E)-N-ethyl-2-((E)-3-(5-nitrofuran-2-yl)allylidene)hydrazinecarbothioamide

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	79%
In ethanol for 2h; Heating;

para-aminophenylsulfonyl hydrazide (5450-86-2) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → C13H12N4O5S

Conditions	Yield
In methanol for 3h; Heating;	72%

naphtho[1,2-b]furan-4,5‑dione (32358-83-1) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → (E)-2-(2-(5-nitrofuran-2-yl)vinyl)furo[3',2':3,4]naphtho[1,2-d]imidazole (1192373-18-4)

Conditions	Yield
With ammonium acetate; acetic acid for 0.5h; Microwave irradiation;	71%

3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) + 4-methylthiosemicarbazide (6610-29-3) → C9H10N4O3S

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	68%
In ethanol for 2h; Heating;

4-((2,7-difluoro-3-oxo-9-(o-tolyl)-3H-xanthen-6-yl)amino)butanehydrazide + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → 4-((2,7-difluoro-3-oxo-9-(o-tolyl)-3H-xanthen-6-yl)amino)-N'-((1E,2E)-3-(5-nitrofuran-2-yl)allylidene)butanehydrazide

Conditions	Yield
In methanol at 22℃; for 1h;	66%

3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) + 4-Phenyl-3-thiosemicarbazide (5351-69-9) → C14H12N4O3S

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	64%

4-butyl-3-semicarbazide (20605-19-0) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → C12H16N4O4

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	62%

N4-hexylsemicarbazide (79353-76-7) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → C14H20N4O4

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	58%

acetic acid hydrazide (1068-57-1) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → N'-((1E,2E)-3-(5-nitrofuran-2-yl)allylidene)acetohydrazide

Conditions	Yield
In methanol for 1h;	58%

1-(3-(4-chlorophenyl)-1-(2-hydrazinyl-2-oxoethyl)-5,5-dimethyl-2-oxoimidazolidin-4-yl)-1-hydroxy-3-(4-(2-methoxyethoxy)phenyl)urea + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → 1-(3-(4-chlorophenyl)-5,5-dimethyl-1-(2-((E)-2-((E)-3-(5-nitrofuran-2-yl)allylidene)hydrazinyl)-2-oxoethyl)-2-oxoimidazolidin-4-yl)-1-hydroxy-3-(4-(2-methoxyethoxy)phenyl)urea

Conditions	Yield
In methanol at 20℃; for 7h;	54%

L-butoxycarbonylhydrazine (52709-73-6) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → N'-[(E)-3-(5-Nitro-furan-2-yl)-prop-2-en-(E)-ylidene]-hydrazinecarboxylic acid butyl ester

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	52%

3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) + aniline (62-53-3) → N-[3-(5-nitrofur-2-yl)-2-propenylidene]aniline

Conditions	Yield
With 4 Angstroem MS In benzene at 20℃; for 4h; Condensation;	50%

hydrazinecarboxylic acid methyl ester (6294-89-9) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → N'-[(E)-3-(5-Nitro-furan-2-yl)-prop-2-en-(E)-ylidene]-hydrazinecarboxylic acid methyl ester

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	50%

heptyl carbazate (90203-34-2) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → N'-[(E)-3-(5-Nitro-furan-2-yl)-prop-2-en-(E)-ylidene]-hydrazinecarboxylic acid heptyl ester

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	50%

benzo[d][1,3]dioxole-5-carbohydrazide (22026-39-7) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → C15H11N3O6

Conditions	Yield
With hydrogenchloride In ethanol; water at 20℃; for 0.5h;	50%

3-trifluoromethylaniline (98-16-8) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → N-[3-(5-nitrofur-2-yl)-2-propenylidene]-3-trifluoromethylaniline

Conditions	Yield
With 4 Angstroem MS In benzene at 20℃; for 12h; Condensation;	45%

3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) + phenyl hydrazinecarboxylate (20605-43-0) → C14H11N3O5

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	45%

allyloxycarbazate (98071-77-3) + 3-(5-nitrofuran-2-yl)-2-propenal (1874-22-2) → C11H11N3O5

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	40%

Upstream product

• 698-63-5 5-nitrofurane-2-carboxaldehyde 
• 75-07-0 acetaldehyde 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 

Downstream Products

• 3318-78-3 3-[3-(5-nitro-[2]furyl)-allylidenamino]-oxazolidin-2-one 
• 10048-74-5 [3t-(5-nitro-[2]furyl)-allylidene]-[1,2,4]triazol-4-yl-amine 
• 1672-88-4 1-{[(1E,2E)-3-(5-nitrofuran-2-yl)prop-2-ene-1-ylidene]amino}imidazolidin-2,4-dione 
• 100621-40-7 4-amino-2-hydroxy-benzoic acid-[3t-(5-nitro-[2]furyl)-allylidenehydrazide] 
• 90871-23-1 3t-(5-nitro-[2]furyl)-acrylaldehyde-[2-(2-hydroxy-ethyl)-semicarbazone] 
• 721-71-1 3t-(5-nitro-[2]furyl)-acrylaldehyde semicarbazone 
• 92150-32-8 3t-(5-nitro-[2]furyl)-acrylaldehyde-(4-phenyl semicarbazone) 
• 101094-95-5 4-chloro-benzoic acid-[3t-(5-nitro-[2]furyl)-allylidenehydrazide] 
• 132861-70-2 N-[3t-(5-nitro-[2]furyl)-allylidene]-p-phenetidine 
• 3455-60-5 3t-(5-nitro-[2]furyl)-acrylaldehyde-(Z)-oxime 
• 3455-60-5 β-(5-nitrofuryl-2)acrolein oxime 
• 19105-42-1 1-(2-Chinolyl)-4-(5-nitro-2-furyl)butadien 
• 3318-79-4 (+/-)-5-morpholinomethyl-3-[3t-(5-nitro-[2]furyl)-allylidenamino]-oxazolidin-2-one 

Relevant articles and documents

Synthesis of Fluorophores that Target Small Molecules to the Endoplasmic Reticulum of Living Mammalian Cells

The endoplasmic reticulum (ER) plays critical roles in the processing of secreted and transmembrane proteins. To deliver small molecules to this organelle, we synthesized fluorinated hydrophobic analogues of the fluorophore rhodol. These cell-permeable fluorophores are exceptionally bright, with quantum yields of around 0.8, and they were found to specifically accumulate in the ER of living HeLa cells, as imaged by confocal laser scanning microscopy. To target a biological pathway controlled by the ER, we linked a fluorinated hydrophobic rhodol to 5-nitrofuran-2-acrylaldehyde. In contrast to an untargeted nitrofuran warhead, delivery of this electrophilic nitrofuran to the ER by the rhodol resulted in cytotoxicity comparable to the ER-targeted cytotoxin eeyarestatin I, and specifically inhibited protein processing by the ubiquitin-proteasome system. Fluorinated hydrophobic rhodols are outstanding fluorophores that enable the delivery of small molecules for targeting ER-associated proteins and pathways.

-

-

Process for the production of β-(5-nitro-2-furyl)-acrolein

An improved process for the production of β-(5-nitro-2-furyl)-acrolein by reacting 5-nitro-furfural and acetaldehyde in the presence of a secondary amine, the improvement comprises effecting the reaction in an aliphatic carboxylic acid of 2 to 4 carbon atoms.