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320102 Sigma-Aldrich

Acetic anhydride

ReagentPlus®, ≥99%

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Properties

grade   ReagentPlus®
vapor density   3.5 (vs air)
vapor pressure   10 mmHg ( 36 °C)
  4 mmHg ( 20 °C)
assay   ≥99%
autoignition temp.   629 °F
expl. lim.   10.3 %
refractive index   n20/D 1.390(lit.)
bp   138-140 °C(lit.)
mp   −73 °C(lit.)
density   1.08 g/mL(lit.)

Description

Packaging

1 L in glass bottle

100, 4×100, 500 mL in glass bottle

Application

Acetic anhydride was used in the following studies:
• Lipozyme TL IM (commercial immobilized lipase from Thermomyces lanuginosus) catalyzed acetylation of essential clove oil.1
• As acetyl donor to investigate the lipase catalyzed acetylation of nanofibrillated cellulose (NFC).2
• Synthesis of N-substituted pyrazolines.3
• Acetylation of Barnyardgrass (Echinochloa crus-galli) starch.4

General description

Acetic anhydride participates in the Friedel-Craft′s intramolecular cyclization reaction of cyclopropyl ketones to afford the tetralones.5 It has been reported to promote the Knoevenagel condensation of various aldehydes and activated methylene compounds.6

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 1715 3(8) / PGII
WGK Germany 
1
RTECS 
AK1925000
Flash Point(F) 
120.2 °F
Flash Point(C) 
49 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Friedel–Crafts Acylation

The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form m...
Keywords: Acylations, Catalysis, Electrophilic aromatic substitution, Microwave synthesis, Substitutions

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. Lipozyme TL IM as Catalyst for the Synthesis of Eugenyl Acetate in Solvent-Free Acetylation. Silva MJ, Loss RA, Laroque DA, et al. Appl. Biochem. Biotechnol., (2015)

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2. New findings about the lipase acetylation of nanofibrillated cellulose using acetic anhydride as acyl donor. Božič M, Vivod V, Kavčič S, et al. Carbohydr. Polym. 125, 340-51, (2015)

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3. An efficient synthesis of new caffeine-based chalcones, pyrazolines and pyrazolo[3,4-b][1,4]diazepines as potential antimalarial, antitrypanosomal and antileishmanial agents. Insuasty B, Ramírez J, Becerra D, et al. Eur. J. Med. Chem. 93, 401-13, (2015)

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4. Acetylation of barnyardgrass starch with acetic anhydride under iodine catalysis. Bartz J, Goebel JT, Giovanaz MA, et al. Food Chem. 178, 236-42, (2015)

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5. Synthesis and pharmacological studies of new pyrazole analogues of podophyllotoxin. Umesha B and Basavarajuk YB Bioorg. Khim. 40(4), 503-12, (2014)

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6. Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter. Ogiwara Y, Takahashi K, Kitazawa T, et al. J. Org. Chem. 80(6), 3101-10, (2015)

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Spatial and temporal expression of the 23 murine Prolactin/Placental Lactogen-related genes is not associated with their position in the locus. Simmons DG BMC Genomics 9, 352, (2008)

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[Improved methodology for quantitative determination of thiabendazole]. Furusho N, Otsuki N, Ohtsuki T, et al. Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho. Hokoku. (130), 46-9, (2012)

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[Biotechnological production of acetylated thymosin beta4]. Beĭrakhova KA, Stepanenko VN, Miroshnikov AI, et al. Bioorg. Khim. 37(2), 223-32, (2011)

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Molt-inhibiting hormone stimulates vitellogenesis at advanced ovarian developmental stages in the female blue crab, Callinectes sapidus 2: novel specific binding sites in hepatopancreas and cAMP as a second messenger. Zmora N Saline Systems 5, 6, (2009)

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Stir bar sorptive extraction coupled to gas chromatography-mass spectrometry for the determination of bisphenols in canned beverages and filling liquids of canned vegetables. Cacho JI, Campillo N, Viñas P, et al. J. Chromatogr. A 1247, 146-53, (2012)

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Synthesis and characterization of acetyloxypropylene dimethacrylate as a new dental monomer. Podgórski M Dent. Mater. 27(8), 748-54, (2011)

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Acetylation of chicken feathers for thermoplastic applications. Hu C, Reddy N, Yan K, et al. J. Agric. Food Chem. 59(19), 10517-23, (2011)

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Insights in starch acetylation in sub- and supercritical CO2. Muljana H, Picchioni F, Knez Z, et al. Carbohydr. Res. 346(10), 1224-31, (2011)

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Derivatization with acetic anhydride: applications to the analysis of biogenic amines and psychiatric drugs by gas chromatography and mass spectrometry. Baker GB, Coutts RT, and Holt A J. Pharmacol. Toxicol. Methods 31(3), 141-8, (1994)

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Pd(II)-catalyzed regio-, enantio-, and diastereoselective 1,4-addition of azlactones formed in situ from racemic unprotected amino acids and acetic anhydride. Weber M and Peters R J. Org. Chem. 77(23), 10846-55, (2012)

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Isolation of cellulose from rice straw and its conversion into cellulose acetate catalyzed by phosphotungstic acid. Fan G, Wang M, Liao C, et al. Carbohydr. Polym. 94(1), 71-6, (2013)

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Paclitaxel-incorporated nanoparticles of hydrophobized polysaccharide and their antitumor activity. Lee SJ, Hong GY, Jeong YI, et al. Int. J. Pharm. 433(1-2), 121-8, (2012)

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microRNA 376a regulates follicle assembly by targeting Pcna in fetal and neonatal mouse ovaries. Zhang H, Jiang X, Zhang Y, et al. Reproduction 148(1), 43-54, (2014)

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Direct titanium-mediated conversion of ketones into enamides with ammonia and acetic anhydride. Reeves JT, Tan Z, Han ZS, et al. Angew. Chem. Int. Ed. Engl. 51(6), 1400-4, (2012)

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Improvement and validation the method using dispersive liquid-liquid microextraction with in situ derivatization followed by gas chromatography-mass spectrometry for determination of tricyclic antidepressants in human urine samples. Ito R, Ushiro M, Takahashi Y, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 879(31), 3714-20, (2011)

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Facile one-pot preparation, surface functionalization, and toxicity assay of APTS-coated iron oxide nanoparticles. Shen M, Cai H, Wang X, et al. Nanotechnology 23(10), 105601, (2012)

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The corticofugal neuron-associated genes ROBO1, SRGAP1, and CTIP2 exhibit an anterior to posterior gradient of expression in early fetal human neocortex development. Ip, B.K., et al. Cereb. Cortex 21, 1395-407, (2011)

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Acetylation of αA-crystallin in the human lens: effects on structure and chaperone function. Nagaraj RH, Nahomi RB, Shanthakumar S, et al. Biochim. Biophys. Acta 1822(2), 120-9, (2012)

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Synthesis, characterization and functional properties of low substituted acetylated corn starch. Han F, Liu M, Gong H, et al. Int. J. Biol. Macromol. 50(4), 1026-34, (2012)

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Dual mode single agent thermochemical ablation by simultaneous release of heat energy and acid: hydrolysis of electrophiles. Cressman EN and Jahangir DA Int. J. Hyperthermia 29(1), 71-8, (2013)

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Copper-catalyzed Perkin-acyl-Mannich reaction of acetic anhydride with pyridine: expeditious entry to unconventional piperidines. Crotti S, Berti F, and Pineschi M Org. Lett. 13(19), 5152-5, (2011)

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Probing the mechanisms of electron capture dissociation mass spectrometry with nitrated peptides. Andrew W. Jones et al Phys. Chem. Chem. Phys. 12 , 13394-9, (2010)

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Understanding the factors affecting the activation of alkane by Cp'Rh(CO)2 (Cp' = Cp or Cp*). George MW, Hall MB, Jina OS, et al. Proc. Natl. Acad. Sci. U. S. A. 107(47), 20178-83, (2010)

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Examination of the kinetic isotopic effect to the acetylation derivatization for the gas chromatographic-combustion-isotope ratio mass spectrometric doping control analysis of endogenous steroids. Angelis YS, Kioussi MK, Kiousi P, et al. Drug Test. Anal. 4(12), 923-7, (2012)

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Synthesis and characterization of 5-nitro-2-nitratomethyl-1,2,3,4-tetrazole: a high nitrogen energetic compound with good oxygen balance. Li Y, Liu W, and Pang S Molecules 17(5), 5040-9, (2012)

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Enzymatic primer-extension with glycerol-nucleoside triphosphates on DNA templates. Chen JJ, et al. PLoS ONE 4(3), e4949, (2009)

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A facile synthesis of highly functionalized 4-arylcoumarins via Kostanecki reactions mediated by DBU. Hwang IT, Lee SA, Hwang JS, et al. Molecules 16(8), 6313-21, (2011)

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Synthesis, molecular properties prediction, and anti-staphylococcal activity of N-acylhydrazones and new 1,3,4-oxadiazole derivatives. de Oliveira CS, Lira BF, dos Santos Falcão-Silva V, et al. Molecules 17(5), 5095-107, (2012)

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The solvolysis of topotecan in alcohols and acetic anhydride. Li J, Wang G, Dong M, et al. Bioorg. Med. Chem. Lett. 21(8), 2324-6, (2011)

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Synthesis of eugenol esters by lipase-catalyzed reaction in solvent-free system. Chiaradia V, Paroul N, Cansian RL, et al. Appl. Biochem. Biotechnol. 168(4), 742-51, (2012)

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Regioselective cleavage of 22-oxo-23-spiroketals. Novel cholestanic frameworks with pyranone and cyclopentenone E rings on the side chain. López Y, Rodríguez L, del Río RE, et al. Steroids 77(5), 534-41, (2012)

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Studies on the chemical modification of goat liver cystatin and the effect on its anti-papain inhibitory activity. Shah A, Aatif M, Priyadarshini M, et al. J. Fluoresc. 22(6), 1627-32, (2012)

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Determination of dihydroxyacetone and glycerol in fermentation process by GC after n-methylimidazole catalyzed acetylation. Wu J, Li MH, Lin JP, et al. J. Chromatogr. Sci. 49(5), 375-8, (2011)

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Biocompatible hydrogels based on chitosan and poly(p-dioxanone). Zhai Y, Wang X, Li X, et al. J. Control. Release 152 Suppl 1, e94-5, (2011)

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Merck 14,56

Beil. 2,IV,386

Fieser 1,3 / Fieser 2,7 / Fieser 5,3 / Fieser 6,1 / Fieser 7,1 / Fieser 8,1 / Fieser 9,1 / Fieser 11,1

Aldrich MSDS 1, 10:C / Corp MSDS 1 (1), 17:D / FT-IR 2 (1), 1204:D / FT-IR 1 (1), 711:A / FT-NMR 1 (1), 1165:A / IR-Spectra (2), 368:A / IR-Spectra (3), 416:A / NMR-Reference 2 (1), 601:A / RegBook 1 (1), 827:H / Sax 6, 85 / Sigma FT-IR 1 (2), 232:A / Structure Index 1, 129:A:1 / Vapor Phase 3, 760:C

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