Standard Article

Acetic Formic Anhydride

  1. Regina Zibuck1,
  2. Ravinder Raju2,
  3. Amy R. Howell2

Published Online: 15 SEP 2008

DOI: 10.1002/047084289X.ra009.pub2

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Zibuck, R., Raju, R. and Howell, A. R. 2008. Acetic Formic Anhydride. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. 1

    Wayne State University, Detroit, MI, USA

  2. 2

    University of Connecticut, Storrs, CT, USA

Publication History

  1. Published Online: 15 SEP 2008

Chemistry Terms

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Abstract

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[2258-42-6] C3H4O3 (MW 88.06)

(useful formylating agent for the hydroxyl,2 phenol,3 and amine groups4 as well as other heteroatoms;5 useful for the synthesis of aldehydes from aromatic Grignard reagents,6 for the preparation of formyl fluoride,7 and for the preparation of diazoacetaldehyde8)

Alternate Name: AFA.

Physical Data: bp 27–28 °C/10 mmHg.

Analysis of Reagent Purity: IR, NMR, MS.1

Preparative Methods:acetic formic anhydride is not comercially available. The easiest method of preparation is by the reaction of sodium formate and Acetyl Chloride in dry ether as reported by Krimen.9 Alternatively, Ketene and Formic Acid form the title compound at room temperature or below.10 Acetic formic anhydride can be prepared rapidly in situ by stirring formic acid, acetyl chloride, and Triethylamine in THF at −70 °C for 10 min.11 AFA is found in a mixture of formic acid (excess) with Acetic Anhydride.1 The mixture is more accurately described as formic acid–acetic anhydride mixture (FAM) and is also used as a formylating agent.

Purification: by fractional distillation at low pressure.

Handling, Storage, and Precautions:acetic formic anhydride decomposes slowly at room temperature and faster at elevated temperatures, giving acetic acid and carbon monoxide. Due to gas evolution, AFA is best stored at 4 °C in a flask fitted with a polyethylene stopper since sealed samples can explode. The compound is an eye and skin irritant and should be handled in a fume hood.

Featured Compounds

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  1. 1 - 72
Compound Information
Molecular Weight:1.00794
Molecular Formula:H
InChIKey:GPRLSGONYQIRFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.3125
Molecular Formula:C13H21N
InChIKey:VKNNTGAVAVGHLZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:153.823
Molecular Formula:CCl4
InChIKey:VZGDMQKNWNREIO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.172
Molecular Formula:C9H8N2O2
InChIKey:AHAGTFJLGJGKNN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:88.0621
Molecular Formula:C3H4O3
InChIKey:ORWKVZNEPHTCQE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:136.1512
Molecular Formula:C7H8N2O
InChIKey:WARCRYXKINZHGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:284.215
Molecular Formula:C12H28O4Ti
InChIKey:VXUYXOFXAQZZMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:178.1415
Molecular Formula:C9H6O4
InChIKey:NYCXYKOXLNBYID-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0501
Molecular Formula:C2H2N2O
InChIKey:PIMASLJEYMYKCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.1284
Molecular Formula:C8H4N2O4
InChIKey:HSVNFUBGPAYPPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:46.0254
Molecular Formula:CH2O2
InChIKey:BDAGIHXWWSANSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:48.0164
Molecular Formula:CHFO
InChIKey:NHGVZTMBVDFPHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:297.2655
Molecular Formula:C15H11N3O4
InChIKey:UPUYWBHITOMKFN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1506
Molecular Formula:C7H8N2O2
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:202.638
Molecular Formula:C8H11ClN2O2
InChIKey:YJQDCBSPMOIYHF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:105.9884
Molecular Formula:CNa2O3
InChIKey:CDBYLPFSWZWCQE-UHFFFAOYSA-L
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:361.411
Molecular Formula:C15H23NO7S
InChIKey:PMPFITJXVRJPKJ-ILSJRFRISA-N
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Compound Information
Molecular Weight:96.106
Molecular Formula:CH4O3S
InChIKey:AFVFQIVMOAPDHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:45.0406
Molecular Formula:CH3NO
InChIKey:ZHNUHDYFZUAESO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.0338
Molecular Formula:C2H3NaO2
InChIKey:VMHLLURERBWHNL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:177.286
Molecular Formula:C12H19N
InChIKey:WKBALTUBRZPIPZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.0072
Molecular Formula:CHNaO2
InChIKey:Not Available
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:259.2558
Molecular Formula:C11H17NO6
InChIKey:JKZBMMLLXSEKGG-KYXWUPHJSA-N
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Compound Information
Molecular Weight:17.0305
Molecular Formula:H3N
InChIKey:QGZKDVFQNNGYKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:162.1454
Molecular Formula:C8H6N2O2
InChIKey:BKKUMKNIRBIPHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.2855
Molecular Formula:C18H15P
InChIKey:RIOQSEWOXXDEQQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:13.835
Molecular Formula:BH3
InChIKey:UORVGPXVDQYIDP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:SKZKKFZAGNVIMN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.2961
Molecular Formula:C13H19NO
InChIKey:HGCULERWAGEILG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.1525
Molecular Formula:C7H9NO
InChIKey:BHAAPTBBJKJZER-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.1461
Molecular Formula:C8H7NO3
InChIKey:DGVIISLJHPSLCH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:181.1256
Molecular Formula:C7H6N2O4
InChIKey:UEALKTCRMBVTFN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:428.298
Molecular Formula:C17H18BrNO5S
InChIKey:BTRAORQGFHVIIV-XJKSGUPXSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:42.04
Molecular Formula:CH2N2
InChIKey:YXHKONLOYHBTNS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:249.3071
Molecular Formula:C17H15NO
InChIKey:IYTJPLJAJCAYDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:164.1613
Molecular Formula:C8H8N2O2
InChIKey:FJYTWSATJDPRNY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:221.297
Molecular Formula:C16H15N
InChIKey:PFWAZPRTKFIJDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:565.523
Molecular Formula:C23H21BrN2O4S3
InChIKey:HPRRISWBJHQPAW-GHTZIAJQSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:172.202
Molecular Formula:C7H8O3S
InChIKey:JOXIMZWYDAKGHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:168.1467
Molecular Formula:C8H8O4
InChIKey:XLEYFDVVXLMULC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:67.806
Molecular Formula:BF3
InChIKey:WTEOIRVLGSZEPR-UHFFFAOYSA-N
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