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320129

Sigma-Aldrich

Acetyl chloride

reagent grade, 98%

Synonym(s):

Acetic acid chloride, Acetic chloride, Ethanoyl chloride

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About This Item

Linear Formula:
CH3COCl
CAS Number:
75-36-5
Molecular Weight:
78.50
Beilstein:
605303
EC Number:
200-865-6
MDL number:
MFCD00000719
UNSPSC Code:
12352100
PubChem Substance ID:
24859250
NACRES:
NA.22
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grade

reagent grade

Quality Level

200

vapor density

2.7 (vs air)

vapor pressure

11.69 psi ( 20 °C)
32.33 psi ( 55 °C)

Assay

98%

form

liquid

autoignition temp.

1353 °F

expl. lim.

19 %

refractive index

n20/D 1.389 (lit.)

bp

52 °C (lit.)

mp

−112 °C (lit.)

density

1.104 g/mL at 25 °C (lit.)

functional group

acyl chloride

SMILES string

CC(Cl)=O

InChI

1S/C2H3ClO/c1-2(3)4/h1H3

InChI key

WETWJCDKMRHUPV-UHFFFAOYSA-N

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General description

Acetyl chloride undergoes reaction with decalin and aluminum trichloride to afford a tricyclic enol ether.[1] It promotes the cyclopropanation of alkene with dibromomethane or diiodomethane in the presence of Zn dust and copper chloride in ether.[2] Friedel-Crafts reaction of acetyl chloride with benzene in the presence of MCl3 (M = Al or Fe) in the ionic liquid 1-butyl-3-methylimidazolium chloride affords MCl3 adducts of the acetyl chloride, the acetylium ion [CH3CO]+[MCl4]- and the MCl3 adduct of acetophenone.[3]

Application

  • Synthesis, Characterization, and Evaluation of Thiazolidine Derivatives of Cysteine for Suppressing Eumelanin Production.: The study discusses the synthesis and evaluation of thiazolidine derivatives of cysteine, where acetyl chloride is used as a reagent, underscoring its importance in pharmaceutical intermediate development. (Amino et al., 2016).
  • New URJC-1 Material with Remarkable Stability and Acid-Base Catalytic Properties.: This research introduces the new URJC-1 material, noting its stability and catalytic properties, with acetyl chloride being pivotal in the synthesis process, illustrating its role in material science and catalysis. (Leo et al., 2016).

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H225,H314

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

41.0 °F - closed cup

Flash Point(C)

5 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0881
STBL4167
STBL4166
SDBB1861
MKCV7127

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Acetyl chloride promoted cyclopropanations of alkenes with dibromomethane using zinc dust and copper (I) chloride in ether.
Friedrich EC and Lewis EJ.
The Journal of Organic Chemistry, 55(8), 2491-2494 (1990)
In situ infrared spectroscopic studies of the Friedel-Crafts acetylation of benzene in ionic liquids using AlCl3 and FeCl3.
Csihony S, et al.
Green Chemistry, 3(6), 307-309 (2001)
Catherine L Lyall et al.
Journal of the American Chemical Society, 136(39), 13745-13753 (2014-09-10)
Decalin undergoes reaction with aluminum trichloride and acetyl chloride to form a tricyclic enol ether in good yield, as first reported by Baddeley. This eye-catching transformation, which may be considered to be an aliphatic Friedel-Crafts reaction, has not previously been
Facile catalyzed acylation of alcohols, phenols, amines and thiols based on ZrOCl 2? 8H 2 O and acetyl chloride in solution and in solvent-free conditions.
Ghosh R, et al.
Tetrahedron Letters, 46(1), 147-151 (2005)
Oxetanes. VII. Synthesis from 1, 3-Diols. Reactions of Oxetanes and of 1, 3-Butanediol with Hydrogen Chloride, Hydrogen Bromide and Acetyl Chloride1, 2.
Searles JS, et al.
Journal of the American Chemical Society, 79(4), 952-956 (1957)
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Articles

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. Is this chemical react with eppendorf tubes? Especially when heated?

    1 answer

    1. The most stable materials for use with Acetyl Chloride are FEP and PVDF. Fluoroethylenepropylene (FEP) is not recommended for high heat conditions. While the product number has not been provided, most Eppendorf tubes are polypropylene. Polypropylene is not compatible with this Acetyl Chloride.

      Further information may be available from our Technical Service team who can assist you further. We kindly ask you to navigate to the link https://www.sigmaaldrich.com/techservice, click on "Product Technical Inquires" under the Products Section with all the required information so that a member of our team can reach out to you to assist further. Thank you.

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