Basic information
- Standard SMILES
CCOC(=O)C(NC(C)=O)C(=O)OCC- InChIKey
ISOLMABRZPQKOV-UHFFFAOYSA-N- Molecular formula
- C9H15NO5
- Average molar mass
- 217.22 g/mol
- Monoisotopic mass
- 217.09502258
Names & identifiers
- Preferred name
- Acetamidomalonic acid diethyl ester
- IUPAC
- diethyl 2-acetamidopropanedioate
- English name
- Diethyl acetamidomalonate
- Molecular formula
- C9H15NO5
- Molecular weight
- 217.22
Names & synonyms
Diethyl acetamidomalonate1068-90-2Diethyl 2-acetamidomalonateDiethyl acetaminomalonateACETAMIDOMALONIC ACID DIETHYL ESTERDiethyl acetylaminomalonatePropanedioic acid, (acetylamino)-, diethyl esterDiethyl (N-acetylamino)malonate(Acetylamino)propanedioic acid diethyl esterMalonic acid, acetamido-, diethyl esterNSC 7645Diethylester kyseliny acetylaminomalonove
Show more names
ETHYL ACETAMIDOMALONATEAA-DEMAURORA KA-3269ACETAMIDO DIETHYL MALONATEdiethyl 2-acetamidopropanedioate2-ACETYLAMINO-MALONIC ACID DIETHYL ESTER2-(Acetylamino)propanedioic acid diethyl ester
HSDB 2664EINECS 213-952-9Propanedioic acid, 2-(acetylamino)-, 1,3-diethyl esterBRN 07838834VDX81E00WAI3-52334NSC-7645Diethylester kyseliny acetylaminomalonove [Czech]
Database identifiers
- CAS
1068-90-2- PubChem CID
- 14041
- DTXSID
DTXSID6061446- ChEMBL
CHEMBL3278808- UNII
- 4VDX81E00W
- EC Number
- 213-952-9
- Nikkaji
- J41.609F
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 81.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 233
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
Color/FormCRYSTALS FROM ALCOHOL OR BENZENE-PETROLEUM ETHER
SolubilitySLIGHTLY SOL IN HOT WATER & ETHER; SOL IN HOT ALCOHOL
Boiling Point185 °C @ 20 MM HG
Melting Point95-96 °C
Physical DescriptionSolid; [HSDB] White crystalline powder; [MSDSonline]
Physicochemical properties
- Melting point
- 95 · 95-98 °C (lit.)
- Boiling point
- 185 °C/20 · 185 °C/20 mmHg (lit.)
- Density
- 1.285 · 1.2850 (rough estimate)
- refractive index
- 1.464 · 1.4640 (estimate)
- Flash point
- 185 °C/20mm · 185°C/20mm
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 11.93 · 11.93±0.59(Predicted)
- form
- Crystalline Powder
- color
- White to light yellow
- Water Solubility
- Soluble in chloroform and methanol. Slightly soluble in water.
- BRN
- 783883 · 783883
- InChI
- 1S/C9H15NO5/c1-4-14-8(12)7(10-6(3)11)9(13)15-5-2/h7H,4-5H2,1-3H3,(H,10,11)
- InChIKey
- ISOLMABRZPQKOV-UHFFFAOYSA-N
- SMILES
- CCOC(=O)C(NC(C)=O)C(=O)OCC
- CAS DataBase Reference
- 1068 · 1068-90-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 VDX81E00W · 4VDX81E00W
- NIST Chemistry Reference
- Propanedioic acid, (acetylamino)-, diethyl ester(1068-90-2)
- EPA Substance Registry System
- 2 · Propanedioic acid, 2-(acetylamino)-, 1,3-diethyl ester (1068-90-2)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314-H290
- Precautionary statements
- 501 · P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36-36/37/38
- Safety Statements
- 39 · 39-36-26-44
- WGK Germany
- 3 · 3
- RTECS
- 360000 · OO0360000
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29241900 · 29241900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazardous Substances Data
- 1068 · 1068-90-2(Hazardous Substances Data)
- Toxicity
- 500 mg/24H · eye-rbt 500 mg/24H MLD 28ZPAK -,130,72
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 35% (7 of 20) of reports.
Warning
H302 (40%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 20 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 09-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/21961
Propanedioic acid, (acetylamino)-, diethyl ester: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryEmergency treatment: Irritants; [HSDB] A mild eye irritant; [RTECS] An irritant; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (40%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- OO0360000
- hs_code
- 29241900
- Toxicity
- eye-rbt 500 mg/24H MLD 28ZPAK -,130,72
- risk_code
- 36-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- safety_code
- 39-36-26-44
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H314-H290
- REACH Registrations
- Active
- Precautionary statements
- P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
- Hazardous Substances Data
- 1068-90-2(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationPropanedioic acid, 2-(acetylamino)-, 1,3-diethyl ester: ACTIVE
Applications
UsesDiethyl acetamidomalonate is a versatile building block used for the synthesis of various pharmaceutical and biologically active compounds. It is an intermediate for the preparation of Novobiocin analogues as potential heat shock protein 90 inhibitors. It is also used as a important intermediates in syntheses of vitamins B1 and B6, barbiturates, non-steroidal anti-inflammatory agents, other numerous pharmaceuticals.
Upstream & downstream products
Upstream raw materials
Downstream products
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