Basic information
- Standard SMILES
O=Cc1ccc([N+](=O)[O-])o1- InChIKey
SXINBFXPADXIEY-UHFFFAOYSA-N- Molecular formula
- C5H3NO4
- Average molar mass
- 141.08 g/mol
- Monoisotopic mass
- 141.00620758
Overview
5-Nitrofurfural is a member of furans and a C-nitro compound.
Names & identifiers
- Preferred name
- 5-Nitrofurfural
- IUPAC
- 5-nitrofuran-2-carbaldehyde
- English name
- 5-Nitrofurfural
- Molecular formula
- C5H3NO4
- Molecular weight
- 141.08
Names & synonyms
5-NITRO-2-FURALDEHYDE5-Nitrofurfural698-63-55-NitrofurfuraldehydeNitrofurfural5-Nitro-2-furfural2-Furancarboxaldehyde, 5-nitro-5-Nitro-2-furancarboxaldehyde2-Furaldehyde, 5-nitro-Furfural, 5-nitro-5-NitrofuraldehydeXXX18AU0Z3
Show more names
AKOS B0042445-Nitrofurural5-nitro-furfuraNiftyer Impurity 7Nitrofuraldehyde,97%
NSC-5574NSC-111144DTXSID30220097RefChem:103254DTXCID30142588211-816-35-nitrofuran-2-carbaldehydeC5H3NO4
Database identifiers
- CAS
698-63-5- PubChem CID
- 12774
- DTXSID
DTXSID30220097- ChEMBL
CHEMBL351937- ChEBI
CHEBI:34459- UNII
- XXX18AU0Z3
- EC Number
- 211-816-3
- Nikkaji
- J60.118G
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 76 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 152
Experimental & physicochemical properties
SpringerMaterials PropertiesBoiling point
LogP1.01
Color/FormPALE YELLOW IN PETROLEUM ETHER
SolubilitySLIGHTLY SOL IN WATER, SOL IN PETROLEUM ETHER
Boiling Point128-132 °C @ 10 MM HG
Melting Point35-36 °C
Physicochemical properties
- Melting point
- 37 · 37-39 °C(lit.)
- Boiling point
- 121 °C10 · 121 °C10 mm Hg(lit.)
- Density
- 1.349 g/mL · 1.349 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.59(lit.)
- Flash point
- 92 °F · 92 °F
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
- form
- Crystalline Low Melting Solid
- color
- Yellow to brown
- Water Solubility
- sparingly soluble
- Sensitive
- Air & Light Sensitive
- BRN
- 120539 · 120539
- InChI
- 1S/C5H3NO4/c7-3-4-1-2-5(10-4)6(8)9/h1-3H
- InChIKey
- SXINBFXPADXIEY-UHFFFAOYSA-N
- SMILES
- [H]C(=O)c1ccc(o1)[N+]([O-])=O
- CAS DataBase Reference
- 698 · 698-63-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 18 AU0Z3 · XXX18AU0Z3
- NIST Chemistry Reference
- 2 · 2-Furancarboxaldehyde, 5-nitro-(698-63-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Danger
- Hazard statements
- 228 · H228
- Precautionary statements
- 210 · P210
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- F,Xi,Xn
- Risk Statements
- 11 · 11-68-10
- Safety Statements
- 16 · 16-36/37
- RIDADR
- 1325 · UN 1325 4.1/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 7200000 · LT7200000
- Hazard Note
- Irritant
- HazardClass
- 3.2 · 3.2
- PackingGroup
- III
- HS Code
- 29321900 · 29321900
- Storage Class
- 4.1 B · 4.1B - Flammable solid hazardous materials
- Hazard Classifications
- 1 · Flam. Sol. 1
- Hazardous Substances Data
- 698 · 698-63-5(Hazardous Substances Data)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H228 (90%): Flammable solid [Danger Flammable solids]
P203, P210, P240, P241, P280, P318, P370+P378, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 12-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24617
5-Nitrofurfural: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesFlam. Sol. 2 (90%)
Toxicology
Non-Human Toxicity Excerpts
MUTAGENICITY: MUTATION RESEARCH 76: 169 (1980). ESCHERICHIA COLI WP2 - REVERSE MUTATION STUDIES: NEGATIVE.
A BREAKDOWN PRODUCT, 5-NITRO-2-FURALDEHYDE, LIBERATED FROM FURADANTIN & FUROXONE, INDUCED MASS MUTATIONS IN BOTH DIVIDING & NONDIVIDING CELLS OF EUGLENA GRACILIS.
5-NITRO-2-FURALDEHYDE WAS MUTAGENIC FOR MYCOBACTERIUM PHLEI, THE EFFECT BEING MEASURED BY INDUCTION OF REVERSIONS IN AUXOTROPHIC STRAINS, OF MUTANTS RESISTANT TO ISONIAZID, & OF PHENOTYPIC CHANGES.
5 -NITRO-2-FURALDEHYDE SELECTIVELY INFLUENCED THE MITOTIC ACTIVITY OF ONION & BROAD BEAN CELLS. IT WAS ALSO MUTAGENIC IN PLANT CELLS, RESULTING IN MITOTIC & CHROMOSOMAL ABERRATIONS.
A BREAKDOWN PRODUCT, 5-NITRO-2-FURALDEHYDE, LIBERATED FROM FURADANTIN & FUROXONE, INDUCED REVERSE MUTATIONS IN AUXOTROPHIC MYCOBACTERIUM PHLEI.
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- LT7200000
- ridadr
- UN 1325 4.1/PG 2
- hs_code
- 29321900
- risk_code
- 11-68-10
- Signal word
- Danger
- Symbol(GHS)
- GHS02
- hazard_code
- F,Xi,Xn
- hazard_note
- Irritant
- safety_code
- 16-36/37
- hazard_class
- 3.2
- Storage Class
- 4.1B - Flammable solid hazardous materials
- packing_group
- III
- Hazard statements
- H228
- REACH Registrations
- Active
- Hazard Classifications
- Flam. Sol. 1
- Precautionary statements
- P210
- Hazardous Substances Data
- 698-63-5(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
UsesCHEM INT FOR NITROFURAN ANTIBACTERIAL DRUG PRODUCTS
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1977) No Data
(1979) No Data
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN US
(1979) NOT PRODUCED COMMERCIALLY IN US
Methods of ManufacturingNITRATION OF FURFURAL FOLLOWED BY CONVERSION OF THE INTERMEDIATE 2-ACETOXY-2,5-DIHYDROFURAN WITH PYRIDINE
Applications
DescriptionNitrofuran carboxaldehyde (NFC) is used to synthesize many drugs and chemicals such as nifuraldezone, puraguanidine, nifuratrone, furmethoxadone, etc. Furfural the main structure of NFC was determined many years ago to be a byproduct of formic acid synthesis. Furfural is produced from agricultural byproducts such as sugarcane bagasse and corncobs.
UsesNFC and its derivatives have antibacterial and antifungal activities. They destroy both gram-positive and gram-negative organisms such as Staphylococcus aureus, Salmonella schotmuelleri, Pseudomonas aeruginosa, Proteus vulgaris, Escherichia coli, and Streptococcus pyogenes. They may be used as antibacterial agents in a prophylactic manner, for example, in cleaning and disinfecting products. This compound also has antitrichomonal and antifungal activities.
Uses5-Nitro-2-furaldehyde was used in the synthesis of a series of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives. . It was also used in the synthesis of modified mesoporous silica (MCM-41). 5-Nitrofurfural can be commonly used as pharmaceutical intermediates.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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Additional notes
DefinitionChEBI: 5-Nitrofurfural is a C-nitro compound and a member of furans.
Related reactions
96 records
Linked notes
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