1(2H)-Naphthalenone, 3,4-dihydro-3-(4-hydroxyphenyl)-

Base Information

• Chemical Name: 1(2H)-Naphthalenone, 3,4-dihydro-3-(4-hydroxyphenyl)-
• CAS No.: 90035-32-8
• Molecular Formula: C16H14O2
• Molecular Weight: 238.286
• Mol file: 90035-32-8.mol

Synonyms:4'-hydroxyflavanone;

Chemical Property of 1(2H)-Naphthalenone, 3,4-dihydro-3-(4-hydroxyphenyl)-

Chemical Property:

• PSA: 37.30000
• LogP: 3.30490

Purity/Quality:

99.3% ^*data from raw suppliers

3-(4-Hydroxyphenyl)-1,2,3,4-tetrahydronaphthalen-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of 1(2H)-Naphthalenone, 3,4-dihydro-3-(4-hydroxyphenyl)-

There total 16 articles about 1(2H)-Naphthalenone, 3,4-dihydro-3-(4-hydroxyphenyl)- 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: 93.0%

3,4-dihydro-3-(4-methoxyphenyl)naphthalene-1(2H)-one (61696-79-5) → 3-(4-hydroxyphenyl)-3,4-dihydronaphthalen-1(2H)-one (90035-32-8)

Guidance literature:

With hydrogen bromide; acetic acid; for 6h; Heating;

DOI:10.1016/j.bmcl.2004.09.009

Reference yield:

4-methoxyphenyl benzyl ketone (1023-17-2) → 3-(4-hydroxyphenyl)-3,4-dihydronaphthalen-1(2H)-one (90035-32-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / Zn; I₂ / benzene / 1 h / Heating

2: 90 percent / Et₃SiH; TFA; BF₃*Et₂O / CH₂Cl₂ / 8 h / Heating

3: 92 percent / aq. KOH / 8 h / Heating

4: 85 percent / polyphosphoric acid / 1 h / 80 °C

5: 93 percent / HBr; AcOH / 6 h / Heating

With triethylsilane; potassium hydroxide; PPA; boron trifluoride diethyl etherate; hydrogen bromide; iodine; acetic acid; trifluoroacetic acid; zinc; In dichloromethane; benzene; 1: Reformatsky reaction;

DOI:10.1016/j.bmcl.2004.09.009

Reference yield:

3-(4-methoxyphenyl)-4-phenylbutanoic acid (118806-78-3) → 3-(4-hydroxyphenyl)-3,4-dihydronaphthalen-1(2H)-one (90035-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / polyphosphoric acid / 1 h / 80 °C

2: 93 percent / HBr; AcOH / 6 h / Heating

With PPA; hydrogen bromide; acetic acid;

DOI:10.1016/j.bmcl.2004.09.009

upstream raw materials:

3,4-dihydro-3-(4-methoxyphenyl)naphthalene-1(2H)-one

4-methoxyphenyl benzyl ketone

3-(4-methoxyphenyl)-4-phenylbutanoic acid

methoxybenzene

Downstream raw materials:

cis-4-hydroxy-3-[1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl]-1-naphthyl]coumarin

trans-4-hydroxy-3-[1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl]-1-naphthyl]coumarin

1-bromo-3-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-1,2,3,4-tetrahydro-naphthalene

1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl]naphthalen-1-ol

Refernces

• 1、 Jung, Jae-Chul,Jang, Soyong,Oh, Seikwan,Park, Oee-Sook. "Simple synthesis and biological evaluation of flocoumafen and its structural isomers". scheme or table. p. 833 - 838. Retrieved 2011/10/04.
• 2、 -. "Anti-coagulants of the 4-hydroxycoumarin type and rodenticidal compositions (baits) comprising such anti-coagulants". . . Retrieved 2008/06/13.