Welcome to LookChem.com Sign In|Join Free
  • or

105-53-3

Post Buying Request

105-53-3 Suppliers

Recommended suppliersmore

Product FOB Price Min.Order Supply Ability Supplier
Diethyl malonate Manufacturer/High quality/Best price/In stock
Cas No: 105-53-3
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
105-53-3 Diethyl malonate
Cas No: 105-53-3
No Data 1 Metric Ton 20 Metric Ton/Day Henan Tianfu Chemical Co., Ltd. Contact Supplier
Dimethyl Malonate\Malonic acid diethyl ester
Cas No: 105-53-3
USD $ 6.5-6.5 / Metric Ton 1 Metric Ton 36 Metric Ton/Week Hangzhou Johoo Chemical Co., Ltd Contact Supplier
High quality Diethyl malonate for hot sale
Cas No: 105-53-3
No Data No Data No Data Wuxi TAA Chemical Industry Co.,LTD. Contact Supplier
High quality Diethylmalonate supplier in China
Cas No: 105-53-3
No Data 1 Metric Ton 30 Metric Ton/Month Simagchem Corporation Contact Supplier
Diethyl malonate
Cas No: 105-53-3
USD $ 12.0-12.0 / Gram 1000 Gram 1000 Metric Ton/Year Jinan Finer Chemical Co., Ltd Contact Supplier
diethyl malonate
Cas No: 105-53-3
USD $ 1.0-2.0 / Metric Ton 1 Metric Ton 100 Metric Ton/Week Hebei yanxi chemical co.,LTD. Contact Supplier
Diethyl malonate manufacturer
Cas No: 105-53-3
No Data 200 Kilogram Metric Ton/Day Hefei TNJ chemical industry co.,ltd Contact Supplier
Good quality Diethyl malonate Cas 105-53-3 with best purity factory price
Cas No: 105-53-3
USD $ 3.0-3.7 / Kilogram 200 Kilogram 1000 Metric Ton/Year Wuhan Fortuna Chemical Co.,Ltd Contact Supplier
Large Stock 99.0% Ethyl malonate 105-53-3 Producer
Cas No: 105-53-3
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier

105-53-3 Usage

Description

As an organic compound, diethyl malonate belongs to the diethyl ester of malonic acid, which is present naturally in guava fruits, melons, grapes, pineapples, blackberries and strawberries as a colorless liquid with an apple-like odor. It is a flavor ingredient commonly found in perfumes, artificial flavorings, alcoholic beverages, various wines and spirits due to its natural pleasant odor. It is also used as an essential intermediate in the syntheses of numerous pharmaceuticals, such as barbiturates, vitamins B1 and B6, non-steroidal anti-inflammatory agents. Besides, diethyl malonate is also involved in organic synthesis of other compounds, such as alpha-aryl malonates, mono-substituted and di-substituted acetic acid. And it can react with benzaldehyde for the production of diethyl benzylidenemalonate in Knoevenagel condensation reaction.

uses

Diethyl malonate is the diethyl ester of malonic acid. It naturally occuring in grapes and strawberries, is widely used in the manufacture of pharmaceuticals, antioxidants, and dyes.Diethyl malonate is used in organic synthesis for the preparation of alpha-aryl malonates, mono-substituted and di-substituted acetic acid, barbiturates and artificial flavorings. It is also involved in the synthesis of pharmaceuticals like chloroquine, butazolidin and barbital. It acts as intermediate in the synthesis of vitamin B1, vitamin B6, non-steroidal anti-inflammatory agents agrochemicals and perfumes. In Knoevenagel condensation reaction, it reacts with benzaldehyde to get diethyl benzylidenemalonate.

References

https://en.wikipedia.org/wiki/Diethyl_malonate https://pubchem.ncbi.nlm.nih.gov/compound/7761#section=Safety-and-Hazards https://www.alfa.com/zh-cn/catalog/A15468/ http://www.hmdb.ca/metabolites/HMDB29573 http://www.chemicalland21.com/industrialchem/organic/DIETHYL%20MALONATE.htm

Description

Diethyl malonate is a diester derivative of malonic acid, a dicarboxylic acid with two carboxyl groups (-COO-) separated by one methylene group (-CH2-). Diethyl malonate is formed by the replacement of the hydroxyl groups (-OH) of malonic acid with ethoxy groups (-OCH2CH3). The hydrogen atoms on the methylene carbon between the two carboxyl groups make this compound acidic. Because of its unique structure, diethyl malonate is reactive and functions as a reagent for organic synthesis and to make products such as barbiturates, pigments, and agrochemicals. Volatile esters are known to have fruity scents and are often used as fragrances and flavorings. Diethyl malonate is a volatile diester that occurs naturally in fruits such as grapes, strawberries, guava, melon, pineapple, and blackberries.

Chemical Properties

Diethyl malonate has a faint, pleasant, aromatic odor.

Occurrence

Reported found in pineapple, bilberry, Cape gooseberry, cognac, malt whiskey, apple brandy, grape brandy, port, cider, sherry and red, white, strawberry and bilberry wines.

Uses

Diethyl Malonate occurs naturally in grapes and strawberries. It is used in the preparation of barbiturates, artificial flavourings, vitamin B1, and vitamin B6 as well as in perfumes.

Uses

manufacture of barbiturates.

Uses

Diethyl malonate is used in organic synthesis for the preparation of alpha-aryl malonates, mono-substituted and di-substituted acetic acid, barbiturates and artificial flavorings. It is also involved in the synthesis of pharmaceuticals like chloroquine, butazolidin and barbital. It acts as intermediate in the synthesis of vitamin B1, vitamin B6, non-steroidal anti-inflammatory agents agrochemicals and perfumes. In Knoevenagel condensation reaction, it reacts with benzaldehyde to get diethyl benzylidenemalonate.

Preparation

Reacting chloroacetic acid to cyanoacetic acid using sodium cyanide and subsequent saponification; malonic acid is finally esterified by azeotropic distillation with ethanol in benzene

Taste threshold values

Taste characteristics at 50 ppm: sweet and fruity with apple and pineapple nuances.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 3151, 1981 DOI: 10.1021/jo00328a041Tetrahedron Letters, 36, p. 3997, 1995 DOI: 10.1016/0040-4039(95)00697-B

General Description

Diethyl malonate is diethyl ester of malonic acid. Acylation of diethyl malonate using magnesium chloride and triethylamine is reported. K2CO3-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones yields polyfunctionalized β,γ-unsaturated enones.

Safety Profile

Mildly toxic by ingestion. A skin irritant. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use water to blanket fire, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

Metabolism

When the ester was fed to chicks at a level of 5% in the diet, 32% of the energy from diethyl malonate was available (Yoshida et al. 1970). Hydrolysis of diethyl malonate would produce ethanol and malonic acid, which is a relatively strong acid and acts as an inhibitor of enzymes, including succinic dehydrogenase (Fassett, 1963). Malonic acid injected into rats or rabbits is excreted largely unchanged, but also causes increased excretion of citric and a-ketoglutaric acids (Krebs, Salvin & Johnson, 1938). Some malonate may be metabolized through the tricarboxylic acid cycle, with decarboxylation to acetate followed by transformation to succinate, which has been detected in rat urine (Lee & Lifson, 1951). Diethyl malonate was hydrolysed by adipose-tissue lipase (Lynn & Perryman, 1960) and to the monoester by α-chymotrypsin (Cohen & Crossely, 1964). It was oxidized in 110 min to the extent of 34% by the homogenized mycelium of urethane-grown Streptomyces nitrifica (Schatz, Trelawny, Schatz & Mohan, 1957).

Purification Methods

If too impure (IR, NMR) the ester (250g) is heated on a steam bath for 36hours with absolute EtOH (125mL) and conc H2SO4 (75mL), then fractionally distilled under reduced pressure. Otherwise fractionally distil it under reduced pressure and collect the steady boiling middle fraction. [Beilstein 2 IV 1881.]
InChI:InChI:1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3

105-53-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A15468)  Diethyl malonate, 99%    105-53-3 500g 335.0CNY Detail
Alfa Aesar (A15468)  Diethyl malonate, 99%    105-53-3 2500g 1027.0CNY Detail
Alfa Aesar (A15468)  Diethyl malonate, 99%    105-53-3 10000g 3490.0CNY Detail

105-53-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Diethyl malonate

1.2 Other means of identification

Product number -
Other names diethyl propanedioate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:105-53-3 SDS

105-53-3Synthetic route

4-[(3-ethoxy-1,3-dioxopropyl)amino]-benzoic acid
130217-49-1

4-[(3-ethoxy-1,3-dioxopropyl)amino]-benzoic acid

A

N,N'-di-4-carboxyanilide of malonic acid
10256-16-3

N,N'-di-4-carboxyanilide of malonic acid

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 98%
B n/a
2-carboxymalonanilic acid ethyl ester
101646-18-8

2-carboxymalonanilic acid ethyl ester

A

N,N'-di-2-carboxyanilide of malonic acid
77317-57-8

N,N'-di-2-carboxyanilide of malonic acid

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 98%
B n/a
[di-μ-(ethoxycarbonyl-(methylene))-bis(tricarbonyl-cobalt) (Co-Co)]

[di-μ-(ethoxycarbonyl-(methylene))-bis(tricarbonyl-cobalt) (Co-Co)]

carbon monoxide
201230-82-2

carbon monoxide

A

dicobalt octacarbonyl
61091-28-9, 15226-74-1, 61117-58-6

dicobalt octacarbonyl

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
With ethanol In hexane High Pressure; soln. of Co2(CO)8 and EtOH placed in autoclave; pressurized (room temp.,50 bar CO); shaken (60 min); IR; gas chromy.;A 98%
B 95%
4-ethoxymalonanilic acid ethyl ester
4270-39-7

4-ethoxymalonanilic acid ethyl ester

A

N,N'-di-4-ethoxyanilide of malonic acid
4270-37-5

N,N'-di-4-ethoxyanilide of malonic acid

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 97%
B n/a
[μ2-(ethoxycarbonyl(methylene))-μ2-(carbonyl)-(tricarbonyl-cobalt)-(triphenylphosphane-dicarbonyl-cobalt) (Co-Co)]

[μ2-(ethoxycarbonyl(methylene))-μ2-(carbonyl)-(tricarbonyl-cobalt)-(triphenylphosphane-dicarbonyl-cobalt) (Co-Co)]

carbon monoxide
201230-82-2

carbon monoxide

A

Co2(CO)7(PPh3)
15906-55-5, 26534-25-8

Co2(CO)7(PPh3)

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
With ethanol In dichloromethane High Pressure; soln. of cobalt complex and anhyd. ethanol pressurized with CO in autoclave at 25°C and 50 bar for 24 h; IR;A 97%
B 66%
2-methoxymalonanilic acid ethyl ester
90475-72-2

2-methoxymalonanilic acid ethyl ester

A

N1,N3-bis(2-methoxyphenyl)malonamide
7056-72-6

N1,N3-bis(2-methoxyphenyl)malonamide

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 96%
B n/a
2-hydroxy-4-nitromalonanilic acid ethyl ester
43038-58-0

2-hydroxy-4-nitromalonanilic acid ethyl ester

A

N,N'-di-2-hydroxy-4-nitroanilide of malonic acid

N,N'-di-2-hydroxy-4-nitroanilide of malonic acid

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 96%
B n/a
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
With bismuth(III) oxide; N-ethyl-N,N-diisopropylamine; para-thiocresol In dichloromethane for 1h; Irradiation;96%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In 2,2,2-trifluoroethanol at 20℃; for 4h; UV-irradiation; Sealed tube; Green chemistry;91%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; N-ethyl-N,N-diisopropylamine; 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole In N,N-dimethyl-formamide for 2.5h; Inert atmosphere; Irradiation;87%
4-carboethoxymalonanilic acid ethyl ester
159657-36-0

4-carboethoxymalonanilic acid ethyl ester

A

N,N'-di-4-carboethoxyanilide of malonic acid
19288-86-9

N,N'-di-4-carboethoxyanilide of malonic acid

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 96%
B n/a
[μ2-(ethoxycarbonyl(methylene))-μ2-(carbonyl)-bis(triphenylphosphane-dicarbonyl-cobalt) (Co-Co)]

[μ2-(ethoxycarbonyl(methylene))-μ2-(carbonyl)-bis(triphenylphosphane-dicarbonyl-cobalt) (Co-Co)]

carbon monoxide
201230-82-2

carbon monoxide

A

tricarbonyldi(triphenylphosphine)cobalt(1+) tetracarbonylcobaltate(1-)
14243-08-4

tricarbonyldi(triphenylphosphine)cobalt(1+) tetracarbonylcobaltate(1-)

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
With ethanol In dichloromethane High Pressure; soln. of cobalt complex and anhyd. ethanol pressurized with CO in autoclave at 25°C and 50 bar for 24 h; IR;A n/a
B 96%
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

A

tetraethyl ethane-1,1,2,2-tetracarboxylate
632-56-4

tetraethyl ethane-1,1,2,2-tetracarboxylate

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; electrochemical reaction: -1,0 V, 0,1 mol/dm3 Et4NClO4, mercury pool cathode;A 95%
B 5%
With potassium hydrogenphosphate trihydrate; 2,6-di-tert-butyl-4-methyl-phenol In ethanol at 20℃; for 1h; Mechanism; Irradiation; Inert atmosphere; Green chemistry;
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

EtTe(CH2)3OH
189247-71-0

EtTe(CH2)3OH

A

2-Bromo-2-ethyl-2λ4-[1,2]oxatellurolane

2-Bromo-2-ethyl-2λ4-[1,2]oxatellurolane

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;A 71%
B 95%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

A

diethyl malonate
105-53-3

diethyl malonate

B

CO2

CO2

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;A 95%
B n/a
chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
With sodium ethanolate In ethanol95%

105-53-3Downstream Products

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 105-53-3