1,5-Dibromo-2,6-dihydroxynaphthalene

• CAS: 132178-78-0
• Catalog Number: ACM132178780-1
• Category: Main Products
• Molecular Weight: 317.96g/mol
• Molecular Formula: C10H6Br2O2
• IUPAC Name: 1,5-dibromonaphthalene-2,6-diol
• Canonical SMILES: C1=CC(=C(C2=C1C(=C(C=C2)O)Br)Br)O
• InChI: InChI=1S/C10H6Br2O2/c11-9-5-1-3-7(13)10(12)6(5)2-4-8(9)14/h1-4,13-14H
• InChI Key: COJNHIANORGBGY-UHFFFAOYSA-N
• Melting Point: 215 °C (dec.)
• Appearance: Solid
• Complexity: 190
• Covalently-Bonded Unit Count: 1
• Exact Mass: 317.87141g/mol
• Formal Charge: 0
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Heavy Atom Count: 14
• Monoisotopic Mass: 315.87345g/mol
• Rotatable Bond Count: 0
• XLogP3: 3.8

Case Study

1,5-Dibromo-2,6-dihydroxynaphthalene for the Synthesis of π-Conjugated Copolymer Oligomers

Yamaguchi, Isao, et al. Polymer Bulletin, 2018, 75, 1635-1650.

The π-conjugated copolymer oligomers (composed of 2,6-dialkoxynaphthalene-1,5-diyl (RNap), 2,1,3-benzothiadiazole-4,7-diyl, and 1,4-phenylenediethynylene units) were synthesized by a Pd complex-catalyzed condensation reaction, which have self-assembling-ordered structures in the solid state. Among them, 1,5-Dibromo-2,6-dihydroxynaphthalene is an important raw material for the synthesis of several monomers. Monomer-1a, monomer-1b and monomer-1c were synthesized by reacting 1,5-dibromo-2,6-dihydroxynaphthalene with 1-bromohexane, 1-bromooctane and 1-bromodecane, respectively. These monomers were subsequently used in the synthesis of a series of oligomers.
Taking Monomer-1a as an example, the typical synthesis procedure was as follows:
A mixture of 1,5-dibromo-2,6-dihydroxynaphthalene (5.1 g, 16 mmol) and potassium hydroxide (4.2 g, 75 mmol) was dissolved in 120 mL of anhydrous ethanol and heated under reflux until the potassium hydroxide fully dissolved. Following this, 1-bromohexane (11.4 g, 69 mmol) was added dropwise to the solution, which was then refluxed for 47 hours. The resulting precipitate was collected through filtration, rinsed with water, and recrystallized from chloroform. Monomer-1a was filtered, dried in a vacuum, and obtained as a white crystalline product.

1,5-Dibromonaphthalene-2,6-Diol for the Synthesis of Naphthalene Core-Based Noncovalently Fused-Ring Electron Acceptors

Zheng, Rui, et al. Journal of Materials Chemistry C, 2019, 7(48), 15141-15147.

Two mutually isomeric non-covalent fused-ring electron acceptors (NC-FREAs), NOC6F-1 and NOC6F-2, were designed and synthesized. They contain two cyclopentadithiophene (CPDT) moieties attached to the 2,6 and 1,5 positions of the naphthalene ring, respectively, for use in organic solar cells (OSCs).
Synthetic routes of NOC6F-1 and NOC6F-2
· Using 2,6-dibromonaphthalene-1,5-diol (1a) and 1,5-dibromonaphthalene-2,6-diol (1b) as starting materials, compounds 2a and 2b were synthesized through alkylation with 1-bromohexane, yielding 73% and 77%, respectively.
· A Stille coupling reaction of compound 3 with 2a and 2b produced compounds 4a and 4b in approximately 95% yields, using Pd(PPh3)4 as the catalyst precursor.
· Subsequently, compounds 4a and 4b underwent lithiation using n-BuLi in anhydrous tetrahydrofuran at -78 °C, and the resulting dianions were quenched with anhydrous N,N-dimethylformamide (DMF), yielding compounds 5a and 5b in yields of 90% and 86%, respectively.
· Finally, NOC6F-1 and NOC6F-2 were synthesized through Knoevenagel condensation of 5a and 5b with compound 6, achieving yields of 59% and 55%, respectively.

Custom Q&A

What is the molecular formula of 1,5-Dibromo-2,6-dihydroxynaphthalene?

The molecular formula is C10H6Br2O2.

What are the synonyms for 1,5-Dibromo-2,6-dihydroxynaphthalene?

The synonyms include 1,5-dibromonaphthalene-2,6-diol, 132178-78-0, 1,5-Dibromo-2,6-naphthalenediol, and 2,6-Naphthalenediol, 1,5-dibromo-.

What is the molecular weight of 1,5-Dibromo-2,6-dihydroxynaphthalene?

The molecular weight is 317.96 g/mol.

When was 1,5-Dibromo-2,6-dihydroxynaphthalene created?

It was created on February 9, 2007.

When was 1,5-Dibromo-2,6-dihydroxynaphthalene last modified?

It was last modified on October 21, 2023.

What is the IUPAC name of 1,5-Dibromo-2,6-dihydroxynaphthalene?

The IUPAC name is 1,5-dibromonaphthalene-2,6-diol.

What is the InChI of 1,5-Dibromo-2,6-dihydroxynaphthalene?

The InChI is InChI=1S/C10H6Br2O2/c11-9-5-1-3-7(13)10(12)6(5)2-4-8(9)14/h1-4,13-14H.

What is the InChIKey of 1,5-Dibromo-2,6-dihydroxynaphthalene?

The InChIKey is COJNHIANORGBGY-UHFFFAOYSA-N.

What is the Canonical SMILES of 1,5-Dibromo-2,6-dihydroxynaphthalene?

The Canonical SMILES is C1=CC(=C(C2=C1C(=C(C=C2)O)Br)Br)O.

What is the CAS number of 1,5-Dibromo-2,6-dihydroxynaphthalene?

The CAS number is 132178-78-0.

Synthetic Use

Upstream Synthesis Route 1

• 581-43-1

• 132178-78-0

Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 36, p. 6487 - 6490
[2] Patent: WO2013/149001, 2013, A2, . Location in patent: Paragraph 00123
[3] Journal of the Chemical Society, 1937, p. 1859,1861
[4] Patent: US2011/224445, 2011, A1, . Location in patent: Page/Page column 8

Upstream Synthesis Route 2

• 83-56-7

• 132178-78-0

Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 33, p. 4781 - 4784

Upstream Synthesis Route 3

• 581-43-1

• 132178-78-0

Reference: [1]Patent: US10174043,2019,B1 .Location in patent: Page/Page column 15

Downstream Synthesis Route 1

• 132178-78-0

• 132178-77-9

Reference: [1]Chemische Berichte,1943,vol. 76,p. 924,928,936

Downstream Synthesis Route 2

• 132178-78-0

• 133546-47-1

Reference: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 68 - 73

* For details of the synthesis route, please refer to the original source to ensure accuracy.