Basic information
- CAS
36239-09-5- Standard SMILES
CCOC(=O)CC(=O)Cl- InChIKey
KWFADUNOPOSMIJ-UHFFFAOYSA-N- Molecular formula
- C5H7ClO3
- Average molar mass
- 150.56 g/mol
- Monoisotopic mass
- 150.00837176
Names & identifiers
- Preferred name
- Ethyl 3-chloro-3-oxopropionate
- IUPAC
- ethyl 3-chloro-3-oxopropanoate
- English name
- Ethyl malonyl chloride
- Molecular formula
- C5H7ClO3
- Molecular weight
- 150.56
Names & synonyms
36239-09-5ethyl 3-chloro-3-oxopropanoateEthyl 3-chloro-3-oxopropionatePropanoic acid, 3-chloro-3-oxo-, ethyl ester6TYB4UU3RUEINECS 252-934-53-chloro-3-oxopropanoic acid ethyl esterDTXSID80189786RefChem:138683DTXCID40112277252-934-5InChI=1/C5H7ClO3/c1-2-9-5(8)3-4(6)7/h2-3H2,1H
Show more names
ethyl chlorocarbonylacetateEthyl 3-oxo-3-chloropropanoateAURORA KA-3051Ethyl Maloriyl ChlorideEthylMalonylChloride>Tofacitinib Impurity 153Ethylmalonylchloride,95%Ethylmalonoyl dichloride
Ethyl malonyl chlorideEthyl chloroformylacetateEthyl MalonylchlorideMFCD00000736ethyl 3-chloro-3-oxo-propanoateethyl 2-(chlorocarbonyl)acetate(Chloroformyl)acetic Acid Ethyl EsterCarbethoxyacetyl chloride
Database identifiers
- CAS
36239-09-5- PubChem CID
- 118931
- DTXSID
DTXSID80189786- UNII
- 6TYB4UU3RU
- EC Number
- 252-934-5
- Nikkaji
- J148.007C
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 121
Physicochemical properties
- Boiling point
- 79 · 79-80 °C25 mm Hg(lit.)
- Density
- 1.196 g/mL · 1.196 g/mL at 20 °C
- refractive index
- 20 · n20/D 1.429(lit.)
- Flash point
- 154 °F · 154 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Soluble), DMSO (Sparingly), Ethyl Acetate (Slightly)
- form
- Liquid
- pka
- 9.35 · 9.35±0.46(Predicted)
- Specific Gravity
- 1.176 · 1.176
- color
- Clear yellow to brown
- Water Solubility
- REACTS
- Sensitive
- Moisture Sensitive
- BRN
- 636215 · 636215
- Stability
- Hygroscopic, Moisture Sensitive
- InChI
- 1S/C5H7ClO3/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3
- InChIKey
- KWFADUNOPOSMIJ-UHFFFAOYSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 55 reports by companies from 7 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Status: Active Update: 25-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20725
Propanoic acid, 3-chloro-3-oxo-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Corr. 1B (100%)
Safety data
- F
- 10-21
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- ridadr
- UN 3265 8/PG 3
- hs_code
- 29171900
- risk_code
- 14-34
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C
- hazard_note
- Corrosive
- safety_code
- 7-26-36/37/39-45-36/39
- hazard_class
- 8
Chemistry & industry
Applications
UsesEmployed in the synthesis of 3-pyrrolin-2-ones via amidation with propargylamines and subsequent base catalyzed 5-exo-dig cyclization.1
UsesEthyl 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.
General DescriptionEthyl malonyl chloride is a versatile acylating agent for propargyl alcohols, hydrazines and amines.
Upstream & downstream products
Downstream products
Related reactions
163 records
Compound notes
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