51927-48-1

Basic information

• Product Name: 1-Naphthalenol, 7,8-dihydro-
• Synonyms: 8-Hydroxy-1.2-dihydro-naphthalin;7,8-dihydro-1-naphthol;7,8-Dihydro-[1]naphthol;7,8-dihydro-1-hydroxynaphthalene;7,8-dihydronaphthalen-1-ol
• CAS NO: 51927-48-1
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• Mol File: 51927-48-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1-Naphthalenol, 7,8-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenol, 7,8-dihydro-(51927-48-1)
• EPA Substance Registry System: 1-Naphthalenol, 7,8-dihydro-(51927-48-1)

Safety Data

• Hazardous Substances Data: 51927-48-1(Hazardous Substances Data)

Usage

General Description

1-Naphthalenol, 7,8-dihydro- is a chemical compound that originates from naphthalene, the primary constituent of mothballs. As with other variations of naphthalene, it is a polycyclic aromatic hydrocarbon. The 7,8-dihydro- specification refers to the two added hydrogen atoms on the 7th and 8th carbon in the naphthalene structure. It is used in specialized industrial and scientific contexts, often related to the synthesis of other organic compounds. Like other naphthalene derivatives, it must be handled carefully due to potential health risks, particularly when it's metabolized in the body.

Synthetic route

8-Methoxy-1,2-dihydronaphthalene (60573-59-3) → 7,8-dihydro-naphthalen-2-ol (51927-48-1)

Conditions	Yield
With sodium thioethylate In N,N-dimethyl-formamide at 120℃;	97%

1,2,3,4-tetrahydro-1,5-dihydroxy-naphthalene (40771-26-4) → 7,8-dihydro-naphthalen-2-ol (51927-48-1)

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 20℃; for 12h; Inert atmosphere;	82.82%
With toluene-4-sulfonic acid In benzene Heating / reflux;	22%
With phosphoric acid In tetrahydrofuran at 80℃; for 2h;	0.614 g

7,8-dihydronaphthalen-1-yl acetate (51927-50-5) → 7,8-dihydro-naphthalen-2-ol (51927-48-1)

Conditions	Yield
With [hydroxy(tosyloxy)iodo]benzene In methanol at 0℃; for 5h;	55%

tetrachloromethane (56-23-5) + ethanol (64-17-5) + 5,8-dihydro-1-naphthol (27673-48-9) + potassium ethoxide (917-58-8) → 5,6-dihydro-1-naphthol (1429-22-7) + 7,8-dihydro-naphthalen-2-ol (51927-48-1)

α-naphthol (90-15-3) → 5,6-dihydro-1-naphthol (1429-22-7) + 7,8-dihydro-naphthalen-2-ol (51927-48-1)

5,8-dihydro-1-naphthol (27673-48-9) + potassium ethoxide (917-58-8) → 5,6-dihydro-1-naphthol (1429-22-7) + 7,8-dihydro-naphthalen-2-ol (51927-48-1)

Conditions	Yield
With ethanol; xylene

7,8-dihydro-naphthalen-2-ol (51927-48-1) + acetic anhydride (108-24-7) → 7,8-dihydronaphthalen-1-yl acetate (51927-50-5)

Conditions	Yield
With dmap; triethylamine at 20℃; for 1h;	96%
With pyridine at 20℃; for 26h;	89.83%

7,8-dihydro-naphthalen-2-ol (51927-48-1) + benzoyl chloride (98-88-4) → 7,8-dihydronaphthalen-1-yl benzoate

Conditions	Yield
With triethylamine In dichloromethane	94%
With triethylamine In dichloromethane	94%

7,8-dihydro-naphthalen-2-ol (51927-48-1) + 2-(trifluoromethyl)benzyl chloride (21742-00-7) → 8-((2-(trifluoromethyl)benzyl)oxy)-1,2-dihydronaphthalene

Conditions	Yield
Stage #1: 7,8-dihydro-naphthalen-2-ol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Sealed tube; Stage #2: 2-(trifluoromethyl)benzyl chloride With sodium iodide In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; Sealed tube;	89%

7,8-dihydro-naphthalen-2-ol (51927-48-1) → (+/-)-cis-1,2,3,4-tetrahydronaphthalene-1,2,5-triol

Conditions	Yield
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In water; tert-butyl alcohol at 100℃; for 48h;	73.5%

7,8-dihydro-naphthalen-2-ol (51927-48-1) → 5,6,7,8-Tetrahydronaphthalen-1-ol (529-35-1)

Conditions	Yield
With ethanol; sodium

trifluoromethylsulfonic anhydride (358-23-6) + 7,8-dihydro-naphthalen-2-ol (51927-48-1) → trifluoromethanesulfonic acid 7,8-dihydronaphthalen-1-yl ester (802918-37-2)

Conditions	Yield
With pyridine at 20℃;

7,8-dihydro-naphthalen-2-ol (51927-48-1) → 7,8-dihydronaphthalene-1-carboxylic acid methyl ester (508219-95-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 20 °C 2: 3.5 g / palladium(II) acetate; 1,1'-bis(diphenylphosphino)ferrocene; triethylamine / dimethylsulfoxide / 8 h / 60 °C View Scheme

7,8-dihydro-naphthalen-2-ol (51927-48-1) → 1a,2,3,7b-tetrahydro-1-oxa-cyclopropa[a]naphthalene-4-carboxylic acid methyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 20 °C 2: 3.5 g / palladium(II) acetate; 1,1'-bis(diphenylphosphino)ferrocene; triethylamine / dimethylsulfoxide / 8 h / 60 °C 3: m-chloroperoxybenzoic acid / CH2Cl2 / 0 - 5 °C View Scheme

7,8-dihydro-naphthalen-2-ol (51927-48-1) → 5,6,7,8-tetrahydro-6-oxonaphthalene-1-carboxylic acid methyl ester (508219-96-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 20 °C 2: 3.5 g / palladium(II) acetate; 1,1'-bis(diphenylphosphino)ferrocene; triethylamine / dimethylsulfoxide / 8 h / 60 °C 3: m-chloroperoxybenzoic acid / CH2Cl2 / 0 - 5 °C 4: 2.4 g / (C6H5)3P; palladium(II) acetate / benzene / 5 h / Heating View Scheme

7,8-dihydro-naphthalen-2-ol (51927-48-1) → 2-hydroxy-3,4-dihydro-naphthalene-1,5-dicarboxylic acid dimethyl ester (508219-97-4)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: pyridine / 20 °C 2.1: 3.5 g / palladium(II) acetate; 1,1'-bis(diphenylphosphino)ferrocene; triethylamine / dimethylsulfoxide / 8 h / 60 °C 3.1: m-chloroperoxybenzoic acid / CH2Cl2 / 0 - 5 °C 4.1: 2.4 g / (C6H5)3P; palladium(II) acetate / benzene / 5 h / Heating 5.1: lithium di(isopropyl)amide / tetrahydrofuran / 1 h / -78 - 0 °C 5.2: 35 percent / hexamethylphosphoramide / tetrahydrofuran / 0.17 h / -78 °C View Scheme

7,8-dihydro-naphthalen-2-ol (51927-48-1) + benzoyl chloride (98-88-4) → (R)-1-(bis(2,2,2-trifluoroethoxy)methyl)-2,3-dihydro-1H-inden-4-yl benzoate + (S)-1-(bis(2,2,2-trifluoroethoxy)methyl)-2,3-dihydro-1H-inden-4-yl benzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: (2R,2'R)-diethyl 2,2'-(2-iodo-1,3-phenylene)bis(oxy)dipropanoate; 3-chloro-benzenecarboperoxoic acid; (1S)-10-camphorsulfonic acid / dichloromethane / -40 °C View Scheme

7,8-dihydro-naphthalen-2-ol (51927-48-1) → 1-(bis(2,2,2-trifluoroethoxy)methyl)-2,3-dihydro-1H-inden-4-yl benzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: [hydroxy(tosyloxy)iodo]benzene / 0.08 h / 0 °C View Scheme

7,8-dihydro-naphthalen-2-ol (51927-48-1) → 1-(bis(2,2,2-trifluoroethoxy)methyl)-2,3-dihydro-1H-inden-4-yl acetate

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; dmap / 1 h / 20 °C 2: [hydroxy(tosyloxy)iodo]benzene / 0.08 h / 0 °C View Scheme

7,8-dihydro-naphthalen-2-ol (51927-48-1) → (R)-5-((2-(trifluoromethyl)benzyl)oxy)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile + 5-((2-(trifluoromethyl)benzyl)oxy)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile

Conditions

Yield

Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere; Sealed tube 1.2: 18 h / 20 °C / Inert atmosphere; Sealed tube 2.1: bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; sodium trimethylsilanolate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; Dimethylphenylsilane; C76H103CuO10P2 / tetrahydrofuran / 16 h / 45 °C / Inert atmosphere; Sealed tube 3.1: acetylenedicarboxylate dioctyl ester / toluene / 8 h / 110 °C / Inert atmosphere; Sealed tube View Scheme

7,8-dihydro-naphthalen-2-ol (51927-48-1) → C28H24F3NO2

Conditions

Yield

Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere; Sealed tube 1.2: 18 h / 20 °C / Inert atmosphere; Sealed tube 2.1: bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; sodium trimethylsilanolate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; Dimethylphenylsilane; C76H103CuO10P2 / tetrahydrofuran / 16 h / 45 °C / Inert atmosphere; Sealed tube View Scheme

Upstream product

• 90-15-3 α-naphthol 
• 60573-59-3 8-Methoxy-1,2-dihydronaphthalene 
• 51927-50-5 7,8-dihydronaphthalen-1-yl acetate 
• 28315-93-7 5-Hydroxy-1-tetralone 
• 40771-26-4 1,2,3,4-tetrahydro-1,5-dihydroxy-naphthalene 
• 27673-48-9 5,8-dihydro-1-naphthol 
• 917-58-8 potassium ethoxide 
• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 

Downstream Products

• 529-35-1 5,6,7,8-Tetrahydronaphthalen-1-ol 

Relevant articles and documents

Lipase-catalyzed resolution of 5-acetoxy-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene. Application to the synthesis of (+)-(3R,4S)-cis-4-hydroxy-6-deoxyscytalone, a metabolite isolated from Colletotrichum acutatum

(+)-cis-4-Hydroxy-6-deoxyscytalone, a natural product bio-synthesized by Colletotrichum sp., has been prepared and its absolute configuration confirmed as 3R,4S, the key step being a kinetic racemic resolution of a cis-diol easily obtained from commercial 1,2,3,4-tetrahydronaphthalen-1,5-diol. Four lipases and different reaction conditions were tested in order to obtain the best yield and enantiomeric excess. Confirmation of absolute configuration was made by NMR using a single-derivatization low-temperature procedure and MPA as the auxiliary reagent.

Iodine(III)-mediated ring contraction reactions: Synthesis of oxygen-And nitrogen-substituted indanes

The synthesis of oxygen-And nitrogen-substituted indanes was successfully performed by iodine(III)-mediated ring contraction of 1,2-dihydronaphthalenes. Acetoxy and benzoyloxy alkenes afforded indanes in 60-71percent yield, irrespective of their position on aromatic ring. Similarly, the nitrogen containing substrates protected with 9-fluorenylmethyloxycarbonyl (Fmoc) and benzoyl (Bz) groups smoothly undergoes ring contraction giving indanes in 64-77percent yield. The tosyl-protected substrate resulted only in addition products.

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