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| CAS No.: | 83-13-6 |
|---|---|
| Name: | Diethyl phenylmalonate |
| Article Data: | 74 |
| Molecular Structure: | |
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| Formula: | C13H16O4 |
| Molecular Weight: | 236.268 |
| Synonyms: | Propanedioic acid, phenyl-, diethyl ester;diethyl 2-phenylpropanedioate;Malonic acid, phenyl-, diethyl ester (8CI);Phenylmalonic acid diethyl ester;Malonic acid, phenyl-, diethyl ester;phenyl ethyl malonic acid diethylester;Diethyl phenyl malonate;Phenyldiethylmalonate; |
| EINECS: | 201-456-5 |
| Density: | 1.111 g/cm3 |
| Melting Point: | 16 °C |
| Boiling Point: | 301 °C at 760 mmHg |
| Flash Point: | 141.8 °C |
| Solubility: | immiscible with water |
| Appearance: | clear colourless to yellowish liquid after melting |
| Safety: | 23-24/25 |
| PSA: | 52.60000 |
| LogP: | 1.89640 |
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| Conditions | Yield |
|---|---|
| With barium dihydroxide; sodium tetrachloropalladate(II) In N,N-dimethyl acetamide at 100℃; for 14h; | 100% |
| With N,N'-(1R,2R)-cyclohexane-1,2-diyl-bis-[1-(pyridine-2-yl)methanimine]; 3 A molecular sieve; caesium carbonate; copper(l) iodide In acetonitrile at 70℃; for 30h; | 93% |
| With copper(l) iodide; caesium carbonate In 1,4-dioxane at 70℃; for 2h; | 93% |
| Conditions | Yield |
|---|---|
| With barium dihydroxide; sodium tetrachloropalladate(II) In N,N-dimethyl acetamide at 100℃; for 14h; | 99% |
| With di-tert-butyl(neopentyl)phosphine; sodium hydride; bis(dibenzylideneacetone)-palladium(0) In toluene; mineral oil at 70℃; for 24h; | 89% |
| With tri-tert-butyl phosphine; sodium hydride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 70℃; for 1h; | 87% |
| Conditions | Yield |
|---|---|
| With barium dihydroxide; sodium tetrachloropalladate(II) In N,N-dimethyl acetamide at 100℃; for 14h; | 93% |
| With potassium phosphate; (1-adamantyl)di(tert-butyl) phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; | 85% |
| Conditions | Yield |
|---|---|
| With polystyrene-trityllithium In tetrahydrofuran Ambient temperature; | 92% |
- 154377-07-8
diethyl (methylsulfonyl)phenylmalonate
- 83-13-6
diethyl 2-phenylmalonate
| Conditions | Yield |
|---|---|
| Stage #1: diethyl phenyl(methylsulfonyl)malonate With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 20℃; for 8h; Reflux; Stage #2: With water | 83% |
| With 1,4-diaza-bicyclo[2.2.2]octane; water 1.) toluene, reflux, 2.) room temperature; Yield given. Multistep reaction; |
| Conditions | Yield |
|---|---|
| With trifluorormethanesulfonic acid In neat (no solvent) at 60℃; for 0.5h; Temperature; Friedel-Crafts Alkylation; | 82% |
- 19213-72-0
ethyl 1-imidazolecarboxylate
- 101-97-3
Ethyl 2-phenylethanoate
- 83-13-6
diethyl 2-phenylmalonate
| Conditions | Yield |
|---|---|
| Stage #1: Ethyl 2-phenylethanoate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: ethyl 1-imidazolecarboxylate In tetrahydrofuran at -78 - 20℃; | 81% |
- 107365-54-8
diethyl 2-chloro-2-phenylmalonate
- 83-13-6
diethyl 2-phenylmalonate
| Conditions | Yield |
|---|---|
| With zinc In water; acetic acid for 4h; Heating; | 80% |
- 47252-14-2
triphenylbismuth carbonate
- 105-53-3
diethyl malonate
A
- 97080-43-8
diethyl 2,2-diphenylmalonate
B
- 83-13-6
diethyl 2-phenylmalonate
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at 67℃; for 11h; | A 77% B 18% |
| In tetrahydrofuran at 67℃; for 11h; | A 13% B 53% |
- 5256-74-6
1,3-diethyl 2-diazopropanedioate
- 934-56-5
trimethyl(phenyl)stannane
- 83-13-6
diethyl 2-phenylmalonate
| Conditions | Yield |
|---|---|
| With potassium fluoride; [Rh(OH)(cod)]2; XPhos In tetrahydrofuran; water at 70℃; for 1h; Stille Cross Coupling; Heating; Inert atmosphere; | 76% |
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Specification
The IUPAC name of Diethyl phenylmalonate is diethyl 2-phenylpropanedioate. With the CAS registry number 83-13-6, it is also named as Phenylmalonic acid diethyl ester. The product's categories are Pharmaceutical Intermediates; C12 to C63; Carbonyl Compounds; Esters. Besides, it is clear colourless to yellowish liquid after melting, which should be stored in dark, dry and sealed place. In addition, its molecular formula is C13H16O4 and molecular weight is 236.26. When you are using this chemical, please do not breathe vapour. And you should avoid contact with skin and eyes.
The other characteristics of this product can be summarized as: (1)EINECS: 201-456-5; (2)ACD/LogP: 2.71; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.71; (5)ACD/LogD (pH 7.4): 2.71; (6)ACD/BCF (pH 5.5): 67.03; (7)ACD/BCF (pH 7.4): 67.02; (8)ACD/KOC (pH 5.5): 706.06; (9)ACD/KOC (pH 7.4): 706.03; (10)#H bond acceptors: 4; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 7; (13)Index of Refraction: 1.5; (14)Molar Refractivity: 62.51 cm3; (15)Molar Volume: 212.4 cm3; (16)Surface Tension: 38.9 dyne/cm; (17)Density: 1.111 g/cm3; (18)Flash Point: 141.8 °C; (19)Melting Point: 16 °C; (20)Enthalpy of Vaporization: 54.11 kJ/mol; (21)Boiling Point: 301 °C at 760 mmHg; (22)Vapour Pressure: 0.00108 mmHg at 25 °C.
Preparation of Diethyl phenylmalonate: this chemical can be prepared by condensation, acidification and elimination of Ethyl phenylacetate. It is also produced by the reaction of Malonic acid diethyl ester with Bromobenzene.
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This reaction needs Ba(OH)2, Na2PdCl4 and N,N-Dimethyl-acetamide at temperature of 100 °C. The reaction time is 14 hours. The yield is 99 %.
Uses of Diethyl phenylmalonate: this chemical is a pharmaceutical intermediate that can be used to produce Phenobarbital. Similarly, it can react with 2-Amino-benzenethiol to get Bis-benzothiazol-2-yl-phenyl-methane.
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This reaction needs Polyphosphoric acid at temperature of 80-90 °C for 2 hours. The yield is 92 %.
People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(OCC)C(C(=O)OCC)c1ccccc1
(2)InChI: InChI=1/C13H16O4/c1-3-16-12(14)11(13(15)17-4-2)10-8-6-5-7-9-10/h5-9,11H,3-4H2,1-2H3
(3)InChIKey: FGYDHYCFHBSNPE-UHFFFAOYAH