Diethyl (ethoxymethylene)malonate

HCID 6871CAS 87-13-8
Substructure searchFind similar structures

Basic information

Standard SMILES
CCOC=C(C(=O)OCC)C(=O)OCC
InChIKey
LTMHNWPUDSTBKD-UHFFFAOYSA-N
Molecular formula
C10H16O5
Average molar mass
216.23 g/mol
Monoisotopic mass
216.09977361

Names & identifiers

Preferred name
Diethyl (ethoxymethylene)malonate
IUPAC
diethyl 2-(ethoxymethylidene)propanedioate
English name
Diethyl ethoxymethylenemalonate
Molecular formula
C10H16O5
Molecular weight
216.23

Names & synonyms

Diethyl ethoxymethylenemalonate87-13-8Diethyl (ethoxymethylene)malonateEthoxymethylenemalonic acid diethyl esterDiethyl EMMEPropanedioic acid, (ethoxymethylene)-, diethyl esterDTXSID5052591NSC-9068MALONIC ACID, (ETHOXYMETHYLENE)-, DIETHYL ESTER6KF8220SZ8NSC-62117DTXCID2031164
Show more names
EMMEDEEMMDiethyl 2-(ethoxymethylene)propanedioatediethyl (ethoxymethylidene)propanedioate2-Ethoxymethylene-malonic acid diethyl esteronatetl1483enemaL
Propanedioic acid, 2-(ethoxymethylene)-, 1,3-diethyl esterRefChem:133377Propanedioic acid, 2-(ethoxymethylene)-, diethyl ester201-725-7Diethyl 2-(ethoxymethylene)malonateDiethyl Ethoxymethylidenemalonate1,3-diethyl 2-(ethoxymethylidene)propanedioateMFCD00009148

Database identifiers

CAS
87-13-8
PubChem CID
6871
DTXSID
DTXSID5052591
UNII
6KF8220SZ8
EC Number
201-725-7
Nikkaji
J61.661C

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
61.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
8
Heavy atoms
15

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Esters, Other

Industrial compound

Physical DescriptionColorless liquid; [Alfa Aesar MSDS]
Ionization Efficiency · 6 items

Positive

2.1

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section146.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID5052591]

Physicochemical properties

Melting point
-33 °C · -33°C
Boiling point
279 · 279-283 °C(lit.)
Density
1.08 g/mL · 1.080 g/mL at 20 °C(lit.)
vapor pressure
0.1 hPa · <0.1 hPa
refractive index
20 · n20/D 1.463
Flash point
311 °F · 311 °F

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (99.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 111 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 29-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/12518

Diethyl ethoxymethylenemalonate: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

A moderate skin irritant; Causes somnolence and gastrointestinal changes in oral lethal-dose studies of rats; [RTECS] An irritant; May cause skin and respiratory sensitization; Harmful by ingestion; [Alfa Aesar MSDS] Search for (87-13-8[EC/RN Number]) AND (allergic OR dermatitis OR asthma OR sensitizer OR sensitization): no results; [PubMed]

Peroxide Forming Chemical · 3 items

Diethyl ethoxymethylenemalonate

D: Other compounds that may form peroxides

Kelly

Hazard Classes and CategoriesAcute Tox. 4 (99.1%)

Toxicology

Toxicity DataLCLo (mouse) = 44 mg/m3

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
OO1100000
hs_code
29189090
Toxicity
LD50 orally in Rabbit: 925 mg/kg LD50 dermal Rat > 2000 mg/kg

Chemistry & industry

Uses & manufacturing

UsesUsed to make fine chemicals; [ExPub: ECHA REACH Registrations]
General Manufacturing InformationPropanedioic acid, 2-(ethoxymethylene)-, 1,3-diethyl ester: ACTIVE
Applications · 1 item

UsesDiethyl ethoxymethylenemalonate is used for synthesis of pyrido[3,2-e]pyrimido[1,2-c]pyrimidines. Initially, it was used to monitor lysine decarboxylase activity. It is useful in the determination of amino acids by precolumn derivatization by using reversed-phase high-performance liquid chromatography (HPLC). It plays an important role in the Gould-Jacobs reaction to prepare quinolines. For example, anile reacts with this reagent to give 4-hydroxyquinoline. It acts as an intermediate in the production of flumequine, which is a fluoroquinolone antibiotic.

Upstream & downstream products

Downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京一化生物科技有限公司13429882898; 13429882898

Related reactions

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Linked notes

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