N-((1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl)glycine

Base Information

• Chemical Name: N-((1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl)glycine
• CAS No.: 3916-40-3
• Molecular Formula: C12H10N2O5
• Molecular Weight: 262.222
• Hs Code.: 2925190090
• European Community (EC) Number: 223-481-0
• NSC Number: 29726
• DSSTox Substance ID: DTXSID60192399
• Nikkaji Number: J195.974C
• Wikidata: Q83065058
• Mol file: 3916-40-3.mol

Synonyms:3916-40-3;2-(2-(1,3-dioxoisoindolin-2-yl)acetamido)acetic acid;Phthaloylglycylglycine;N-((1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl)glycine;2-[[2-(1,3-dioxoisoindol-2-yl)acetyl]amino]acetic acid;EINECS 223-481-0;N-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]glycine;2-[2-(1,3-Dioxoisoindolin-2-yl)acetamido]acetic acid;N-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl]glycine;NSC29726;Glycine, N-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl]-;CBKinase1_001888;CBKinase1_014288;Oprea1_395041;Oprea1_458539;PHTHALOYLGLY CYLGLYCINE;SCHEMBL16057586;DTXSID60192399;MFCD00057146;NSC 29726;NSC-29726;STK182860;AKOS000612138;SB65897;CS-0349106;EU-0038860;(2-(1,3-dioxoisoindolin-2-yl)acetyl)glycine;2-(2-(1,3-dioxoisoindolin-2-yl)acetamido)aceticacid;BRD-K06623473-001-01-4;Z57152604;F0850-1885;2-[[2-(1,3-dioxo-isoindol-2-yl)-acetyl]amino]-acetic acid;([(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]amino)acetic acid #

Chemical Property of N-((1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl)glycine

Chemical Property:

• Vapor Pressure: 1.78E-14mmHg at 25°C
• Boiling Point: 583.9°Cat760mmHg
• Flash Point: 306.9°C
• PSA: 103.78000
• Density: 1.509g/cm³
• LogP: -0.18780
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 262.05897142
• Heavy Atom Count: 19
• Complexity: 410

Purity/Quality:

99%min ^*data from raw suppliers

N-Phthaloylglycylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CC(=O)NCC(=O)O
• Uses: N-Phthaloylglycylglycine is an intermediate used in the synthesis of Rilmazafone Hydrochloride (R509715), which can be used in biological study of nitrazepam or rilmazafone hydrochloride combined with ethanol effects on human memory. It is also used as sleep aid medication.

Technology Process of N-((1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl)glycine

There total 12 articles about N-((1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl)glycine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

N-phthaloylglycine chloride (6780-38-7) + glycine (56-40-6,18875-39-3,25718-94-9) → N-phthaloylglycylglycine (3916-40-3)

Guidance literature:

glycine; With magnesium oxide; In water; at 25 ℃; for 4h;

N-phthaloylglycine chloride; In 1,4-dioxane; water; at 25 ℃; for 2h;

DOI:10.1021/ja030297b

Reference yield: 39.0%

phthalic anhydride (85-44-9) + glycylglycine (556-50-3) → N-phthaloylglycylglycine (3916-40-3)

Guidance literature:

at 175 ℃;

DOI:10.1002/ejic.200600219

Reference yield:

N-phthaloylglycine chloride (6780-38-7) → N-phthaloylglycylglycine (3916-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene

2: dioxane / und einer gepufferten wss.Loesung vom pH 7.4

With 1,4-dioxane; benzene;

DOI:10.1021/ja01159a066

upstream raw materials:

Glycine anhydride

benzene-1,2-dicarboxylic acid

phthalic anhydride

glycylglycine

Downstream raw materials:

N-({[4-Chloro-2-(2-fluoro-benzoyl)-phenyl]-methyl-carbamoyl}-methyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide

4-chloro-2-(o-chlorobenzoyl)-N-methyl-N^α-(phthalylglycyl)glycinanilide

N-({[4-Chloro-2-(hydroxy-phenyl-methyl)-phenyl]-methyl-carbamoyl}-methyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide

4-chloro-2-(o-chloro-α-hydroxybenzyl)-N-methyl-N^α-(phthalylglycyl)glycinanilide

Refernces

• 1、 Sato,Nakai,Wada,Mizoguchi,Hatanaka,Kanaoka. "Application of remote photocyclization with a pair system of phthalimide and methylthio groups. A photochemical synthesis of cyclic peptide models". . p. 3174 - 3180. Retrieved 1992.