HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,4-Dibromonaphthalene
1,4-DBN · 1,4-dibromo-naphthalen · SKL252 · 1,4-DibromonaphthaL · 1,4-DIBROMONAPHTHALE · Glycerol Impurity 58 · ,4-dibromonaphthalene · 1,4-DIBROMONAPTHALENE
Identifiers & Physical Properties
| CAS No. | 83-53-4 |
|---|---|
| Molecular formula | C10H6Br2 |
| Average molar mass | 285.96 g/mol |
| Monoisotopic mass | 283.88362439 g/mol |
| SMILES | Brc1ccc(Br)c2ccccc12 |
| InChIKey | IBGUDZMIAZLJNY-UHFFFAOYSA-N |
| PubChem CID | 66521 |
| EC No. | 201-484-8 |
| DTXSID | DTXSID6058893 |
Chemical & Physical Properties
| XLogP | 4.8 |
|---|---|
| Topological polar surface area | 0 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 0 |
| Heavy atoms | 12 |
| Formal charge | 0 |
| Complexity | 140 |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Melting point | 80-82 °C |
| Boiling point | 288.1°C (rough estimate) |
| Density | 1.8199 (estimate) |
| Vapor pressure | 0-93.326Pa at 25℃ |
| Refractive index | 1.6000 (estimate) |
| Storage conditions | Sealed in dry,Room Temperature |
| Solubility | Chloroform, DMSO (Slightly), Methanol (Slightly)347.9ug/L(25 ºC) |
| Physical state | Crystalline Powder or Crystals |
| Color | White to light beige |
| Henry's law constant | 5.8×10-2 mol/(m3Pa) at 25℃, Ebert et al. (2023) |
| InChI | InChI=1S/C10H6Br2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H |
| InChIKey | IBGUDZMIAZLJNY-UHFFFAOYSA-N |
| SMILES | C1(Br)=C2C(C=CC=C2)=C(Br)C=C1 |
| LogP (partition coefficient) | 4.95-5.02 |
| CAS DataBase Reference | 83-53-4(CAS DataBase Reference) |
| EPA Substance Registry System | Naphthalene, 1,4-dibromo- (83-53-4) |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 24/25-26 |
| TSCA inventory status | TSCA listed |
| Hazard class | IRRITANT |
| Customs code | 29039990 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | WarningH315 (69.2%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 13 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Status: Active Update: 02-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/27156 |
| Hazard Classes and Categories | Skin Irrit. 2 (69.2%) |
| TSCA inventory status | TSCA listed |
| Customs code | 29039990 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 24/25-26 |
| Hazard class | IRRITANT |
| GHS hazard statements | H315-H319-H335 |
| REACH registrations | Active |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
Applications & Uses
Uses
1,4-Dibromonaphthalene is used in the annelation of PAHs. Also used in the synthesis of novel, orally active dual NK1/NK2 antagonists.
Preparation & Synthesis
Preparation
An environment-friendly method was developed to synthesize 1,4-dibromonaphthalene (1,4-DBN) using 1,3-dialkylimidazolium and pyridinium ionic liquids as catalysts, over which the yields of 1,4-DBN were obtained as high as 100%.An environment-friendly method for synthesis of 1,4-dibromo-naphthalene in aqueous solution of ionic liquids