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| | 9-(Chloromethyl)anthracene Basic information |
| | 9-(Chloromethyl)anthracene Chemical Properties |
| Melting point | 138-140 °C (lit.) | | Boiling point | 294.66°C (rough estimate) | | density | 1.1510 (rough estimate) | | refractive index | 1.6281 (estimate) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | solubility | chloroform: soluble | | form | Powder | | color | Yellow | | Water Solubility | Soluble in chloroform. Insoluble in water. | | Sensitive | Light Sensitive | | BRN | 1873394 | | CAS DataBase Reference | 24463-19-2(CAS DataBase Reference) | | NIST Chemistry Reference | 9-(Chloromethyl)anthracene(24463-19-2) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | RIDADR | UN 3261 8/PG 2 | | WGK Germany | 3 | | RTECS | CA9600000 | | F | 19 | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29039990 | | Toxicity | mouse,LDLo,intravenous,2267ug/kg (2.267mg/kg),Cancer Research. Vol. 36, Pg. 2423, 1976. |
| | 9-(Chloromethyl)anthracene Usage And Synthesis |
| Chemical Properties | YELLOW POWDER | | Uses | 9-(Chloromethyl)anthracene is used as a blocking group reagent used for carboxylic acids, phenols, mercaptans and thiophenols. It is a derivatizing agent for carboxylic acids giving esters with enhanced UV and fluorescence detection in HPLC. | | Application | 9-Anthracenylmethyl Chloride is a derivative of Anthracene which is an important source of dyestuffs. It is a reagent for the protection of carboxylic acids, alcohols, phenols and thiols as their 9-anthrylmethyl derivatives, which are stable to mild acid or base, but specifically cleaved by NaSMe. | | Reactions | Lepidopterene, a tetrabenzotetracyclotetradecatetraene, was first synthesized by reaction of 9-(chloromethyl)anthracene with methylmagnesium iodide. Through this methodology, lepidopterene and 1,2-bis(9-anthracenyl)ethane were obtained in 35% and 30% yield, respectively.
An easy synthesis of lepidopterene from 9-chloromethylanthracene | | Purification Methods | If it is free from OH in the IR then recrystallisation from hexane/*C6H6 or *C6H6 (as needles). If OH is present, then some solvolysis has occurred. In this case treat 8.5g of it with SOCl2 (4.8g) in dioxane (60mL) and reflux for 5hours, then evaporate to dryness and wash the residue with cold *C6H6 and recrystallise it. With KI/Me2CO it forms the iodomethyl derivative. [Fierens et al. Helv Chim Acta 38 2009 1955, Hunter et al. J Org Chem 21 1512 1956, Beilstein 5 III 3152, 5 IV 2313.] |
| | 9-(Chloromethyl)anthracene Preparation Products And Raw materials |
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