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Dimethyl succinylo succinate
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Name

Dimethyl succinylo succinate

 EINECS 228-528-9
CAS No. 6289-46-9 Density 1.306 g/cm3
PSA 86.74000 LogP -0.50320
Solubility Soluble in water 0.0016 g/L. Melting Point 154-157 °C
Formula C10H12O6 Boiling Point 350.5 °C at 760 mmHg
Molecular Weight 228.202 Flash Point 156.1 °C
Transport Information N/A Appearance white to light yellow-green fine crystalline powder
Safety 37/39-26-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 6289-46-9 (2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester) Hazard Symbols IrritantXi
Synonyms

1,4-Cyclohexanedicarboxylicacid, 2,5-dioxo-, dimethyl ester (7CI,8CI,9CI);Dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate;Dimethyl succinosuccinate;NSC 122567;NSC 5670;Succinosuccinic acid dimethyl ester;

Article Data 18

Dimethyl succinylo succinate Synthetic route

106-65-0

Dimethyl succinate

6289-46-9

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions
ConditionsYield
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%
124-41-4

sodium methylate

106-65-0

Dimethyl succinate

6289-46-9

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions
ConditionsYield
at 100℃; for 6h; Claisen Condensation; Inert atmosphere;75.4%
67-56-1

methanol

124-41-4

sodium methylate

106-65-0

Dimethyl succinate

6289-46-9

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions
ConditionsYield
With sulfuric acid In water68%
32807-28-6

Methyl 4-chloroacetoacetate

(R)-(phenyl)(phenylmethoxycarbonylamino)acetic acid potassium salt

A

6289-46-9

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

B

261963-22-8

(-)-3-oxo-4-[(R)-(phenyl)(phenylmethoxycarbonylamino)acetoxy]butanoic acid methyl ester

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl-formamide at 20℃; for 5h; Condensation; esterification; cyclisation;A n/a
B 65%
32807-28-6

Methyl 4-chloroacetoacetate

6289-46-9

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 20 - 60℃; for 13h;52%
67-56-1

methanol

124-41-4

sodium methylate

123-25-1

succinic acid diethyl ester

A

110-15-6

succinic acid

B

6289-46-9

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions
ConditionsYield
bei laengerem Erhitzen;
79-20-9

acetic acid methyl ester

106-65-0

Dimethyl succinate

6289-46-9

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions
ConditionsYield
With sodium at 90 - 100℃;
32807-28-6

Methyl 4-chloroacetoacetate

Potassium; (S)-benzyloxycarbonylamino-phenyl-acetate

A

17609-52-8

Z-D-phenylglycine

B

6289-46-9

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

C

4-((S)-2-Benzyloxycarbonylamino-2-phenyl-acetoxy)-3-oxo-butyric acid methyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature;
105-45-3

acetoacetic acid methyl ester

6289-46-9

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bromine / 0.5 h
2: potassium carbonate / ethanol
View Scheme
3600-18-8

methyl 2-bromo-3-oxobutanoate

6289-46-9

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions
ConditionsYield
With potassium carbonate In ethanol

Dimethyl succinylo succinate Specification

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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