6-Aminotetramethylrhodamine

Base Information

• Chemical Name: 6-Aminotetramethylrhodamine
• CAS No.: 159435-10-6
• Molecular Formula: C24H23N3O3
• Molecular Weight: 401.46
• DSSTox Substance ID: DTXSID80402169
• Wikidata: Q82205545
• Mol file: 159435-10-6.mol

Synonyms:6-Aminotetramethylrhodamine;159435-10-6;6-Aminotetramethyl Rhodamine;5-amino-3',6'-bis(dimethylamino)spiro[2-benzofuran-3,9'-xanthene]-1-one;Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 6-amino-3',6'-bis(dimethylamino)-;DTXSID80402169;AKOS030254248;FT-0662078;J-009606;6-amino-3',6'-bis(dimethylamino)-3h-spiro[2-benzofuran-1,9'-xanthen]-3-one

Chemical Property of 6-Aminotetramethylrhodamine

Chemical Property:

• Vapor Pressure: 4.46E-18mmHg at 25°C
• Melting Point: >300°C (dec.)
• Refractive Index: 1.712
• Boiling Point: 675 °C at 760 mmHg
• PKA: 4.10±0.20(Predicted)
• Flash Point: 362 °C
• PSA: 68.03000
• Density: 1.36 g/cm³
• LogP: 4.55000
• Storage Temp.: -20°C Freezer
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 401.17394160
• Heavy Atom Count: 30
• Complexity: 636

Purity/Quality:

99% ^*data from raw suppliers

6-AminotetramethylRhodamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC2=C(C=C1)C3(C4=C(O2)C=C(C=C4)N(C)C)C5=C(C=CC(=C5)N)C(=O)O3
• Uses: Biulding Block Synthetic Intermediat

Technology Process of 6-Aminotetramethylrhodamine

There total 7 articles about 6-Aminotetramethylrhodamine 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: 77.0%

6-acetamido-3',6'-bis(dimethylamino)spiro<1,3-dihydroisobenzofuran-1,9'-xanthen>-3-one (159435-06-0) → 6-amino-3',6'-bis(dimethylamino)spiro<1,3-dihydroisobenzofuran-1,9'-xanthen>-3-one (159435-10-6)

Guidance literature:

With hydrogenchloride; In ethanol; for 2h; Heating;

Reference yield: 62.0%

6-azidotetramethylrhodamine → 6-amino-3',6'-bis(dimethylamino)spiro<1,3-dihydroisobenzofuran-1,9'-xanthen>-3-one (159435-10-6)

Guidance literature:

With sodiumsulfide nonahydrate; In methanol; water; at 60 - 70 ℃; for 2h;

DOI:10.1016/j.tet.2020.131087

Reference yield:

4-nitrophthalic anhydride (5466-84-2) → 6-amino-3',6'-bis(dimethylamino)spiro<1,3-dihydroisobenzofuran-1,9'-xanthen>-3-one (159435-10-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 3 percent / 2.) conc. H₂SO₄ / 1) toluene, reflux, 6 h; 2) reflux, 8 h

2: H₂ / Pd/C / acetic acid / 5 h / Ambient temperature

3: 1.) pyridine, 2.) aq. NaOH / 1) room temperature, 16 h; 2) methanol, reflux, 1 h

4: 26 percent / trimethylsilyl polyphosphate / dimethylformamide / 4 h / 130 °C

5: 77 percent / aq. HCl / ethanol / 2 h / Heating

With pyridine; hydrogenchloride; sodium hydroxide; trimethylsilylphosphate; sulfuric acid; hydrogen; palladium on activated charcoal; In ethanol; acetic acid; N,N-dimethyl-formamide;

upstream raw materials:

6-acetamido-3',6'-bis(dimethylamino)spiro<1,3-dihydroisobenzofuran-1,9'-xanthen>-3-one

4-nitrophthalic anhydride

4-nitrophthalic acid

4-Amino-2-(4-dimethylamino-2-hydroxy-benzoyl)-benzoic acid methyl ester

Downstream raw materials:

6-iodoacetamido-3',6'-bis(dimethylamino)spiro<1,3-dihydroisobenzofuran-1,9'-xanthen>-3-one

6-chloroacetamido-3',6'-bis(dimethylamino)spiro<1,3-dihydroisobenzofuran-1,9'-xanthen>-3-one

Refernces

• 1、 Corrie, John E. T.,Craik, James S.. "Synthesis and Characterisation of Pure Isomers of Iodoacetamidotetramethylrhodamine". . p. 2967 - 2974. Retrieved 2007/10/02.