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1587-20-8

Basic Information
CAS No.: 1587-20-8
Name: TRIMETHYL CITRATE
Article Data: 28
Molecular Structure:
Molecular Structure of 1587-20-8 (TRIMETHYL CITRATE)
Formula: C9H14O7
Molecular Weight: 234.206
Synonyms: Citric acid, trimethyl ester(6CI,7CI,8CI);1,2,3-Propanetricarboxylicacid, 2-hydroxy-, trimethyl ester (9CI);3-Hydroxy-3-methoxycarbonylpentanedioic acid dimethyl ester;NSC75824;
EINECS: 216-449-2
Density: 1.265 g/cm3
Melting Point: 75-78 °C
Boiling Point: 238.8 °C at 760 mmHg
Flash Point: 79.2 °C
Solubility: 53.2g/L at 20℃
Safety: 22-24/25
PSA: 99.13000
LogP: -0.98330
Synthetic route
67-56-1

methanol

77-92-9

citric acid

1587-20-8

trimethyl citrate

Conditions
ConditionsYield
With zirconium(IV) oxychloride In toluene at 120℃; for 1h;99%
With thionyl chloride at 0 - 20℃;98%
With thionyl chloride In methanol at 0 - 20℃; Inert atmosphere;98%
67-56-1

methanol

141-82-2

malonic acid

1587-20-8

trimethyl citrate

Conditions
ConditionsYield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 70℃; for 20h;94%
77-92-9

citric acid

1587-20-8

trimethyl citrate

Conditions
ConditionsYield
In methanol; diethyl ether at 0℃;90%
In methanol; diethyl ether
67-56-1

methanol

sym-dimethyl citrate * H2O

1587-20-8

trimethyl citrate

Conditions
ConditionsYield
With sulfuric acid; 2,2-dimethoxy-propane for 7h; Heating;88%
67-56-1

methanol

77-92-9

citric acid

A

1830-54-2

3-oxopentanedioic acid dimethyl ester

B

100009-70-9

dimethyl 2-methoxypropene-1,3-dicarboxylate

C

20820-77-3

trimethyl aconitate

D

1587-20-8

trimethyl citrate

E

105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
Stage #1: citric acid With chlorosulfonic acid In dichloromethane at 10 - 15℃; for 5 - 6h;
Stage #2: methanol In dichloromethane at 3 - 35℃; for 2h; Conversion of starting material;
A 87.3%
B n/a
C n/a
D n/a
E n/a
26163-65-5

2-Hydroxy-1,2,3-propanetricarboxylic Acid 2-Methyl Ester

1587-20-8

trimethyl citrate

Conditions
ConditionsYield
In methanol; diethyl ether at 0℃;85%
540-88-5

acetic acid tert-butyl ester

53798-96-2

1,5-dimethyl citrate

A

1587-20-8

trimethyl citrate

B

114340-51-1

2-tert-butyl 1,3-dimethyl 2-hydroxypropane-1,2,3-tricarboxylate

Conditions
ConditionsYield
With perchloric acid for 72h; Ambient temperature;A n/a
B 78%
53798-96-2

1,5-dimethyl citrate

77-76-9

2,2-dimethoxy-propane

1587-20-8

trimethyl citrate

Conditions
ConditionsYield
With sulfuric acid for 7h; Reflux;62%
77-92-9

citric acid

1587-20-8

trimethyl citrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 29 percent / 98percent H2SO4 / 1 h / Heating
2: 60percent HClO4 / 72 h / Ambient temperature
View Scheme
67-56-1

methanol

77-93-0

citric acid triethyl ester

A

1587-20-8

trimethyl citrate

B

1242516-57-9

1,6-dimethyl 5-ethyl citrate

C

1242516-58-0

1,2-diethyl-3-methyl-2-hydroxypropane-1,2,3-tricarboxylate

Conditions
ConditionsYield
With SEC-BUTYLAMINE at 20℃; Product distribution / selectivity;
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  • 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-trimethyl ester

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    1587-20-8

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Specification

The 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-trimethyl ester is an organic compound with the formula C9H14O7. The IUPAC name of this chemical is Trimethyl 2-hydroxypropane-1,2,3-tricarboxylate. With the CAS registry number 1587-20-8, it is also named as Citric acid, trimethyl ester. The product's categories are Functional Materials; Hydroxycarboxylic Acid Esters (Plasticizer); Plasticizer; C8 to C9; Carbonyl Compounds; Esters. Besides, its molecular weight is 234.2.

Physical properties about 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-trimethyl ester are: (1)ACD/LogP: -0.10; (2)ACD/LogD (pH 5.5): -0.1; (3)ACD/LogD (pH 7.4): -0.1; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 20.98; (7)ACD/KOC (pH 7.4): 20.96; (8)#H bond acceptors: 7; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 9; (11)Polar Surface Area: 88.13 Å2; (12)Index of Refraction: 1.458; (13)Molar Refractivity: 50.56 cm3; (14)Molar Volume: 185 cm3; (15)Polarizability: 20.04×10-24 cm3; (16)Surface Tension: 43.8 dyne/cm; (17)Density: 1.265 g/cm3; (18)Flash Point: 79.2 °C; (19)Enthalpy of Vaporization: 55.29 kJ/mol; (20)Boiling Point: 238.8 °C at 760 mmHg; (21)Vapour Pressure: 0.00732 mmHg at 25 °C.

Preparation: this chemical can be prepared by 2-Hydroxy-propane-1,2,3-tricarboxylic acid. This reaction will need solvents methanol; diethyl ether. The reaction temperature is 0 °C. The yield is about 90%.

Uses of 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-trimethyl ester: it can be used to produce Citric acid β-methyl ester. It will need reagent 1 N NaOH and solvents methanol; H2O with reaction time of 2 hours. The yield is about 73%.

When you are using this chemical, please be cautious about it as the following:
When you are using it, do not breathe dust, and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)InChI: InChI=1/C9H14O7/c1-14-6(10)4-9(13,8(12)16-3)5-7(11)15-2/h13H,4-5H2,1-3H3
(2)InChIKey: HDDLVZWGOPWKFW-UHFFFAOYAJ
(3)Std. InChI: InChI=1S/C9H14O7/c1-14-6(10)4-9(13,8(12)16-3)5-7(11)15-2/h13H,4-5H2,1-3H3
(4)Std. InChIKey: HDDLVZWGOPWKFW-UHFFFAOYSA-N