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52267-39-7

Basic Information
CAS No.: 52267-39-7
Name: Benzyl methyl malonate
Article Data: 7
Molecular Structure:
Molecular Structure of 52267-39-7 (Benzyl methyl malonate)
Formula: C11H12O4
Molecular Weight: 208.214
Synonyms: Propanedioicacid, methyl phenylmethyl ester (9CI);Benzyl methyl malonate;Methyl benzylmalonate;
Density: 1.164g/cm3
Boiling Point: 333.5 °C at 760 mmHg
Flash Point: 129.5 °C
Solubility: Slightly soluble in water.
Safety: 24/25
PSA: 52.60000
LogP: 1.29290
Synthetic route
40204-26-0

malonic acid monobenzyl ester

79-22-1

methyl chloroformate

A

52267-39-7

benzyl methyl malonate

B

CO2

CO2

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;A 100%
B n/a
16695-14-0

Malonic acid monomethyl ester

501-53-1

benzyl chloroformate

A

52267-39-7

benzyl methyl malonate

B

CO2

CO2

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;A 99%
B n/a
38330-80-2

monomethyl monopotassium malonate

100-39-0

benzyl bromide

52267-39-7

benzyl methyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 22h;97%
67-56-1

methanol

1416169-71-5

C10H7IO2

52267-39-7

benzyl methyl malonate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate In water; acetonitrile at 20℃; for 0.0833333h;94%
108-59-8

malonic acid dimethyl ester

100-51-6

benzyl alcohol

A

15014-25-2

malonic acid dibenzyl ester

B

52267-39-7

benzyl methyl malonate

Conditions
ConditionsYield
at 140 - 170℃; Transesterification;A 9%
B 86%
89238-09-5

methoxycarbonylketene

100-51-6

benzyl alcohol

52267-39-7

benzyl methyl malonate

Conditions
ConditionsYield
80%
1621424-09-6

benzyl (E)-β-methoxyacrylate

52267-39-7

benzyl methyl malonate

Conditions
ConditionsYield
With methanol; silver(I) acetate; palladium diacetate; sodium nitrite at 80℃; for 24h; Inert atmosphere;60%
2495-35-4

benzylacrylate

52267-39-7

benzyl methyl malonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium diacetate; silver(I) acetate; sodium nitrite / 8 h / 25 °C / Inert atmosphere
2: methanol; palladium diacetate; silver(I) acetate; sodium nitrite / 24 h / 80 °C / Inert atmosphere
View Scheme
67-56-1

methanol

2495-35-4

benzylacrylate

A

52267-39-7

benzyl methyl malonate

B

1621424-09-6

benzyl (E)-β-methoxyacrylate

Conditions
ConditionsYield
With silver(I) acetate; palladium diacetate; sodium nitrite at 110℃; for 6h;A 14 %Spectr.
B 80 %Spectr.
52267-39-7

benzyl methyl malonate

118283-56-0

2-[(Z)-Hydroxyimino]-malonic acid benzyl ester methyl ester

Conditions
ConditionsYield
With acetic acid; sodium nitrite In water Ambient temperature;95.4%
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Specification

The Propanedioicacid, 1-methyl 3-(phenylmethyl) ester, with CAS registry number 52267-39-7, has the systematic name of benzyl methyl propanedioate. Besides this, it is also called Benzyl methyl malonate. And the chemical formula of this chemical is C11H12O4. Its molecular weight is 208.21.

Physical properties of Propanedioicacid, 1-methyl 3-(phenylmethyl) ester: (1)ACD/LogP: 1.49; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.49; (4)ACD/LogD (pH 7.4): 1.49; (5)ACD/BCF (pH 5.5): 7.97; (6)ACD/BCF (pH 7.4): 7.97; (7)ACD/KOC (pH 5.5): 153.76; (8)ACD/KOC (pH 7.4): 153.75; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 52.6 Å2; (13)Index of Refraction: 1.507; (14)Molar Refractivity: 53.25 cm3; (15)Molar Volume: 178.7 cm3; (16)Polarizability: 21.11×10-24cm3; (17)Surface Tension: 41.1 dyne/cm; (18)Density: 1.164 g/cm3; (19)Flash Point: 129.5 °C; (20)Enthalpy of Vaporization: 57.64 kJ/mol; (21)Boiling Point: 333.5 °C at 760 mmHg; (22)Vapour Pressure: 0.000136 mmHg at 25°C.

Preparation: this chemical can be prepared by phenylmethanol and 3-Oxo-2-propenoic acid methyl ester. The yield is about 80%.

Uses of Propanedioicacid, 1-methyl 3-(phenylmethyl) ester: it can be used to produce 2-hydroxyimino-malonic acid benzyl ester methyl ester. This reaction will need reagents acetic acid, sodium nitrite and solvent H2O. The yield is about 95.4%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)CC(=O)OCc1ccccc1
(2)InChI: InChI=1/C11H12O4/c1-14-10(12)7-11(13)15-8-9-5-3-2-4-6-9/h2-6H,7-8H2,1H3
(3)InChIKey: IAUZDBFOEWAQFE-UHFFFAOYAS
(4)Std. InChI: InChI=1S/C11H12O4/c1-14-10(12)7-11(13)15-8-9-5-3-2-4-6-9/h2-6H,7-8H2,1H3
(5)Std. InChIKey: IAUZDBFOEWAQFE-UHFFFAOYSA-N