56181-82-9

Basic information

• Product Name: 3-(4'-Bromo[1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthalenol
• Synonyms: 3-(4'-bromo[1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthol;3-(4''-BROMO[1,1''-BIPHENYL]-4-YL)-1,2,3,4-TETRAHYDRO-1-NAPHTHALENOL;3-(4′-brome-4-biphenyl-4-yl)-1，2，3，4-tetrahydro-1-naphthanol;3-(4'-Bromo-4-biphenyl-4-yl)-1,2,3,4-tetenol;1-Naphthalenol, 3-(4'-bromo(1,1'-biphenyl)-4-yl)-1,2,3,4-tetrahydro-;Einecs 260-038-0;3-[4-(4-broMophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-ol
• CAS NO: 56181-82-9
• Molecular Formula: C₂₂H₁₉BrO
• Molecular Weight: 379.29
• EINECS: 260-038-0
• Mol File: 56181-82-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 512.8 °C at 760 mmHg
• Flash Point: 263.9 °C
• Appearance: Cream To Pale Solid Powder.
• Density: 1.359 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slig
• PKA: 14.15±0.40(Predicted)
• CAS DataBase Reference: 3-(4'-Bromo[1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthalenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4'-Bromo[1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthalenol(56181-82-9)
• EPA Substance Registry System: 3-(4'-Bromo[1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthalenol(56181-82-9)

Safety Data

• Hazardous Substances Data: 56181-82-9(Hazardous Substances Data)

Usage

Uses

3-(4''-Bromo[1,1''-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthalenol is used to prepare 4-hydroxycoumarin derivatives with antitumor activities. It is also used to synthesize diphenacoum and brodifacoum (B677900) as the rodenticides.

Synthetic route

3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-one (60313-01-1) → (+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 2h;	85%

4-bromo-1,1'-biphenyl (92-66-0) + K4[Fe(CN)6] → (+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: 88 percent / AlCl3 / CH2Cl2 / 16 h / -10 °C 2: 95 percent / Zn; I2 / benzene / 1 h / Heating 3: 85 percent / Et3SiH; TFA; BF3*Et2O / CH2Cl2 / 8 h / Heating 4: 93 percent / aq. KOH / 8 h / Heating 5: 80 percent / polyphosphoric acid / 1 h / 80 °C 6: 85 percent / NaBH4 / ethanol / 2 h / 20 °C View Scheme

1-[4'-bromo(1,1'-biphenyl)-4-yl]-2-phenylethan-1-one (60312-95-0) → (+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / Zn; I2 / benzene / 1 h / Heating 2: 85 percent / Et3SiH; TFA; BF3*Et2O / CH2Cl2 / 8 h / Heating 3: 93 percent / aq. KOH / 8 h / Heating 4: 80 percent / polyphosphoric acid / 1 h / 80 °C 5: 85 percent / NaBH4 / ethanol / 2 h / 20 °C View Scheme

phenylacetyl chloride (103-80-0) → (+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: 88 percent / AlCl3 / CH2Cl2 / 16 h / -10 °C 2: 95 percent / Zn; I2 / benzene / 1 h / Heating 3: 85 percent / Et3SiH; TFA; BF3*Et2O / CH2Cl2 / 8 h / Heating 4: 93 percent / aq. KOH / 8 h / Heating 5: 80 percent / polyphosphoric acid / 1 h / 80 °C 6: 85 percent / NaBH4 / ethanol / 2 h / 20 °C View Scheme

3-(4'-Bromo-biphenyl-4-yl)-4-phenyl-butyric acid ethyl ester (124325-90-2) → (+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / aq. KOH / 8 h / Heating 2: 80 percent / polyphosphoric acid / 1 h / 80 °C 3: 85 percent / NaBH4 / ethanol / 2 h / 20 °C View Scheme

3-(4'-Bromo-biphenyl-4-yl)-4-phenyl-butyric acid (124325-89-9) → (+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / polyphosphoric acid / 1 h / 80 °C 2: 85 percent / NaBH4 / ethanol / 2 h / 20 °C View Scheme

3-(4'-bromo-biphenyl-4-yl)-3-hydroxy-4-phenyl-butyric acid ethyl ester (124325-88-8) → (+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / Et3SiH; TFA; BF3*Et2O / CH2Cl2 / 8 h / Heating 2: 93 percent / aq. KOH / 8 h / Heating 3: 80 percent / polyphosphoric acid / 1 h / 80 °C 4: 85 percent / NaBH4 / ethanol / 2 h / 20 °C View Scheme

(+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9) → 1-Bromo-3-(4'-bromo-biphenyl-4-yl)-1,2,3,4-tetrahydro-naphthalene (70942-04-0)

Conditions	Yield
With phosphorus tribromide In dichloromethane at 0℃;	94%
With phosphorus tribromide In dichloromethane at -10℃; for 1h;

4-hydroxy[1]benzopyran-2-one (1076-38-6) + (+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9) → (3-[(1R,3S)-3-[4-(4-bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-4-hydroxychromen-2-one) + (3-[(1R,3R)-3-[4-(4-bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-4-hydroxychromen-2-one)

Conditions	Yield
With hydrogenchloride at 160℃; for 0.5h; Yield given. Yields of byproduct given;

(+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9) → 3-[3-(4'-bromo-biphenyl-4-yl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-4-hydroxy-6-methyl-6-phenyl-5,6-dihydro-pyran-2-one

Conditions	Yield
Multi-step reaction with 2 steps 1.1: PBr3 / CH2Cl2 / 1 h / -10 °C 2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 2.2: 61 percent / tetrahydrofuran / 2 h / Heating View Scheme

(+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9) → 3-[3-(4'-bromo-biphenyl-4-yl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-6-ethyl-4-hydroxy-6-phenyl-5,6-dihydro-pyran-2-one

Conditions	Yield
Multi-step reaction with 2 steps 1.1: PBr3 / CH2Cl2 / 1 h / -10 °C 2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 2.2: 71 percent / tetrahydrofuran / 2 h / Heating View Scheme

(+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9) → 3-[3-(4'-bromo-biphenyl-4-yl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-pyran-2-one

Conditions	Yield
Multi-step reaction with 2 steps 1.1: PBr3 / CH2Cl2 / 1 h / -10 °C 2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 2.2: 72 percent / tetrahydrofuran / 2 h / Heating View Scheme

(+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9) → 2-(4'-Bromo-biphenyl-4-yl)-1,2-dihydro-naphthalene

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / PBr3 / CH2Cl2 / 0 °C 2: HCl / 0.5 h / 160 °C View Scheme

(+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (56181-82-9) → (3-[(1R,3S)-3-[4-(4-bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-4-hydroxychromen-2-one)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / PBr3 / CH2Cl2 / 0 °C 2: HCl / 0.5 h / 160 °C View Scheme

Upstream product

• 92-66-0 4-bromo-1,1'-biphenyl 
• 124325-88-8 3-(4'-bromo-biphenyl-4-yl)-3-hydroxy-4-phenyl-butyric acid ethyl ester 
• 124325-89-9 3-(4'-Bromo-biphenyl-4-yl)-4-phenyl-butyric acid 
• 124325-90-2 3-(4'-Bromo-biphenyl-4-yl)-4-phenyl-butyric acid ethyl ester 
• 103-80-0 phenylacetyl chloride 
• 60312-95-0 1-[4'-bromo(1,1'-biphenyl)-4-yl]-2-phenylethan-1-one 
• 60313-01-1 3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-one 

Downstream Products

• 70942-04-0 1-Bromo-3-(4'-bromo-biphenyl-4-yl)-1,2,3,4-tetrahydro-naphthalene 
• 56073-10-0 (3-[(1R,3S)-3-[4-(4-bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-4-hydroxychromen-2-one) 
• 56073-10-0 (3-[(1R,3R)-3-[4-(4-bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-4-hydroxychromen-2-one) 

Relevant articles and documents

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.