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A15616 Ethyl malonyl chloride, 95%

CAS Number
36239-09-5
Synonyms
Ethyl (chloroformyl)acetate
Malonic acid monoethyl ester chloride

Stock No. Size Price ($) Quantity Availability
A15616-06 5g 52.40
A15616-14 25g 181.00
A15616-22 100g 573.00
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Ethyl malonyl chloride, 95%

MDL
MFCD00000736
EINECS
252-934-5

Chemical Properties

Formula
C5H7ClO3
Formula Weight
150.56
Boiling Point
83°/22mm
Flash Point
67°(152°F)
Density
1.189
Refractive Index
1.4290
Storage & Sensitivity
Keep Cold. Moisture Sensitive.
Solubility
Miscible with water.

Applications

Ethyl malonyl chloride is used in the syntheses of methanofullerodendimers and 3-pyrrolin-2-ones. It plays a vital role in the preparation of 3,5-disubstituted 1,2,4-oxadiazole derivatives, which are potential peptidomimetic building blocks. It is a versatile acylating agent for propargyl alcohols, hydrazines and amines.

Notes

Store in cool place. Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with alcohols. It reacts with water.

Literature References

Useful synthetic building block, e.g. in an oxazole synthesis: J. Med. Chem., 36, 3871 (1993):

Formation of amides has been used in the syntheses of 1,2,4-triazine-3,6-diones, and of a vicinal tricarbonyl amide derivative of L-phenylalanine: J. Org. Chem., 60, 5992 (1995); 61, 1872 (1996).

Yang, Z.; Li, S.; Zhang, Z.; Xu, J. Base-switched annuloselectivity in the reactions of ethyl malonyl chloride and imines. Org. Biomol. Chem. 2014, 12 (48), 9822-9830.

Hayat, F.; Kang, L.; Lee, C. Y.; Shin, D. Synthesis of arylnaphthalene lignan lactone using benzoin condensation, intramolecular thermal cyclization and Suzuki coupling. Tetrahedron 2015, 71 (19), 2945-2950.

GHS Hazard and Precautionary Statements

Hazard Statements: H227-H314-H335

Combustible liquid. Causes severe skin burns and eye damage. May cause respiratory irritation.

Precautionary Statements: P210-P235-P260-P264b-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
636215
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2917.19
TSCA
No

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