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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

Price and Availability

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

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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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Serum and adipose tissue amino acid homeostasis in the metabolically healthy obese. Badoud F, Lam KP, DiBattista A, et al. J. Proteome Res. 13(7), 3455-66, (2014)

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Gas chromatography time-of-flight mass spectrometry (GC-TOF-MS)-based metabolomics for comparison of caffeinated and decaffeinated coffee and its implications for Alzheimer's disease. Chang KL, Ho PC, et al. PLoS ONE 9(8), e104621, (2014)

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Cntnap4 differentially contributes to GABAergic and dopaminergic synaptic transmission. Karayannis T, Au E, Patel JC, et al. Nature 511(7508), 236-40, (2014)

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Sox11 is required to maintain proper levels of Hedgehog signaling during vertebrate ocular morphogenesis. Pillai-Kastoori L, Wen W, Wilson SG, et al. PLoS Genet. 10(7), e1004491, (2014)

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The sinus venosus contributes to coronary vasculature through VEGFC-stimulated angiogenesis. Chen HI, Sharma B, Akerberg BN, et al. Development 141(23), 4500-12, (2014)

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Quantitative determination of free and total bisphenol A in human urine using labeled BPA glucuronide and isotope dilution mass spectrometry. Kubwabo C, Kosarac I, Lalonde K, et al. Anal. Bioanal. Chem 406(18), 4381-92, (2014)

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Selective intracellular delivery of proteasome inhibitors through pH-sensitive polymeric micelles directed to efficient antitumor therapy. Quader S, Cabral H, Mochida Y, et al. J. Control. Release 188, 67-77, (2014)

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Mobility of the Arg-Gly-Asp ligand on the outermost surface of biomaterials suppresses integrin-mediated mechanotransduction and subsequent cell functions. Kakinoki S, Seo JH, Inoue Y, et al. Acta Biomater. 13, 42-51, (2015)

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Mass spectrometric behavior of anabolic androgenic steroids using gas chromatography coupled to atmospheric pressure chemical ionization source. Part I: ionization. Raro M, Portolés T, Sancho JV, et al. J. Mass Spectrom. 49(6), 509-21, (2014)

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Hoxb8 intersection defines a role for Lmx1b in excitatory dorsal horn neuron development, spinofugal connectivity, and nociception. Szabo NE, da Silva RV, Sotocinal SG, et al. J. Neurosci. 35(13), 5233-46, (2015)

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Urinary metabolic fingerprinting of mice with diet-induced metabolic derangements by parallel dual secondary column-dual detection two-dimensional comprehensive gas chromatography. Bressanello D, Liberto E, Collino M, et al. J. Chromatogr. A. 1361, 265-76, (2014)

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The early fetal development of human neocortical GABAergic interneurons. Al-Jaberi N, Lindsay S, Sarma S, et al. Cereb. Cortex 25(3), 631-45, (2015)

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Analysis of beers from an 1840s' shipwreck. Londesborough J, Dresel M, Gibson B, et al. J. Agric. Food Chem. 63(9), 2525-36, (2015)

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Development and validation of a specific and sensitive gas chromatography tandem mass spectrometry method for the determination of bisphenol A residues in a large set of food items. Deceuninck Y, Bichon E, Durand S, et al. J. Chromatogr. A. 1362, 241-9, (2014)

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Condensed tannin biosynthesis and polymerization synergistically condition carbon use, defense, sink strength and growth in Populus. Harding SA, Xue LJ, Du L, et al. Tree Physiol. 34(11), 1240-51, (2014)

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Combinatorialization of fungal polyketide synthase-peptide synthetase hybrid proteins. Kakule TB, Lin Z, Schmidt EW, et al. J. Am. Chem. Soc. 136(51), 17882-90, (2014)

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Remarkably regioselective deacylation of cellulose esters using tetraalkylammonium salts of the strongly basic hydroxide ion. Zheng X, Gandour RD, Edgar KJ, et al. Carbohydr. Polym. 111, 25-32, (2014)

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Lung deposition and cellular uptake behavior of pathogen-mimicking nanovaccines in the first 48 hours. Ross KA, Haughney SL, Petersen LK, et al. Adv. Healthc. Mater. 3(7), 1071-7, (2014)

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Exploratory analysis of urinary tract infection using a GC-APCI-MS platform. Pacchiarotta T, Derks RJ, Nevedomskaya E, et al. Analyst 140(8), 2834-41, (2015)

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Steam explosion distinctively enhances biomass enzymatic saccharification of cotton stalks by largely reducing cellulose polymerization degree in G. barbadense and G. hirsutum. Huang Y, Wei X, Zhou S, et al. Bioresour. Technol. 181, 224-30, (2015)

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SOXC proteins amplify canonical WNT signaling to secure nonchondrocytic fates in skeletogenesis. Bhattaram P, Penzo-Méndez A, Kato K, et al. J. Cell Biol. 207(5), 657-71, (2014)

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A metabolic profiling strategy for the dissection of plant defense against fungal pathogens. Aliferis KA, Faubert D, Jabaji S, et al. PLoS ONE 9(11), e111930, (2014)

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Cholesterol-induced non-alcoholic fatty liver disease and atherosclerosis aggravated by systemic inflammation. Kim EJ, Kim BH, Seo HS, et al. PLoS ONE 9(6), e97841, (2014)

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The effect of hyperpolarization-activated cyclic nucleotide-gated ion channel inhibitors on the vagal control of guinea pig airway smooth muscle tone. McGovern AE, Robusto J, Rakoczy J, et al. Br. J. Pharmacol. 171(15), 3633-50, (2014)

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OVCAR-3 spheroid-derived cells display distinct metabolic profiles. Vermeersch KA, Wang L, Mezencev R, et al. PLoS ONE 10(2), e0118262, (2015)

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Safety and biocompatibility of carbohydrate-functionalized polyanhydride nanoparticles. Vela-Ramirez JE, Goodman JT, Boggiatto PM, et al. AAPS J. 17(1), 256-67, (2015)

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Spectrum and mechanisms of inflammasome activation by chitosan. Bueter CL, Lee CK, Wang JP, et al. J. Immunol. 192(12), 5943-51, (2014)

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Abnormal retinal development associated with FRMD7 mutations. Thomas MG, Crosier M, Lindsay S, et al. Hum. Mol. Genet. 23(15), 4086-93, (2014)

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Association between sensitisation and pain-related behaviours in an experimental canine model of osteoarthritis. Rialland P, Otis C, Moreau M, et al. Pain 155(10), 2071-9, (2014)

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Simultaneous gas-chromatographic urinary measurement of sugar probes to assess intestinal permeability: use of time course analysis to optimize its use to assess regional gut permeability. Shaikh M, Rajan K, Forsyth CB, et al. Clin. Chim. Acta 442, 24-32, (2015)

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Metabolite profiling for the identification of altered metabolic pathways in Alzheimer's disease. González-Domínguez R, García-Barrera T, Gómez-Ariza JL, et al. J. Pharm. Biomed. Anal. 107, 75-81, (2015)

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Development and validation of a GC/MS method for the simultaneous determination of levetiracetam and lamotrigine in whole blood. Nikolaou P, Papoutsis I, Dona A, et al. J. Pharm. Biomed. Anal. 102, 25-32, (2014)

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Effects of resveratrol, oxyresveratrol, and their acetylated derivatives on cellular melanogenesis. Park J, Park JH, Suh HJ, et al. Arch. Dermatol. Res. 306(5), 475-87, (2014)

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Profiling Chlamydomonas metabolism under dark, anoxic H2-producing conditions using a combined proteomic, transcriptomic, and metabolomic approach. Subramanian V, Dubini A, Astling DP, et al. J. Proteome Res. 13(12), 5431-51, (2014)

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Sensitive and selective plasmon ruler nanosensors for monitoring the apoptotic drug response in leukemia. Tajon CA, Seo D, Asmussen J, et al. ACS Nano 8(9), 9199-208, (2014)

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Effect of nanovaccine chemistry on humoral immune response kinetics and maturation. Haughney SL, Ross KA, Boggiatto PM, et al. Nanoscale 6(22), 13770-8, (2014)

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Identification of organic acids as potential biomarkers in the urine of autistic children using gas chromatography/mass spectrometry. Ka?u?na-Czapli?ska J, ?urawicz E, Struck W, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 966, 70-6, (2014)

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Structural features of a novel polysaccharide isolated from a New Zealand Maori mushroom Iliodiction cibarium. Ren L, Edwards PJ, Perera CO, et al. Carbohydr. Res. 406, 19-26, (2015)

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Gas chromatography-mass spectrometry-based metabolite profiling of Salmonella enterica serovar Typhimurium differentiates between biofilm and planktonic phenotypes. Wong HS, Maker GL, Trengove RD, et al. Appl. Environ. Microbiol. 81(8), 2660-6, (2015)

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Metabolomic analysis of simvastatin and fenofibrate intervention in high-lipid diet-induced hyperlipidemia rats. Xu QY, Liu YH, Zhang Q, et al. Acta Pharmacol. Sin. 35(10), 1265-73, (2014)

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Aminorex associated with possible idiopathic pulmonary hypertension in a cocaine user. Karch SB, Defraia B, Messerini L, et al. Forensic Sci. Int. 240, e7-10, (2014)

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Three-dimensional cultures of trophoblast stem cells autonomously develop vascular-like spaces lined by trophoblast giant cells. Rai A and Cross JC Dev. Biol. 398(1), 110-9, (2015)

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Ficolins and the lectin pathway of complement in patients with systemic lupus erythematosus. Hein E, Nielsen LA, Nielsen CT, et al. Mol. Immunol. 63(2), 209-14, (2014)

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An evaluation of acute hydrogen sulfide poisoning in rats through serum metabolomics based on gas chromatography-mass spectrometry. Zhang M, Deng M, Ma J, et al. Chem. Pharm. Bull. 62(6), 505-7, (2014)

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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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