Alpha-naphtholbenzein

• CAS: 6948-88-5
• Catalog Number: ACM6948885
• Category: Other Products
• Molecular Weight: 392.45
• Molecular Formula: C27H18O2
• Description: Alpha-naphtholbenzein is a derivative of the aromatic hydrocarbon naphthalene, consisting of two benzene rings and one naphthalene ring.
• Synonyms: α-Naphtholbenzein;LABOTEST-BB LT00441167;BIS(4-HYDROXY-1-NAPHTHYL)PHENYLMETHANOL;Bis-(4-hydroxy-1-naphtyl)phenylmethanol;1-NAPHTHOLBENZEIN;4,4'-[ALPHA-HYDROXYBENZYLIDENE]-DI-1-NAPHTHOL;4-hydroxy-alpha-(4-hydroxynaphthyl)-alpha-phenylnaphthalene-1-methano
• IUPAC Name: 4-[hydroxy-(4-hydroxynaphthalen-1-yl)-phenylmethyl]naphthalen-1-ol
• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=C(C3=CC=CC=C32)O)(C4=CC=C(C5=CC=CC=C54)O)O
• InChI: InChI=1S/C27H20O3/c28-25-16-14-23(19-10-4-6-12-21(19)25)27(30,18-8-2-1-3-9-18)24-15-17-26(29)22-13-7-5-11-20(22)24/h1-17,28-30H
• InChI Key: OUYLDJXFDLBCTQ-UHFFFAOYSA-N
• Boiling Point: 685.6ºC at 760mmHg
• Melting Point: 230-235 °C(lit.)
• Flash Point: 313.1ºC
• Density: 1.328 g/mL
• Appearance: RED-BROWN POWDER
• Application: It has been used as a model to study the structure and dynamics of aromatic molecules. It is also used as a fluorescent dye for biological imaging.
• Storage: Store at 2-8 ℃
• EC Number: 230-116-9
• Exact Mass: 392.141
• HTS Code: 2907199090
• MDL Number: MFCD00003979
• PSA: 60.69
• WGK Germany: 3
• XLogP3: 5.6884

Case Study

Synthesis of Phthalocyanine Compounds Containing α-Naphtholbenzene Units

Özçeşmeci M. Journal of Organometallic Chemistry, 2014, 767: 16-21.

Alpha-naphtholquinone is a pH indicator that changes color when a neutral solution becomes alkaline. The precursors required for the synthesis of phthalocyanine complexes can be prepared through the nucleophilic aromatic substitution reaction between 4-nitrophthalonitrile and α-naphtholbenzene.
Synthetic procedure of phthalocyanine complexes
·α-Naphtholbenzein (1.081 g, 2.890 mmol) and 4-nitrophthalonitrile (0.500 g, 2.890 mmol) were stirred and dissolved in 50 mL dry DMF at room temperature.
· Anhydrous K2CO3 (0.800 g, 5.780 mmol) was added portionwise over 2 h under a nitrogen atmosphere, then the reaction mixture was stirred vigorously for further 3 days. After the reaction was completed, the mixture was purified to obtain compound 1.
· Cyclotetramerization reactions of the new dinitrile derivative were accomplished in dry dimethylformamide at refluxed temperature. Then metal-free phthalocyanine (2) and zinc(II) phthalocyanine (3) were prepared respectively.