Diethyl malonate
Description uses References- Product Name
- Diethyl malonate
- CAS No.
- 105-53-3
- Chemical Name
- Diethyl malonate
- Synonyms
- DEM;ETHYL MALONATE;MALONIC ESTER;DIETHYL PROPANEDIOATE;MALONIC ACID DIETHYL ESTER;Diethyi malonate;Diethyl malonat;FEMA 2375;JACS-105-53-3;DIETHYL MALONATE
- CBNumber
- CB8852658
- Molecular Formula
- C7H12O4
- Formula Weight
- 160.17
- MOL File
- 105-53-3.mol
Diethyl malonate Property
- Melting point:
- -51--50 °C (lit.)
- 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)
- refractive index
- n20/D 1.413(lit.)
- FEMA
- 2375 | DIETHYL MALONATE
- Flash point:
- 212 °F
- storage temp.
- Store below +30°C.
- solubility
- 20.8g/l (External MSDS)
- pka
- 13.5(at 25℃)
- form
- Liquid
- color
- colourless liquid
- Odor
- Sweet ester odor
- Odor Type
- fruity
- explosive limit
- 0.8-12.8%(V)
- Water Solubility
- Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water.
- Merck
- 14,3823
- JECFA Number
- 614
- BRN
- 774687
- Dielectric constant
- 7.9（21℃）
- Stability:
- Stable. Combustible. Incompatible with strong oxidizing agents,
- InChIKey
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N
- LogP
- 0.96 at 20℃
- 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)
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
- Hazardous Substances Data
- 105-53-3(Hazardous Substances Data)
- Toxicity
- LD50 orally in Rabbit: 15720 mg/kg LD50 dermal Rabbit > 16000 mg/kg
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- 8.00898
- Product name
- Diethyl malonate
- Purity
- for synthesis
- Packaging
- 100mL
- Price
- $39.7
- Updated
- 2024/03/01
- Product number
- 8.00898
- Product name
- Diethyl malonate
- Purity
- for synthesis
- Packaging
- 500mL
- Price
- $57.9
- Updated
- 2024/03/01
- Product number
- 8.00898
- Product name
- Diethyl malonate
- Purity
- for synthesis
- Packaging
- 1L
- Price
- $87.5
- Updated
- 2024/03/01
- Product number
- 8.00898
- Product name
- Diethyl malonate
- Purity
- for synthesis
- Packaging
- 2.5L
- Price
- $159
- Updated
- 2024/03/01
- Product number
- 04151
- Product name
- Diethyl malonate
- Purity
- analytical standard
- Packaging
- 5ml
- Price
- $250
- Updated
- 2022/05/15
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.
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.
Definition
ChEBI: Ethyl malonate is a dicarboxylic acid.
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/jo00328a041
Tetrahedron 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.]
Diethyl malonate Preparation Products And Raw materials
Raw materials
Preparation Products
Diethyl malonate Suppliers
- Tel
- 18906359122
- 258225957@qq.com
- Country
- China
- ProdList
- 53
- Advantage
- 58
- Tel
- 400-400-6206333 18521732826
- Fax
- 021-50323701
- market@aladdin-e.com
- Country
- China
- ProdList
- 25003
- Advantage
- 65
- Tel
- 133-96369453 18678026865
- Fax
- 0536-2101172
- sdfantai@163.com
- Country
- China
- ProdList
- 862
- Advantage
- 58
- Tel
- 18560028598
- 2584792069@qq.com
- Country
- China
- ProdList
- 74
- Advantage
- 58
- Tel
- 1735-4997695 17715859063
- 1204996172@qq.com
- Country
- China
- ProdList
- 245
- Advantage
- 58
- Tel
- 18551497631 18551497631
- 507167383@qq.com
- Country
- China
- ProdList
- 4956
- Advantage
- 58
- Tel
- 027-19371278 19371278702
- Fax
- QQ：2729801554
- nuodina@163.com
- Country
- China
- ProdList
- 2904
- Advantage
- 58
- Tel
- 18014482516
- 977144864@qq.com
- Country
- China
- ProdList
- 402
- Advantage
- 58
- Tel
- 18207128853 18207128853
- 3860188266@qq.com
- Country
- China
- ProdList
- 914
- Advantage
- 58
- Tel
- 022-66880623
- Fax
- 86(0)22-66880086
- sales@tjzxchem.com
- Country
- China
- ProdList
- 613
- Advantage
- 60
- Tel
- 0838-5675166 15883665058
- Fax
- 0838-5675535
- nbcxkj@126.com
- Country
- China
- ProdList
- 667
- Advantage
- 55
- Tel
- 010-82848833 400-666-7788
- Fax
- 86-10-82849933
- jkinfo@jkchemical.com
- Country
- China
- ProdList
- 94657
- Advantage
- 76
- Tel
- 021-61259108 18621169109
- Fax
- 86-21-61259102
- market03@meryer.com
- Country
- China
- ProdList
- 40228
- Advantage
- 62
- Tel
- 400-6106006
- Fax
- 021-67582001/03/05
- saleschina@alfa-asia.com
- Country
- China
- ProdList
- 30123
- Advantage
- 84
- Tel
- 021-67121386
- Fax
- 021-67121385
- Sales-CN@TCIchemicals.com
- Country
- China
- ProdList
- 24529
- Advantage
- 81
- Tel
- 010-89508211 18501085097
- Fax
- 010-89508210
- sales.bj@hwrkchemical.com
- Country
- China
- ProdList
- 8415
- Advantage
- 55
- Tel
- 021-021-58432009 400-005-6266
- Fax
- 021-58436166
- sales8178@energy-chemical.com
- Country
- China
- ProdList
- 44689
- Advantage
- 61
- Tel
- 010-82967028 13552068683
- Fax
- +86-10-82967029
- 2355560935@qq.com
- Country
- China
- ProdList
- 12438
- Advantage
- 60
- Tel
- 13817811078
- Fax
- 86-021-50426522,50426273
- sales@jingyan-chemical.com
- Country
- China
- ProdList
- 9976
- Advantage
- 60
- Tel
- 0573-85285100 18627885956
- Fax
- 0573-85285100
- isenchem@163.com
- Country
- China
- ProdList
- 9414
- Advantage
- 66
- Tel
- 021-50795510 4000665055
- Fax
- 021-50795055
- sales@accelachem.com
- Country
- China
- ProdList
- 11655
- Advantage
- 64
- Tel
- 021-58099652-8005 13585536065
- Fax
- 021-58099609
- bin.wu@shlschem.com
- Country
- China
- ProdList
- 9809
- Advantage
- 59
- Tel
- 021-54306202 13764082696
- info@hanhongsci.com
- Country
- China
- ProdList
- 42958
- Advantage
- 64
- Tel
- 021-50135380
- shchemsky@sina.com
- Country
- China
- ProdList
- 32321
- Advantage
- 50
- Tel
- 21-62165282 15801962796;
- Fax
- 021 61153784
- bidingchem@163.com
- Country
- China
- ProdList
- 1183
- Advantage
- 60
- Tel
- 010-82954736 13391601435
- sales@isomersyn.com
- Country
- China
- ProdList
- 3295
- Advantage
- 57
- Tel
- 4009903999 13355009207
- Fax
- 0539-6365991
- 3007715519@qq.com
- Country
- China
- ProdList
- 18738
- Advantage
- 57
- Tel
- 400-1166-196 18981987031
- Fax
- 028-84555506 800101999
- cdhxsj@163.com
- Country
- China
- ProdList
- 11707
- Advantage
- 57
- Tel
- 0086-21-58956006
- Fax
- 0086-21-58956100
- Country
- China
- ProdList
- 7811
- Advantage
- 57
- Tel
- 400 638 7771
- sales@heowns.com
- Country
- China
- ProdList
- 14435
- Advantage
- 57
- Tel
- 86-21-63210123
- Fax
- 86-21-63290778 86-21-63218885
- sj_scrc@sinopharm.com
- Country
- China
- ProdList
- 9815
- Advantage
- 79
- Tel
- Please Send Email 18652950785
- Fax
- 025-87193546
- chemweiao@163.com
- Country
- China
- ProdList
- 4378
- Advantage
- 65
- Tel
- +86 (573) 82222445 (0)18006601000 452520369
- Fax
- +86 (573) 82222643
- sales@maya-r.com
- Country
- China
- ProdList
- 11707
- Advantage
- 57
- Tel
- 021-33690831-8001 13552411790
- Fax
- 021-33690831
- postmaster@tyjchem.cn
- Country
- China
- ProdList
- 1541
- Advantage
- 55
- Tel
- 021-021-021-67601398-809-809-809 15221380277
- Fax
- 021-57711696
- marketing_china@spectrumchemical.com
- Country
- China
- ProdList
- 9658
- Advantage
- 60
- Tel
- 021-021-52212593 18049974220
- Fax
- +86 (21) 51062076
- 2982497773@qq.com
- Country
- China
- ProdList
- 1622
- Advantage
- 60
- Tel
- 4008-755-333 18080918076
- Fax
- 028-86757656
- 800078821@qq.com
- Country
- China
- ProdList
- 9718
- Advantage
- 55
- Tel
- 0755-4000505016 13380397412
- Fax
- 0755 28094224
- 3001272453@qq.com
- Country
- China
- ProdList
- 5047
- Advantage
- 50
- Tel
- 022-60116533 13207668525
- Fax
- 022-60979672
- saleskc@scipharmacn.com
- Country
- China
- ProdList
- 684
- Advantage
- 58
- Tel
- 86-21-34053660
- Fax
- 86-21-34053661
- sale@labgogo.com
- Country
- China
- ProdList
- 9865
- Advantage
- 52
- Tel
- 800-810-5118
- Fax
- +86-10-84193589
- cnchemical@thermofisher.com
- Country
- China
- ProdList
- 17770
- Advantage
- 75
- Tel
- 400-810-7969 010-59572699
- Fax
- 010-59572688
- ningzi.li@inno-chem.com.cn
- Country
- China
- ProdList
- 6134
- Advantage
- 55
- Tel
- 21-50456736 13818239876
- Fax
- 021-50761379
- sales21@riyngroup.com
- Country
- China
- ProdList
- 1052
- Advantage
- 30
- Tel
- +86 21 61551611
- Fax
- +86 21 50676805
- Country
- China
- ProdList
- 9891
- Advantage
- 58
- Tel
- 18017383231 18017383231
- Fax
- qq：2817624287
- lyh_antaeus@163.com
- Country
- China
- ProdList
- 9347
- Advantage
- 55
- Tel
- 4009209199
- Fax
- 86-021-52271987
- sales@9dingchem.com
- Country
- China
- ProdList
- 22514
- Advantage
- 55
- Tel
- 021-69180038
- Fax
- 0086-21-39177059
- zhuoruichem@163.com
- Country
- China
- ProdList
- 105
- Advantage
- 58
- Tel
- 021-62960152
- Fax
- 021-52212593
- 934678158@qq.com
- Country
- China
- ProdList
- 9899
- Advantage
- 55
- Tel
- +86-021-50935922
- Fax
- +86-021-33847795
- Country
- China
- ProdList
- 7865
- Advantage
- 55
- Tel
- 021-021-33632979 15002134094
- Fax
- 021-33632979
- marketing@targetmol.com
- Country
- China
- ProdList
- 7783
- Advantage
- 58
View Lastest Price from Diethyl malonate manufacturers
- Product
- Diethyl malonate 105-53-3
- Price
- US $100.00-75.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 5000Ton
- Release date
- 2024-08-13
- Product
- Diethyl malonate 105-53-3
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- 99%
- Supply Ability
- 1000kg
- Release date
- 2024-03-26
- Product
- Diethyl malonate 105-53-3
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 ton
- Release date
- 2024-11-15