alpha-Methylbutyrolactone
Basic information
- CAS
1679-47-6- Standard SMILES
CC1CCOC1=O- InChIKey
QGLBZNZGBLRJGS-UHFFFAOYSA-N- Molecular formula
- C5H8O2
- Average molar mass
- 100.12 g/mol
- Monoisotopic mass
- 100.0524295
Overview
Dihydro-3-methyl-2(3H)-furanone is a gamma-lactone.
Names & identifiers
- Preferred name
- alpha-Methylbutyrolactone
- IUPAC
- 3-methyloxolan-2-one
- English name
- alpha-Methyl-gamma-butyrolactone
- Molecular formula
- C5H8O2
- Molecular weight
- 100.12
Names & synonyms
3-methyldihydrofuran-2(3H)-onealpha-Methyl-gamma-butyrolactone3-methyloxolan-2-oneDihydro-3-methyl-2(3H)-furanone2-Methylbutanolide.alpha.-Methylbutyrolactone4-Hydroxy-2-methylbutyric acid lactonealpha-Methylbutyrolactone2(3H)-Furanone, dihydro-3-methyl-2-methylbutyrolactone3-methyltetrahydrofuran-2-one.alpha.-Methyl-.gamma.-butyrolactone
Show more names
2-Methyl-4-butanolideα-Methyl-γ-butyrolactone2(3H)-Furanone,dihydro-3-methyl-4,5-DIHYDRO-3-METHYL-2(3H)-FURANONE
2-Methyl-.gamma.-butyrolactone4-Hydroxy-2-methylbutanoic acid lactone140H0G0P5W3-methyldihydrofuran-2-one2-Methyl-gamma-butyrolactoneEINECS 216-846-0NSC 102837NSC-102837
Database identifiers
- CAS
1679-47-6- PubChem CID
- 98323
- DTXSID
DTXSID401030919- ChEMBL
CHEMBL36365- ChEBI
CHEBI:173343- UNII
- 140H0G0P5W
- EC Number
- 216-846-0
- Nikkaji
- J141.781I
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 88.1
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Lactones
Physical DescriptionClear light yellow liquid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Boiling point
- 78 · 78-81 °C/10 mmHg (lit.)
- Density
- 1 · 1,06 g/cm3
- refractive index
- 20 · n20/D 1.432(lit.)
- Flash point
- 163 °F · 163 °F
- storage temp.
- 2 · 2-8°C
- solubility
- THF: soluble
- form
- clear liquid
- color
- Colorless to Almost colorless
- BRN
- 80418 · 80418
- InChI
- 1S/C5H8O2/c1-4-2-3-7-5(4)6/h4H,2-3H2,1H3
- InChIKey
- QGLBZNZGBLRJGS-UHFFFAOYSA-N
- SMILES
- CC1CCOC1=O
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
Warning
H227 (100%): Combustible liquid [Warning Flammable liquids]
P210, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory Information2(3H)-Furanone, dihydro-3-methyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS] See Butyrolactone.
Hazard Classes and CategoriesFlam. Liq. 4 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- hs_code
- 2932209090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 23-24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H227
- Precautionary statements
- P210-P280-P370+P378-P403+P235-P501
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
Usesα-Methyl-γ-butyrolactone was used as model compound in Bracketing experiments to investigate the thermodynamically favored site of reaction of pilocarpine.
UsesALPHA-METHYL-GAMMA-BUTYROLACTONE was used as model compound in Bracketing experiments to investigate the thermodynamically favored site of reaction of pilocarpine.
General Descriptionα-Methyl-γ-butyrolactone undergoes benzylation to give racemic α-benzyl-α-methyl-γ-butyrolactone.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: Dihydro-3-methyl-2(3H)-furanone is a gamma-lactone.
Related reactions
21 records
Compound notes
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