Basic information
- CAS
288-14-2- Standard SMILES
c1cnoc1- InChIKey
CTAPFRYPJLPFDF-UHFFFAOYSA-N- Molecular formula
- C3H3NO
- Average molar mass
- 69.06 g/mol
- Monoisotopic mass
- 69.02146372
Names & identifiers
- Preferred name
- Isoxazole
- IUPAC
- 1,2-oxazole
- English name
- Isoxazole
- Molecular formula
- C3H3NO
- Molecular weight
- 69.06
Names & synonyms
ISOXAZOLE288-14-21,2-oxazole1-Oxa-2-azacyclopentadieneIsoxazoles00SRW0M6PWNSC-137774DTXSID7059775CHEBI:35595RefChem:150159DTXCID9037874CHEBI:55373
Show more names
IsoxazolIsoxazolecIsoxazole>Isoxazole 99%Isoxazole,99%ISOXAZOLE 98+%Isoxazole, 95%
206-018-7IsooxazoleMFCD00003149UNII-00SRW0M6PW2-azafuranEINECS 206-018-7Isoxazole, 99%NSC 137774
Database identifiers
- CAS
288-14-2- PubChem CID
- 9254
- DTXSID
DTXSID7059775- ChEMBL
CHEMBL13257- ChEBI
CHEBI:35595- UNII
- 00SRW0M6PW
- EC Number
- 206-018-7
- Nikkaji
- J2.565H
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 26 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 5
- Formal charge
- 0
- Complexity
- 30
Experimental & physicochemical properties
Vapor Pressure45.5 [mmHg]
Physical DescriptionClear light brown liquid; [Sigma-Aldrich MSDS]
Kovats Retention Index590；590
Physicochemical properties
- Melting point
- -67.1 °C · -67.1°C
- Boiling point
- 93 · 93-95 °C(lit.)
- Density
- 1.078 g/mL · 1.078 g/mL at 25 °C(lit.)
- vapor density
- 2.4 · 2.4 (vs air)
- refractive index
- 20 · n20/D 1.427(lit.)
- Flash point
- 48 °F · 48 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 167 g/l · 167g/l
- pka
- -2 · -2.0(at 25℃)
- form
- clear liquid
- color
- Colorless to Light yellow
- BRN
- 103773 · 103773
- Henry's Law Constant
- 4 · 4.0×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- InChI
- 1S/C3H3NO/c1-2-4-5-3-1/h1-3H
- InChIKey
- CTAPFRYPJLPFDF-UHFFFAOYSA-N
- SMILES
- c1cnoc1
- CAS DataBase Reference
- 288 · 288-14-2(CAS DataBase Reference)
- FDA UNII
- 0 SRW0M6PW · 00SRW0M6PW
- NIST Chemistry Reference
- Isoxazole(288-14-2)
- EPA Substance Registry System
- Isoxazole (288-14-2)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Danger
- Hazard statements
- 225 · H225
- Precautionary statements
- 210 · P210
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11
- Safety Statements
- 16 · 16-23/33-33-29-7/9
- RIDADR
- 1993 · UN 1993 3/PG 2
- WGK Germany
- 3 · 3
- F
- 10 · 10
- Hazard Note
- Highly Flammable
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29349990 · 29349990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 · Flam. Liq. 2
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]；H314 (69.5%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H318 (68.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 151 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory InformationIsoxazole: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummarySee 3-Amino-5-methylisoxazole.
Hazard Classes and CategoriesFlam. Liq. 2 (100%)；Skin Corr. 1B (69.5%)；Eye Dam. 1 (68.9%)
Regulatory information
Regulatory InformationIsoxazole: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- F
- 10
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 1993 3/PG 2
- hs_code
- 29349990
- risk_code
- 11
- Signal word
- Danger
- Symbol(GHS)
- GHS02
- hazard_code
- F,Xi
- hazard_note
- Highly Flammable
- safety_code
- 16-23/33-33-29-7/9
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H225
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Flam. Liq. 2
- Precautionary statements
- P210
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationIsoxazole: ACTIVE
Applications
DescriptionIsoxazole, an important class of heterocycles, is a five membered heterocyclic compound that exhibits various pharmacological actions. It is present in some natural products such as ibotenic acid and is also used as a foundation for several drugs such as the COX-2 inhibitor valdecoxib and anti-inflammatory drugs. Isoxazoles are largely applied in the area of pharmaceuticals and therapeutics, including insecticidal, antibacterial, antibiotic, antitumour, antifungal, antituberculosis, anticancer and ulcerogenic. Besides, it has a great effect on reducing blood glucose, eliminating pain, resisting inflammation, killing harmful bacteria, controlling and reducing the risk of HIV.
UsesNatural insecticide.
General DescriptionIsoxazole(288-14-2) are described as inhibitors of acetylcholinesterase (AChE). Isoxazole ligands bind to and inhibit the Sxc- antiporter.
Preparation methods
PreparationIsoxazoles can be synthesized by various methods, such as the 1,3-dipolar cycloaddition reaction of nitrile oxides with alkynes, the reaction of hydroxylamine with 1,3-diketones or propiolic acid derivatives, etc.www.organic-chemistry.org
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: Isoxazole is a monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles. It is a mancude organic heteromonocyclic parent, a monocyclic heteroarene and a member of isoxazoles.
Related reactions
12 records
Compound notes
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