Basic information
- Standard SMILES
CCOC(=O)CC(=O)CCl- InChIKey
OHLRLMWUFVDREV-UHFFFAOYSA-N- Molecular formula
- C6H9ClO3
- Average molar mass
- 164.59 g/mol
- Monoisotopic mass
- 164.02402183
Names & identifiers
- Preferred name
- Ethyl 4-chloroacetoacetate
- IUPAC
- ethyl 4-chloro-3-oxobutanoate
- English name
- Ethyl 4-chloroacetoacetate
- Molecular formula
- C6H9ClO3
- Molecular weight
- 164.59
Names & synonyms
Ethyl 4-chloroacetoacetate638-07-3Ethyl 4-chloro-3-oxobutanoateButanoic acid, 4-chloro-3-oxo-, ethyl esterEthyl gamma-chloroacetoacetateDTXSID4044454Acetoacetic acid, 4-chloro-, ethyl ester5AE82250CMDTXCID2024454COBE cpdECA cpdRefChem:595395
Show more names
oroacetoacetateAKOS BBS-00004336Ethyl 4-chloroacetoa4-Chloro-acetoaceticAmlodipine Impurity 66Oxiracetam Impurity 15
211-317-04-Chloroacetoacetic acid ethyl esterMFCD00000939Ethyl (Chloroacetyl)acetateEthyl 4-Chloro-3-oxobutyrate4-chloro-3-oxobutanoic acid ethyl esterAmlodipine Impurity Rethyl 4-chloro-3-oxo-butanoate
Database identifiers
- CAS
638-07-3- PubChem CID
- 69484
- DTXSID
DTXSID4044454- ChEMBL
CHEMBL3187729- UNII
- 5AE82250CM
- EC Number
- 211-317-0
- Nikkaji
- J24.754E
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 133
Experimental & physicochemical properties
SpringerMaterials PropertiesOptical coefficient
Physicochemical properties
- Melting point
- -8 °C · -8 °C
- Boiling point
- 115 °C/14 · 115 °C/14 mmHg (lit.)
- Density
- 1.218 g/mL · 1.218 g/mL at 25 °C (lit.)
- vapor pressure
- 7 hPa · 7hPa at 20℃
- refractive index
- 20 · n20/D 1.452(lit.)
- Flash point
- 206 °F · 206 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 47 g/l · 47.0g/l
- form
- Liquid
- pka
- 9.56 · 9.56±0.46(Predicted)
- color
- Clear colorless to pale reddish-yellow
- PH
- 2.9 · 2.9 (10g/l, H2O, 20℃)
- explosive limit
- 1.8 % · 1.8%(V)
- Water Solubility
- 47.5 g/L · 47.5 g/L (20 ºC)
- BRN
- 1761275 · 1761275
- InChI
- 1S/C6H9ClO3/c1-2-10-6(9)3-5(8)4-7/h2-4H2,1H3
- InChIKey
- OHLRLMWUFVDREV-UHFFFAOYSA-N
- SMILES
- CCOC(=O)CC(=O)CCl
- LogP
- 0.68 at · 0.68 at 25℃
- CAS DataBase Reference
- 638 · 638-07-3(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 5 AE82250CM · 5AE82250CM
- NIST Chemistry Reference
- 4 · Butanoic acid, 4-chloro-3-oxo-, ethyl ester(638-07-3)
- EPA Substance Registry System
- 4 · Ethyl 4-chloroacetoacetate (638-07-3)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS06,GHS09
- Signal word
- Danger
- Hazard statements
- 301 · H301+H311-H314-H411
- Precautionary statements
- 270 · P270-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- T,N,C
- Risk Statements
- 25 · 25-34-51/53-24/25-36
- Safety Statements
- 26 · 26-36-45-61-36/37/39-27
- RIDADR
- 2922 · UN 2922 8/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 5110000 · AK5110000
- F
- 8 · 8-10-19-21
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29183000 · 29183000
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Skin Corr. 1B
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P261, P262, P264, P264+P265, P270, P272, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 77 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Butanoic acid, 4-chloro-3-oxo-, ethyl ester
Status: Active Update: 24-11-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21272
Ethyl 4-chloroacetoacetate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- F
- 8-10-19-21
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AK5110000
- ridadr
- UN 2922 8/PG 2
- hs_code
- 29183000
- risk_code
- 25-34-51/53-24/25-36
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06,GHS09
- hazard_code
- T,N,C
- safety_code
- 26-36-45-61-36/37/39-27
- hazard_class
- 8
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- Hazard statements
- H301+H311-H314-H411
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Skin Corr. 1B
- Precautionary statements
- P270-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationButanoic acid, 4-chloro-3-oxo-, ethyl ester: ACTIVE
Applications
DescriptionEthyl 4-chloroacetoacetate is a chemical compound, which for the ethyl esters of acetoacetic acid belongs. It is a starting material in various syntheses.
UsesEthyl-4-chloracetoacetate (CAAEt) is used as intermediate for organic syntheses, e.g. ethyl 4-chloro-3-arylaminocrotonates, diethyl succinylsuccinate, 2-alkyl-4-hydroxy-6-chloromethylpyrimidines, 4- chloromethylcoumarines. Product Data Sheet
UsesEthyl 4-chloroacetoacetate is used as a precursor in the preparation of phosphorous ylides. It finds application in regular film coating, pharmaceutical coating and formulation.
Preparation methods
PreparationPreparative Methods of Ethyl 4-chloroacetoacetate: the industrial production of the esters is made exclusively by chlorination of diketene followed by reaction of the intermediate acid chloride with the corresponding alcohol.[2]
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
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