M1601

Sigma-Aldrich

Malonyl chloride

97%

Synonym(s):
Malonyl dichloride
Linear Formula:
CH2(COCl)2
CAS Number:
Molecular Weight:
140.95
Beilstein/REAXYS Number:
774044
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

refractive index

n20/D 1.465 (lit.)

bp

53-55 °C/19 mmHg (lit.)

density

1.449 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClC(=O)CC(Cl)=O

InChI

1S/C3H2Cl2O2/c4-2(6)1-3(5)7/h1H2

InChI key

SXYFKXOFMCIXQW-UHFFFAOYSA-N

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Application

Malonyl chloride can be used as a reactant for the synthesis of:
  • Alkaloids with tetracyclic cores such as cyclopiamide A and speradine E.
  • 6-tetrathiafulvalene(TTF)-polymer by condensation polymerization with TTF-based dihydroxy monomer.
  • N-doped TiO2 films by molecular layer deposition.
  • Alkyne-substituted 1,3-oxazines by reaction with arylpropynamides.

It can also be used as a coupling agent in the synthesis of block copolymers by anionic polymerization.

Packaging

5, 25, 100 g in ampule

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Supp Hazards

EUH014

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2920 3(8) / PGII

WGK Germany

WGK 1

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

Total synthesis of cyclopiamide A and speradine E
Nakhla MC, et al.
Tetrahedron, 74(38), 5085-5088 (2018)
Nanoporous Nitrogen-Doped Titanium Dioxide with Excellent Photocatalytic Activity under Visible Light Irradiation Produced by Molecular Layer Deposition
Chen C, et al.
Angewandte Chemie (International Edition in English), 125(35), 9366-9370 (2013)
Synthesis and Characterization of a Tetrathiafulvalene-Based Polymer
Lee SH, et al.
Bull. Korean Chem. Soc., 33(5), 1451-1456 (2012)
Preparation of Arylpropynamides and Their Reaction with Malonyl Acid Derivatives
Petina OA, et al.
Synthesis, 45(06), 803-809 (2013)
Mechanistic Pathway for the Formation of Radial Polystyrenes Using Diacyl Chloride
Kumar S, et al.
Macromolecules, 45(6), 2675-2681 (2012)

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