5-carboxy-X-rhodamine

Base Information

• Chemical Name: 5-carboxy-X-rhodamine
• CAS No.: 216699-35-3
• Molecular Formula: C33H30 N2 O5
• Molecular Weight: 534.612
• European Community (EC) Number: 683-410-8
• DSSTox Substance ID: DTXSID701314908
• Wikidata: Q27122698
• Mol file: 216699-35-3.mol

Synonyms:5-carboxy-X-rhodamine

Chemical Property of 5-carboxy-X-rhodamine

Chemical Property:

• PSA: 97.05000
• LogP: 5.12340
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 534.21547206
• Heavy Atom Count: 40
• Complexity: 1200

Purity/Quality:

99% ^*data from raw suppliers

5-ROX ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=CC3=C(C4=C2N(C1)CCC4)OC5=C6CCC[N+]7=C6C(=CC5=C3C8=C(C=C(C=C8)C(=O)[O-])C(=O)O)CCC7
• Uses: 5-ROX is the purified isomer of 5(6)-ROX. It is preferred for some complicated biological applications where reproducibility is really critical. The minor positional difference between 5-ROX and 6-ROX might significantly affect some biological properties 5-ROX is a purified isomer of carboxy-X-rhodamine. 5-ROX is widely used for oligonucleotide labeling and automated DNA sequencing applications.

Technology Process of 5-carboxy-X-rhodamine

There total 3 articles about 5-carboxy-X-rhodamine 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: 87.0%

8-hydroxyjulolidine (41175-50-2) + 5-carboxyphthalaldehydic acid → 5-carboxy-X-rhodamine (216699-35-3)

Guidance literature:

With oxygen; In 2,2,2-trifluoroethanol; at 75 ℃; for 21h; regioselective reaction;

DOI:10.1021/acs.orglett.6b02635

Reference yield: 34.0%

8-hydroxyjulolidine (41175-50-2) + trimellitic Anhydride (552-30-7,145253-53-8) → 6-carboxy-X-rhodamine (194785-18-7) + 5-carboxy-X-rhodamine (216699-35-3)

Guidance literature:

With sulfuric acid; In n-PrCO₂H; for 12h; Reflux;

DOI:10.1021/ol801904k

Reference yield:

m-Anisidine (536-90-3,918666-97-4) → 5-carboxy-X-rhodamine (216699-35-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium carbonate / 19 h / 70 - 150 °C

2: pyridine hydrochloride / 2 h / 200 °C

3: toluene-4-sulfonic acid / propionic acid / 24 h / Reflux

With pyridine hydrochloride; sodium carbonate; toluene-4-sulfonic acid; In propionic acid;

upstream raw materials:

8-hydroxyjulolidine

trimellitic Anhydride

m-Anisidine

Downstream raw materials:

5-carboxy-X-rhodamine N-succinimidyl ester

Refernces

• 1、 -. "METHODS FOR SYNTHESIZING RHODAMINE DYES". Paragraph 0100. . Retrieved 2017/05/17.
• 2、 Uddin, Md Jashim,Marnett, Lawrence J.. "Synthesis of 5- and 6-carboxy-x-rhodamines". supporting information; experimental part. p. 4799 - 4801. Retrieved 2009/05/31.