Benzoic acid, 2-(3,6-diamino-2-iodo-9H-xanthen-9-yl)-, methyl ester

Base Information

• Chemical Name: Benzoic acid, 2-(3,6-diamino-2-iodo-9H-xanthen-9-yl)-, methyl ester
• CAS No.: 109244-59-9
• Molecular Formula: C21H17IN2O3
• Molecular Weight: 472.282
• DSSTox Substance ID: DTXSID10426070
• ChEMBL ID: CHEMBL50874
• Mol file: 109244-59-9.mol

Synonyms:Iododihydrorhodamine 123;109244-59-9;Benzoic acid, 2-(3,6-diamino-2-iodo-9H-xanthen-9-yl)-, methyl ester;Iodo-reduced Rhodamine 123;CHEMBL50874;DTXSID10426070

Chemical Property of Benzoic acid, 2-(3,6-diamino-2-iodo-9H-xanthen-9-yl)-, methyl ester

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 472.02839
• Heavy Atom Count: 27
• Complexity: 548

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=CC=C1C2C3=C(C=C(C=C3)N)OC4=CC(=C(C=C24)I)N

Technology Process of Benzoic acid, 2-(3,6-diamino-2-iodo-9H-xanthen-9-yl)-, methyl ester

There total 3 articles about Benzoic acid, 2-(3,6-diamino-2-iodo-9H-xanthen-9-yl)-, methyl ester 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: 21.0%

Dihydrorhodamine 123 (109244-58-8) → 4'-iododihydrorhodamine 123 (109282-63-5) + 2'-iododihydrorhodamine 123 (109244-59-9) + 4',7'-diiododihydrorhodamine 123 (109244-61-3) + 2',7'-diiododihydrorhodamine 123 (109244-60-2)

Guidance literature:

With N-chloro-succinimide; ammonium acetate; sodium iodide; In methanol; tetrachloromethane; dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1021/jm00393a013

Reference yield: 5.0%

Dihydrorhodamine 123 (109244-58-8) → 4'-iododihydrorhodamine 123 (109282-63-5) + 2'-iododihydrorhodamine 123 (109244-59-9) + 2',7'-diiododihydrorhodamine 123 (109244-60-2)

Guidance literature:

With N-chloro-succinimide; ammonium acetate; sodium iodide; In methanol; tetrachloromethane; dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jm00393a013

Reference yield:

rhodamin 123 (62669-70-9) → 2'-iododihydrorhodamine 123 (109244-59-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / CH₂Cl₂; H₂O / 1 h

2: 21 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH₄OAc / methanol; CH₂Cl₂; CCl₄ / 1 h / 0 - 20 °C

With sodium tetrahydroborate; N-chloro-succinimide; ammonium acetate; sodium iodide; In methanol; tetrachloromethane; dichloromethane; water;

DOI:10.1021/jm00393a013

upstream raw materials:

Dihydrorhodamine 123

rhodamin 123

Refernces