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CAS No.: | 87-13-8 |
---|---|
Name: | Diethyl ethoxymethylenemalonate |
Article Data: | 33 |
Molecular Structure: | |
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 |
orthoformic acid triethyl ester
diethyl malonate
diethyl 2-ethoxymethylenemalonate
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% |
Conditions | Yield |
---|---|
With pyridine for 0.25h; Ambient temperature; | 96% |
phosphoric acid
orthoformic acid triethyl ester
diethyl malonate
diethyl 2-ethoxymethylenemalonate
Conditions | Yield |
---|---|
With acetic anhydride | 92.6% |
acetic anhydride
(E)-3-Ureido-but-2-enoic acid ethyl ester
orthoformic acid triethyl ester
diethyl malonate
diethyl 2-ethoxymethylenemalonate
acetic anhydride
orthoformic acid triethyl ester
diethyl malonate
diethyl 2-ethoxymethylenemalonate
Conditions | Yield |
---|---|
With zinc(II) chloride |
carbon monoxide
orthoformic acid triethyl ester
ethyl iodoacetae
A
ethyl 2-ethoxyethanoate
B
ethyl acetate
C
diethyl 2-ethoxymethylenemalonate
D
diethyl malonate
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; |
diethyl malonate
A
diethoxymethylmalonic acid diethyl ester
B
diethyl 2-ethoxymethylenemalonate
Conditions | Yield |
---|---|
at 116℃; |
diethoxymethyl acetate
diethyl malonate
A
diethoxymethylmalonic acid diethyl ester
B
diethyl 2-ethoxymethylenemalonate
Conditions | Yield |
---|---|
at 116℃; |
diethyl 2-(hydroxymethylene)malonate
A
diethyl 2-ethoxymethylenemalonate
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 |
7-(4-morpholinylmethyl)-3,4-dihydro-2H-1,4-benzoxazine
diethyl 2-ethoxymethylenemalonate
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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. |