(1R,2S)-1,2-Dihydronaphthalene-1,2-diol

Base Information

• Chemical Name: (1R,2S)-1,2-Dihydronaphthalene-1,2-diol
• CAS No.: 51268-88-3
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Hs Code.: 2907299090
• UNII: E8MH7SV5YM
• Nikkaji Number: J89.614D
• Wikidata: Q27097486
• Metabolomics Workbench ID: 52374
• Mol file: 51268-88-3.mol

Synonyms:(1R,2S)-1,2-Dihydronaphthalene-1,2-diol;51268-88-3;(1R, 2S)-CIS 1,2 DIHYDROXY-1,2-DIHYDRONAPHTHALENE;Naphthalene dihydrodiol;cis-1,2-Dihydroxy-1,2-dihydronaphthalene;E8MH7SV5YM;cis naphthalene dihydrodiol;cis-1,2-Dihydronaphthalene-1,2-diol;3,4-dihydronaphthalene-3,4-diol;(1R,2S)-cis-1,2-Dihydro-1,2-naphthalenediol;(+)-(1R,2S)-1,2-Dihydro-1,2-naphthalenediol;(1R,2S)-naphthalene-1,2-dihydrodiol;(1R,2S)-1,2-Dihydro-1,2-naphthalenediol;(1R,2S)-1,2-dihydro-1,2-dihyroxynaphthalene;1,2-Dihydronaphthalene-1,2-diol, (1R,2S)-;Rel-(1R,2S)-1,2-dihydronaphthalene-1,2-diol;1,2-Naphthalenediol, 1,2-dihydro-, (1R,2S)-;cis-(1R,2S)-1,2-Dihydro-1,2-dihydroxynaphthalene;(+)-cis-1(R),2(S)-Dihydroxy-1,2-dihydronaphthalene;(+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2-DIHYDRONAPHTHALENE;1,2-dihydro-1,2-naphthalenediol;31966-70-8;starbld0001810;UNII-E8MH7SV5YM;bmse000655;SCHEMBL639420;CHEBI:44343;(1R,1S)-CIS-1,2-DIHYDRO-1,2-DIHYDROXYNAPHTHALENE;AKOS015915949;DB08264;1,2-Dihydro-1beta,2beta-naphthalenediol;CIS-12-DIHYDRONAPHTHALENE-12-DIOL;cis-1,2-dihydroxy-1,2-dihydronaphtha-lene;(1R-cis)-1,2-Dihydro-1,2-naphthalenediol;(1R, 2S)-1,2-dihydronaphthalene-1,2-diol;C04314;(1R,2S)-cis-1,2-Dihydro-1,2-dihydroxynaphthalene;Q27097486;(1R,2S)-cis-1,2-Dihydro-1,2-naphthalenediol, >=98.0%

Chemical Property of (1R,2S)-1,2-Dihydronaphthalene-1,2-diol

Chemical Property:

• Vapor Pressure: 6.23E-05mmHg at 25°C
• Melting Point: 121-127 °C(lit.)
• Refractive Index: 1.664
• Boiling Point: 331.4°C at 760 mmHg
• PKA: 13.58±0.40(Predicted)
• Flash Point: >230 °F
• PSA: 40.46000
• Density: 1.312g/cm³
• LogP: 1.10770
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

99.3% ^*data from raw suppliers

(+)-(1R,2S)-1,2-Dihydro-1,2-naphthalenediol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(C(C=CC2=C1)O)O
• Isomeric SMILES: C1=CC=C2[C@H]([C@H](C=CC2=C1)O)O
• Uses: (-)-(1R,2S)-1,2-Dihydro-1,2-naphthalenediol is a derivative of Naphthalene (N345600), an abundant polycyclic aromatic hydrocarbon that is persistent, bioaccumulative, toxic and found in tobacco smoke and urban air.

Technology Process of (1R,2S)-1,2-Dihydronaphthalene-1,2-diol

There total 12 articles about (1R,2S)-1,2-Dihydronaphthalene-1,2-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

1,4-epoxy-1,4-dihydronaphthalene (573-57-9) → (1R,2R)-1,2-dihydronaphthalene-1,2-diol (771-16-4,7234-04-0,13011-97-7,19216-89-8,31966-70-8,51268-88-3,62697-15-8,81655-35-8,90365-29-0)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-1-[(S)-2-(di-tert-butylphosphino)ferrocenyl]ethyl-di-2-methylphenylphosphine; water; In tetrahydrofuran; at 25 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201200390

Reference yield: 53.0%

1,4-epoxy-1,4-dihydronaphthalene (573-57-9) → (1R,2R)-1,2-dihydronaphthalene-1,2-diol (771-16-4,7234-04-0,13011-97-7,19216-89-8,31966-70-8,51268-88-3,62697-15-8,81655-35-8,90365-29-0) + 2-hydroxy-1-tetralone (64559-97-3)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-1-[(S)-2-(di-tert-butylphosphino)ferrocenyl]ethyl-di-2-methylphenylphosphine; water; In tetrahydrofuran; at 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201200390

Reference yield:

naphthalene (91-20-3,71998-51-1,72931-45-4) → α-naphthol (90-15-3) + cis-1,2-dihydroxy-1,2-dihydronaphthalene (771-16-4,7234-04-0,13011-97-7,19216-89-8,31966-70-8,51268-88-3,62697-15-8,81655-35-8,90365-29-0) + β-naphthol (135-19-3) + [1,4]naphthoquinone (130-15-4)

Guidance literature:

With [Fe(tpa)(CH₃CN)2](OTf)2; water; dihydrogen peroxide; In acetonitrile; at 25 ℃;

DOI:10.1039/b817222f

upstream raw materials:

1,4-epoxy-1,4-dihydronaphthalene

1,2-Dihydronaphthalene

(R)-(+)-1-hydroxy-1,2-dihydronaphthalene

naphthalene

Downstream raw materials:

benzene-1,2-dicarboxylic acid

1,2,3,4-tetrahydro-1,2,3,4-tetrahydroxynaphthalene

β-naphthol

α-naphthol

Refernces

• 1、 Kudavalli, Jaya S.,Boyd, Derek R.,Coyne, Dara,Keeffe, James R.,Lawlor, David A.,MacCormac, Aoife C.,More O'Ferrall, Rory A.,Rao, S. Nagaraja,Sharma, Narain D.. "Hyperaromatic stabilization of arenium ions". supporting information; experimental part. p. 5550 - 5553. Retrieved 2011/02/27.
• 2、 Chun,Ohnishi,Misawa,Shindo,Hayashi,Harayama,Horinouchi. "Biotransformation of phenanthrene and 1-methoxynaphthalene with Streptomyces lividans cells expressing a marine bacterial phenanthrene dioxygenase gene cluster.". . p. 1774 - 1781. Retrieved 2007/10/03.