Benzyl methyl malonate supplier

Name
Benzyl methyl malonate
EINECS
CAS No. 52267-39-7
Article Data7
CAS DataBase
Density 1.164g/cm³
Solubility Slightly soluble in water.
Melting Point
Formula C₁₁H₁₂O₄
Boiling Point 333.5 °C at 760 mmHg
Molecular Weight 208.214
Flash Point 129.5 °C
Transport Information
Appearance
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Propanedioicacid, methyl phenylmethyl ester (9CI);Benzyl methyl malonate;Methyl benzylmalonate;
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

Conditions	Yield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;	A 100% B n/a

...Expand

: 16695-14-0
Malonic acid monomethyl ester

: 501-53-1
benzyl chloroformate

A: 52267-39-7
benzyl methyl malonate

B CO2: CO2

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;	A 99% B n/a

...Expand

: 38330-80-2
monomethyl monopotassium malonate

: 100-39-0
benzyl bromide

: 52267-39-7
benzyl methyl malonate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 22h;	97%

: 67-56-1
methanol

: 1416169-71-5
C10H7IO2

: 52267-39-7
benzyl methyl malonate

Conditions

Conditions	Yield
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

Conditions	Yield
at 140 - 170℃; Transesterification;	A 9% B 86%

...Expand

: 89238-09-5
methoxycarbonylketene

: 100-51-6
benzyl alcohol

: 52267-39-7
benzyl methyl malonate

Conditions

Conditions	Yield
	80%

: 1621424-09-6
benzyl (E)-β-methoxyacrylate

: 52267-39-7
benzyl methyl malonate

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 52267-39-7
benzyl methyl malonate

: 118283-56-0
2-[(Z)-Hydroxyimino]-malonic acid benzyl ester methyl ester

Conditions

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

: 52267-39-7
benzyl methyl malonate

: N-methyl-N-phenylthiocarbamoyl fluoride

: 1-benzyl 3-methyl 2-(methyl(phenyl)carbamothioyl)malonate

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 80℃; for 12h;	95%

: 1260224-12-1
(1S,3R,4S,6R,8R,9R)-6-methyl-12-methylene-10-azatetracyclo[7.2.2.03,8.04,10]tridecan-13-one

: 52267-39-7
benzyl methyl malonate

: 1422437-40-8
α-{(1S,3R,4S,6S,8R,9R,10R)-6-methyl-13-oxo-10-azatetracyclo[7.2.2.03,8.04,10]tridecan-12-yl}methyl malonic acid benzyl methyl ester

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃;	91.3%

: 52267-39-7
benzyl methyl malonate

: 100420-10-8
4-phenyl-1-(pyrrolidin-1-yl)butan-1-one

: 1-benzyl 3-methyl 2-[1-oxo-4-phenyl-1-(pyrrolidin-1-yl)butan-2-yl]malonate

Conditions

Conditions	Yield
Stage #1: 4-phenyl-1-(pyrrolidin-1-yl)butan-1-one With 2-iodopyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: With 2,6-lutidine N-oxide In dichloromethane at 0℃; for 0.0166667h; Inert atmosphere; Stage #3: benzyl methyl malonate With sodium hydride In tetrahydrofuran; dichloromethane at 0 - 25℃; for 1h; Inert atmosphere; chemoselective reaction;	89%

Yield

Stage #1: 4-phenyl-1-(pyrrolidin-1-yl)butan-1-one With 2-iodopyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: With 2,6-lutidine N-oxide In dichloromethane at 0℃; for 0.0166667h; Inert atmosphere;
Stage #3: benzyl methyl malonate With sodium hydride In tetrahydrofuran; dichloromethane at 0 - 25℃; for 1h; Inert atmosphere; chemoselective reaction;

89%

: 66086-33-7
Di-tert-butyl acetylenedicarboxylate

: 52267-39-7
benzyl methyl malonate

: trans-1-benzyl 2,3-di-tert-butyl 1-methyl cyclopropane-1,1,2,3-tetracarboxylate

Conditions

Conditions	Yield
With triphenyl-arsane In ethanol at 0 - 20℃; for 240h;	85.9%

: 52267-39-7
benzyl methyl malonate

: 132873-63-3
1-benzyl 3-methyl 2-bromomalonate

Conditions

Conditions	Yield
With bromine In tetrachloromethane	85%
With bromine In tetrachloromethane Irradiation;	68%
Stage #1: benzyl methyl malonate With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; Stage #2: With carbon tetrabromide In tetrahydrofuran at -78℃; for 3h; Inert atmosphere;	60%

: 52267-39-7
benzyl methyl malonate

: 107-18-6
allyl alcohol

A: 1-benzyl 3-methyl 2,2-diallylmalonate

B: 1-benzyl 3-methyl 2-allylmalonate

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) bromide trihydrate; tetrabutylammonium acetate; zinc In N,N-dimethyl acetamide at 50℃; for 66h; Inert atmosphere;	A 14% B 84%

...Expand

: 52267-39-7
benzyl methyl malonate

: 106-96-7
propargyl bromide

: 162107-25-7
methyl benzyl 2,2-diprop-2-ynylmalonate

Conditions

Conditions	Yield
With potassium carbonate In acetone for 65h; Heating;	83%

: 1421045-80-8
(S)-2-chloro-1-(2-ethyl-8-methoxyquinolin-5-yl)propan-1-one

: 52267-39-7
benzyl methyl malonate

: 1-benzyl 3-methyl 2-[1-(2-ethyl-8-methoxyquinolin-5-yl)-1-oxopropan-2-yl]malonate

Conditions

Conditions	Yield
Stage #1: (S)-2-chloro-1-(2-ethyl-8-methoxyquinolin-5-yl)propan-1-one; benzyl methyl malonate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 14h; Inert atmosphere; Stage #2: Inert atmosphere;	83%

: 52267-39-7
benzyl methyl malonate

: (S)-4-[(E)-6-(3-Formyl-phenyl)-hex-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 2-[1-{3-[(E)-6-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-hex-3-enyl]-phenyl}-meth-(Z)-ylidene]-malonic acid benzyl ester methyl ester

Conditions

Conditions	Yield
With piperidine; benzoic acid In toluene for 6h; Heating;	82%

: 51673-84-8
dimethoxyacetaldehyde

: 52267-39-7
benzyl methyl malonate

: 161681-84-1
2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester

Conditions

Conditions	Yield
With piperidine In toluene Heating;	82%

: 1171908-44-3
methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate

: 52267-39-7
benzyl methyl malonate

: 1228377-57-8
methyl 5-acetamido-2,6-anhydro-4-C-[(benzyloxycarbonyl)(methoxycarbonyl)methyl]-7-O-(tert-butyldimethylsilyl)-3,4,5-trideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tributylphosphine; sodium In tetrahydrofuran; mineral oil at 60℃; for 18h; Inert atmosphere; stereoselective reaction;	80%

: 1171908-44-3
methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate

: 52267-39-7
benzyl methyl malonate

: 1228377-56-7
methyl 5-acetamido-2,6-anhydro-2-C-[(benzyloxycarbonyl)(methoxycarbonyl)methyl]-7-O-(tert-butyldimethylsilyl)-3,4,5-trideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-3-enoate

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran; mineral oil at 60℃; for 2h; Inert atmosphere; stereoselective reaction;	75%

: 52267-39-7
benzyl methyl malonate

: methyl (S)-5-(3-hydroxybut-1-yn-1-yl)-1-methyl-1H-pyrazole-4-carboxylate

: 1-benzyl 3-methyl 2-((S)-4-(4-(methoxycarbonyl)-1-methyl-1H-pyrazol-5-yl)but-3-yn-2-yl)malonate

Conditions

Conditions	Yield
Stage #1: methyl (S)-5-(3-hydroxybut-1-yn-1-yl)-1-methyl-1H-pyrazole-4-carboxylate With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 1.75h; Stage #2: benzyl methyl malonate With cesium fluoride In 1,4-dioxane at 80℃; for 16h;	74%

: 50-00-0
formaldehyd

: 52267-39-7
benzyl methyl malonate

: 41609-04-5
N-benzyl-3-amino-2-cyclohexen-1-one

: 1-benzyl 3-methyl 2-((2-(benzylamino)-6-oxocyclohex-1-en-1-yl)methyl)malonate

Conditions

Conditions	Yield
With lithium perchlorate; acetic anhydride In acetonitrile at 60℃; Sealed tube;	73%

...Expand

: 52267-39-7
benzyl methyl malonate

: 17435-72-2
ethyl 2-bromomethyl-2-propenoate

: 4-Benzyloxycarbonyl-2,6-bis(ethoxycarbonyl)-4-methoxycarbonyl-1,6-heptadiene

Conditions

Conditions	Yield
In water; acetonitrile	72.4%

: 493-05-0
isochromane

: 52267-39-7
benzyl methyl malonate

: 1246668-97-2
1-benzyl 3-methyl 2-(isochroman-1-yl)malonate

Conditions

Conditions	Yield
With iron(II) triflate; 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 20℃; Inert atmosphere;	72%

: 82843-06-9
1-(2-nitro-vinyl)-naphthalen-2-ol

: 52267-39-7
benzyl methyl malonate

: 2-benzyl 2-methyl 1-(nitromethyl)naphtho[2,1-b]furan-2,2(1H)-dicarboxylate

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; iodine; sodium hydrogencarbonate In tetrahydrofuran; decane at 30℃; for 24h;	67%

: 52267-39-7
benzyl methyl malonate

: (S)-4-[(E)-5-(2-Formyl-phenyl)-pent-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 2-[1-{2-[(E)-5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pent-3-enyl]-phenyl}-meth-(E)-ylidene]-malonic acid benzyl ester methyl ester

Conditions

Conditions	Yield
With piperidine; benzoic acid In toluene for 6h; Heating;	66%

: 52267-39-7
benzyl methyl malonate

: N-benzyloxymethyl-3'-O-(tert-butyldimethylsilyl)-5'-deoxy-5'-iodothymidine

: C-(N3-benzyloxymethyl-3'-O-(tert-butyldimethylsilyl)-5'-deoxythymidin-5'-yl)benzyl methyl malonate

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil	66%

: 52267-39-7
benzyl methyl malonate

: 107-11-9
1-amino-2-propene

A: 1-benzyl 3-methyl 2,2-diallylmalonate

B: 1-benzyl 3-methyl 2-allylmalonate

Conditions

Conditions	Yield
With nickel(II) bromide trihydrate; 1,4-di(diphenylphosphino)-butane; zinc In N,N-dimethyl-formamide at 80℃; for 22h; Inert atmosphere;	A 20% B 64%

...Expand

: 52267-39-7
benzyl methyl malonate

: Methyl-benzyl-hydroxymalonat

Conditions

Conditions	Yield
With cerium; ammonium nitrate; oxygen In methanol for 6h; Ambient temperature;	62%

: 104-54-1
3-Phenylpropenol

: 52267-39-7
benzyl methyl malonate

: 1-benzyl 3-methyl 2-(cinnamyloxy)malonate

Conditions

Conditions	Yield
Stage #1: benzyl methyl malonate With 4-toluenesulfonyl azide; triethylamine In acetonitrile at 0 - 20℃; Stage #2: 3-Phenylpropenol With rhodium(II) acetate dimer In dichloromethane at 0 - 20℃; Inert atmosphere;	59%

Benzyl methyl malonate 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

Product Name

Benzyl methyl malonate

Synthetic route

Benzyl methyl malonate Specification

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