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Details

Stereochemistry ACHIRAL
Molecular Formula C4H6O3
Molecular Weight 102.0888
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETIC ANHYDRIDE

SMILES

CC(=O)OC(=O)C

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 102.0888
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
The effects of acyl chain length on the micelle properties of poly(ethylene oxide)-block-poly(N-hexyl-L-aspartamide)-acyl conjugates.
2002
Oxidized cellulose esters: I. Preparation and characterization of oxidized cellulose acetates--a new class of biodegradable polymers.
2002
Final report on the safety assessment of ethoxyethanol and ethoxyethanol acetate.
2002
Reaction of glycosyl isothiocynates with 3-indolylaminomethyl-ketone hydrochloride.
2002 Apr-May
Scandium(III) trifluoromethanesulfonate catalyzed aromatic nitration with inorganic nitrates and acetic anhydride.
2002 Aug
Dorsal horn-enriched genes identified by DNA microarray, in situ hybridization and immunohistochemistry.
2002 Aug 20
Functional expression of NF1 tumor suppressor protein: association with keratin intermediate filaments during the early development of human epidermis.
2002 Aug 29
Determination of maleic anhydride in occupational atmospheres.
2002 Dec 27
Catalytic asymmetric synthesis of O-acetyl cyanohydrins from KCN, Ac2O and aldehydes.
2002 Feb 7
Quantitation of neuropeptides in Cpe(fat)/Cpe(fat) mice using differential isotopic tags and mass spectrometry.
2002 Jul 1
Formation of 2'-deoxy-2-nitroadenosines by reaction of 2'-deoxyadenosines with copper(II) nitrate/acetic anhydride.
2002 Jun-Jul
Synthesis and antimicrobial activities of N-substituted imides.
2002 May
Pseudorabies virus DNA-binding protein stimulates the exonuclease activity and regulates the processivity of pseudorabies virus DNase.
2002 May 17
Dihapto coordination of carboxylic acid derivatives with an asymmetric rhenium pi-base: a new mechanism for amide isomerization?
2002 Nov 13
[3-nitrobenzylidene-2,3(3H,5H)-furandione in the Hantzsch pyridine synthesis. 1. A new approach to furo(3,4-b)pyridines].
2002 Oct
Structural characterization of acetylpyridinium-ethyl pyruvate adducts by electrospray ionization mass spectrometry.
2002 Oct
Properties and application of a partially purified alkaline xylanase from an alkalophilic fungus Aspergillus nidulans KK-99.
2002 Oct
Determination of some histamine H1-receptor antagonists in dosage forms.
2002 Oct 15
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 Oct 21
Acetylation of rice straw with or without catalysts and its characterization as a natural sorbent in oil spill cleanup.
2002 Oct 23
A facile synthesis of natural products chaetomellic acid A and 1,7(Z)- nonadecadiene-2,3-dicarboxylic acid.
2002 Oct 4
4-Dimethylaminopyridine as a catalyst in heroin synthesis.
2002 Oct 9
Levels of trace and major elements in illicit heroin.
2002 Sep
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
Preparation and characterization of chitosan microspheres containing doxifluridine.
2003 Apr
Spectrophotometric and titrimetric determination of nizatidine in capsules.
2003 Apr 1
Aspartic proteinase napsin is a useful marker for diagnosis of primary lung adenocarcinoma.
2003 Apr 22
Preparation of sulfoacetate derivatives of cellulose by direct esterification.
2003 Apr 4
Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile.
2003 Apr 9
Cis,cis,cis-1,2,4,5-cyclohexanetetracarboxylic acid and its dianhydride.
2003 Aug
Anhydride prodrugs for nonsteroidal anti-inflammatory drugs.
2003 Feb
Synthesis and circular dichroism study of the human salivary proline-rich protein IB7.
2003 Feb
Effects of deletion of the prolactin receptor on ovarian gene expression.
2003 Feb 6
Palladium-catalyzed reaction of aryl iodides with acetic anhydride. A carbon monoxide-free synthesis of acetophenones.
2003 Feb 6
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 Jan 15
Study of 1-deoxy-1-(indol-3-yl)-L-sorbose, 1-deoxy-1-(indol-3-yl)-L-tagatose, and their analogs.
2003 Jan 20
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 Jul
Urinary monitoring method of 3,3'-dichlorobenzidine (DCB) and its metabolites, N-acetyl-DCB and N,N'-diacetyl-DCB.
2003 Jul
Simultaneous quantification of lyso-neutral glycosphingolipids and neutral glycosphingolipids by N-acetylation with [3H]acetic anhydride.
2003 Jul
New cationized LDL-DNA complexes: their targeted delivery to fibroblasts in culture.
2003 Jul-Sep
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 Jun
Development of enzyme-linked immunosorbent assay for therapeutic drug monitoring of mexiletine.
2003 Jun
Synthesis of (Z)-(2,3-bis-hydroxymethyl)methylenecyclopropane analogues of purine nucleosides.
2003 Mar
On-column derivatization of the antibiotics teicoplanin and ristocetin coupled to affinity capillary electrophoresis.
2003 Mar
Synergism of ultrasound and solid acids in intensification of Friedel-Crafts acylation of 2-methoxynaphthalene with acetic anhydride.
2003 May
Acetylation of aromatic ethers using acetic anhydride over solid acid catalysts in a solvent-free system. Scope of the reaction for substituted ethers.
2003 May 7
[Effect of the degree of acetylation of chitosan on its enzymatic hydrolysis with the preparation Celloviridin G20x].
2003 May-Jun
Derivatisation in gas chromatographic determination of acidic herbicides in aqueous environmental samples.
2003 Oct
Myotoxicity induced by an acidic Asp-49 phospholipase A(2) isolated from Lachesis muta snake venom. Comparison with lysophosphatidylcholine.
2003 Oct
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:59:25 UTC 2021
Edited
by admin
on Sat Jun 26 00:59:25 UTC 2021
Record UNII
2E48G1QI9Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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, 1,1'-ANHYDRIDE
Common 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 Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
CFR 21 CFR 172.892
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
Code System Code Type Description
WIKIPEDIA
ACETIC ANHYDRIDE
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY
EPA CompTox
108-24-7
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY
NCI_THESAURUS
C76285
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY
PUBCHEM
7918
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY
MESH
C031800
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY
MERCK INDEX
M1325
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY Merck Index
HSDB
233
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY
ECHA (EC/EINECS)
203-564-8
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY
FDA UNII
2E48G1QI9Q
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
CONCEPT Industrial Aid
RXCUI
1370450
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY RxNorm
CAS
108-24-7
Created by admin on Sat Jun 26 00:59:26 UTC 2021 , Edited by admin on Sat Jun 26 00:59:26 UTC 2021
PRIMARY