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M9653

Sigma-Aldrich

Methoxyacetyl chloride

97%

Synonym(s):

2-methoxyacetyl chloride, Methoxyacetic acid chloride

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About This Item

Linear Formula:
CH3OCH2COCl
CAS Number:
38870-89-2
Molecular Weight:
108.52
Beilstein:
1740244
EC Number:
254-169-2
MDL number:
MFCD00000728
UNSPSC Code:
12352100
PubChem Substance ID:
24897347
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.419 (lit.)

bp

112-113 °C (lit.)

density

1.187 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

COCC(Cl)=O

InChI

1S/C3H5ClO2/c1-6-2-3(4)5/h2H2,1H3

InChI key

JJKWHOSQTYYFAE-UHFFFAOYSA-N

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Application

Methoxyacetyl chloride can be used for methoxyacetylation of:
  • Bilocularin A to synthesize 8-Methoxyacetoxybilocularin A.
  • Substituted and unsubstituted benzamides to synthesize N-(2-methoxyacetyl)-benzamides.

It can also be used for the synthesis of β-lactams by reacting with imines. and in the post-synthetic modification of the metal-organic framework (MOF), MIL-101, to synthesize a catalyst for cycloaddition reaction of CO2 with propylene oxide.

Signal Word

Danger

Hazard Statements

H226,H314,H331,H335

Hazard Classifications

Acute Tox. 3 Inhalation - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

82.4 °F

Flash Point(C)

28 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of Quinolinone Alkaloids via Aryne Insertions into Unsymmetric Imides in Flow.
Schwan J, et al.
Organic Letters, 20(23), 7661?7664-7661?7664 (2018)
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PloS one, 7(9), e43657-e43657 (2012-09-13)
Three different variants of photoactivatable caged paclitaxel (PTX) have been synthesized and their bioactivity was characterized in in vitro assays and in living cells. The caged PTXs contain the photoremovable chromophore 4,5-dimethoxy-2-nitrobenzyloxycarbonyl (Nvoc) attached to position C7, C2' and to
Functionalized MIL-101 with imidazolium-based ionic liquids for the cycloaddition of CO2 and epoxides under mild condition.
Liu D, et al.
Applied Surface Science, 428(45), 218-225 (2018)
An investigation towards the diastereoselective synthesis of 3-acetoxy/methoxy/phthalimido-β-lactams using chiral imines.
Bhalla A, et al.
Tetrahedron Asymmetry, 28(2), 307-316 (2017)
Bioactive dihydro-?-agarofuran sesquiterpenoids from the Australian rainforest plant Maytenus bilocularis.
Wibowo M, et al.
Journal of Natural Products, 79(5), 1445-1453 (2016)
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