| Identification | More | [Name]
Diethyl ethoxymethylenemalonate | [CAS]
87-13-8 | [Synonyms]
1,1-DICARBETHOXY-2-ETHOXYETHYLENE
2,2-DICARBETHOXYVINYL ETHYL ETHER
AKOS BBS-00004230
DIETHYL ETHOXYMETHYLENEMALONATE
EMME
ETHOXYMETHYLENEMALONIC ACID DIETHYL ESTER
(Ethoxymethylene)-propanedioic acid diethyl ester
ETHOXYMETHYLENMALONIC ACID DIETHYL ESTER
ETHYL 3-ETHOXY-2-(ETHOXYCARBONYL)ACRYLATE
ETHYL A-CARBETHOXY-B-ETHOXYACRYLATE
ETHYL ETHOXYMETHYLENE MALONATE
LABOTEST-BB LT02094814
(ethoxymethylene)-malonicacidiethylester
(ethoxymethylene)-propanedioicacidiethylester
Diethyl 2-(ethoxymethylene)malonate
diethylemme
ethoxymethylenemalonicacid,ethylester
Malonic acid, (ethoxymethylene)-, diethyl ester
Propanedioicacid,(ethoxymethylene)-,diethylester
tl1483 | [EINECS(EC#)]
201-725-7 | [Molecular Formula]
C10H16O5 | [MDL Number]
MFCD00009148 | [Molecular Weight]
216.23 | [MOL File]
87-13-8.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS TO LIGHT YELLOW LIQUID | [Melting point ]
-33°C | [Boiling point ]
279-283 °C(lit.)
| [density ]
1.080 g/mL at 20 °C(lit.)
| [vapor pressure ]
<0.1 hPa | [refractive index ]
n20/D 1.463
| [Fp ]
311 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Liquid | [color ]
Clear colorless to light yellow | [Water Solubility ]
insoluble | [BRN ]
880058 | [InChI]
1S/C10H16O5/c1-4-13-7-8(9(11)14-5-2)10(12)15-6-3/h7H,4-6H2,1-3H3 | [InChIKey]
LTMHNWPUDSTBKD-UHFFFAOYSA-N | [SMILES]
CCO\C=C(\C(=O)OCC)C(=O)OCC | [LogP]
1.5-2.1 at pH7 | [CAS DataBase Reference]
87-13-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Propanedioic acid, (ethoxymethylene)-, diethyl ester(87-13-8) | [EPA Substance Registry System]
87-13-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
1
| [RTECS ]
OO1100000
| [Autoignition Temperature]
215 °C | [TSCA ]
Yes | [HS Code ]
29189090 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 2
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1A | [Safety Profile]
Moderately toxic by
ingestion. A skin irritant. A combustible
liquid. When heated to decomposition it
emits acrid smoke and irritating fumes. | [Toxicity]
LD50 orally in Rabbit: 925 mg/kg LD50 dermal Rat > 2000 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Triethyl orthoformate-->Diethyl malonate | [Preparation Products]
Norfloxacin-->Alachlor-->Lomefloxacin-->Orotic acid-->ETHYL 4-CHLORO-3-METHYLTHIENO[2,3-B]PYRIDINE-5-CARBOXYLATE-->Ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate-->ETHYL 4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLATE-->Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate-->5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one-->Levofloxacin-->7-TRIFLUOROMETHYL-4-QUINOLINETHIOL-->1,4-DIHYDRO-2-(METHYLTHIO)-4-OXO-5-PYRIMIDINE-CARBOXYLATE ACID ETHYL ESTER-->7-BROMO-3,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID-->7-(TRIFLUOROMETHYL)-4-QUINOLINOL-->4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID-->Fleroxacin-->4-HYDROXY-2-METHYL-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER-->Nalidixic acid-->ETHYL 4-CHLOROTHIENO[2,3-B]PYRIDINE-5-CARBOXYLATE-->4-HYDROXY-2-PHENYL-5-PYRIMIDINECARBOXYLIC ACID-->3,4-DIHYDRO-8-HYDROXY-4-OXOQUINOLINE-3-CARBOXYLIC ACID-->Ethyl 7-bromo-3,4-dihydro-4-oxoquinoline-3-carboxylate ,97%-->4-AMINO-2-METHYLSULFANYL-PYRIMIDINE-5-CARBOXYLIC ACID-->4-HYDROXY-8-METHOXYQUINOLINE-3-CARBOXYLIC ACID-->6-CHLORO-[1,2,4]TRIAZOLO[4,3-B]PYRIDAZINE-->ETHYL 4-HYDROXY-7-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE-->Ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylate-->Decoquinate-->4-HYDROXY-8-METHOXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR COLOURLESS TO LIGHT YELLOW LIQUID | [Uses]
Intermediate in the production of Flumequine | [Synthesis]
The synthesis of diethyl ethoxymethylidenemalonate is usually carried out using diethyl malonate and triethyl orthoformate in a condensation reaction and the removal of a molecule of ethanol to obtain the condensation intermediate, which then eliminate | [Purification Methods]
Likely impurity is diethyl diethoxymethylene malonate which is difficult to separate from diethyl ethoxymethylene malonate by distillation, and it is necessary to follow the course of the distillation by the change in refractive index instead of boiling point. After a low boiling fraction is collected, there is obtained an intermediate fraction (n 20 1.414—1.458), the size of which depends on the amount of the diethoxymethylene compound. This fraction is fractionated through a 5inch Vigreux column (p 11) at low pressure avoiding interruption in heating. Fraction b 108-110o/0.25mm is ca 10o lower than the submitters' fraction (b 97.2o/0.25mm, n D 1.4612—1.4623) [Org Synth Coll Vol III 395 1955, Fuson et al. J Org Chem 11 197 1946, Duff & Kendal J Chem Soc 893 1948]. [Beilstein 3 IV 1192.] |
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