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

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

Used in Pharmaceutical Industry:
1,2,3,4-TETRAHYDRO-1,5-NAPHTHALENEDIOL is used as a key intermediate 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). These compounds have potential applications in the development of new pharmaceutical agents, particularly in the treatment of various diseases.
Used in Chemical Synthesis:
1,2,3,4-TETRAHYDRO-1,5-NAPHTHALENEDIOL is used as a versatile building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and reactivity make it a valuable component in the development of new chemical entities with diverse applications.

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

• 61982-91-0 1,2,3,4-tetrahydro-5-methoxynaphthalen-1-ol 
• 121-69-7 N,N-dimethyl-aniline 
• 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 
• 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%.

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.

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.

Dihydronaphthalene compounds, compositions, uses thereof, and methods for synthesis

The present invention relates to novel dihydronaphthalene compounds, compositions, methods for using the same, and processes for preparing the same. The present invention also relates to novel total synthesis approaches for preparing these compounds. In addition, the present invention relates to methods of producing quantities of isomers of these compounds and separating and purifying them using chiral separation techniques. The present invention also relates to methods of producing quantities of a single isometric compound without the need for chiral separation techniques.

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.

Synthesis of some substituted naphthalenes as potential intermediates for polyethers and terpenoids

1-Benzyloxy-5-hydroxynaphthalene and 1,6-dimethyl-5-hydroxynaphthalene were prepared from 5-methoxy-α-tetralone. 6-Methoxy-α-tetralone was converted to 1,6-dimethoxy-2-isopropylnaphthalene.

Regio- and Chemo-selective Properties of Lipase from Candida cylindracea

Lipase from Candida cylindracea allows discrimination between the two connectively non-equivalent hydroxy groups in primary diols or their esters via acylation-hydrolysis, with high regioselectivity.The same technique is used to distinguish between hydroxy groups of different nature in phenolic compounds.