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63406

Sigma-Aldrich

Methyl malonyl chloride

purum, ≥97.0% (AT)

Synonym(s):

Methyl chloroformylacetate

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About This Item

Linear Formula:
CH3OCOCH2COCl
CAS Number:
37517-81-0
Molecular Weight:
136.53
Beilstein:
1754078
EC Number:
253-540-6
MDL number:
MFCD00013657
UNSPSC Code:
12352100
PubChem Substance ID:
329759858
NACRES:
NA.22

grade

purum

Quality Level

200

Assay

≥97.0% (AT)

refractive index

n20/D 1.432 (lit.)
n20/D 1.432

bp

57-59 °C/12 mmHg (lit.)

density

1.273 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

COC(=O)CC(Cl)=O

InChI

1S/C4H5ClO3/c1-8-4(7)2-3(5)6/h2H2,1H3

InChI key

UTBCRHAMJFMIIR-UHFFFAOYSA-N

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Application

Methyl malonyl chloride can be used in the synthesis of methyl 7-hydroxy[1,3]thiazolo[5,4-b]pyridin-5(4H)-one-6-carboxylates and 6-carboxamides, which can act like HIV integrase strand transfer inhibitors. It can also be used in the synthesis of Strychnos alkaloids like (-)-leuconicine A and (-)-leuconicine B.

Caution

may discolor to yellow on storage

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314 - H335

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

176.0 °F - closed cup

Flash Point(C)

80 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC0301
BCBJ3603V
1425257
1425257V
1426039V

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"Total synthesis of (-)-leuconicine A and B"
Sirasani G and Andrade.BR
Organic Letters, 13(17), 4736-4737 (2011)
"Synthesis and HIV-integrase strand transfer inhibition activity of 7-hydroxy [1, 3] thiazolo [5, 4-b]pyridin-5 (4H)-ones"
Boros.EE, et al.
Bioorganic & Medicinal Chemistry, 16(21), 5668-5672 (2006)
Elif Okutan et al.
Journal of fluorescence, 26(6), 2333-2343 (2016-11-01)
Colorimetric fluorescent chemosensors 4 and 5 based on mono- and di- styryl borondipyrromethenes (BODIPY) linked methyl malonyl were designed for detection of hemoglobin (HgB). Their sensing behavior toward various analytes (Br

Protocols

Analytical Method: Copper (total) in feedstuffs

Photometric determination with Cuprizon subsequent to acid mineralisation

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