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% |
ethanol
diethyl 2-(chloromethylene)malonate
diethyl 2-ethoxymethylenemalonate
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
Conditions | Yield |
---|---|
With propionic acid; orthoformic acid triethyl ester; Zinc chloride | |
With FeCl3; acetic anhydride; orthoformic acid triethyl ester |
6-methoxy-pyridin-3-ylamine
diethyl 2-ethoxymethylenemalonate
diethyl {[(6-methoxypyridin-3-yl)amino]methylidene}propanedioate
Conditions | Yield |
---|---|
In ethanol for 4h; Heating / reflux; | 100% |
In ethanol for 4h; Heating / reflux; | 100% |
In ethanol for 4h; Heating / reflux; | 100% |
1-amino-naphthalene
diethyl 2-ethoxymethylenemalonate
2-[(naphthalen-1-ylamino)methylidene]malonic acid diethyl ester
Conditions | Yield |
---|---|
High vacuum; | 100% |
In ethanol at 28℃; for 6h; | 98% |
at 130℃; for 2.75h; Substitution; | 91% |
2-methoxy-phenylamine
diethyl 2-ethoxymethylenemalonate
2-[(2-methoxyphenylamino)-methylene]-malonic acid diethyl ester
Conditions | Yield |
---|---|
In ethanol at 90℃; for 18h; | 100% |
at 130℃; | 99% |
In neat (no solvent) at 120℃; for 0.75h; | 98% |
3-trifluoromethylaniline
diethyl 2-ethoxymethylenemalonate
diethyl 2-({[3-(trifluoromethyl)phenyl]amino}methylidene)propanedioate
Conditions | Yield |
---|---|
at 90 - 110℃; for 1h; | 100% |
In ethanol at 90℃; for 18h; | 100% |
In toluene at 110℃; for 24h; | 98% |
4-chloro-aniline
diethyl 2-ethoxymethylenemalonate
diethyl 4-chloroanilinomethylenemalonate
Conditions | Yield |
---|---|
In toluene at 110℃; | 100% |
In neat (no solvent) at 120℃; for 0.75h; | 98% |
at 110℃; for 0.75h; | 95% |
4-methoxy-aniline
diethyl 2-ethoxymethylenemalonate
diethyl 2-(((4-methoxyphenyl)amino)methylene)malonate
Conditions | Yield |
---|---|
at 14 - 95℃; for 2.91667h; | 100% |
In ethanol for 4h; Heating / reflux; | 100% |
at 100 - 125℃; for 18.5h; | 100% |
4-nitro-aniline
diethyl 2-ethoxymethylenemalonate
ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate
Conditions | Yield |
---|---|
at 120℃; for 3h; Heating / reflux; | 100% |
for 0.025h; Gould-Jacob reaction; Irradiation; | 98% |
In ethanol at 28℃; for 6h; | 95% |
aniline
diethyl 2-ethoxymethylenemalonate
diethyl (anilinomethylene)malonate
Conditions | Yield |
---|---|
at 120 - 130℃; for 16.5h; Temperature; | 100% |
In ethanol at 28℃; for 0.333333h; | 98% |
In neat (no solvent) at 120℃; for 0.75h; | 98% |
3-chloro-aniline
diethyl 2-ethoxymethylenemalonate
2-(3-chlorophenylamino)methylenemalonic acid diethyl ester
Conditions | Yield |
---|---|
In toluene at 110℃; for 24h; | 100% |
In neat (no solvent) at 120℃; for 0.75h; | 98% |
In ethanol for 3h; Reflux; | 91% |
diethyl 2-ethoxymethylenemalonate
3-Iodoaniline
diethyl 2-(((3-iodophenyl)amino)methylene)malonate
Conditions | Yield |
---|---|
at 90 - 110℃; for 1h; | 100% |
In ethanol | 100% |
at 110℃; | 97% |
diethyl 2-ethoxymethylenemalonate
3-bromoaniline
ethyl α-carbethoxy-β-m-bromoanilinoacrylate
Conditions | Yield |
---|---|
at 90 - 110℃; for 1h; | 100% |
In toluene at 110℃; for 24h; | 100% |
In toluene for 1h; Inert atmosphere; Reflux; | 91% |
diethyl 2-ethoxymethylenemalonate
methylamine
Diethyl ethoxymethylenemalonate
Conditions | Yield |
---|---|
In toluene at 100℃; for 2h; Condensation; | 100% |
In ethanol; water Heating; |
diethyl 2-ethoxymethylenemalonate
benzylamine
2-(benzylamino-methylene)-malonic acid diethyl ester
Conditions | Yield |
---|---|
In ethanol at 28℃; | 100% |
propylamine
diethyl 2-ethoxymethylenemalonate
diethyl 2-((propylamino)methylene)malonate
Conditions | Yield |
---|---|
In methanol for 0.5h; | 100% |
In methanol for 0.25h; Ambient temperature; | 81% |
In ethanol Heating; |
Conditions | Yield |
---|---|
With ammonia In ethanol | 100% |
With ammonia In ethanol at 20℃; for 1h; | 96% |
With ammonium hydroxide |
benzo[1,3]dioxolo-5-ylamine
diethyl 2-ethoxymethylenemalonate
diethyl [[3,4-(methylenedioxy)phenylamino]methylene]malonate
Conditions | Yield |
---|---|
In ethanol at 90℃; for 18h; | 100% |
In benzene for 3.5h; Reflux; | 96% |
In benzene for 3.5h; Heating; | 71% |
In benzene for 3h; Reflux; |
isopropylamine
diethyl 2-ethoxymethylenemalonate
ethyl 3-isopropylamino-2-ethoxycarbonylpropenoate
Conditions | Yield |
---|---|
at 20℃; for 1.08333h; Cooling with ice; | 100% |
In methanol for 0.25h; Ambient temperature; | 93% |
5-Amino-1-ethylpyrazole
diethyl 2-ethoxymethylenemalonate
[[(1-ethyl-5-pyrazolyl)amino]methylene]malonic acid diethyl ester
Conditions | Yield |
---|---|
at 120℃; for 1h; | 100% |
at 120℃; for 1h; | 100% |
at 120℃; for 4h; | 86% |
diethyl 2-ethoxymethylenemalonate
Cyclopropylamine
<(Cyclopropylamino)methylene>propanedioic acid diethyl ester
Conditions | Yield |
---|---|
In methanol at 0℃; for 0.25h; | 100% |
at 20℃; for 0.683333h; Cooling with ice; | 100% |
98.1% | |
In ethanol at 320℃; for 0.5h; | 98% |
In acetonitrile at 20 - 80℃; |
diethyl 2-ethoxymethylenemalonate
3,4-dimethoxyaniline
[[(3,4-Dimethoxyphenyl)amino]methylene]malonic acid,diethyl ester
Conditions | Yield |
---|---|
In ethanol at 90℃; for 18h; | 100% |
In acetonitrile Ambient temperature; | 68% |
at 90 - 100℃; for 1h; |
3-chloro-4-fluorophenylamine
diethyl 2-ethoxymethylenemalonate
diethyl 2-[(3-chloro-4-fluorophenylamino)methylene]malonate
Conditions | Yield |
---|---|
at 120 - 130℃; for 2h; | 100% |
for 0.0333333h; Gould-Jacob reaction; Irradiation; | 99% |
at 110℃; for 1h; Microwave irradiation; | 99% |
3,4-difluoro-2-(2-hydroxypropyl)aniline
diethyl 2-ethoxymethylenemalonate
<<(3,4-difluoro-2-(2-hydroxypropyl)phenyl)amino>methylene>propanedioic acid diethyl ester
Conditions | Yield |
---|---|
at 150 - 160℃; for 0.333333h; | 100% |
In hexane | 62% |
m-Anisidine
diethyl 2-ethoxymethylenemalonate
Diethyl 2-<(3-methoxyphenylamino)methylene>malonate
Conditions | Yield |
---|---|
at 90 - 110℃; for 1h; | 100% |
at 125℃; for 3h; | 99% |
In neat (no solvent) at 120℃; for 0.75h; | 98% |
meta-fluoroaniline
diethyl 2-ethoxymethylenemalonate
diethyl 2-(((3-fluorophenyl)amino)methylene)malonate
Conditions | Yield |
---|---|
for 2h; Heating; | 100% |
at 90 - 110℃; for 1h; | 100% |
In toluene at 110℃; for 24h; | 100% |
2-phenylaniline
diethyl 2-ethoxymethylenemalonate
diethyl 2-((biphenyl-2-ylamino)methylene)malonate
Conditions | Yield |
---|---|
at 120℃; for 1h; Gould-Jacobs Reaction; | 100% |
p-benzylaniline
diethyl 2-ethoxymethylenemalonate
diethyl {[(4-benzylphenyl)amino]methylidene}propanedioate
Conditions | Yield |
---|---|
at 130℃; for 2h; | 100% |
at 130℃; for 3h; | 100% |
3-methylmercaptoaniline
diethyl 2-ethoxymethylenemalonate
diethyl 2-[[(3-methylthio)phenylamino]methylene]malonate
Conditions | Yield |
---|---|
In ethanol at 90℃; for 18h; | 100% |
In toluene Heating; |
allyl bromide
aniline
diethyl 2-ethoxymethylenemalonate
diethyl (anilinomethylene)malonate
Conditions | Yield |
---|---|
Stage #1: allyl bromide With indium In tetrahydrofuran at 20℃; for 1h; Stage #2: aniline; diethyl 2-ethoxymethylenemalonate In tetrahydrofuran for 2h; | 100% |
4-Isopropylaniline
diethyl 2-ethoxymethylenemalonate
diethyl 4-i-propylanilinomethylenemalonate
Conditions | Yield |
---|---|
at 130℃; for 2h; | 100% |
at 120℃; for 4h; Inert atmosphere; |
Conditions | Yield |
---|---|
at 130℃; for 2h; | 100% |
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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