Name: Diethyl ethoxymethylenemalonate
SKU: 87-13-8

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Basic Information

Molecular Structure:
CAS No.:	87-13-8
Name:	Diethyl ethoxymethylenemalonate

Formula:	C₁₀H₁₆O₅
Molecular Weight:	216.234
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;
EINECS:	201-725-7
Density:	1.08 g/cm³
Melting Point:	-33 °C
Boiling Point:	280 °C at 760 mmHg
Flash Point:	107.6 °C
Solubility:	Insoluble in water
Appearance:	clear colourless to light yellow liquid
Hazard Symbols:	Xn
Risk Codes:	22-36/37/38-42/43
Safety:	26-36/37/39-27-24/25
PSA:	61.83000
LogP:	1.03300

Synthetic route

: 122-51-0
orthoformic acid triethyl ester

: 105-53-3
diethyl malonate

: 87-13-8
diethyl 2-ethoxymethylenemalonate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With acetic anhydride	92.6%

...Expand

: 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

...Expand

: 108-24-7
acetic anhydride

: 122-51-0
orthoformic acid triethyl ester

: 105-53-3
diethyl malonate

: 87-13-8
diethyl 2-ethoxymethylenemalonate

Conditions

Conditions	Yield
With zinc(II) chloride

...Expand

: 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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
at 116℃;

...Expand

: 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

Conditions	Yield
at 116℃;

...Expand

: 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

Conditions	Yield
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

Raw Materials

623-48-3

122-51-0

64-17-5

Downstream Products

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Consensus Reports

Reported in EPA TSCA Inventory.

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.

87-13-8

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Consensus Reports

Specification