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Diethyl malonate

Product Name:
Diethyl malonate
CAS No.
105-53-3
Chemical Name:
Diethyl malonate
CBNumber:
CB8852658
Molecular Formula:
C7H12O4
Formula Weight:
160.17
MOL File:
105-53-3.mol
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Diethyl malonate Property

Melting point:
-50 °C
Boiling point:
199 °C(lit.)
Density 
1.055 g/mL at 25 °C(lit.)
vapor density 
5.52 (vs air)
vapor pressure 
1 mm Hg ( 40 °C)
FEMA 
2375 | DIETHYL MALONATE
refractive index 
n20/D 1.413(lit.)
Flash point:
212 °F
storage temp. 
Store below +30°C.
solubility 
20.8g/l (External MSDS)
pka
13.5(at 25℃)
form 
Liquid
explosive limit
0.8-12.8%(V)
Water Solubility 
Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water.
JECFA Number
614
Merck 
14,3823
BRN 
774687
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents,
InChIKey
IYXGSMUGOJNHAZ-UHFFFAOYSA-N
CAS DataBase Reference
105-53-3(CAS DataBase Reference)
NIST Chemistry Reference
Propanedioic acid, diethyl ester(105-53-3)
EPA Substance Registry System
Diethyl malonate (105-53-3)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38-36
Safety Statements 
24/25-26
WGK Germany 
1
RTECS 
OO0700000
Autoignition Temperature
435 °C DIN 51794
Hazard Note 
Irritant
TSCA 
Yes
HS Code 
29171910
Toxicity
LD50 orally in Rabbit: 15720 mg/kg LD50 dermal Rabbit > 16000 mg/kg
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N-Bromosuccinimide Price More Price(19)

Sigma-Aldrich Gold
Product number:
04151
Product name :
Diethyl malonate
Purity:
analytical standard
Packaging:
1ml
Price:
$51.8
Updated:
2019/12/02
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Sigma-Aldrich Gold
Product number:
04151
Product name :
Diethyl malonate
Purity:
analytical standard
Packaging:
5ml
Price:
$206
Updated:
2019/12/02
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TCI Chemical Gold
Product number:
M0029
Product name :
Diethyl Malonate
Purity:
>99.0%(GC)
Packaging:
25mL
Price:
$14
Updated:
2020/06/24
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TCI Chemical Gold
Product number:
M0029
Product name :
Diethyl Malonate
Purity:
>99.0%(GC)
Packaging:
500mL
Price:
$24
Updated:
2020/06/24
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Alfa Aesar Gold
Product number:
A15468
Product name :
Diethyl malonate, 99%
Packaging:
500g
Price:
$31
Updated:
2020/06/24
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Diethyl malonate Chemical Properties,Usage,Production

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.

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

Chemical Properties

colourless liquid

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.

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.

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.]

Diethyl malonate Preparation Products And Raw materials Raw materials

Raw materials

Preparation Products

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Diethyl malonate Suppliers

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Description References