Dimethyl succinylo succinate supplier

Name
2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester
EINECS 228-528-9
CAS No. 6289-46-9
Article Data18
CAS DataBase
Density 1.306 g/cm³
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
Appearance white to light yellow-green fine crystalline powder
Safety 37/39-26-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 86.74000
LogP -0.50320

Synthetic route

: 106-65-0
Dimethyl succinate

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions

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%

: 124-41-4
sodium methylate

: 106-65-0
Dimethyl succinate

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions

Conditions	Yield
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

Conditions	Yield
With sulfuric acid In water	68%

...Expand

: 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

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

...Expand

: 32807-28-6
Methyl 4-chloroacetoacetate

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions

Conditions	Yield
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

Conditions	Yield
bei laengerem Erhitzen;

...Expand

: 79-20-9
acetic acid methyl ester

: 106-65-0
Dimethyl succinate

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions

Conditions	Yield
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

Conditions	Yield
In N,N-dimethyl-formamide Ambient temperature;

...Expand

: 105-45-3
acetoacetic acid methyl ester

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions

Conditions	Yield
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

Conditions	Yield
With potassium carbonate In ethanol

: C10H10O6(2-)*2Na(1+)

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

Conditions

Conditions	Yield
With sulfuric acid In methanol pH=2; Inert atmosphere;

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 62-53-3
aniline

: 4898-58-2
2,5-bis(phenylamino)-1,4-cyclohexadiene-1,4-dicarboxylic acid dimethyl ester

Conditions

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

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 106-49-0
p-toluidine

: 10291-28-8
2,5-di(4'-methylphenylamino)terephthalic acid

Conditions

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%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 5870-37-1
2,5-Dihydroxybenzol-1,4-dicarbonsaeure-dimethylester

Conditions

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;

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 107-21-1
ethylene glycol

: 4746-97-8
cyclohexanedione monoethylene ketal

Conditions

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water; 1-ethylimidazolium tetrafluoroborate at 110 - 132℃; for 5.5h; Temperature; Reagent/catalyst;	97.8%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 610-92-4
2,5-dihydroxy-1,4-benzenedicarboxylic acid

Conditions

Conditions	Yield
With 2-ethylanthraquinone; dihydrogen peroxide; potassium hydroxide In methanol Reagent/catalyst; Inert atmosphere; Reflux;	97%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 62-53-3
aniline

: 10109-95-2
2,5-di(phenylamino)-terephthalic acid

Conditions

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;

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: C11H12O5

Conditions

Conditions	Yield
With N-chloro-succinimide; acetic acid at 80℃; for 1.5h;	96%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 106-49-0
p-toluidine

: 114508-42-8
2,5-di-p-toluidino-terephthalic acid dimethyl ester

Conditions

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;

: 1132796-42-9
9,9-dihexyl-9H-fluoren-2-ylamine

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: C60H76N2O4

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 12h; Reflux;	92%

: 9,9-diethyl-9H-fluoren-2-amine

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: C44H44N2O4

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 12h; Reflux;	89%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 75-04-7
ethylamine

: dimethyl 2,5-dihydro-3,6-bis(ethylamino)terephthalate

Conditions

Conditions	Yield
In methanol; water for 16h; Inert atmosphere; Reflux;	88%

: 959417-85-7
9,9-dioctyl-9H-fluoren-2-amine

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: C68H92N2O4

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 12h; Reflux;	86%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 75-31-0
isopropylamine

: dimethyl 2,5-dihydro-3,6-bis(isopropylamino)terephthalate

Conditions

Conditions	Yield
In methanol; water Inert atmosphere; Reflux;	86%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 62-53-3
aniline

: 5862-38-4
5,6,12,13-tetrahydro-quino[2,3-b]acridine-7,14-dione

Conditions

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%

: 95-23-8
5-amino-1,3-dihydro-benzoimidazol-2-one

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: C16H15N3O6

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 8h;	85%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 25186-39-4
2,5-Dichlor-3,6-dioxo-1,4-cyclohexadien-1,4-dicarbonsaeure-dimethylester

Conditions

Conditions	Yield
With N-chloro-succinimide; acetic acid at 70 - 90℃;	84%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 106-49-0
p-toluidine

: 13796-22-0
2,9-dimethyl-6,13-dihydroquinacridone

Conditions

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%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 104-94-9
4-methoxy-aniline

: 114399-42-7
2,5-di(p-methoxyanilino)-3,6-dihydroterephthalate dimethyl ester

Conditions

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;

: 1225055-70-8
2-amino-9,9-didodecyl-9H-fluorene

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: C84H124N2O4

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 12h; Reflux;	81%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 75-04-7
ethylamine

: dimethyl 2,5-bis(ethylamino)terephthalate

Conditions

Conditions	Yield
With oxygen; acetic acid In methanol; water for 30h; Reflux;	81%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 371-40-4
4-fluoroaniline

: dimethyl 2,5-bis[(4-fluorophenyl)amino]terephthalate

Conditions

Conditions	Yield
With acetic acid In ethanol Reflux;	78%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 75-31-0
isopropylamine

: dimethyl 2,5-bis(isopropylamino)terephthalate

Conditions

Conditions	Yield
With oxygen; acetic acid In methanol for 30h; Reflux;	77%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 62-53-3
aniline

: 14297-60-0
2,5-dianilinoterephthalic acid dimethyl ester

Conditions

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;

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 109-73-9
N-butylamine

: C18H28N2O4

Conditions

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;

: 111-86-4
n-Octylamine

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: dimethyl (3,6-bis(octylamino)terephthalate)

Conditions

Conditions	Yield
With oxygen; acetic acid In methanol for 30h; Reflux;	71%

: 6289-46-9
dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

: 106-93-4
ethylene dibromide

: 57293-62-6
dimethyl 1,4-dioxobicyclo<2.2.2>octane-2,5-dicarboxylate

Conditions

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

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

Product Name

2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester

Synthetic route

Dimethyl succinylo succinate Specification

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