2-Acetylbutyrolactone

HCID 10601CAS 517-23-7

Basic information

Standard SMILES
CC(=O)C1CCOC1=O
InChIKey
OMQHDIHZSDEIFH-UHFFFAOYSA-N
Molecular formula
C6H8O3
Average molar mass
128.13 g/mol
Monoisotopic mass
128.04734412

Overview

3-Acetyldihydro-2(3H)-furanone is a gamma-lactone.

Names & identifiers

Preferred name
2-Acetylbutyrolactone
IUPAC
3-acetyloxolan-2-one
English name
2-Acetylbutyrolactone
Molecular formula
C6H8O3
Molecular weight
128.13

Names & synonyms

2-Acetylbutyrolactone517-23-7ALPHA-ACETYLBUTYROLACTONE2(3H)-Furanone, 3-acetyldihydro-2-Oxo-3-acetyltetrahydrofuranDihydro-3-acetyl-2(3H)-furanonealpha-AcetobutyrolactoneI3D73T5K0QNSC-2019RefChem:5553584,5-dihydro-3-acetylfuran-2(3H)-one208-235-2
Show more names
ABLα-Acetyl-γ-butyrolactoneACETYLBUTYROLACTONEα-Acetylbutyrolactonea-Acetyl-y-Butyrolactone
3-acetyldihydrofuran-2(3H)-one3-acetyloxolan-2-one3-Acetyldihydro-2(3H)-furanonealpha-Acetyl-gamma-butyrolactone2-Acetylbutanolide2-Acetyl-gamma-butyrolactone3-acetyltetrahydrofuran-2-one3-Acetyltetrahydro-2-furanone

Database identifiers

CAS
517-23-7
PubChem CID
10601
DTXSID
DTXSID6044436
ChEMBL
CHEMBL3187921
ChEBI
CHEBI:179633
UNII
I3D73T5K0Q
EC Number
208-235-2
Nikkaji
J6.575G

Properties

Computed structural properties

XLogP
0.1
Topological polar surface area
43.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
9

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Lactones
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704]
Physical Description · 2 items

Liquid

Liquid with an ester-like odor; [Merck Index] Clear colorless to pale yellow liquid; [Acros Organics MSDS]

Physicochemical properties

Melting point
25 °C · <25 °C
Boiling point
107 · 107-108 °C5 mm Hg(lit.)
Density
1.19 g/mL · 1.19 g/mL at 25 °C(lit.)
vapor pressure
0.131 Pa · 0.131Pa at 20℃
refractive index
20 · n20/D 1.459(lit.)
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 0.5% (1 of 202) of reports.

Warning

H315 (97.5%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 202 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 2(3H)-Furanone, 3-acetyldihydro-

2(3H)-Furanone, 3-acetyldihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2(3H)-Furanone, 3-acetyldihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 26-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/25715

2-Acetyl-gamma-butyrolactone: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin and mucous membrane irritant; [Merck Index] A skin and strong eye irritant; [ECHA REACH Registrations] An irritant; [Acros Organics MSDS] See beta-Butyrolactone and Butyrolactone.
Hazard Classes and CategoriesSkin Irrit. 2 (97.5%)

Safety data

PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
LU3456000
hs_code
29322980
risk_code
36/37/38-61

Chemistry & industry

Uses & manufacturing

UsesUsed to make 3,4-disubstituted pyridines and 5-(beta-hydroxethyl)-4-methylthiazole; [Merck Index] Used as an intermediate; [ECHA REACH Registrations]
U.S. Production2023: 5,000,000 - <10,000,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 items

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

2(3H)-Furanone, 3-acetyldihydro-: ACTIVE

Applications · 3 items

DescriptionIt is an important intermediate involved in the synthesis of chemical and pharmaceutical products such as vitamin B, 3,4-substituted pyridine, 5-(2-Hydroxyethyl)-4-methylthiazole. In presence of 2-acetylbutyrolactone, reaction of tert-butyl isocyanide with dialkyl acetylenedicarboxylates leads to the formation of dialkyl (E)-2-{(tert-butylamino)[2-oxo-4,5-dihydro-3(2H)-furanylidene]methyl}-2-butenedioates.1 Moreover, reaction of 2-acetylbutyrolactone with thiosemicarbazide and 3-(2-bromo-acetyl)-chromen-2-one in anhydrous ethanol produced 3-{2-[5-hydroxyl-4-(2-hydroxyl-ethyl)-3-methyl-pyrazol-1-yl]-thiazol-4-yl}-chromen-2-one in good yields.2 In addition, 2-acetylbutyrolactone can also function as the raw material for synthesizing pilocarpine that is a leading therapeutic agent for the treatment of narrow and wide angle glaucoma.3 Besides, this chemical can also act as a fluorogenic reagent in the quantitative spectrofluorometric determination of primary amines, which has been demonstrated to be equally accurate and precise as the officially or other reported methods.4

UsesAn intermediate in the synthesis of 2,4-disubstituted pyridines. A fluorogenic reagent for the spectrofluorimetric determination of primary amines.

UsesIn synthesis of 3,4-disubstituted pyridines; of 5-(b-hydroxethyl)-4-methylthiazole.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]

Additional notes

DefinitionChEBI: 3-Acetyldihydro-2(3H)-furanone is a gamma-lactone.

Related reactions

100 records

Linked notes

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