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C19651

Sigma-Aldrich

Chloroacetonitrile

99%

Synonym(s):

α-Chloroacetonitrile, 2-Chloroacetonitrile, Chloromethyl cyanide, Cyanomethyl chloride, Monochloroacetonitrile

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100 G
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About This Item

Linear Formula:
ClCH2CN
CAS Number:
Molecular Weight:
75.50
Beilstein:
506028
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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vapor density

3 (vs air)

vapor pressure

1.78 psi ( 20 °C)

Assay

99%

form

liquid

refractive index

n20/D 1.422 (lit.)

bp

124-126 °C (lit.)

density

1.193 g/mL at 25 °C (lit.)

SMILES string

ClCC#N

InChI

1S/C2H2ClN/c3-1-2-4/h1H2

InChI key

RENMDAKOXSCIGH-UHFFFAOYSA-N

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Application

Chloroacetonitrile can be used:
  • For the synthesis of ionic liquids containing nitrile functionalized imidazolium salts.[1]
  • For the synthesis of cyanomethyl dodecyl trithiocarbonate, a reversible addition-fragmentation chain transfer (RAFT) agent.[2]
  • As an alkylating reagent for the synthesis of derivatives of triazolyl thiazoles to be used as anti-tuberculosis agents.[3]
  • As a reagent in photo Meerwein addition reaction for amino-arylation of alkenes.[4]
  • As an esterifying agent in the synthesis of a cytotoxic natural product: apicularen A.[5]

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

129.2 °F

Flash Point(C)

54 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis and characterization of ionic liquids incorporating the nitrile functionality.
Zhao D, et al.
Inorganic Chemistry, 43(6), 2197-2205 (2004)
Synthesis of new S-derivatives of clubbed triazolyl thiazole as anti-Mycobacterium tuberculosis agents.
Shiradkar MR, et al.
Bioorganic & Medicinal Chemistry, 15(12), 3997-4008 (2007)
The photoredox-catalyzed Meerwein addition reaction: intermolecular amino-arylation of alkenes.
Prasad Hari D, et al.
Angewandte Chemie (International Edition in English), 53(3), 725-728 (2014)
Total synthesis of (-)-apicularen A.
Su Q and Panek JS
Journal of the American Chemical Society, 126(8), 2425-2430 (2004)
Yukako Komaki et al.
Journal of environmental sciences (China), 58, 231-238 (2017-08-05)
Disinfection by-products occur widely as the unintended effect of water disinfection and are associated with toxicity and adverse human health effects. Yet the molecular mechanisms of their toxicity are not well understood. To investigate the molecular basis of hyperploidy induction

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    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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  2. 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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