13011-97-7

Basic information

• Product Name: (1S,2S)-1,2-Dihydronaphthalene-1,2-diol
• Synonyms: (1S,2S)-1,2-Dihydronaphthalene-1,2-diol;[1S,2S,(+)]-1,2-Dihydro-1,2-naphthalenediol;1,2-Dihydro-1,2-naphthalenediol (1S-trans)-;1,2-Naphthalenediol, 1,2-dihydro-, (1S,2S)-(+)-;1,2-Naphthalenediol, 1,2-dihydro-, (1S-trans)-;(1S,2S)-trans-1,2-Dihydro-1,2-naphthalenediol
• CAS NO: 13011-97-7
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Mol File: 13011-97-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (1S,2S)-1,2-Dihydronaphthalene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-1,2-Dihydronaphthalene-1,2-diol(13011-97-7)
• EPA Substance Registry System: (1S,2S)-1,2-Dihydronaphthalene-1,2-diol(13011-97-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 13011-97-7(Hazardous Substances Data)

Usage

General Description

(1S,2S)-1,2-Dihydronaphthalene-1,2-diol is a chemical compound with the molecular formula C10H10O2. It is a diol, which means it contains two hydroxyl groups (-OH) attached to adjacent carbon atoms within a naphthalene ring. (1S,2S)-1,2-Dihydronaphthalene-1,2-diol can be synthesized through various chemical reactions, and it has applications in organic synthesis and medicinal chemistry. Its stereochemistry (1S,2S) refers to the spatial arrangement of its atoms, indicating that the hydroxyl groups are on the same side of the molecule. Overall, (1S,2S)-1,2-Dihydronaphthalene-1,2-diol is an important building block for creating other organic compounds and has potential uses in pharmaceutical research and chemical manufacturing.

Upstream product

• 91-20-3 naphthalene 
• 524-42-5 1,2-naphthoquinone 
• 573-57-9 1,4-epoxy-1,4-dihydronaphthalene 

Downstream Products

• 90-15-3 α-naphthol 
• 91-20-3 naphthalene 
• 135-19-3 β-naphthol 
• 14211-53-1 cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 574-00-5 1,2-Dihydroxynaphthalene 

Relevant articles and documents

Bioconversion of substituted naphthalenes to the corresponding 1,2-dihydro derivatives by Escherichia coli recombinant strains

1,2-dihydroxynaphthalenes are produced by bioconversion of the corresponding hydrocarbons using Escherichia coli recombinant strains containing the naphthalene dioxygenase and dehydrogenase genes cloned from pseudomonas fluorescens N3. Conversions are lead by a two step procedure without isolation of the dihydrodiol intermediate. Conversion rates depend on the position and nature of the naphthalene substituent.

Hyperaromatic stabilization of arenium ions

Benzene-cis- and trans-1,2-dihydrodiols undergo acid-catalyzed dehydration at remarkably different rates: kcis/ktrans = 4500. This is explained by formation of a β-hydroxycarbocation intermediate in different initial conformations, one of which is stabilized by hyperconjugation amplified by an aromatic no-bond resonance structure (HOC6H6 + HOC6H5 H+). MP2 calculations and an unfavorable effect of benzoannelation on benzenium ion stability, implied by pKR measurements of -2.3, -8.0, and -11.9 for benzenium, 1-naphthalenium, and 9-phenanthrenium ions, respectively, support the explanation.

Biotransformation of phenanthrene and 1-methoxynaphthalene with Streptomyces lividans cells expressing a marine bacterial phenanthrene dioxygenase gene cluster.

The phdABCD gene cluster in a marine bacterium Nocardioides sp. strain KP7 codes for the multicomponent enzyme phenanthrene dioxygenase. phdA encoding an iron-sulfur protein large subunit alpha, phdB encoding its small subunit beta, phdC encoding ferredoxin, and phdD encoding ferredoxin reductase, were replaced in such a way that the termination codons of the preceding open reading frames were overlapped with the initiation codons of the following genes. This manipulated phdABCD gene cluster was positioned downstream of the thiostrepton-inducible promoter PtipA in a high-copy-number vector pIJ6021, and introduced into the gram-positive, soil-inhabiting, filamentous bacterium Streptomyces lividans. The recombinant S. lividans cells converted phenanthrene into a cis-diol form, which was determined to be cis-3,4-dihydroxy-3,4-dihydrophenanthrene by its UV spectral data as well as HPLC property, using the authentic sample for comparison. This biotransformation proceeded very efficiently; 200 microM and 2 mm of phenanthrene were almost completely converted to its cis-diol form in 6 h and 32 h, respectively. In addition, the S. lividans cells carrying the phdABCD gene cluster were found to transform 1-methoxynaphthalene to two products, which were identified to be 8-methoxy-2-naphthol in addition to 8-methoxy-1,2-dihydro-1,2-naphthalenediol by their EI-MS, 1H- and 13C-NMR spectral data.