Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 60 - 80℃; for 2h; Temperature; | 95% |
With sodium methylate at 140 - 145℃; for 3.5h; Temperature; Inert atmosphere; | 86.42% |
With sodium methylate In methanol for 20h; | 65% |
sodium methylate
Dimethyl succinate
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
at 100℃; for 6h; Claisen Condensation; Inert atmosphere; | 75.4% |
methanol
sodium methylate
Dimethyl succinate
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
With sulfuric acid In water | 68% |
Methyl 4-chloroacetoacetate
A
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
B
(-)-3-oxo-4-[(R)-(phenyl)(phenylmethoxycarbonylamino)acetoxy]butanoic acid methyl ester
Conditions | Yield |
---|---|
With potassium iodide In N,N-dimethyl-formamide at 20℃; for 5h; Condensation; esterification; cyclisation; | A n/a B 65% |
Methyl 4-chloroacetoacetate
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 20 - 60℃; for 13h; | 52% |
methanol
sodium methylate
succinic acid diethyl ester
A
succinic acid
B
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
bei laengerem Erhitzen; |
acetic acid methyl ester
Dimethyl succinate
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
With sodium at 90 - 100℃; |
Methyl 4-chloroacetoacetate
A
Z-D-phenylglycine
B
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Ambient temperature; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: bromine / 0.5 h 2: potassium carbonate / ethanol View Scheme |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
With sulfuric acid In methanol pH=2; Inert atmosphere; |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
aniline
2,5-bis(phenylamino)-1,4-cyclohexadiene-1,4-dicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 2-methyl-propan-1-ol at 20 - 100℃; for 4h; Product distribution / selectivity; | 99.7% |
at 80 - 90℃; for 4h; | 95% |
With ethanol; acetic acid |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
p-toluidine
2,5-di(4'-methylphenylamino)terephthalic acid
Conditions | Yield |
---|---|
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; p-toluidine With acetic acid In ethanol at 102 - 105℃; for 4h; Inert atmosphere; Stage #2: With potassium hydroxide In ethanol at 60 - 70℃; for 1h; Inert atmosphere; Stage #3: With sodium anthraquinone-2-sulfonate; potassium hydroxide In ethanol for 0.5h; Inert atmosphere; | 98.6% |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
2,5-Dihydroxybenzol-1,4-dicarbonsaeure-dimethylester
Conditions | Yield |
---|---|
With sulfuric acid | 98% |
With iodine; dimethyl sulfoxide at 80℃; for 12h; Sealed tube; Green chemistry; | 87% |
With bromine | |
With N-Bromosuccinimide; acetic acid | |
With N-chloro-succinimide; acetic acid at 80℃; for 1h; |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
ethylene glycol
cyclohexanedione monoethylene ketal
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium hydrogen sulfate; water; 1-ethylimidazolium tetrafluoroborate at 110 - 132℃; for 5.5h; Temperature; Reagent/catalyst; | 97.8% |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
2,5-dihydroxy-1,4-benzenedicarboxylic acid
Conditions | Yield |
---|---|
With 2-ethylanthraquinone; dihydrogen peroxide; potassium hydroxide In methanol Reagent/catalyst; Inert atmosphere; Reflux; | 97% |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
aniline
2,5-di(phenylamino)-terephthalic acid
Conditions | Yield |
---|---|
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; aniline With acetic acid In methanol at 102 - 105℃; for 4h; Inert atmosphere; Stage #2: With potassium hydroxide In methanol at 60 - 70℃; for 1h; Inert atmosphere; Stage #3: With sodium anthraquinone-2-sulfonate; dihydrogen peroxide In methanol for 0.5h; Inert atmosphere; | 96% |
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; aniline With toluene-4-sulfonic acid In 2-methyl-propan-1-ol at 20 - 100℃; for 4h; Stage #2: With sodium hydroxide; water; sodium 3-nitrobenzenesulfonate for 4h; Heating / reflux; |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
With N-chloro-succinimide; acetic acid at 80℃; for 1.5h; | 96% |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
p-toluidine
2,5-di-p-toluidino-terephthalic acid dimethyl ester
Conditions | Yield |
---|---|
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; p-toluidine With toluene-4-sulfonic acid In 2-methyl-propan-1-ol at 20 - 100℃; for 4h; Stage #2: With sodium methylate; sodium 3-nitrobenzenesulfonate In methanol for 4h; Product distribution / selectivity; Heating / reflux; | 95.5% |
With acetic acid In ethanol Reflux; | 69% |
With hydrogenchloride In ethanol for 6h; Reflux; Inert atmosphere; |
9,9-dihexyl-9H-fluoren-2-ylamine
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol for 12h; Reflux; | 92% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol for 12h; Reflux; | 89% |
Conditions | Yield |
---|---|
In methanol; water for 16h; Inert atmosphere; Reflux; | 88% |
9,9-dioctyl-9H-fluoren-2-amine
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol for 12h; Reflux; | 86% |
Conditions | Yield |
---|---|
In methanol; water Inert atmosphere; Reflux; | 86% |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
aniline
5,6,12,13-tetrahydro-quino[2,3-b]acridine-7,14-dione
Conditions | Yield |
---|---|
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; aniline With phosphoric acid In 2-methyl-propan-1-ol at 20 - 100℃; for 4h; Stage #2: With PPA at 70 - 130℃; for 1.5h; | 85% |
5-amino-1,3-dihydro-benzoimidazol-2-one
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 100℃; for 8h; | 85% |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
2,5-Dichlor-3,6-dioxo-1,4-cyclohexadien-1,4-dicarbonsaeure-dimethylester
Conditions | Yield |
---|---|
With N-chloro-succinimide; acetic acid at 70 - 90℃; | 84% |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
p-toluidine
2,9-dimethyl-6,13-dihydroquinacridone
Conditions | Yield |
---|---|
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; p-toluidine With phosphoric acid In 2-methyl-propan-1-ol at 20 - 100℃; for 4h; Stage #2: at 280℃; for 1.5h; Product distribution / selectivity; | 83% |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
4-methoxy-aniline
2,5-di(p-methoxyanilino)-3,6-dihydroterephthalate dimethyl ester
Conditions | Yield |
---|---|
With acetic acid In ethanol Reflux; | 81% |
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; 4-methoxy-aniline With acetic acid In ethanol at 120℃; for 2h; Stage #2: With iodine In ethanol; chloroform at 80℃; for 6h; |
2-amino-9,9-didodecyl-9H-fluorene
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol for 12h; Reflux; | 81% |
Conditions | Yield |
---|---|
With oxygen; acetic acid In methanol; water for 30h; Reflux; | 81% |
Conditions | Yield |
---|---|
With acetic acid In ethanol Reflux; | 78% |
Conditions | Yield |
---|---|
With oxygen; acetic acid In methanol for 30h; Reflux; | 77% |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
aniline
2,5-dianilinoterephthalic acid dimethyl ester
Conditions | Yield |
---|---|
With acetic acid In ethanol Reflux; | 75% |
With oxygen | |
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; aniline With acetic acid In ethanol at 120℃; for 2h; Stage #2: With iodine In ethanol; chloroform at 80℃; for 6h; | |
With hydrogenchloride In ethanol for 6h; Reflux; Inert atmosphere; |
Conditions | Yield |
---|---|
With oxygen; acetic acid In methanol for 30h; Reflux; | 74% |
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; N-butylamine In diethyl ether at 40℃; for 48h; Stage #2: With air Solvent; Temperature; Time; |
Conditions | Yield |
---|---|
With oxygen; acetic acid In methanol for 30h; Reflux; | 71% |
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
ethylene dibromide
dimethyl 1,4-dioxobicyclo<2.2.2>octane-2,5-dicarboxylate
Conditions | Yield |
---|---|
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate With sodium hydride In 1,2-dimethoxyethane at 20℃; Inert atmosphere; Reflux; Stage #2: ethylene dibromide Inert atmosphere; Reflux; | 70% |
With sodium hydride In 1,2-dimethoxyethane at 60 - 90℃; for 20h; | 57% |
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate With sodium hydride In 1,2-dimethoxyethane Inert atmosphere; Reflux; Stage #2: ethylene dibromide for 72h; Inert atmosphere; Reflux; | 51% |
With sodium hydride 1.) 1,2-dimethoxyethane, 2.) 1,2-dimethoxyethane, reflux; Yield given. Multistep reaction; | |
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate With sodium hydride In 1,2-dimethoxyethane; mineral oil at 130℃; for 4h; Cooling with ice; Stage #2: ethylene dibromide for 72h; Reflux; | 2.2 g |
The IUPAC name of Dimethyl succinylo succinate is dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate. With the CAS registry number 6289-46-9, it is also named as Succinosuccinic acid, dimethyl ester. The product's categorie is pharmaceutical intermediates. It is white to light yellow-green fine crystalline powder.
The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.23; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.23; (4)ACD/LogD (pH 7.4): -0.24; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 17.87; (8)ACD/KOC (pH 7.4): 17.47; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.482; (13)Molar Refractivity: 49.83 cm3; (14)Molar Volume: 174.6 cm3; (15)Polarizability: 19.75×10-24 cm3; (16)Surface Tension: 47.3 dyne/cm; (17)Enthalpy of Vaporization: 59.51 kJ/mol; (18)Vapour Pressure: 4.38E-05 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Tautomer Count: 15; (21)Exact Mass: 228.063388; (22)MonoIsotopic Mass: 228.063388; (23)Topological Polar Surface Area: 86.7; (24)Heavy Atom Count: 16; (25)Complexity: 311.
Preparation of Dimethyl succinylo succinate: It can be obtained by succinic acid dimethyl ester. This reaction needs reagent sodium methylate
dioxane.
Uses of Dimethyl succinylo succinate: It is used in the production of pigments such as Pigment Red 122 and Pigment Violet 19. It also can react with 2,4-diamino-phenol to get 2,5-bis-(3-amino-4-hydroxy-phenylamino)-cyclohexa-1,4-diene-1,4-dicarboxylic acid dimethyl ester. This reaction needs reagent N-ethylpiperidine at temperature of 105 °C. The reaction time is 7 hours. The yield is 80%.
When you are using this chemical, please be cautious about it as the following:
It 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 gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OC)C1C(=O)CC(C(=O)C1)C(=O)OC
2. InChI:InChI=1/C10H12O6/c1-15-9(13)5-3-8(12)6(4-7(5)11)10(14)16-2/h5-6H,3-4H2,1-2H3
3. InChIKey:MHKKFFHWMKEBDW-UHFFFAOYAT
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