NSC 8864

NSC 8864 - Names and Identifiers

Name	Ethyl malonate
Synonyms	NSC 8864 AI3-00656 Malonic ester MALONIC ESTER FEMA No. 2375 Ethyl malonate ETHYL MALONATE UNII-53A58PA183 Diethyl malonate Diethyi malonate Dicarbethoxymethane Ethyl propanedioate Ethyl malonate (VAN) Diethyl propanedioate Carbethoxyacetic ester MALONIC ACID DIETHYL ESTER Ethyl methanedicarboxylate Malonic acid, diethyl ester Propanedioic acid, diethyl ester Propanedioic acid, 1,3-diethyl ester Methanedicarboxylic acid, diethyl ester Malonic Acid Diethyl EsterEthyl Malonate Diethyl malonate,Malonic acid diethyl ester
CAS	105-53-3 145601-68-9
EINECS	203-305-9
InChI	InChI:1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3
InChIKey	IYXGSMUGOJNHAZ-UHFFFAOYSA-N

NSC 8864 - Physico-chemical Properties

Molecular Formula	C7H12O4
Molar Mass	160.17
Density	1.055 g/mL at 25 °C (lit.)
Melting Point	-51--50 °C (lit.)
Boling Point	199 °C (lit.)
Flash Point	212°F
JECFA Number	614
Water Solubility	Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water.
Solubility	20.8g/l (External MSDS)
Vapor Presure	1 mm Hg ( 40 °C)
Vapor Density	5.52 (vs air)
Appearance	Colorless liquid
Color	colourless liquid
Odor	Sweet ester odor
Merck	14,3823
BRN	774687
pKa	13.5(at 25℃)
Storage Condition	Store below +30°C.
Stability	Stable. Combustible. Incompatible with strong oxidizing agents,
Sensitive	Sensitive to humidity
Explosive Limit	0.8-12.8%(V)
Refractive Index	n20/D 1.413(lit.)
MDL	MFCD00009195
Physical and Chemical Properties	Character colorless liquid, with a sweet ether odor. melting point -50 ℃ boiling point 199.3 ℃ relative density 1.0551 refractive index 1.4135 flash point 100 ℃ solubility miscible with alcohols and ethers, soluble in chloroform, benzene and other organic solvents. Slightly soluble in water. The solubility in water is 2.08g/100ml at 20 °c.
Use	It is used as an intermediate of sulfanilamide and barbiturate in medicine, and is also an intermediate of perfume and dye.

NSC 8864 - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	R36/37/38 - Irritating to eyes, respiratory system and skin. R36 - Irritating to the eyes
Safety Description	S24/25 - Avoid contact with skin and eyes. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany	1
RTECS	OO0700000
TSCA	Yes
HS Code	29171910
Hazard Note	Irritant
Toxicity	LD50 orally in Rabbit: 15720 mg/kg LD50 dermal Rabbit > 16000 mg/kg

NSC 8864 - Upstream Downstream Industry

Raw Materials	Sodium carbonate Sulfuric acid Chloroacetic acid Sodium cyanide Cyanoacetic acid Hydrochloric acid Chloroacetic acid Ethyl Alcohol
Downstream Products	malonic acid Diethyl n-butylmalonate 4,6-Dihydroxypyrimidine Diethyl ethoxymethylenemalonate sulfamonomethoxine enoxacin Phenylbutazone Chloroquine diphosphate Gliclazide

NSC 8864 - Nature

Open Data Verified Data

a colorless liquid with a sweet ether odor. The relative density was 1. 0551. Melting Point -50 °c. Boiling point 199.3 °c. Refractive index 4135. Flash point 100 ° C and alcohol, ether miscible, soluble in chloroform, benzene and other organic solvents. Slightly soluble in water, 20 ° C water solubility of 2. 08g/lOOmL.

Last Update：2024-01-02 23:10:35

NSC 8864 - Preparation Method

Open Data Verified Data

sodium chloroacetate method sodium chloroacetic acid is neutralized with sodium carbonate at 30 ° C. To form sodium chloroacetate, cyanated with sodium cyanide at 92-95 ° C., and then hydrolyzed with alkali to form sodium malonate. After drying, sodium malonate is esterified with ethanol at 70-72 °c in the presence of sulfuric acid. The esterification product was washed and distilled to obtain the final diethyl malonate.
The sodium cyanoacetate method is derived from the direct esterification of cyanoacetic acid with ethanol.

Last Update：2022-01-01 10:33:40

NSC 8864 - Introduction

Slightly aromatic. Soluble in alcohol, ether, benzene and chloroform, insoluble in water.

Last Update：2022-10-16 17:11:43

NSC 8864 - Use

Open Data Verified Data

mainly used in organic synthesis, is the intermediate of dyes, spices, but also the synthesis of chloroquine, phenylbutazone, barbiturate and other pharmaceutical raw materials.

Last Update：2022-01-01 10:33:40

NSC 8864 - Safety

Open Data Verified Data

This product is of low toxicity, rat oral LD50 >1600mg/kg, but in the body will be hydrolyzed into acid, to avoid contact. Wash after contact. Operators should wear rubber gloves.
This product is packaged in iron drum or galvanized iron drum with a specification of 200kg. According to the provisions of combustible chemicals storage and transportation.

Last Update：2022-01-01 10:33:41

NSC 8864 - Reference Information

FEMA	2375 \| DIETHYL MALONATE
LogP	0.96 at 20℃
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
overview	malonic acid and its derivatives are widely used in pharmaceutical, perfume, food additive, polyester and other industries, and are important fine chemical raw materials and intermediates. Especially in pharmaceutical intermediates, diethyl malonate is widely used in the synthesis of barbian acid, amino acids, vitamins B1, B2 and B6, sleeping pills and phenylbutazone and other drugs.
properties	diethyl malonate is an important fine chemical raw material, because the methylene hydrogen in its molecule is easily replaced by a variety of groups, And then generate a variety of important derivatives, which are widely used in various chemical production fields, including food, medicine, pesticides, industrial dyes, liquid crystal materials and other industries.
Use	Diethyl malonate is an important intermediate for the preparation of 2-amino -4, 6-dimethoxypyrimidine, and can be used to prepare sulfonylurea Herbicides, such as bensulfuron-methyl, pyrisulfuron-methyl, nicosulfuron-methyl, etc., are also intermediates for sulfa drugs and barbiturates in medicine. It can also be used in gas chromatography stationary liquid (the maximum use temperature is 40 ℃, the solvent is benzene, chloroform, ethanol) to verify ammonia and potassium. In addition, diethyl malonate is also a edible spice permitted by GB 2760-96. It is mainly used to prepare fruit flavors such as pears, apples, grapes, cherries, etc.
production method	chloroacetic acid is used as raw material, dissolved in water, sodium carbonate aqueous solution is added to pH = 7 at <30 ℃, sodium cyanide is added to the sodium chloroacetate solution after being dissolved in water, cyanidation reaction at 92~95 ℃ for 1h, alkali solution is added, heating reaction at 100~105 ℃ for 1h, hydrolysis is carried out, and then heating to remove water, ethanol and toluene are added, a little sulfuric acid is added dropwise, and the reaction is carried out at 68~70 ℃ for 3h, esterification is carried out, and then the ester layer is taken for vacuum distillation to obtain the finished product. ClCH2COOH + Na2CO3 → ClCH2COONaClCH2COONa + NaCH → NCCH2COONa + NaClNCCH2COONa + NaOH[H2O]→ NaOOC-CH2-COONa + NH3 The production methods of diethyl malonate are mainly cyanide esterification and catalytic carbonylation. At present, the traditional cyanide esterification method is still widely used in industry. It is obtained by neutralization, cyanidation, hydrolysis and esterification of chloroacetic acid. Chloroacetic acid is neutralized with sodium carbonate at 30°C to generate sodium chloroacetate, cyanated with sodium cyanide at 92-95°C, and then hydrolyzed with alkali to generate sodium malonate. After drying, sodium malonate is esterified with ethanol in the presence of sulfuric acid at 70-72°C. The esterification product is washed and distilled to obtain the finished diethyl malonate. Raw material consumption quota: chloroacetic acid (95%)650 kg/t, sodium cyanide (95%)340 kg/t, ethanol (95%)910 kg/t. The new process developed abroad is mainly based on catalytic carbonylation, that is, using chloroacetate, carbon monoxide, and ethanol as raw materials to synthesize diethyl malonate in the next step of the catalyst. In contrast, the catalytic carbonylation process is also the sodium cyanoacetate process, which is obtained by direct esterification of cyanoacetic acid and ethanol. It is obtained by co-boiling, distillation, and esterification of malonic acid and ethanol in benzene medium. It is obtained by esterification of sodium malonate and ethanol under sulfuric acid catalysis and then distillation.
spontaneous combustion temperature	435°C DIN 51794
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)