6349-98-0

Basic information

• Product Name: PHTHALYL-DL-GLUTAMIC ACID
• Synonyms: 2-PHTHALIMIDINO-GLUTARIC ACID;PHTHALOYL-DL-GLUTAMIC ACID;PHTHALYL-DL-GLUTAMIC ACID;PHT-DL-GLU-OH;N-PHTHALOYL-DL-GLUTAMIC ACID;2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)glutaric acid;N-Phthalimido-glutamicacid;2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid
• CAS NO: 6349-98-0
• Molecular Formula: C₁₃H₁₁NO₆
• Molecular Weight: 277.23
• EINECS: 228-754-8
• Mol File: 6349-98-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 189.0 to 193.0 °C
• Boiling Point: 519.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.566±0.06 g/cm3(Predicted)
• Solubility: almost transparency in Methanol
• PKA: 3.45±0.10(Predicted)
• CAS DataBase Reference: PHTHALYL-DL-GLUTAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: PHTHALYL-DL-GLUTAMIC ACID(6349-98-0)
• EPA Substance Registry System: PHTHALYL-DL-GLUTAMIC ACID(6349-98-0)

Safety Data

• RTECS: MA3810000
• Hazardous Substances Data: 6349-98-0(Hazardous Substances Data)

Usage

Uses

2-Phthalimidino-glutaric acid is a stable analog of thalidomide.

InChI:InChI=1/C13H11NO6/c15-10(16)6-5-9(13(19)20)14-11(17)7-3-1-2-4-8(7)12(14)18/h1-4,9H,5-6H2,(H,15,16)(H,19,20)

Upstream product

• 85-44-9 phthalic anhydride 
• 56-86-0 L-glutamic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 617-65-2 Glutamic acid 
• 3350-06-9 2-cyclopentenamine 
• 3343-28-0 N-phthaloylglutamic acid anhydride 
• 204922-61-2 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-nitro-pentanedioic acid 5-ethyl ester 1-methyl ester 
• 100727-30-8 2-(cyclopent-2-en-1-yl)isoindoline-1,3-dione 

Downstream Products

• 617-65-2 Glutamic acid 
• 50-35-1 thalidomide 
• 56-85-9 GLUTAMINE 
• 7607-72-9 2-phthalimidoglutaramic acid 
• 912893-81-3 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(4-methoxy-benzylcarbamoyl)-butyric acid 
• 600721-43-5 2-(1-benzyloxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 600721-44-6 1-benzyloxy-3-(1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione 
• 222713-09-9 1-(4-methoxy-benzyl)-3-(1-oxo-3-phenylsulfanyl-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione 
• 222713-07-7 2-[1-(4-methoxybenzyl)-2,6-dioxopiperidin-3-yl]isoindoline-1,3-dione 
• 222713-08-8 3-(1-hydroxy-3-oxo-1,3-dihydro-isoindol-2-yl)-1-(4-methoxy-benzyl)-piperidine-2,6-dione 
• 222713-10-2 1-(4-methoxybenzyl)-3-(1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione 
• 94547-37-2 N⁵-benzyl-N²,N²-phthaloyl-glutamine 
• 24666-53-3 2-(1-benzyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 

Relevant articles and documents

Facile Synthesis of Thalidomide

We report a simple and facile procedure for the preparation of thalidomide in two steps with a high overall yield (56%). The preparation was composed of a reaction between anhydride phthalic and l-glutamic acid to form N-phthaloyl-dl-glutamic acid (IV), and a cyclization step using IV reacted with ammonium acetate in diphenyl ether to create thalidomide. Reaction parameters reaction time, temperature, solvent, and molar ratio of reagents in the procedure are optimized so that the reaction performance is highest while ensuring environmental friendliness. Moreover, this process has great potential for the industrial scale of thalidomide. These compounds were identified through IR, MS, 1H NMR, and 13C NMR.

Synthesis and evaluation of some N-Mannich bases of isoindole-1,3(2H)-dione derivatives as potential antimicrobial, anthelmintic and insecticidal agents

A series of some novel N-Mannich bases of benzimidazolyl substituted 1H-isoindole-1,3(2H) dione have been synthesized by cyclo-condensation of phthalic anhydride with different amino acids and thereafter, condensed with o-phenylenediamine following the Mannich protocol with different amines and formaldehyde to yield the titled compounds 5a-k. The structures of the newly synthesized compounds have been confirmed by FTIR, 1H NMR, mass spectral studies and elemental analyses. All the synthesized compounds have been evaluated for their in vitro antimicrobial, anthelmintic and insecticidal activities against selected microbes, helminthes and insects, compared to standard drugs streptomycin, nystatin, piperazine hydrochloride and cypermethrin respectively. Synthesized compounds 5d, 5j and 5k have shown promising activity against all selected microbes, helminthes and insects, while 5b is strongly toxic against S. aureus, 5g and 5k against B. subtilis, 5i against K. pneumoniae, 5a against T. viride and C. albicans, and 5h against A. niger. Compounds 5f, 5h, 5j, and 5k exhibited good antifungal activity, while 5b, 5g, 5e and 5i are sufficiently toxic for selected bacterial strains. Compounds 5a, 5b, 5c, 5e and 5f are strongly toxic against selected helminthes, while 5a, 5b, 5f, 5g, 5h and 5i have shown promising insecticidal activity.

Synthesis and enantiomeric separation of 2-phthalimidino-glutaric acid analogues: Potent inhibitors of tumor metastasis [2]

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