2,6-Dibromonaphthalene-1,5-diol

Base Information

• Chemical Name: 2,6-Dibromonaphthalene-1,5-diol
• CAS No.: 84-59-3
• Molecular Formula: C10H6Br2O2
• Molecular Weight: 317.964
• Hs Code.: 2908199090
• European Community (EC) Number: 201-543-8
• NSC Number: 62684
• UNII: D3BHJ6NH78
• DSSTox Substance ID: DTXSID00232889
• Nikkaji Number: J40.503E
• Wikidata: Q29706742
• Mol file: 84-59-3.mol

Synonyms:2,6-Dibromonaphthalene-1,5-diol;84-59-3;2,6-Dibromo-1,5-dihydroxynaphthalene;2,6-Dibromo-1,5-naphthalenediol;1,5-Naphthalenediol, 2,6-dibromo-;1,5-Dihydroxy-2,6-dibromonaphthalene;C10H6Br2O2;EINECS 201-543-8;NSC 62684;D3BHJ6NH78;NSC-62684;NSC62684;1, 2,6-dibromo-;UNII-D3BHJ6NH78;SCHEMBL2367986;2,6-dibromnaphthalen-1,5-diol;C10-H6-Br2-O2;DTXSID00232889;WLN: L66J BQ CE GQ HE;MFCD00021473;STK378142;AKOS003602218;2,6-bis(bromanyl)naphthalene-1,5-diol;2,6-dibromo-1,5-di hydroxynaphthalene;2,6-dibromo-1,5-dihydroxy naphtha-lene;BS-44028;LS-94575;CS-0157296;D2593;FT-0610538;1 5-DIHYDROXY-2 6-DIBROMONAPHTHALENE;D85425;A840871

Chemical Property of 2,6-Dibromonaphthalene-1,5-diol

Chemical Property:

• Vapor Pressure: 6.92E-07mmHg at 25°C
• Melting Point: 78-81?°C(lit.)
• Refractive Index: 1.766
• Boiling Point: 397.4 °C at 760 mmHg
• PKA: 6.19±0.50(Predicted)
• Flash Point: 194.2 °C
• PSA: 40.46000
• Density: 2.081 g/cm³
• LogP: 3.77600
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 317.87141
• Heavy Atom Count: 14
• Complexity: 190

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,6-Dibromo-1,5-naphthalenediol ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C2=C1C(=C(C=C2)Br)O)O)Br
• Uses: 2,6-Dibromo-1,5-naphthalenediol is a useful synthetic intermediate. It is used to prepare semiconducting polyphenyls and polythiophenes via microwave-assisted Suzuki and Stille cross-coupling reactions. It is also used to prepare and polymerize adamantane or phenylenevinylene or naphthalenevinylene-containing monomers.

Technology Process of 2,6-Dibromonaphthalene-1,5-diol

There total 2 articles about 2,6-Dibromonaphthalene-1,5-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%

1,5-dihydroxynaphthalene (83-56-7) → 2,6-dibromo-1,5-naphthalenediol (84-59-3)

Guidance literature:

With bromine; In chloroform; at 0 - 20 ℃; for 3h;

DOI:10.1021/acs.joc.7b01001

Reference yield:

1,5-dihydroxynaphthalene (83-56-7) + bromine (7726-95-6) + iodine (7553-56-2,12190-71-5,8031-47-8) + acetic acid (64-19-7,77671-22-8) → 2,6-dibromo-1,5-naphthalenediol (84-59-3)

Guidance literature:

at 80 ℃;

DOI:10.1021/ja01375a032

Reference yield: 93.0%

2,6-dibromo-1,5-naphthalenediol (84-59-3) + benzyl bromide (100-39-0) → 1,5-dibenzoxy-2,6-dibromonaphthalene

Guidance literature:

2,6-dibromo-1,5-naphthalenediol; With sodium hydroxide; In N,N-dimethyl-formamide; at 0 ℃; for 1.5h; Inert atmosphere; Cooling with ice;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c4dt02300e

upstream raw materials:

1,5-dihydroxynaphthalene

bromine

iodine

acetic acid

Downstream raw materials:

8-amino-2,6-dibromo-5-hydroxy-[1,4]naphthoquinone

2,6-dibromo-1,5-bis(methoxy)naphthalene

2,6-dibromo-5-methoxy-[1]naphthol

9-bromo-3-(4-methoxyphenyl)naphtho<1,8-bc>pyran-2,6-dione

Refernces

• 1、 Cha, Hyojung,Baek, Jang Yeol,An, Tae Kyu,Kim, Seul-Ong,Kwon, Soon-Ki,Kim, Yun-Hi,Park, Chan Eon. "Development of bulk heterojunction morphology by the difference of intermolecular interaction behaviors". . p. 3558 - 3567. Retrieved 2014.
• 2、 Gonzalez, Silvia,Martin, Nazario,Segura, Jose L.,Seoane, Carlos. "Convenient regioselective syntheses of isomeric bis(tetrathiafulvalenylethenyl)naphthalene π-donors". . p. 3051 - 3054. Retrieved 1998.
• 3、 Urban, Mateusz,Durka, Krzysztof,Jankowski, Piotr,Serwatowski, Janusz,Luliński, Sergiusz. "Highly Fluorescent Red-Light Emitting Bis(boranils) Based on Naphthalene Backbone". . p. 8234 - 8241. Retrieved 2017/08/14.