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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/REAXYS Number:
1740244
EC Number:
254-169-2
MDL number:
MFCD00000728
UNSPSC Code:
12352100
PubChem Substance ID:
24897347
NACRES:
NA.22

Quality Level

100

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.

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Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

82.4 °F

flash_point_c

28 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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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Bioactive dihydro-?-agarofuran sesquiterpenoids from the Australian rainforest plant Maytenus bilocularis.
Wibowo M, et al.
Journal of Natural Products, 79(5), 1445-1453 (2016)
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)
Radu A Gropeanu et al.
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
A telescopic one-pot synthesis of ?-lactam rings using amines as a convenient source of imines.
Rajamaki SHM, et al.
Royal Society of Chemistry Advances, 6(45), 38553-38557 (2016)
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