9-(Chloromethyl)anthracene Property

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)

Safety

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.

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H290May be corrosive to metals

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H318Causes serious eye damage

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P234Keep only in original container.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

P390Absorb spillage to prevent material damage.

P405Store locked up.

P406Store in corrosive resistant/… container with a resistant inner liner.

P501Dispose of contents/container to..…

9-(Chloromethyl)anthracene Chemical Properties,Usage,Production

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.]