ChemicalBook CAS DataBase List 5-(bromophenyl)-10,15,20-phenylporphyrin

5-(bromophenyl)-10,15,20-phenylporphyrin synthesis

5synthesis methods

Product Name:5-(bromophenyl)-10,15,20-phenylporphyrin
CAS Number:123444-60-0
Molecular formula:C44H29BrN4
Molecular Weight:693.63

67605-64-5 Synthesis

4-(10,15,20-Triphenyl-21H,23H-porphin-5-yl)benzenamine

67605-64-5
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5-(bromophenyl)-10,15,20-phenylporphyrin

123444-60-0
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Yield:123444-60-0 79%

Reaction Conditions:

Stage #1: 5-(4-aminophenyl)-10,15,20-triphenylporphyrinwith sulfuric acid;sodium nitrite in water at -10; for 0.166667 h;
Stage #2: in water; for 0.166667 h;
Stage #3: with hydrogen bromide;urea;copper(I) bromide in water;Cooling with ice;

Steps:

4.2.8 5-(4-bromophenyl)-10,15,20-triphenylporphyrin (TPP-7)

TPP-7 was prepared partly according to Lin's method.^13f TPP-6 (3.15g, 5mmol) was dissolved in 600mL 50% H₂SO₄ aq. and the mixture was stirring in cryohydrate bath. Sodium nitrite solution consisted of NaNO₂ (6.90g, 100mmol) and H₂O (200mL) was slowly added into the porphyrin solution. The reaction was stirring for 10min below 0°C. Then urea (69.37g, 1.16mol) was added and the mixture was stirring for additional 10min. After that, CuBr (7.17g, 50mmol) in cold hydrobromic acid (300mL, ≥40.0%) was poured into the above reaction mixture and the reaction mixture was stirred for additional 2h with the ice melting. Then the reaction mixture was diluted with water and the solution was adjusted to pH=10 with 3M NaOH. The aqueous phase was extracted with chloroform and the obtained organic phase was dried over Na₂SO₄. The residue was purified over silica gel column using CH₂Cl₂/ PE (1:3) as eluent to afford TPP-7 as a purple solid (2.75g, 79% yield). ¹H NMR (400MHz, CDCl₃) δ 8.92-8.79 (m, 8H), 8.25-8.19 (m, 6H), 8.12-8.06 (m, 2H), 7.93-7.87 (m, 2H), 7.83-7.72 (m, 9H),-2.79 (s, 2H).

References:

Tang, Xiao-fei;Feng, Shi-hao;Wang, Ya-kun;Yang, Fan;Zheng, Ze-hao;Zhao, Jing-nan;Wu, Yu-feng;Yin, Hang;Liu, Guang-zhi;Meng, Qing-wei [Tetrahedron,2018,vol. 74,# 27,p. 3624 - 3633]

109-97-7 Synthesis