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M35304

Sigma-Aldrich

Methyl chloroformate

99%

Synonym(s):

MCF, Chloroformic acid methyl ester

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5 G
$46.80
100 G
$54.90
500 G
$89.10

About This Item

Linear Formula:
ClCOOCH3
CAS Number:
79-22-1
Molecular Weight:
94.50
Beilstein/REAXYS Number:
605437
EC Number:
201-187-3
MDL number:
MFCD00000639
UNSPSC Code:
12352100
PubChem Substance ID:
24896852
NACRES:
NA.22

$46.80

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vapor density

3.26 (vs air)

Quality Level

200

vapor pressure

4.8 psi ( 20 °C)

assay

99%

autoignition temp.

905 °F

refractive index

n20/D 1.387 (lit.)

bp

70-72 °C (lit.)

density

1.223 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

COC(Cl)=O

InChI

1S/C2H3ClO2/c1-5-2(3)4/h1H3

InChI key

XMJHPCRAQCTCFT-UHFFFAOYSA-N

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Application

Methyl chloroformate (MCF) is generally used for the derivatization of functional groups such as carboxylic acids, amines, and phenols.[1]
MCF can also be used:
  • To activate 3-acylpyridines for nucleophilic addition with alkynyltin reagents to form 2,3-disubstituted 1,2-dihydropyridines.[2]
  • Chloroesterification of terminal alkynes to form β-chloro-α,β-unsaturated esters.[3]
  • As an electrophilic reagent to mediate the reaction of pyridine with lithium dialkyl- or diarylcuprates to form 4-substituted 1,4-dihydropyridine derivatives.[4]
  • To convert nitronates into methoxycarbonyl nitronates.[5]

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

50.0 °F - closed cup

flash_point_c

10 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB3204
STBL0805
STBK0604
STBJ8556
STBJ5986

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Thibaut D J Delplancke et al.
Scientific reports, 8(1), 36-36 (2018-01-10)
The hair metabolome has been recognized as a valuable source of information in pregnancy research, as it provides stable metabolite information that could assist with studying biomarkers or metabolic mechanisms of pregnancy and its complications. We tested the hypothesis that
Kathleen F Smart et al.
Nature protocols, 5(10), 1709-1729 (2010-10-05)
This protocol describes an analytical platform for the analysis of intra- and extracellular metabolites of microbial cells (yeast, filamentous fungi and bacteria) using gas chromatography-mass spectrometry (GC-MS). The protocol is subdivided into sampling, sample preparation, chemical derivatization of metabolites, GC-MS
M G Zampolli et al.
Journal of chromatography. A, 1150(1-2), 162-172 (2007-01-16)
This work describes a GC-MS method for enantioselective separation of amino acids. The method is based on a derivatization reaction which employs a mixture of alkyl chloroformate-alcohol-pyridine, as reagents to obtain the N(O,S)-alkyl alkoxy carbonyl esters of amino acids. Various
One-pot synthesis of five-membered cyclic thioethers or ethers via intramolecular nitrile oxide-olefin cycloaddition (INOC) or intramolecular alkoxycarbonyl nitronate-olefin cycloaddition (IAOC) by the use of methyl chloroformate.
Yan M C, et al.
Tetrahedron, 55(43), 12493-12514 (1999)
Ruth Jakobs et al.
Oecologia, 186(1), 173-184 (2017-11-17)
Plant chemistry is one of the main drivers of herbivore distribution. Monophagous herbivore species are highly specialized, but even within their only host species the chemistry varies. The herbivore's choice is initially mainly guided by volatile plant compounds. Once on
View All Related Papers

Questions

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  1. 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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  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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