40771-26-4

Basic information

• Product Name: 1,2,3,4-TETRAHYDRO-1,5-NAPHTHALENEDIOL
• Synonyms: 1,5-Naphthalenediol, 1,2,3,4-tetrahydro-;1,5-DIHYDROXYTETRALIN;1,5-DIHYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE;1,2,3,4-TETRAHYDRO-1,5-NAPHTHALENEDIOL;1,2,3,4-tetrahydronaphthalene-1,5-diol;1,5-DIHYDROXY-1,2,3,4-TETRAHYDRO-NAPHTHA LENE, TECH.;1,5-DIHYDROXY-1,2,3,4-TETRAHYDRO-NAPHTHALENE 95%;1,5-Dihydroxy-1,2,3,4- tetrahydronaphthalene, 90%,tech
• CAS NO: 40771-26-4
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: 255-070-7
• Mol File: 40771-26-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 132-134 °C(lit.)
• Boiling Point: 251.67°C (rough estimate)
• Flash Point: 162.4 °C
• Appearance: /
• Density: 1.0326 (rough estimate)
• Vapor Pressure: 9.08E-05mmHg at 25°C
• Refractive Index: 1.5180 (estimate)
• PKA: 10.40±0.40(Predicted)
• CAS DataBase Reference: 1,2,3,4-TETRAHYDRO-1,5-NAPHTHALENEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRAHYDRO-1,5-NAPHTHALENEDIOL(40771-26-4)
• EPA Substance Registry System: 1,2,3,4-TETRAHYDRO-1,5-NAPHTHALENEDIOL(40771-26-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 40771-26-4(Hazardous Substances Data)

Usage

Uses

1,5-Dihydroxy-1,2,3,4-tetrahydronaphthalene was used in the synthesis of 1,5-bis(4-aminobenzoate)-1,2,3,4-tetrahydronapthalene(4-DABTN) and 1,5-bis(3-aminobenzoate)-1,2,3,4-tetrahydronapthalene (5-DABTN).

General Description

1,5-Dihydroxy-1,2,3,4-tetrahydronaphthalene is a complexing agent and forms complexes with cephradine. It reacts with 4- or 3-nitrobenzoyl chloride to yield 4-DABTN and 3-DABTN .

InChI:InChI=1/C10H12O2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1,3,5,10-12H,2,4,6H2/t10-/m0/s1

Upstream product

• 61982-91-0 1,2,3,4-tetrahydro-5-methoxynaphthalen-1-ol 
• 33892-75-0 5-Methoxy-1-tetralone 
• 690232-04-3 1-benzyl-5-methoxy-1,2,3,4-tetrahydronaphthalene 
• 28315-93-7 5-Hydroxy-1-tetralone 
• 91028-14-7 1,2,3,4-Tetrahydronaphthalene-1,5-diyl diacetate 
• 83-56-7 1,5-dihydroxynaphthalene 

Downstream Products

• 51927-48-1 7,8-dihydro-naphthalen-2-ol 
• 1020414-33-8 [1-(7,8-dihydronaphthalen-1-yl)-ethyl]-[3-(3-trifluoromethylphenyl)propyl]amine hydrochloride 
• 802918-36-1 [(R)-1-(5,6-Dihydro-naphthalen-1-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)-propyl]-amine 
• 802918-36-1 [(S)-1-(5,6-Dihydro-naphthalen-1-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)-propyl]-amine 
• 802918-46-3 [1-(7,8-dihydro-naphthalen-1-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)-propyl]-amine 
• 802918-47-4 [1-(5,6-dihydronaphthalen-1-yl)ethyl]-[3-(3-trifluoromethylphenyl)propyl]amine 
• 41552-07-2 1-oxo-5-hydroxy-6-methyl-1,2,3,4-tetrahydronaphthalene 
• 61982-91-0 1,2,3,4-tetrahydro-5-methoxynaphthalen-1-ol 
• 121-69-7 N,N-dimethyl-aniline 
• 28315-93-7 5-Hydroxy-1-tetralone 

Relevant articles and documents

4,8-dihydroxy-1-Tetralone chemical synthesis method

The invention discloses a chemical synthesis method of 4,8- dihydroxyl-1-tetralone. The chemical synthesis method comprises the following steps: by taking 5-hydroxyl- tetralone as a raw material, firstly, adding NaBH4 to synthesize 5-hydroxyl-tetralol by taking methanol as a solvent, and adding benzoyl chloride to synthesize 1,5-dibenzoyl- tetrahydronaphthalene by taking pyridine as a solvent; then, adding benzene, diatomite, pyridinium dichromate and tert-butyl hydroperoxide to synthesize 4,8- dibenzoyl-1-tetralone; and finally, adding cesium carbonate to synthesize 4,8- dihydroxyl-1-tetralon by taking methanol as a solvent. The chemical synthesis method disclosed by the invention is simple in process, green and environmentally friendly and high in product purity which reaches 99.82%, and has a reaction total yield of 39-47%.

Efficient synthesis of substances related to cinacalcet hydrochloride via heck coupling

Efficient synthetic methods to process substances related to cinacalcet hydrochloride 1, generated during the preparation, were described. The compounds were identified as [1-(7,8-dihydro-naphthalen-1-yl)-ethyl]-[3-(3- trifluoromethyl-phenyl)-propyl]-amine hydrochloride 2,[1-(5,6,7,8-tetrahydro- naphthalen-1-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)-propyl]-amine hydrochloride 3 and [1-(naphthalen-2-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)- propyl]-amine hydrochloride 4. All were prepared from commercially available materials in several linear steps and characterized by their respective spectral data.

Synthesis of Cinacalcet congeners

Two related substances 1 and 2 of Cinacalet were prepared. Two racemic isomeric dihydronaphthalenes 1 and 2 were prepared from commercially available 5-hydroxytetralone in five linear steps. A key palladium-catalyzed double bond migration led to the synthesis of both isomers from the same starting material. Preparative chiral HPLC separation provided the enantiomerically pure materials. An asymmetric synthesis employing CBS reduction to furnish 1 was also developed.