ChemicalBook > CAS DataBase List > 4-Bromo-1,8-naphthalic anhydride

4-Bromo-1,8-naphthalic anhydride

Product Name: 4-Bromo-1,8-naphthalic anhydride
CAS No.: 81-86-7
Chemical Name: 4-Bromo-1,8-naphthalic anhydride
Synonyms: 4-BROMO-1,8-NAPHTHALENEDICARBOXYLIC ANHYDRIDE;4-BROMONAPHTHALIC ANHYDRIDE;4-Bromo-1,8-phthalic anhydride;4-Bromo-1,8-Napthalic Anhydride;4-Bromo-1,8-naphthalic anhydride;4-BroMo-1,8-naphthalic anhydride 95%;4-Bromo-1,8-naphthalic Anhydride >4-Bromo-1,8-Naphthalic Anhydride,>98%;6-BROMO-BENZO[DE]ISOCHROMENE-1,3-DIONE;7-Bromo-1H,3H-naphtho[1,8-cd]pyran-1,3-dione
CBNumber: CB8364504
Molecular Formula: C12H5BrO3
Formula Weight: 277.07
MOL File: 81-86-7.mol

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4-Bromo-1,8-naphthalic anhydride Property

Melting point:: 217-219 °C (lit.)
Boiling point:: 467.2±28.0 °C(Predicted)
Density: 1.812±0.06 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
color: Off-White to Pale Yellow
InChI: InChI=1S/C12H5BrO3/c13-9-5-4-8-10-6(9)2-1-3-7(10)11(14)16-12(8)15/h1-5H
InChIKey: DTUOTSLAFJCQHN-UHFFFAOYSA-N
SMILES: C1(=O)OC(=O)C2=CC=C(Br)C3=C2C1=CC=C3
CAS DataBase Reference: 81-86-7(CAS DataBase Reference)
EPA Substance Registry System: 1H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-bromo- (81-86-7)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-37/39
WGK Germany: 3
HS Code: 29173990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 324248
Product name: 4-Bromo-1,8-naphthalic anhydride
Purity: 95%
Packaging: 5g
Price: $54.53
Updated: 2025/07/31

TCI Chemical

Product number: B0858
Product name: 4-Bromo-1,8-naphthalic Anhydride
Purity: >95.0%(T)
Packaging: 5g
Price: $45
Updated: 2025/07/31

TCI Chemical

Product number: B0858
Product name: 4-Bromo-1,8-naphthalic Anhydride
Purity: >95.0%(T)
Packaging: 25g
Price: $155
Updated: 2025/07/31

TRC

Product number: B697930
Product name: 4-Bromo-1,8-naphthalic Anhydride
Packaging: 500mg
Price: $50
Updated: 2021/12/16

TRC

Product number: B697930
Product name: 4-Bromo-1,8-naphthalic Anhydride
Packaging: 5g
Price: $85
Updated: 2021/12/16

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4-Bromo-1,8-naphthalic anhydride Chemical Properties,Usage,Production

Uses

4-Bromo-1,8-naphthalic Anhydride is used as a starting material in the synthesis of a fluorescent probe for the detection of copper ions in living human LO-2 cell lines.

Synthesis

81-84-5

81-86-7

1. Oxidation: 1,8-Naphthalenedicarboxylic anhydride (2.31 g, 15.0 mmol) was dissolved in acetic acid (60 mL) and sodium dichromate (11.17 g, 40.0 mmol) was added under stirring conditions at room temperature. The suspension was heated to 75 °C and the reaction was carried out for 8 hours. After the reaction was completed, cold water was added to precipitate the product, which was filtered and washed with water to obtain white 1,8-naphthalenedicarboxylic anhydride (2.6 g, 80%, melting point 266-268 °C). 2. Bromination: 1,8-naphthalenedicarboxylic anhydride (1.98 g, 10.0 mmol) was dissolved in aqueous KOH (2.8 g KOH in 12 mL of water), cooled, and bromine was added dropwise. The reaction mixture was heated to 60 °C and kept for 6 h, then acidified with HCl solution. The crude product was obtained by filtration, the solid was dissolved by heating with 5% NaOH solution, filtered and neutralized with HCl solution, filtered again and washed with cold water, and dried to obtain yellow 4-bromo-1,8-naphthalenedicarboxylic anhydride (2.05 g, 82%, melting point 117-119 °C). 3. Condensation: 4-bromo-1,8-naphthalenedicarboxylic anhydride (2.00 g, 5.0 mmol) was refluxed with o-phenylenediamine (0.618 g, 5.0 mmol) in THF for 6 hours. After completion of the reaction (monitored by TLC), the reaction mixture was cooled, filtered and washed with THF to afford brown 3-bromo-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one (2.51 g, 63%, melting point 190-192 °C). Product characterization: 1H NMR (CDCl3 + TFA) δ 8.90 (dd, J=8.48, 0.68 Hz, 1H, ArH), 8.79 (dd, J=7.36, 0.84 Hz, 1H, ArH), 8.53 (d, J=7.92 Hz, 1H, ArH), 8.24 (d, J=7.92 Hz, 1H, ArH), 8.04 (dd, J=7.92 Hz, 1H, ArH), 8.04 (dd, J=7.92 Hz, 1H, ArH), 8.05 (dd, J=7.92 Hz, 1H, ArH). 8.04 (dd, J=8.48, 7.48 Hz, 1H, ArH), 7.74 (m, 3H, ArH), 7.56 (m, 1H, ArH); 13C NMR (CDCl3 + TFA) δ 165.76, 136.55, 134.50, 134.42, 133.44, 131.92, 131.75, 131.68, 131.15, 130.90, 129.30, 128.64, 128.20, 127.26, 124.97, 121.02, 119.98; EIMS m/z: 350 (M+ + 1). Calculated elemental analysis (C18H9BrN2O): C, 61.91; H, 2.60; N, 8.08. Measured values: C, 61.76; H, 2.81; N, 8.45.

References

[1] Chemistry - A European Journal, 2011, vol. 17, # 44, p. 12257 - 12261
[2] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 352 - 360
[3] RSC Advances, 2015, vol. 5, # 52, p. 41803 - 41813
[4] New Journal of Chemistry, 2011, vol. 35, # 8, p. 1690 - 1700
[5] Dyes and Pigments, 2018, vol. 158, p. 353 - 361

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View Lastest Price from 4-Bromo-1,8-naphthalic anhydride manufacturers

Honest Joy Holdings Limited

Product: 4-Bromo-1,8-naphthalic anhydride 81-86-7
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98.2%
Supply Ability: 100 tons
Release date: 2022-02-18

Career Henan Chemical Co

Product: Benzothioxanthene dicarboxylic anhydride 81-86-7
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1
Release date: 2018-08-09

81-86-7, 4-Bromo-1,8-naphthalic anhydrideRelated Search:

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6-BROMO-BENZO[DE]ISOCHROMENE-1,3-DIONE

6-Bromo-1H,3H-naphtho[1,8-cd]pyran-1,3-dione

4-BROMONAPHTHALIC ANHYDRIDE

1H,3H-Naphtho(1,8-cd)pyran-1,3-dione, 6-bromo-

4-Bromo-1,8-naphthalic anhydride

7-Bromo-1H,3H-naphtho[1,8-cd]pyran-1,3-dione

6-Bromo-1H,3H-benzo[de]isochromene-1,3-dione, 6-Bromo-1,3-dioxo-1H,3H-benzo[de]isochromene

4-BroMo-1,8-naphthalic anhydride 95%

4-BROMO-1,8-NAPHTHALENEDICARBOXYLIC ANHYDRIDE

4-Bromo-1,8-naphthalic Anhydride &gt

4-Bromo-1,8-Naphthalic Anhydride,>98%

4-Bromo-1,8-Napthalic Anhydride

8-bromo-3-oxatricyclo[7.3.1.0?13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione

4-Bromo-1,8-phthalic anhydride

81-86-7

Pyridines

Anhydride Monomers

Monomers

Polymer Science