90035-32-8

Basic information

• Product Name: 1(2H)-Naphthalenone, 3,4-dihydro-3-(4-hydroxyphenyl)-
• Synonyms: 4'-hydroxyflavanone
• CAS NO: 90035-32-8
• Molecular Formula: C16H14O2
• Molecular Weight: 238.286
• Mol File: 90035-32-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1(2H)-Naphthalenone, 3,4-dihydro-3-(4-hydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1(2H)-Naphthalenone, 3,4-dihydro-3-(4-hydroxyphenyl)-(90035-32-8)
• EPA Substance Registry System: 1(2H)-Naphthalenone, 3,4-dihydro-3-(4-hydroxyphenyl)-(90035-32-8)

Safety Data

• Hazardous Substances Data: 90035-32-8(Hazardous Substances Data)

Usage

Uses

3-(4-Hydroxyphenyl)-1,2,3,4-tetrahydronaphthalen-1-one is an intermediate in synthesizing Flocoumafen-d4 (F401502), an isotope labelled Flocoumafen is a second generation anticoagulant rodenticide. Flocoumafen is extremely effective against strains of pest rodents resistant to conventional anticoagulants. Flocoumafen is highly toxic and is used strictly in sewers and indoors in some places such as UK.

Upstream product

• 61696-79-5 3,4-dihydro-3-(4-methoxyphenyl)naphthalene-1(2H)-one 
• 103-82-2 phenylacetic acid 
• 100-66-3 methoxybenzene 
• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 118806-75-0 3-p-methoxyphenyl-2-carboxy-4-phenylbutyric acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 7443-25-6 dimethyl 2-(4-methoxybenzylidene)malonate 
• 1333110-92-1 C₂₀H₂₂O₅ 
• 118806-78-3 3-(4-methoxyphenyl)-4-phenylbutanoic acid 
• 171818-87-4 3-hydroxy-3-(4-methoxy-phenyl)-4-phenyl-butyric acid ethyl ester 
• 171818-88-5 ethyl 3-(4-methoxyphenyl)-4-phenylbutanoate 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 104563-61-3 cis-4-hydroxy-3-[1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl]-1-naphthyl]coumarin 
• 104563-61-3 trans-4-hydroxy-3-[1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl]-1-naphthyl]coumarin 
• 807609-63-8 1-bromo-3-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-1,2,3,4-tetrahydro-naphthalene 
• 103772-30-1 1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl]naphthalen-1-ol 
• 287974-84-9 3-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-3,4-dihydro-2H-naphthalen-1-one 

Relevant articles and documents

Borontribromide-mediated C-C bond formation in cyclic ketones: A transition metal free approach

Borontribromide (BBr3) is a well-known demethylating agent. The current investigation was focused on a new application of borontribromide as a C-C bond forming agent in cyclic ketones. In this study, borontribromide mediated C-C bond formation reactions of tetralones, chromenone, thiochromenone and indanones were explored. A methoxy group containing ketones showed selective C-C bond formation reaction instead of demethylation of the methoxy group. MM2 steric energy calculations for the final products showed that the reaction favored the formation of exo- or endo-cyclic double bond containing products, depending upon their low MM2 steric energy in a specific frame structure, as observed in X-ray crystallography. A comprehensive crystallographic and pi-stacking analysis of product 10a demonstrated the formation of 10a as an enantiomeric mixture, and its centre of inversion was stabilized by a set of three unique pi-pi interactions.

Synthesis and antitumor activity of 4-hydroxycoumarin derivatives

A series of 4-hydroxycoumarin derivatives was prepared and evaluated for antitumor activity against five human tumor cell lines. A series of 4-hydroxycoumarin derivatives was prepared and evaluated for antitumor activity. The key fragments were 2a-c, 5c, 12b, 13b, 17, and 18 which were prepared via dianion ring cyclization, Friedel-Crafts acylation, and Reformatsky reaction. Compound 20b showed the most potent antitumor activity among the total 12 derivatives and compounds 19a and 19b exhibited efficacy comparable to etoposide in vitro antitumor activity.