4-carboxy-2-methyl silicon rhodamine

Base Information

• Chemical Name: 4-carboxy-2-methyl silicon rhodamine
• CAS No.: 1329676-57-4
• Molecular Formula: C₂₇H₃₁N₂O₂Si
• Molecular Weight: 443.641
• Mol file: 1329676-57-4.mol

Synonyms:4-carboxy-2-methyl silicon rhodamine

Chemical Property of 4-carboxy-2-methyl silicon rhodamine

Chemical Property:

Purity/Quality:

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Technology Process of 4-carboxy-2-methyl silicon rhodamine

There total 2 articles about 4-carboxy-2-methyl silicon 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: 36.0%

tert-butyl 4-bromo-3-methylbenzoate (347174-28-1) + 3,7-bis(N,N-dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-one (1290536-55-8) → 4-carboxy-2-methyl silicon rhodamine (1329676-57-4)

Guidance literature:

tert-butyl 4-bromo-3-methylbenzoate; With sec.-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

3,7-bis(N,N-dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-one; In tetrahydrofuran; at -78 - 20 ℃; Further stages; Inert atmosphere;

DOI:10.1021/ja205809h

Reference yield:

C19H25N2Si(1+) (913177-21-6) → 4-carboxy-2-methyl silicon rhodamine (1329676-57-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium cyanide / water / 4 h / Reflux

1.2: 0.5 h / 90 °C

2.1: sec.-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C

2.3: 20 °C

With potassium cyanide; sec.-butyllithium; In tetrahydrofuran; water;

DOI:10.1021/ja303931b

Reference yield: 78.0%

N-BOC-1,2-diaminoethane (57260-73-8) + 4-carboxy-2-methyl silicon rhodamine (1329676-57-4) → N-(10-(4-((2-((tert-butoxycarbonyl)amino)ethyl)carbamoyl)-2-methylphenyl)-7-(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-3(5H)-ylidene)-N-methyl-methanaminium hexafluorophosphate

Guidance literature:

4-carboxy-2-methyl silicon rhodamine; With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h; Schlenk technique; Inert atmosphere;

N-BOC-1,2-diaminoethane; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01717

upstream raw materials:

tert-butyl 4-bromo-3-methylbenzoate

3,7-bis(N,N-dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-one

C₁₉H₂₅N₂Si⁽¹⁺⁾

Downstream raw materials:

C₃₁H₃₄N₃O₄Si⁽¹⁺⁾