1-Bromo-2,3-dimethoxynaphthalene

Base Information

• Chemical Name: 1-Bromo-2,3-dimethoxynaphthalene
• CAS No.: 222555-02-4
• Molecular Formula: C12H11 Br O2
• Molecular Weight: 267.12
• Hs Code.: 2909309090
• European Community (EC) Number: 625-786-8
• DSSTox Substance ID: DTXSID00584592
• Nikkaji Number: J3.591.719E
• Wikidata: Q82476275
• Mol file: 222555-02-4.mol

Synonyms:1-Bromo-2,3-dimethoxynaphthalene;222555-02-4;SCHEMBL13302148;DTXSID00584592;AKOS015913652;AT25602;1-Bromo-2,3-dimethoxynaphthalene, 97%;1-BROMO-2 3-DIMETHOXYNAPHTHALENE 97;EN300-7547178;J-014612

Chemical Property of 1-Bromo-2,3-dimethoxynaphthalene

Chemical Property:

• Vapor Pressure: 0.000211mmHg at 25°C
• Melting Point: 48-52 °C(lit.)
• Refractive Index: 1.61
• Boiling Point: 337°C at 760 mmHg
• Flash Point: 110 °C
• PSA: 18.46000
• Density: 1.422g/cm³
• LogP: 3.61950
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 265.99424
• Heavy Atom Count: 15
• Complexity: 210

Purity/Quality:

95-99% ^*data from raw suppliers

1-Bromo-2,3-dimethoxynaphthalene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 41-50/53
• Safety Statements: 26-39-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=CC=CC=C2C(=C1OC)Br

Technology Process of 1-Bromo-2,3-dimethoxynaphthalene

There total 3 articles about 1-Bromo-2,3-dimethoxynaphthalene 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: 86.0%

2,3-dimethoxynaphthalene (10103-06-7) → 1-bromo-2,3-dimethoxynaphthalene (222555-02-4)

Guidance literature:

With bromine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1055/s-1999-3424

Reference yield: 65.0%

2,3-dimethoxynaphthalene (10103-06-7) → dibromo-1,4 dimethoxy-2,3 naphtalene (7311-17-3) + 1-bromo-2,3-dimethoxynaphthalene (222555-02-4)

Guidance literature:

With aluminum tri-bromide; [bis(acetoxy)iodo]benzene; In acetonitrile; at 23 ℃;

DOI:10.1039/c8ra02982b

Reference yield:

2,3-naphthalenediol (92-44-4) → 1-bromo-2,3-dimethoxynaphthalene (222555-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 50 °C

2: N-Bromosuccinimide / acetonitrile / 20 °C

With N-Bromosuccinimide; potassium carbonate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.1c01671

upstream raw materials:

2,3-dimethoxynaphthalene

2,3-naphthalenediol

Refernces

• 1、 Baker,Brkic,Sargent,Skelton,White. "Atropisomerism of 2,2′-binaphthalenes". . p. 925 - 938. Retrieved 2000.
• 2、 Satkar, Yuvraj,Ramadoss, Velayudham,Nahide, Pradip D.,García-Medina, Ernesto,Juárez-Ornelas, Kevin A.,Alonso-Castro, Angel J.,Chávez-Rivera, Ruben,Jiménez-Halla, J. Oscar C.,Solorio-Alvarado, César R.. "Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system". . p. 17806 - 17812. Retrieved 2018/05/28.