Naphthalene-1,4-diboronic acid

Base Information

• Chemical Name: Naphthalene-1,4-diboronic acid
• CAS No.: 22871-75-6
• Molecular Formula: C10H10B2O4
• Molecular Weight: 215.809
• DSSTox Substance ID: DTXSID10440756
• Nikkaji Number: J1.281.595F
• Wikidata: Q82257151
• Mol file: 22871-75-6.mol

Synonyms:22871-75-6;NAPHTHALENE-1,4-DIBORONIC ACID;NAPHTHALENE-1,4-DIYLDIBORONIC ACID;(4-borononaphthalen-1-yl)boronic Acid;Boronic acid,1,1'-(1,4-naphthalenediyl)bis-;1,4-naphthalenediboronic acid;SCHEMBL1427222;YSZC1573;DTXSID10440756;UQQNPIILEFDCRF-UHFFFAOYSA-N;1,4-Bis(dihydroxyboryl)naphthalene;AKOS004116599;AB30030;NAPHTHALENE-1,4-DIYLDIBORONICACID;CS-0169824;F87615;[4-(dihydroxyboranyl)naphthalen-1-yl]boronic acid

Chemical Property of Naphthalene-1,4-diboronic acid

Chemical Property:

• Melting Point: >300 °C
• Boiling Point: 514.229 °C at 760 mmHg
• PKA: 7.89±0.30(Predicted)
• Flash Point: 264.796 °C
• PSA: 80.92000
• Density: 1.367 g/cm³
• LogP: -1.80060
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 216.0765191
• Heavy Atom Count: 16
• Complexity: 213

Purity/Quality:

98%min ^*data from raw suppliers

Naphthalene-1,4-diboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C2=CC=CC=C12)B(O)O)(O)O
• Uses: Naphthalene-1,4-diboronic Acid is a reagent used in the synthesis of carcinogenic oxidized metaboites of benzo[s]picene, benzo[rst]pentaphene, and dibenzo[b,def]chrysene.

Technology Process of Naphthalene-1,4-diboronic acid

There total 2 articles about Naphthalene-1,4-diboronic acid 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:

1,4-dibromonaphthalene (83-53-4) → naphthalene-1,4-diyldiboronic acid (22871-75-6)

Guidance literature:

1,4-dibromonaphthalene; With iodine; magnesium; In tetrahydrofuran; for 12h; Heating;

With Trimethyl borate; In tetrahydrofuran; at 20 ℃;

With hydrogenchloride; In tetrahydrofuran; at 0 - 5 ℃; Further stages.;

DOI:10.1021/jo9918044

Reference yield:

→ naphthalene-1,4-diyldiboronic acid (22871-75-6)

Guidance literature:

1,4-Dibromnaphthalin/Mg, Trimethylborat;

DOI:10.1002/jps.2600580321

Reference yield: 91.0%

naphthalene-1,4-diyldiboronic acid (22871-75-6) + ortho-bromobenzaldehyde (6630-33-7) → 2,2'-(naphthalene-1,4-diyl)dibenzaldehyde (285571-20-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; ethanol; Heating;

DOI:10.1021/jo9918044

upstream raw materials:

1,4-dibromonaphthalene

Downstream raw materials:

1,4-bis(2-formyl-3,4-dimethoxyphenyl)naphthalene

2,2'-(naphthalene-1,4-diyl)dibenzaldehyde

1,4-bis(2-vinyl-3,4-dimethoxyphenyl)naphthalene

C₃₄H₃₆O₈

Refernces

• 1、 Zhang, Fang-Jie,Cortez, Cecilia,Harvey, Ronald G.. "New synthetic approaches to polycyclic aromatic hydrocarbons and their carcinogenic oxidized metabolites: Derivatives of benzo[s]picene, benzo[rst]pentaphene, and dibenzo[b,def]chrysene". . p. 3952 - 3960. Retrieved 2007/10/03.