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Methyl glycolate

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Name

Methyl glycolate

EINECS 202-502-7
CAS No. 96-35-5 Density 1.14 g/cm3
PSA 46.53000 LogP -0.84830
Solubility Miscible with water. Melting Point 149-151 °C
Formula C3H6O3 Boiling Point 151.099 °C at 760 mmHg
Molecular Weight 90.0788 Flash Point 67.222 °C
Transport Information N/A Appearance Clear colorless liquid
Safety 23-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 96-35-5 (Methyl glycolate) Hazard Symbols IrritantXi
Synonyms

Methyl hydroxyacetate;NSC 27786;Acetic acid, hydroxy-, methyl ester;Glycolic acid, methyl ester (8CI);

Article Data 109

Methyl glycolate Synthetic route

93-58-3

benzoic acid methyl ester

96-35-5

glycolic acid methyl ester

Conditions
ConditionsYield
With C33H32Cl2N2P2Ru; hydrogen; sodium methylate In para-xylene; toluene at 5 - 100℃; under 37503.8 Torr; for 4h; Reagent/catalyst; Glovebox;100%
553-90-2

Dimethyl oxalate

96-35-5

glycolic acid methyl ester

Conditions
ConditionsYield
With (o-PPh2C6H4NH2)[EtNH(CH2)2NHEt]RuCl2; hydrogen; sodium methylate In tetrahydrofuran; para-xylene at 5 - 100℃; under 7500.75 Torr; for 1.5h; Reagent/catalyst; Pressure; Temperature; Glovebox;99%
With hydrogen In methanol at 219.84℃; under 18751.9 Torr; Temperature; Reagent/catalyst; Autoclave;32%
With 1,1,1-tris(n-butylthiomethyl)ethane; hydrogen; zinc; Λ(+)-tris(pentane-2,5-dionato)ruthenium In methanol at 100℃; under 60004.8 Torr; for 69h; Kinetics; Product distribution; Further Variations:; Reagents;
67-56-1

methanol

50-00-0

formaldehyd

201230-82-2

carbon monoxide

96-35-5

glycolic acid methyl ester

Conditions
ConditionsYield
Stage #1: formaldehyd; carbon monoxide With 1,3,5-Trioxan; methanesulfonic acid; phosphoric acid In dichloromethane; benzene at 150℃; under 54005.4 Torr;
Stage #2: methanol In dichloromethane; benzene at 190℃; under 9000.9 Torr; for 24h; Temperature; Reagent/catalyst; Solvent; Pressure;
97.4%
Stage #1: formaldehyd; carbon monoxide With 4-n-butyl-4-(3-sulfopropyl)thiomorpholinium 1,1-dioxide trifluoromethane sulfonate In sulfolane at 160℃; under 37503.8 Torr; for 8h; Autoclave;
Stage #2: methanol With 4-n-butyl-4-(3-sulfopropyl)thiomorpholinium 1,1-dioxide trifluoromethane sulfonate In sulfolane at 80℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Pressure; Time; Temperature; Concentration; Autoclave;
92%
Stage #1: formaldehyd; carbon monoxide In sulfolane at 200℃; under 60006 Torr; Autoclave;
Stage #2: methanol With nitric acid for 4h; Reflux; chemoselective reaction;
47.7 %Chromat.
67-56-1

methanol

79-14-1

glycolic Acid

96-35-5

glycolic acid methyl ester

Conditions
ConditionsYield
With amberlyst-15 for 16h;96%
With toluene-4-sulfonic acid for 10h; Reflux;87.2%
With boric acid at 20℃; for 18h;80%
146351-72-6

[(1,1-dimethylethyl)(dimethyl)silyloxy]acetic acid methyl ester

96-35-5

glycolic acid methyl ester

Conditions
ConditionsYield
With formic acid In water; acetonitrile at 20℃;95%
553-90-2

Dimethyl oxalate

67-56-1

methanol

A

96-35-5

glycolic acid methyl ester

B

107-21-1

ethylene glycol

Conditions
ConditionsYield
With hydrogen at 199.84℃; under 22502.3 Torr; Reagent/catalyst;A 90.6%
B n/a
67-56-1

methanol

79-14-1

glycolic Acid

A

502-97-6

glycolide

B

96-35-5

glycolic acid methyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 10h; Reflux;A n/a
B 87.2%
553-90-2

Dimethyl oxalate

A

96-35-5

glycolic acid methyl ester

B

107-21-1

ethylene glycol

Conditions
ConditionsYield
With C32H32Cl2N2P2Ru; hydrogen; sodium methylate In para-xylene; toluene at 5 - 100℃; under 37503.8 Torr; for 4h; Reagent/catalyst; Glovebox;A 86%
B 13%
With hydrogen In methanol at 219.84℃; under 18751.9 Torr; Autoclave;A 76%
B n/a
With hydrogen In methanol at 219.84℃; under 18751.9 Torr; Autoclave;A 31%
B n/a
67-56-1

methanol

96-35-5

glycolic acid methyl ester

Conditions
ConditionsYield
With zeolite Sn-MFI for 18h; Reagent/catalyst; Time; Sealed tube; Green chemistry;83%
553-90-2

Dimethyl oxalate

A

67-56-1

methanol

B

96-35-5

glycolic acid methyl ester

Conditions
ConditionsYield
With hydrogen; <(Ph3P)(Ph2P)RuH2-K+*diglyme>2 In toluene at 90℃; under 4650.4 Torr; for 20h; Title compound not separated from byproducts;A n/a
B 70%
With (K(1+))2<(Ph3P)3(Ph2P)Ru2H4>(2-)*2C6H14O3; hydrogen In toluene at 90℃; under 4650.4 Torr; for 20h;

Methyl glycolate Specification

Methyl glycolate is an organic compound with the formula C3H6O3, and its systematic name is the same with the product name. With the CAS registry number 96-35-5, it is also named as Methyl hydroxyacetate. It belongs to the product categories of Acids and Derivatives; Alcohols and Derivatives; C2 to C5; Carbonyl Compounds; Esters. Its EINECS number is 202-502-7. In addition, the molecular weight is 90.08. This chemical should be sealed and stored in a cool and ventilated place. Moreover, it should be protected from oxides, heat and fire. It is used in organic synthesis, and it is also used as high-grade cleaning solvent.

Physical properties of Methyl glycolate are: (1)ACD/LogP: -0.902; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.90; (4)ACD/LogD (pH 7.4): -0.90; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 7.70; (8)ACD/KOC (pH 7.4): 7.70; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 46.53 Å2; (13)Index of Refraction: 1.402; (14)Molar Refractivity: 19.257 cm3; (15)Molar Volume: 79.044 cm3; (16)Polarizability: 7.634×10-24cm3; (17)Surface Tension: 35.52 dyne/cm; (18)Density: 1.14 g/cm3; (19)Flash Point: 67.222 °C; (20)Enthalpy of Vaporization: 45.19 kJ/mol; (21)Boiling Point: 151.099 °C at 760 mmHg; (22)Vapour Pressure: 1.4 mmHg at 25°C.

Preparation: this chemical can be prepared by methanol and hydroxyacetic acid at the ambient temperature. This reaction will need reagent thionyl chloride with the reaction time of 48 hours. The yield is about 60%.

Methyl glycolate can be prepared by methanol and hydroxyacetic acid at the ambient temperature

Uses of Methyl glycolate: it can be used to produce triisopropylsilanyloxy-acetic acid methyl ester at the ambient temperature. It will need reagent imidazole and solvent dimethylformamide with the reaction time of 73 hours. The yield is about 72%.

Methyl glycolate can be used to produce triisopropylsilanyloxy-acetic acid methyl ester at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. You should not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). When using it, you must avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)CO
(2)Std. InChI: InChI=1S/C3H6O3/c1-6-3(5)2-4/h4H,2H2,1H3
(3)Std. InChIKey: GSJFXBNYJCXDGI-UHFFFAOYSA-N 

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