1-Bromohexadecane
CETYL BROMIDE · 1-Bromhexadecan · HEXADECYL BROMIDE · 1-HEXADECYL BROMIDE · N-HEXADECYL BROMIDE · BROMOHEXADECANE · Hexadecylbromid · Palmitylbromide
Identifiers & Physical Properties
| CAS No. | 112-82-3 |
|---|---|
| Molecular formula | C16H33Br |
| Average molar mass | 305.34 g/mol |
| Monoisotopic mass | 304.17656316 g/mol |
| SMILES | CCCCCCCCCCCCCCCCBr |
| InChIKey | HNTGIJLWHDPAFN-UHFFFAOYSA-N |
| PubChem CID | 8213 |
| ChEMBL | CHEMBL3188886 |
| EC No. | 204-008-7 |
| DTXSID | DTXSID2049397 |
Chemical & Physical Properties
| XLogP | 9.2 |
|---|---|
| Topological polar surface area | 0 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 14 |
| Heavy atoms | 17 |
| Formal charge | 0 |
| Complexity | 123 |
| Chemical classes | Other Classes -> Halogenated Aliphatics, Saturated |
| SpringerMaterials Properties | Boiling point |
| Physical Description | LiquidMelting point = 18 deg C[ChemIDplus] Colorless liquidmp = 16-18 deg C[Alfa Aesar MSDS] |
| Melting point | 16-18 °C(lit.) |
| Boiling point | 190 °C11 mm Hg(lit.) |
| Density | 0.999 g/mL at 25 °C(lit.) |
| Vapor density | 10.6 (vs air) |
| Vapor pressure | <1 mm Hg ( 20 °C) |
| Refractive index | n20/D 1.4609(lit.) |
| Flash point | >230 °F |
| Storage conditions | Inert atmosphere,Room Temperature |
| Solubility | Difficult to mix.INSOLUBLE |
| Physical state | Liquid After Melting |
| Specific gravity | 1.000 (20/4℃) |
| Color | Clear amber to brown-black |
| BRN | 773989 |
| Dielectric constant | 3.71 |
| Stability | Stable. Incompatible with strong oxidizing agents. Combustible. |
| InChI | 1S/C16H33Br/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h2-16H2,1H3 |
| InChIKey | HNTGIJLWHDPAFN-UHFFFAOYSA-N |
| SMILES | CCCCCCCCCCCCCCCCBr |
| LogP (partition coefficient) | 8.54 |
| CAS DataBase Reference | 112-82-3(CAS DataBase Reference) |
| FDA UNII | 76GJI7GVAM |
| NIST Chemistry Reference | Hexadecane, 1-bromo-(112-82-3) |
| EPA Substance Registry System | Hexadecane, 1-bromo- (112-82-3) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315 |
| GHS precautionary statements | P302+P352 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29033036 |
| Storage class | 10 - Combustible liquids |
| Hazard class | Skin Irrit. 2 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | WarningH315 (100%): 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 77 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Hexadecane, 1-bromo-Hexadecane, 1-bromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexadecane, 1-bromo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 10-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/10277Hexadecane, 1-bromo-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | An irritant[Alfa Aesar MSDS] See Hexadecane. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29033036 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36 |
| Storage class | 10 - Combustible liquids |
| GHS hazard statements | H315 |
| REACH registrations | Active |
| Hazard class | Skin Irrit. 2 |
| GHS precautionary statements | P302+P352 |
Applications & Uses
Uses
1-Bromohexadecane has been used:in the preparation of soluble carbon nano-onions by covalent functionalization with hexadecyl chainsas extraction solvent in determination of endocrine-disrupting phenols (EDPs) in water samples by ultrasound-assisted emulsification microextraction (MS-USAEME) methodin the preparation of [2-(methacryloyloxy)ethyl]dimethylhexadecylammonium bromide monomer, required for the synthesis of novel methacrylate based adsorbentsin the synthesis of surfactant, N-hexadecyl ethylenediamine triacetic acid (HED3A)
Uses
1-Bromohexadecane is used in the preparation of soluble carbon nano-onions by covalent functionalization with hexadecyl chains. It is also used to synthesize [2-(methacryloyloxy)ethyl]dimethylhexadecylammonium bromide monomer, required for the synthesis of novel methacrylate based adsorbents.
Preparation & Synthesis
Preparation
Synthesis of 1-Bromohexadecane from hexadecanol by bromination: put hexadecanol into the reaction pot and stir, heat, melt and put in red phosphorus. Add bromine drop by drop at 100℃ with sufficient stirring on one side, control 120-130℃, about 6h drop by drop, continue the reaction and drain the hydrogen bromide. Cool to below 50 ℃, add saturated and sodium chloride, stirring and washing, resting stratification, parting off the lower waste stream, then wash with water to neutral, distillation, collect 220-230 ℃ (2kPa) fraction, to obtain 1-bromohexadecane.