Glutaric anhydride

HCID 7940CAS 108-55-4
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C1CCCC(=O)O1
InChIKey
VANNPISTIUFMLH-UHFFFAOYSA-N
Molecular formula
C5H6O3
Average molar mass
114.1 g/mol
Monoisotopic mass
114.03169405

Overview

Glutaric anhydride is a cyclic dicarboxylic anhydride that is oxane which carries oxo groups at positions 2 and 6. It is used as an intermediate in the production of pharmaceuticals, corrosion inhibitors, and polymers (E.g. epoxy polyesters). It is a cyclic dicarboxylic anhydride and a member of oxanes. It is functionally related to a glutaric acid.

Names & identifiers

Preferred name
Glutaric anhydride
IUPAC
oxane-2,6-dione
English name
Glutaric anhydride
Molecular formula
C5H6O3
Molecular weight
114.1

Names & synonyms

GLUTARIC ANHYDRIDE108-55-4Dihydro-2H-pyran-2,6(3H)-dioneoxane-2,6-dionePentanedioic anhydrideGlutaric acid anhydridePyroglutaric acid2H-Pyran-2,6(3H)-dione, dihydro-Pentanedioic acid anhydrideAnhydrid kyseliny glutaroveDTXSID504436263OFI15S80
Show more names
GANGlutamic AnhydrideTETRAHYDROPYRAN-2,6-DIONEutaric anhydrideGlutaric anhydridpyroglutaricacidGlutarsureanhydrid
NSC-166402H-Pyran-2,6(3H)-dione, dihydroDTXCID3024362CHEBI:167482RefChem:143700203-593-6MFCD00006679dihydro-3H-pyran-2,6-dione

Database identifiers

CAS
108-55-4
PubChem CID
7940
DTXSID
DTXSID5044362
ChEMBL
CHEMBL3188341
ChEBI
CHEBI:167482
UNII
63OFI15S80
EC Number
203-593-6
Nikkaji
J49.215I

Properties

Computed structural properties

XLogP
-0.1
Topological polar surface area
43.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

PolymersPlastics & Rubber -> Acid Anhydrides, Cyclic
SpringerMaterials PropertiesBoiling point
Physical Description · 2 items

CBI; Dry Powder

Off-white flakes or crystals; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
50 · 50-55 °C (lit.)
Boiling point
150 °C/10 · 150 °C/10 mmHg (lit.)
Density
1 · 1,411 g/cm3
bulk density
990 kg/m3 · 990kg/m3
vapor pressure
0.05 hPa · 0.05 hPa (50 °C)
refractive index
1.463 · 1.4630 (estimate)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 0.4% (1 of 270) of reports.

Danger

H302 (98.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 270 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 2H-Pyran-2,6(3H)-dione, dihydro-

2H-Pyran-2,6(3H)-dione, dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-Pyran-2,6(3H)-dione, dihydro- 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: 27-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11130

Glutaric anhydride: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

Causes somnolence, necrotic gastrointestinal changes, and diffuse hepatitis in oral lethal-dose studies of rats; [RTECS] An irritant that may cause serious eye injury; Toxic by ingestion and skin absorption; [Alfa Aesar MSDS] See Acid Anhydrides.

Hazard Classes and CategoriesAcute Tox. 4 (98.5%)

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Safety data

F
2-21
wgk
3
tsca
TSCA listed
rtecs
MA3850000
ridadr
3261
hs_code
29171990

Chemistry & industry

Uses & manufacturing

UsesUsed to make fine chemicals; [ExPub: ECHA REACH Registrations]
U.S. Production2023: 75,000 - <500,000 lb
Consumer UsesFragrance
Industry UsesNot Known or Reasonably Ascertainable
General Manufacturing Information · 2 items

Not Known or Reasonably Ascertainable

2H-Pyran-2,6(3H)-dione, dihydro-: ACTIVE

Applications · 1 item

UsesGlutaric anhydride is used in the production of glutaric acid family pharmaceuticals. Its derivatives are also used in certain corrosion inhibitors, some surfactants and metal finishing compounds. It is also used in the production of polymers, particularly modified unsaturated linear (epoxy) polyesters and as a raw material in the manufacture of flavors. It is also used in improvement of electrode/electrolyte interfaces in High-Voltage Spinel Lithium-Ion batteries as an electrolyte additive.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [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]
Additional notes · 1 item

DefinitionChEBI: Glutaric anhydride is a cyclic dicarboxylic anhydride that is oxane which carries oxo groups at positions 2 and 6. It is used as an intermediate in the production of pharmaceuticals, corrosion inhibitors, and polymers (E.g. epoxy polyesters). It is a cyclic dicarboxylic anhydride and a member of oxanes. It is functionally related to a glutaric acid.

Related reactions

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Linked notes

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