Sydnone, 3-(p-carboxyphenyl)-

Base Information

• Chemical Name: Sydnone, 3-(p-carboxyphenyl)-
• CAS No.: 7614-53-1
• Molecular Formula: C9H7N2O4+
• Molecular Weight: 206.158
• NSC Number: 63255
• DSSTox Substance ID: DTXSID90226999
• Nikkaji Number: J188.325I
• Wikidata: Q83106595
• Mol file: 7614-53-1.mol

Synonyms:3-(4-Carboxyphenyl)sydnone;Sydnone, 3-(p-carboxyphenyl)-;3-(p-Carboxyphenyl)sydnone;N-(p-Carboxyphenyl)sydnone;Sydnone, 3-(4-carboxyphenyl)-;7614-53-1;NSC 63255;N-(p-Karboxyphenyl)-sydnon [German];N-(p-Karboxyphenyl)-sydnon;BRN 3679419;4-27-00-07444 (Beilstein Handbook Reference);SCHEMBL15941121;DTXSID90226999;NSC63255;NSC-63255;LS-148307

Chemical Property of Sydnone, 3-(p-carboxyphenyl)-

Chemical Property:

• PSA: 90.27000
• LogP: 0.79330
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 206.03275668
• Heavy Atom Count: 15
• Complexity: 313

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)[O-])[N+]2=CC(=O)ON2

Technology Process of Sydnone, 3-(p-carboxyphenyl)-

There total 4 articles about Sydnone, 3-(p-carboxyphenyl)- 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: 58.0%

N-(p-carboxyphenyl)glycine (5698-54-4) → 3-(4-carboxyphenyl)-1,2,3λ5-oxadiazol-3-ylium-5-olate (7614-53-1)

Guidance literature:

N-(p-carboxyphenyl)glycine; With tert.-butylnitrite; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

With trifluoroacetic anhydride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.joc.7b03004

Reference yield: 52.0%

4-((carboxymethyl)(nitroso)amino)benzoic acid (111831-83-5) → 3-(4-carboxyphenyl)-1,2,3λ5-oxadiazol-3-ylium-5-olate (7614-53-1)

Guidance literature:

With acetic anhydride; at 100 ℃; for 3h;

DOI:10.1039/c4cc03816a

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 3-(4-carboxyphenyl)-1,2,3λ5-oxadiazol-3-ylium-5-olate (7614-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium acetate / water / 10 h / Reflux

2: hydrogenchloride; sodium nitrite / water / 14.67 h / 0 - 20 °C / Inert atmosphere

3: acetic anhydride / 3 h / 100 °C

With hydrogenchloride; sodium acetate; acetic anhydride; sodium nitrite; In water;

DOI:10.1039/c4cc03816a

upstream raw materials:

4-((carboxymethyl)(nitroso)amino)benzoic acid

N-(p-carboxyphenyl)glycine

4-amino-benzoic acid

Downstream raw materials:

4-bromo-3-(4-carboxyphenyl)-1,2,3λ⁵-oxadiazol-3-ylium-5-olate

3-(4-carboxyphenyl)-4-chloro-1,2,3λ⁵-oxadiazol-3-ylium-5-olate

3-(4-(methoxycarbonyl)phenyl)-1,2,3-oxadiazol-3-ium-5-olate

Refernces

• 1、 -. "SYDNONE DERIVATIVES FOR CONJUGATION OF COMPOUNDS OF INTEREST". Paragraph 0208-0209. . Retrieved 2017/04/11.
• 2、 Specklin, Simon,Decuypere, Elodie,Plougastel, Lucie,Aliani, Soifia,Taran, Frédéric. "One-pot synthesis of 1,4-disubstituted pyrazoles from arylglycines via copper-catalyzed sydnone-alkyne cycloaddition reaction". . p. 7772 - 7777. Retrieved 2014/10/15.