9-(Chloromethyl)anthracene

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 Reference24463-19-2(CAS DataBase Reference)
NIST Chemistry Reference9-(Chloromethyl)anthracene(24463-19-2)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
RIDADR UN 3261 8/PG 2
WGK Germany 3
RTECS CA9600000
19
HazardClass 8
PackingGroup III
HS Code 29039990
Toxicitymouse,LDLo,intravenous,2267ug/kg (2.267mg/kg),Cancer Research. Vol. 36, Pg. 2423, 1976.
MSDS Information
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9-(Chloromethyl)anthracene Usage And Synthesis
Chemical PropertiesYELLOW POWDER
Uses9-(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.
Application9-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.
ReactionsLepidopterene, 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.
reaction of 9-(chloromethyl)anthracene with methylmagnesium iodide
An easy synthesis of lepidopterene from 9-chloromethylanthracene
Purification MethodsIf 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.]
Benzyl chloride Chloromethyl silane 9-ANTHRACENECARBONYL CHLORIDE 6-CHLOROMETHYLBENZO(A)PYRENE DIMETHYLTHEXYLSILYL CHLORIDE Chloromethyl methyl ether 7-chloromethyl-12-methylbenz(a)anthracene tert-Butyldimethylsilyl chloride 4-(Chloromethyl)benzoic acid Vinylbenzyl chloride 9,10-Bis(chloromethyl)anthracene Anthracene ALPHA-CHLORO-9-ANTHRALDOXIME Chloromethane 9-(Chloromethyl)anthracene

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