3-Hydroxycarbofuran
Basic information
- CAS
16655-82-6- Standard SMILES
CNC(=O)Oc1cccc2c1OC(C)(C)C2O- InChIKey
RHSUJRQZTQNSLL-UHFFFAOYSA-N- Molecular formula
- C12H15NO4
- Average molar mass
- 237.25 g/mol
- Monoisotopic mass
- 237.10010796
Overview
3-Hydroxy-carbofuran is a member of 1-benzofurans.
Names & identifiers
- Preferred name
- 3-Hydroxycarbofuran
- IUPAC
- (3-hydroxy-2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate
- English name
- Carbofuran-3-hydroxy
- Molecular formula
- C12H15NO4
- Molecular weight
- 237.25
Names & synonyms
3-HYDROXYCARBOFURAN16655-82-63-Hydroxy-carbofuran3,7-Benzofurandiol, 2,3-dihydro-2,2-dimethyl-, 7-(methylcarbamate)7J7N7A61BJDTXSID20375063-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl N-methylcarbamateRefChem:502538DTXCID00175061-((3-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy)-N-methylmethanimidic acid3-Hydroxy CarbofuranCarbofuran-3-hydroxy
Show more names
MethylcarbaMic acidHydroxycarbofuran3-Hydroxycarbofuranecarbofuran-3-hydroxy solutionC11011000 Carbofuran-3-hydroxyCarbofuran-3-hydroxy in AcetoneCarbofuran-3-hydroxy in Methanol
(3-hydroxy-2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate3-Hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl methylcarbamateCarbofuran 3-ohBRN 1383873Carbofuran, 3-hydroxyCarbamic acid, methyl-, 2,3-dihydro-2,2-dimethyl-3-hydroxy-7-benzofuranyl ester3,7-Benzofurandiol, 2,3-dihydro-2,2-dimethyl-, 7-(N-methylcarbamate)3-Hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamate
Database identifiers
- CAS
16655-82-6- PubChem CID
- 27975
- DTXSID
DTXSID2037506- ChEMBL
CHEMBL1867082- ChEBI
CHEBI:174216- UNII
- 7J7N7A61BJ
- EC Number
- 625-078-9
- Nikkaji
- J124.956H
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 67.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 305
Experimental & physicochemical properties
Pesticides
Environmental transformation -> Pesticide transformation products (metabolite, successor)
Pesticide (3-Hydroxycarbofuran) -> USDA PDB
Pesticide degradation product
Melting Point138 - 140 °C
Physical DescriptionSolid
Collision Cross Section149.06 Ų [M+H]+
Physicochemical properties
- Melting point
- 140 · 140-148 °C
- Boiling point
- 344.7 · 344.7±42.0 °C(Predicted)
- Density
- 1.239 · 1.239±0.06 g/cm3 (20 ºC 760 Torr)
- Flash point
- -4 °C · -4 °C
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform: Soluble; Methanol: Soluble
- pka
- 12.28 · 12.28±0.46(Predicted)
- BRN
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Toxicology
Treatment
If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Health Effects
Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).
Chemistry & industry
Pharmacology
Metabolism/Metabolites
E-hydroxy-carbofuran is a known human metabolite of Carbofuran.
The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)
Cellular LocationsCytoplasm
Uses & manufacturing
Uses3-Hydroxy-carbofuran is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
Use Classification
Environmental transformation -> Pesticide transformation products (metabolite, successor)
Transformation products
Applications
Uses3-Hydroxy Carbofuran is a metabolite of Carbofuran (C176590).
General DescriptionCarbofuran-3-hydroxy is one of the metabolites of the insecticide, carbofuran.
Upstream & downstream products
Upstream raw materials
Additional notes
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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