U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H6O3
Molecular Weight 102.0886
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Acetic anhydride

SMILES

CC(=O)OC(C)=O

InChI

InChIKey=WFDIJRYMOXRFFG-UHFFFAOYSA-N
InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3

HIDE SMILES / InChI

Molecular Formula C4H6O3
Molecular Weight 102.0886
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Acetic anhydride is an esterification agent for use in prepn. of modified food starch and for acetylation of monoglycerides. Acetic anhydride is a versatile reagent for acetylations, the introduction of acetyl groups to organic substrates. Acetic anhydride is the chemical compound with the formula (CH3CO)2O (commonly abbreviated Ac2O). Ac2O is mainly used for acetylations leading to commercially significant materials. Its largest application is for the conversion of cellulose to cellulose acetate, which is a component of photographic film and other coated materials. Similarly it is used in the production of aspirin, acetyl salicylic acid, which is prepared by the acetylation of salicylic acid. It is also used as a wood preservative via autoclave impregnation to make a longer lasting timber. Ac2O is also used in many industrial processes for the production of plastics, textiles, dyes, photochemical agents, perfumes, explosives and cigarette filters. Because of its use for the synthesis of heroin by the diacetylation of morphine, acetic anhydride (known as 'AA' in clandestine chemistry circles) is listed as a U.S. DEA List II Precursor, and restricted in many other countries.

Originator

Curator's Comment: Acetic anhydride was first synthesized in 1852 by the French chemist Charles Frédéric Gerhardt (1816-1856) by heating potassium acetate with benzoyl chloride.

Approval Year

PubMed

PubMed

TitleDatePubMed
Derivatisation in gas chromatographic determination of acidic herbicides in aqueous environmental samples.
2003-10
Myotoxicity induced by an acidic Asp-49 phospholipase A(2) isolated from Lachesis muta snake venom. Comparison with lysophosphatidylcholine.
2003-10
New cationized LDL-DNA complexes: their targeted delivery to fibroblasts in culture.
2003-08-29
Cis,cis,cis-1,2,4,5-cyclohexanetetracarboxylic acid and its dianhydride.
2003-08
Investigations on the influence of terminal groups at the C2-propyl side chain of 1,1-bis(4-hydroxyphenyl)-2-phenylpent-1-ene and 1,1,2-tris(4-hydroxyphenyl)pent-1-ene on the estrogen receptor binding and the estrogenic/anti-estrogenic properties.
2003-07
Urinary monitoring method of 3,3'-dichlorobenzidine (DCB) and its metabolites, N-acetyl-DCB and N,N'-diacetyl-DCB.
2003-07
Simultaneous quantification of lyso-neutral glycosphingolipids and neutral glycosphingolipids by N-acetylation with [3H]acetic anhydride.
2003-07
Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions.
2003-06-13
Oxidative cyclization of D-fructose thiosemicarbazones to 2-amino-5-(D-arabino-1,2,3,4-tetrahydroxybut-1-yl)-1,3,4-thiadiazoles through carbon-carbon bond cleavage of the sugar chain.
2003-06
Development of enzyme-linked immunosorbent assay for therapeutic drug monitoring of mexiletine.
2003-06
[Effect of the degree of acetylation of chitosan on its enzymatic hydrolysis with the preparation Celloviridin G20x].
2003-05-21
Acetylation of aromatic ethers using acetic anhydride over solid acid catalysts in a solvent-free system. Scope of the reaction for substituted ethers.
2003-05-07
Synergism of ultrasound and solid acids in intensification of Friedel-Crafts acylation of 2-methoxynaphthalene with acetic anhydride.
2003-05
Aspartic proteinase napsin is a useful marker for diagnosis of primary lung adenocarcinoma.
2003-04-22
Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile.
2003-04-09
Preparation of sulfoacetate derivatives of cellulose by direct esterification.
2003-04-04
Spectrophotometric and titrimetric determination of nizatidine in capsules.
2003-04-01
Preparation and characterization of chitosan microspheres containing doxifluridine.
2003-04
Synthesis of (Z)-(2,3-bis-hydroxymethyl)methylenecyclopropane analogues of purine nucleosides.
2003-03
On-column derivatization of the antibiotics teicoplanin and ristocetin coupled to affinity capillary electrophoresis.
2003-03
Effects of deletion of the prolactin receptor on ovarian gene expression.
2003-02-06
Palladium-catalyzed reaction of aryl iodides with acetic anhydride. A carbon monoxide-free synthesis of acetophenones.
2003-02-06
Anhydride prodrugs for nonsteroidal anti-inflammatory drugs.
2003-02
Synthesis and circular dichroism study of the human salivary proline-rich protein IB7.
2003-02
Stereoselective synthesis of 1,2:4,5-di-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-beta-D-psicopyranose and its X-ray crystallographic analysis.
2003-01-31
Efficient synthesis of 3H-imidazo[4,5-b]pyridines from malononitrile and 5-amino-4-(cyanoformimidoyl)imidazoles.
2003-01-24
Study of 1-deoxy-1-(indol-3-yl)-L-sorbose, 1-deoxy-1-(indol-3-yl)-L-tagatose, and their analogs.
2003-01-20
Determination of hypnotic benzodiazepines (alprazolam, estazolam, and midazolam) and their metabolites in rat hair and plasma by reversed-phase liquid-chromatography with electrospray ionization mass spectrometry.
2003-01-15
Characterization of an extracellular medium-chain-length poly(3-hydroxyalkanoate) depolymerase from Streptomyces sp. KJ-72.
2003
Lack of evidence for an association of Epstein-Barr virus infection with breast carcinoma.
2003
Determination of maleic anhydride in occupational atmospheres.
2002-12-27
[Benzo(f)furo(3,4-c)(2,7)naphthyridines from furo(3,4-b)pyridines].
2002-12
Formation of 2'-deoxy-2-nitroadenosines by reaction of 2'-deoxyadenosines with copper(II) nitrate/acetic anhydride.
2002-11-22
Dihapto coordination of carboxylic acid derivatives with an asymmetric rhenium pi-base: a new mechanism for amide isomerization?
2002-11-13
Acetylation of rice straw with or without catalysts and its characterization as a natural sorbent in oil spill cleanup.
2002-10-23
New dirhenium(III) compounds bridged by carboxylate ligands: N(C(4)H(9))(4)[Re(2)(OOCCF(3))Cl(6)] and Re(2)(OOCCCHCo(2)(CO)(6))(4)Cl(2).
2002-10-21
Determination of some histamine H1-receptor antagonists in dosage forms.
2002-10-15
4-Dimethylaminopyridine as a catalyst in heroin synthesis.
2002-10-09
A facile synthesis of natural products chaetomellic acid A and 1,7(Z)- nonadecadiene-2,3-dicarboxylic acid.
2002-10-04
[3-nitrobenzylidene-2,3(3H,5H)-furandione in the Hantzsch pyridine synthesis. 1. A new approach to furo(3,4-b)pyridines].
2002-10
Structural characterization of acetylpyridinium-ethyl pyruvate adducts by electrospray ionization mass spectrometry.
2002-10
Properties and application of a partially purified alkaline xylanase from an alkalophilic fungus Aspergillus nidulans KK-99.
2002-10
Levels of trace and major elements in illicit heroin.
2002-09
Functional expression of NF1 tumor suppressor protein: association with keratin intermediate filaments during the early development of human epidermis.
2002-08-29
Dorsal horn-enriched genes identified by DNA microarray, in situ hybridization and immunohistochemistry.
2002-08-20
Reaction of glycosyl isothiocynates with 3-indolylaminomethyl-ketone hydrochloride.
2002-08-17
Scandium(III) trifluoromethanesulfonate catalyzed aromatic nitration with inorganic nitrates and acetic anhydride.
2002-08
Quantitation of neuropeptides in Cpe(fat)/Cpe(fat) mice using differential isotopic tags and mass spectrometry.
2002-07-01
Catalytic asymmetric synthesis of O-acetyl cyanohydrins from KCN, Ac2O and aldehydes.
2002-02-07
The effects of acyl chain length on the micelle properties of poly(ethylene oxide)-block-poly(N-hexyl-L-aspartamide)-acyl conjugates.
2002
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:33:19 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:19 GMT 2025
Record UNII
2E48G1QI9Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACETIC ACID, 1,1'-ANHYDRIDE
Preferred Name English
Acetic anhydride
HSDB   II   MI  
Systematic Name English
ACETIC ACID, ANHYDRIDE
Common Name English
ACETIC ANHYDRIDE [MI]
Common Name English
ACETYL ACETATE
Systematic Name English
ACETIC ACID ANHYDRIDE
Systematic Name English
ACETIC ANHYDRIDE [II]
Common Name English
ACETIC ANHYDRIDE [HSDB]
Common Name English
ETHANOIC ANHYDRIDE
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 44007
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
DEA NO. 8519
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
CFR 21 CFR 172.892
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
Code System Code Type Description
WIKIPEDIA
ACETIC ANHYDRIDE
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID0024395
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
NCI_THESAURUS
C76285
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
PUBCHEM
7918
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
MESH
C031800
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
MERCK INDEX
m1325
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY Merck Index
HSDB
233
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-564-8
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
SMS_ID
300000015360
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
CHEBI
36610
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
FDA UNII
2E48G1QI9Q
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
CONCEPT Industrial Aid
RXCUI
1370450
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY RxNorm
CAS
108-24-7
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY