Diethyl (N-acetylamino)propanedioate
Diethyl acetamidomalonate
CAS: 1068-90-2
Molecular Formula: C9H15NO5
Diethyl (N-acetylamino)propanedioate - Names and Identifiers
Diethyl (N-acetylamino)propanedioate - Physico-chemical Properties
| Molecular Formula | C9H15NO5 |
| Molar Mass | 217.22 |
| Density | 1.2850 (rough estimate) |
| Melting Point | 95-98 °C (lit.) |
| Boling Point | 185 °C/20 mmHg (lit.) |
| Flash Point | 185°C/20mm |
| Water Solubility | Soluble in chloroform and methanol. Slightly soluble in water. |
| Solubility | Soluble in hot alcohol, slightly soluble in ether and hot water. |
| Vapor Presure | 0.000565mmHg at 25°C |
| Appearance | Bright yellow solid |
| Color | White to light yellow |
| BRN | 783883 |
| pKa | 11.93±0.59(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.4640 (estimate) |
| MDL | MFCD00009146 |
| Physical and Chemical Properties | Melting point 94-97°C boiling point 185°C (20 torr) |
| Use | Used in pharmaceutical industry, also used as tryptophan Intermediate |
Diethyl (N-acetylamino)propanedioate - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36 - Irritating to the eyes R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S39 - Wear eye / face protection. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S44 - |
| WGK Germany | 3 |
| RTECS | OO0360000 |
| TSCA | Yes |
| HS Code | 29241900 |
| Hazard Class | IRRITANT |
| Toxicity | eye-rbt 500 mg/24H MLD 28ZPAK -,130,72 |
Diethyl (N-acetylamino)propanedioate - Introduction
Insoluble in water, soluble in alcohol.
Last Update：2022-10-16 17:11:49
Diethyl (N-acetylamino)propanedioate - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | diethyl acetaminomalonate (Diethyl acetamidomalonate, DEAM) is an important intermediate in organic synthesis, mainly used to synthesize desmethylchlorincomycin hydrochloride (LincomycinU-24729A), lincomycin (Lincomycin), pentyl chlorincomycin (Mirincarmycin) and lincomycin phosphate, etc. |
| preparation method | 1. nitrification of newly distilled diethyl malonate (Diethyl malonate, DEM) with sodium nitrite and acetic acid to generate diethyl oxime malonate (Diethyl oximidomalonate, DEOM). after extraction with dichloromethane, it is compounded with sodium acetate to form diethyl oxime malonate sodium compound salt, then reduced with zinc powder and acylated with acetic anhydride to synthesize DEAM. In the process of preparing composite salt, a large amount of sodium acetate and the extractant dichloromethane are used, which requires two-step decompression distillation, long reaction time (about 20h), high energy consumption, complicated operation, and acetic acid and sodium nitrite The amount is large, which is not suitable for industrial production. 2. the raw materials are the same method 1. after DEOM is prepared under the condition of shortening the reaction time (7.5h), DEAM is directly reduced and acylated with ether as extraction solvent. This method is easy to operate, shortens the reaction time and saves energy. However, the consumption of raw materials acetic acid and sodium nitrite is relatively large, especially the solvent ether is flammable and explosive, toxic, and industrial production is more dangerous. 3. there are patent reports that DEOM is prepared under the condition of reducing the feeding of acetic acid and sodium nitrite, then hydrogenated and reduced with Pd-C catalyst, and then acylated with acetic anhydride. Although this method saves raw materials, it Pd-C difficult to regenerate and has low utilization rate. 4. using dichloromethane with low toxicity and flammability as extraction solvent, diethyl oxime malonate was synthesized by phase transfer catalysis method, and then DEOM was reduced by zinc powder in acetic acid medium and acetic anhydride acylation was carried out to obtain the product. This method has less raw material consumption, low energy consumption, simple operation, safer solvent, less consumption, and is suitable for industrial production. fig. 1 is the synthesis route experimental method: (1) synthesis of diethyl oxime malonate (1): 80g (0.5mol) DEM, 69g (1mol) sodium nitrite, 69g (1mol) water and 2g phase transfer catalyst (hexyltrimethylammonium bromide) were added into a 500mL three-mouth bottle, and stirred vigorously. Then, 58.3mL(1mol) of glacial acetic acid was added dropwise at 5 ℃ for about 1h. After dropping the acid, react at 30~40 ℃ for 4 hours. Add 50mL of water and 200 mLCH2 Cl2 for extraction. The organic layer is separated, and the water layer is extracted with 2 × 50 mLCH2Cl2 respectively, the organic phase is combined, and anhydrous Na2SO4 is added to dry overnight. Filter out the precipitate, distill the filtrate, and remove the solvent to obtain a light yellow oily liquid 1. (2) Preparation of diethyl acetaminomalonate (DEAM) (2): 1,130mL acetic anhydride and 300mL glacial acetic acid were added into a 1000mL three-mouth bottle, and 110g zinc powder was slowly added at room temperature. The reaction temperature is controlled between 40~50 ℃, the material is added, the reaction is carried out for 0.5h, the filter cake is filtered while hot, and the filter cake is cleaned twice with 100mL hot acetic acid. Merge the filtrate, distillation under reduced pressure, and recover acetic acid. When crystals appear on the flask wall, stop distillation. Add 150mL of water to heat and dissolve, then place it in an ice bath and stir vigorously, and a large amount of solid is precipitated. Let stand in the ice bath for 2 hours and filter. The filter cake is washed with cold tap water and dried to obtain 85g of white powdery crystals. |
| application | used to synthesize desmethyllincomycin hydrochloride (LincomycinU-24729A), lincomycin (Lincomycin), pentyl lincomycin (Mirincarmycin) and lincomycin phosphate, etc. |
| Main reference materials | /ChemicalProductProperty_CN_CB3491359.htm [1] Qu Bin et al. Study on New Synthesis Process of Diethyl Acetaminomalonate. The chemical world. 2002:587-589. |
| Uses | Used in the synthesis of α-amino acids, such as intermediates for tryptophan and pain-reducing mustard. Alkylation reaction is one of the key reactions in the synthesis of amino acids. When the product is mixed with equimolar benzyl chloride, tetrabutylammonium bromide, sodium iodide and powdered potassium carbonate are added, and stirred at 100 ℃ for 5h, cooling, filtering, washing and drying are performed to obtain diethyl benzylacetaminomalonate with 92% yield. It is used in the pharmaceutical industry and also as a tryptophan intermediate It is mainly used to synthesize desmethylchlorincomycin hydrochloride (LincomycinU-21729A), lincomycin (Lincomycin), pentyl chlorincomycin (Mirincarmycin) and lincomycin phosphate. |
| production method | is obtained by nitrosation, reduction and acetylation of diethyl malonate. |
| category | toxic substances |
| stimulation data | eyes-rabbit 500 mg/24 hours mild |
| flammability hazard characteristics | flammability; heating decomposition releases toxic nitrogen oxide smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand and water |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
Supplier List
Featured ProductsSpot supply
Product Name: Diethyl acetamidomalonate Request for quotationCAS: 1068-90-2
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3787852685
Featured ProductsMultiple SpecificationsSpot supply
Product Name: Diethyl acetamidomalonate Request for quotationCAS: 1068-90-2
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3785839865
Spot supply
Product Name: Diethyl acetamidomalonate Request for quotationCAS: 1068-90-2
Tel: 15335994747
Email: 3521670276@qq.com
Mobile: 15335994747
QQ: 3521670276
Wechat: A2020071098
Product Name: Diethyl acetamidomalonate Request for quotation
CAS: 1068-90-2
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
CAS: 1068-90-2
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
Product Name: Diethyl acetamidomalonate Request for quotation
CAS: 1068-90-2
Tel: 0086-551-65418684
Email: sales@tnjchem.com
info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840
Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
CAS: 1068-90-2
Tel: 0086-551-65418684
Email: sales@tnjchem.com
info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840
Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
Spot supply
Product Name: Diethyl acetamidomalonate Visit Supplier Webpage Request for quotationCAS: 1068-90-2
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Product Name: Diethyl acetamidomalonate Request for quotation
CAS: 1068-90-2
Tel: 0086-13605431940
Email: xuli678323@126.com
Mobile: +86-13605431940
QQ: 56860987
Wechat: 13605431940
WhatsApp: 13605431940
CAS: 1068-90-2
Tel: 0086-13605431940
Email: xuli678323@126.com
Mobile: +86-13605431940
QQ: 56860987
Wechat: 13605431940
WhatsApp: 13605431940
Featured ProductsSpot supply
Product Name: Diethyl acetamidomalonate Request for quotationCAS: 1068-90-2
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3787852685
Featured ProductsMultiple SpecificationsSpot supply
Product Name: Diethyl acetamidomalonate Request for quotationCAS: 1068-90-2
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3785839865
Spot supply
Product Name: Diethyl acetamidomalonate Request for quotationCAS: 1068-90-2
Tel: 15335994747
Email: 3521670276@qq.com
Mobile: 15335994747
QQ: 3521670276
Wechat: A2020071098
Product Name: Diethyl acetamidomalonate Request for quotation
CAS: 1068-90-2
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
CAS: 1068-90-2
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
Product Name: Diethyl acetamidomalonate Request for quotation
CAS: 1068-90-2
Tel: 0086-551-65418684
Email: sales@tnjchem.com
info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840
Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
CAS: 1068-90-2
Tel: 0086-551-65418684
Email: sales@tnjchem.com
info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840
Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
Spot supply
Product Name: Diethyl acetamidomalonate Visit Supplier Webpage Request for quotationCAS: 1068-90-2
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Product Name: Diethyl acetamidomalonate Request for quotation
CAS: 1068-90-2
Tel: 0086-13605431940
Email: xuli678323@126.com
Mobile: +86-13605431940
QQ: 56860987
Wechat: 13605431940
WhatsApp: 13605431940
CAS: 1068-90-2
Tel: 0086-13605431940
Email: xuli678323@126.com
Mobile: +86-13605431940
QQ: 56860987
Wechat: 13605431940
WhatsApp: 13605431940
View History