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Diethyl ethoxymethylenemalonate

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Name

Diethyl ethoxymethylenemalonate

EINECS 201-725-7
CAS No. 87-13-8 Density 1.08 g/cm3
PSA 61.83000 LogP 1.03300
Solubility Insoluble in water Melting Point -33 °C
Formula C10H16O5 Boiling Point 280 °C at 760 mmHg
Molecular Weight 216.234 Flash Point 107.6 °C
Transport Information N/A Appearance clear colourless to light yellow liquid
Safety 26-36/37/39-27-24/25 Risk Codes 22-36/37/38-42/43
Molecular Structure Molecular Structure of 87-13-8 (Diethyl ethoxymethylenemalonate) Hazard Symbols HarmfulXn
Synonyms

Malonicacid, (ethoxymethylene)-, diethyl ester (6CI,7CI,8CI);Propanedioic acid,(ethoxymethylene)-, diethyl ester (9CI);(Ethoxymethylene)malonic acid diethylester;(Ethoxymethylene)propanedioic acid diethyl ester;2-(Ethoxymethylene)malonic acid diethyl ester;2-Ethoxy-1,1-bis(ethoxycarbonyl)ethene;Diethyl (ethoxymethylene)malonate;Diethyl (ethoxymethylene)propanedioate;Diethyl 2-(ethoxymethylene)malonate;Diethyl 2-(ethoxymethylidene)propanedioate;Diethyl[(ethyloxy)methylidene]propanedioate;Ethyl3-ethoxy-2-(ethoxymethylene)-3-oxopropanoate;NSC 62117;NSC 9068;

Article Data 33

Diethyl ethoxymethylenemalonate Synthetic route

122-51-0

orthoformic acid triethyl ester

105-53-3

diethyl malonate

87-13-8

diethyl 2-ethoxymethylenemalonate

Conditions
ConditionsYield
With 1,2-bis(N-methylimidazolium)ethanechloroaluminate; acetic anhydride at 125℃; for 8h; Reagent/catalyst; Temperature;98.86%
With acetic anhydride; zinc(II) chloride for 4h; Inert atmosphere; Reflux;97%
With acetic anhydride; zinc(II) chloride Heating;72%
64-17-5

ethanol

28783-51-9

diethyl 2-(chloromethylene)malonate

87-13-8

diethyl 2-ethoxymethylenemalonate

Conditions
ConditionsYield
With pyridine for 0.25h; Ambient temperature;96%
86119-84-8, 7664-38-2

phosphoric acid

122-51-0

orthoformic acid triethyl ester

105-53-3

diethyl malonate

87-13-8

diethyl 2-ethoxymethylenemalonate

Conditions
ConditionsYield
With acetic anhydride92.6%
108-24-7

acetic anhydride

5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

122-51-0

orthoformic acid triethyl ester

105-53-3

diethyl malonate

87-13-8

diethyl 2-ethoxymethylenemalonate

108-24-7

acetic anhydride

122-51-0

orthoformic acid triethyl ester

105-53-3

diethyl malonate

87-13-8

diethyl 2-ethoxymethylenemalonate

Conditions
ConditionsYield
With zinc(II) chloride
201230-82-2

carbon monoxide

122-51-0

orthoformic acid triethyl ester

623-48-3

ethyl iodoacetae

A

817-95-8

ethyl 2-ethoxyethanoate

B

141-78-6

ethyl acetate

C

87-13-8

diethyl 2-ethoxymethylenemalonate

D

105-53-3

diethyl malonate

Conditions
ConditionsYield
With triphenylphosphine; dodecacarbonyltetrarhodium(0) at 120℃; under 76000 Torr; for 12h; Product distribution; Parr autoclave; further catalysts;
With triphenylphosphine; rhodium(III) chloride at 120℃; under 76000 Torr; for 12h; Parr autoclave; Yield given. Yields of byproduct given;
105-53-3

diethyl malonate

diethoxymethyl acetate

diethoxymethyl acetate

ZnCl2

ZnCl2

A

7251-32-3

diethoxymethylmalonic acid diethyl ester

B

87-13-8

diethyl 2-ethoxymethylenemalonate

Conditions
ConditionsYield
at 116℃;
14036-06-7

diethoxymethyl acetate

105-53-3

diethyl malonate

ZnCl2

ZnCl2

A

7251-32-3

diethoxymethylmalonic acid diethyl ester

B

87-13-8

diethyl 2-ethoxymethylenemalonate

Conditions
ConditionsYield
at 116℃;
20734-18-3

diethyl 2-(hydroxymethylene)malonate

A

87-13-8

diethyl 2-ethoxymethylenemalonate

B

sodium compound of acetonedicarboxylic acid diethyl ester

sodium compound of acetonedicarboxylic acid diethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 77 percent / SOCl2, DMF / toluene / Heating
2: 96 percent / pyridine / 0.25 h / Ambient temperature
View Scheme
333780-72-6

7-(4-morpholinylmethyl)-3,4-dihydro-2H-1,4-benzoxazine

87-13-8

diethyl 2-ethoxymethylenemalonate

Diethyl ethoxymethylenemalonate Consensus Reports

Reported in EPA TSCA Inventory.

Diethyl ethoxymethylenemalonate Specification

The IUPAC name of Ethoxymethylenemalonic acid, ethyl ester is diethyl 2-(ethoxymethylidene)propanedioate. With the CAS registry number 87-13-8, it is also named as Propanedioic acid, (ethoxymethylene)-, diethyl ester; Diethyl (ethoxymethylidene)propanedioate. The product's categories are pharmaceutical intermediates, carbonyl compounds and esters. In addition, it is clear colourless to light yellow liquid which is insoluble in water.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.44; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.44; (4)ACD/LogD (pH 7.4): 1.44; (5)ACD/BCF (pH 5.5): 7.26; (6)ACD/BCF (pH 7.4): 7.26; (7)ACD/KOC (pH 5.5): 143.88; (8)ACD/KOC (pH 7.4): 143.88; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.447; (13)Molar Refractivity: 53.57 cm3; (14)Molar Volume: 200.3 cm3; (15)Polarizability: 21.23×10-24 cm3; (16)Surface Tension: 33.6 dyne/cm; (17)Enthalpy of Vaporization: 51.87 kJ/mol; (18)Vapour Pressure: 0.00388 mmHg at 25°C; (19)Rotatable Bond Count: 8; (20)Exact Mass: 216.099774; (21)MonoIsotopic Mass: 216.099774; (22)Topological Polar Surface Area: 61.8; (23)Heavy Atom Count: 15.

Preparation of Ethoxymethylenemalonic acid, ethyl ester: It can be obtained by triethoxymethane and malonic acid diethyl ester with the reagent acetic acid anhydride and ZnCl.
 

Uses of Ethoxymethylenemalonic acid, ethyl ester: It is an important organic raw materials and it is now mainly used for synthesis of gatifloxacin. For example: It can react with 6-methyl-pyridin-2-ylamine to get [(6-methyl-pyridin-2-ylamino)-methylene]-malonic acid diethyl ester. The reaction temperature is 110 °C.

  

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and is irritating to eyes, respiratory system and skin, so people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES: O=C(OCC)\C(=C\OCC)C(=O)OCC;
2. InChI: InChI=1/C10H16O5/c1-4-13-7-8(9(11)14-5-2)10(12)15-6-3/h7H,4-6H2,1-3H3.

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LCLo inhalation 44mg/m3 (44mg/m3)   National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. 30101, Pg. 11, 1945.
mouse LD50 oral 2227mg/kg (2227mg/kg)   Journal of Pharmaceutical Sciences. Vol. 60, Pg. 1810, 1971.
rat LD50 oral 925mg/kg (925mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES
Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 37, 1990.

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