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Heterocyclic building blocks

Furylfuramide

Also known as Furylamide, Tofuron, 2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide

CAS 3688-53-7Formula C11H8N2O5Molar mass 248.19 g/mol
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Furylfuramide chemical structure, C11H8N2O5, CAS 3688-53-7
2D chemical structure

Key facts

What buyers check first

All properties
Appearance
Reddish-orange needles
Melting point
151 to 152 °C
Solubility
Slightly soluble in water, soluble in dimethyl formamide, ethanol and methanol
HS code
293219
Category
Heterocyclic building blocks
Illustrative photo, a shrink wrapped pallet of kraft paper sacks in a chemical plant
Typical packagingIllustrative packaging image, not the actual product

What is Furylfuramide?

Plain description, key identifiers and synonyms

(Z)-2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide is a member of the class of acrylamides that is acrylamide which is substituted at positions 2 and 3 by 2-furyl and 5-nitro-2-furyl groups, respectively (the trans isomer). Formerly used as a food preservative, it was withdrawn from the market following suspicions of carcenogenicity. It is a primary carboxamide, a member of acrylamides, a C-nitro compound and a nitrofuran antibiotic.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(Z)-2-(furan-2-yl)-3-(5-nitrofuran-2-yl)prop-2-enamide
CAS number
3688-53-7 CAS number cross-checked
Molecular formula
C11H8N2O5
UNII
054NR2135Y
MDL number
MFCD00869231
InChIKey
LYAHJFZLDZDIOH-VURMDHGXSA-N
InChI
InChI=1S/C11H8N2O5/c12-11(14)8(9-2-1-5-17-9)6-7-3-4-10(18-7)13(15)16/h1-6H,(H2,12,14)/b8-6-
Canonical SMILES
NC(=O)C(=Cc1ccc([N+](=O)[O-])o1)c1ccco1
Isomeric SMILES
C1=COC(=C1)/C(=C/C2=CC=C(O2)[N+](=O)[O-])/C(=O)N

Synonyms

  • Furylamide
  • Tofuron
  • 2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide
  • AF 2 (Preservative)
  • Acrylamide, 2-(2-furyl)-3-(5-nitro-2-furyl)-
  • 2-(2-Furyl)-3-(5-nitro-2-furyl)acrylic acid amide
  • 2-(Furyl)-3-(5-nitro-2-furyl)acrylamide
  • 2-Furanacrylamide, alpha-2-furyl-5-nitro-
  • 2-Furanacetamide, alpha-((5-nitro-2-furanyl)methylene)-
  • AF 2
  • (Z)-2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide
  • (Z)-2-(furan-2-yl)-3-(5-nitrofuran-2-yl)prop-2-enamide
  • (2Z)-2-(furan-2-yl)-3-(5-nitrofuran-2-yl)prop-2-enamide
  • (2Z)-2-(2-furyl)-3-(5-nitro-2-furyl)prop-2-enamide
  • (Z)-2-(2-Furyl)-3-(5-nitro-2-furyl)prop-2-enamide
  • cis-Furylfuramide
  • alpha-2-Furyl-5-nitro-2-furanacrylamide
  • cis-AF 2
  • 2-(2-Furyl)-3-(5-nitrofuryl)acrylamide
  • alpha-(Furyl)-beta-(5-nitro-2-furyl)acrylic amide
  • alpha-((5-Nitro-2-furanyl)methylene)-2-furanacetamide
  • (Z)-alpha-2-Furyl-5-nitro-2-furanacrylamide
  • cis-3-(5-Nitro-2-furyl)-2-(2-furyl)acrylamide
  • 2-FURANACRYLAMIDE, alpha-2-FURYL-5-NITRO-, (Z)-
  • AF-2 (TN)
Show all 27 synonyms
  • 2-Furanacetamide, alpha-[(5-nitro-2-furanyl)methylene]-
  • 2-Furanacetamide, alpha-((5-nitro-2-furanyl)methylene)-, (Z)-

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

Appearance
Reddish-orange needlesexp.
Melting point
151 to 152 °Cexp.
Solubility
Slightly soluble in water, soluble in dimethyl formamide, ethanol and methanolexp.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
248.19 g/molcalc.
Exact mass
248.0433 Dacalc.
LogP (octanol/water)
1.81calc.
Topological polar surface area
112.5 Ųcalc.
Hydrogen bond donors
1calc.
Hydrogen bond acceptors
5calc.
Rotatable bonds
4calc.
Heavy atoms
18calc.
Rings
2calc.
Aromatic rings
2calc.
Fraction sp3 carbons
0calc.
Formal charge
0calc.
Stereocentres
0calc.
Lipinski rule of five
Passes (0 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, C(=Cc1ccco1)c1ccco1

C(=Cc1ccco1)c1ccco1

2 rings, 12 atoms.

24 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

No GHS hazard classification is recorded for this substance yet. That does not mean it is harmless.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Furylfuramide suppliers

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Furylfuramide price

Indicative price range per kg from live supplier offers

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Uses and applications

What the substance is used for, by industry and function

AF-2 is a synthetic nitrofuran derivative ... for use as a food preservative in Japan in 1965, it was withdrawn from the market in 1974 ... used at levels up to 50 mg/kg to protect foods of animal and vegetable origin against attack by a large variety of microorganisms, particularly bacteria.

Was used as food additive mainly in japan until...found to be highly mutagenic & carcinogenic.

Pharmacological actions

  • Mutagens

How it is made

AF-2 was first synthesized in 1958. It can be made by the reaction of 5-nitrofurfural with the potassium salt of 2-furfuryl acetic acid in acetic anhydride and treatment of the resulting cmpd with sulfur dichloride to form an acid chloride, which is then heated with ammonia...

Prepared by the condensation of 5-nitro-2-furancarboxaldehyde with 2-furanacetic acid followed by chlorination and amination.

Regulatory status

Inventories, regulations and trade controls that list this substance

No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Furylfuramide is traded under.

HS 2932.19Indicative HS code

Compounds containing an unfused furan ring (whether or not hydrogenated) in the…

World exports in 2024
$2.62B
−6.4% vs 2023, imports $2.56B
2019 to 2024
Top exporters
  1. Germany57.9%
  2. Italy11.5%
  3. China10.4%
Top importers
  1. Greece40.4%
  2. Japan16.3%
  3. Germany12.8%
Reported customs values in USD, not prices.Full trade data

The HS code shown for Furylfuramide is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Furylfuramide, based on the data on this page

What is Furylfuramide?

(Z)-2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide is a member of the class of acrylamides that is acrylamide which is substituted at positions 2 and 3 by 2-furyl and 5-nitro-2-furyl groups, respectively (the trans isomer).

What is the CAS number of Furylfuramide?

The CAS registry number of Furylfuramide is 3688-53-7.

What is the molecular formula and weight of Furylfuramide?

The molecular formula of Furylfuramide is C11H8N2O5 and its molar mass is 248.19 g/mol.

What is Furylfuramide used for?

AF-2 is a synthetic nitrofuran derivative ... for use as a food preservative in Japan in 1965, it was withdrawn from the market in 1974 ... used at levels up to 50 mg/kg to protect foods of animal and vegetable origin against attack by a large variety of microorganisms, particularly bacteria.

Is Furylfuramide hazardous?

No GHS hazard classification for Furylfuramide is recorded on CompoundList yet. That does not prove it is safe. Always read the supplier safety data sheet.

What is the HS code of Furylfuramide?

Furylfuramide is usually classified under HS code 293219 (Compounds containing an unfused furan ring (whether or not hydrogenated) in the…). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Furylfuramide?

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What is the price of Furylfuramide?

Suppliers quote Furylfuramide on request because prices depend on grade, purity, quantity and destination. A free request on CompoundList gets you several quotes to compare.

Guides for buyers

Practical guides that help when you source, ship or handle Furylfuramide

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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