13552-87-9

Basic information

• Product Name: DIETHYL ASPARTATE
• Synonyms: DIETHYL ASPARTATE;[S,(+)]-Aminosuccinic acid diethyl ester;L-Aspartic acid diethyl;L-Aspartic diethyl ester
• CAS NO: 13552-87-9
• Molecular Formula: C₈H₁₅NO₄
• Molecular Weight: 189.209
• EINECS: 256-095-6
• Mol File: 13552-87-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 178-180 °C
• Boiling Point: 259.5°Cat760mmHg
• Flash Point: 97.5°C
• Appearance: /
• Density: 1.102g/cm³
• Vapor Pressure: 0.0129mmHg at 25°C
• Refractive Index: 1.45
• PKA: 6.19±0.33(Predicted)
• CAS DataBase Reference: DIETHYL ASPARTATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL ASPARTATE(13552-87-9)
• EPA Substance Registry System: DIETHYL ASPARTATE(13552-87-9)

Safety Data

• Hazardous Substances Data: 13552-87-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H15NO4/c1-3-12-7(10)5-6(9)8(11)13-4-2/h6H,3-5,9H2,1-2H3/t6-/m0/s1

Upstream product

• 64-17-5 ethanol 
• 70-47-3 L-asparagine 
• 56-84-8 L-Aspartic acid 
• 43101-48-0 DL-aspartic acid diethyl ester 
• 122-51-0 orthoformic acid triethyl ester 
• 16115-68-7 diethyl L-aspartate hydrochloride 
• 39256-89-8 N-Benzyloxycarbonyl-L-asparaginsaeure-β-aethylester 
• 57471-70-2 diethyl N-benzyloxycarbonyl-(S)-aspartate 

Downstream Products

• 101106-34-7 N-phenylsulfanylcarbonyl-L-aspartic acid diethyl ester 
• 16804-55-0 γ-Glu-asp 
• 121395-04-8 diethyl N²,N⁶-bis((benzyloxy)carbonyl)-L-lysyl-L-aspartate 
• 56-84-8 L-Aspartic acid 
• 7554-28-1 diethyl (R)-malate 
• 763-51-9 diethyl 2-bromosuccinate 
• 100658-82-0 N-(N-benzyloxycarbonyl-L-α-glutamyl)-L-aspartic acid diethyl ester 
• 926309-23-1 C₁₄H₁₉ClNO₆P 
• 1276112-67-4 (S)-diethyl 2-(3-[(R)-1-phenylethyl]ureido)succinate 
• 16150-75-7 rac.-N-Benzyl-N-<β,β-dimethoxycarbonyl-β-formamido-aethyl>-asparaginsaeure-diaethylester 

Relevant articles and documents

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Ionic liquids with methotrexate moieties as a potential anticancer prodrug: Synthesis, characterization and solubility evaluation

The technological utility of active pharmaceutical ingredients (APIs) is enormously improved when they are converted into ionic liquids (ILs). API-ILs possess better aqueous solubility and thermal stability than that of solid-state salt or crystalline drugs. However, many such API-ILs are not biocompatible or biodegradable. In the current study, we synthesized a series of IL-APIs using methotrexate (MTX), a potential anticancer prodrug, and biocompatible IL-forming cations (choline and amino acid esters). The MTX-IL moieties were characterized through 1H NMR, FTIR, p-XRD, DSC and thermogravimetric analysis. The solubility of the MTX-ILs was evaluated in simulated body fluids (phosphate-buffered saline, simulated gastric, and simulated intestinal fluids). An assessment of the in vitro antitumor activity of the MTX-ILs in a mammalian cell line (HeLa cells) was used to evaluate their cytotoxicity. The MTX-ILs showed aqueous solubility at least 5000 times higher than that of free MTX and two orders of magnitude higher compared with that of a sodium salt of MTX in both water and simulated body fluids. Importantly, a proline ethyl ester MTX prodrug showed similar solubility as the MTX sodium salt but it provided improved in vitro antitumor activity. These results clearly suggest that the newly synthesized API-ILs represent promising potential drug formulations.

Stereoretentive N-Arylation of Amino Acid Esters with Cyclohexanones Utilizing a Continuous-Flow System

The N-arylation of chiral amino acid esters with minimal racemization is a challenging transformation because of the sensitivity of the α-stereocenter. A versatile synthetic method was developed to prepare N-arylated amino acid esters using cyclohexanones as aryl sources under continuous-flow conditions. The designed flow system, which consists of a coil reactor and a packed-bed reactor containing a Pd(OH)2/C catalyst, efficiently afforded the desired N-arylated amino acids without significant racemization, accompanied by only small amounts of easily removable co-products (i. e., H2O and alkanes). The efficiency and robustness of this method allowed for the continuous synthesis of the desired product in very high yield and enantiopurity with high space-time yield (74.1 g L?1 h?1) and turnover frequency (5.9 h?1) for at least 3 days.