9,10-Bis(chloromethyl)anthracene Chemical Properties

Melting point:

258-260°C

Boiling point:

355.58°C (rough estimate)

Density 

1.1151 (rough estimate)

refractive index 

1.5610 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

very faint turbidity in hot Toluene

form 

powder to crystal

color 

Crystals from xylene; yellow blades from toluene

CAS DataBase Reference

10387-13-0(CAS DataBase Reference)

EPA Substance Registry System

Anthracene, 9,10-bis(chloromethyl)- (10387-13-0)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

RIDADR 

3261

RTECS 

CA9365000

HS Code 

2903.99.8001

HazardClass 

8

PackingGroup 

II

Toxicity

mma-sat 100 ng/plate PNASA6 72,5135,75

MSDS

• Language:English Provider:9,10-Bis(chloromethyl)anthracene

9,10-Bis(chloromethyl)anthracene Usage And Synthesis

Safety Profile

Poison by intravenous route.Questionable carcinogen with experimental neoplastigenicdata. Mutation data reported. When heated todecomposition it emits toxic fumes of Cl-.

Synthesis

A dioxane (20 mL) solution of anthracene (1.78 g, 10 mmol), anhydrous ZnCl2 (1.64 g, 12 mmol), and paraformaldehyde (1.50 g, 50 mmol) was added sequentially to a reactor vessel equipped with a stirrer. A concentrated aqueous hydrochloric acid solution (40 mL) was added slowly and dropwise with stirring, and the reaction temperature was controlled to be below 50 °C. The reaction mixture was stirred at room temperature until homogeneous and then heated to a mild reflux condition and kept for 3 hours. After completion of the reaction, the mixture was allowed to stand at room temperature for 16 hours to complete crystallization. The resulting fine grained solid was separated by diafiltration and washed sequentially with deionized water and dioxane. The crude product was purified by recrystallization with toluene to give 1.8 g of light yellow solid product in 64.1% yield. The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3): δ 8.40 (m, 4H), 7.62 (m, 4H), 5.61 ppm (s, 4H).

References

[1] Journal of Organic Chemistry, 1998, vol. 63, # 18, p. 6153 - 6159
[2] Journal of Physical Chemistry B, 2005, vol. 109, # 10, p. 4377 - 4390
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 46, p. 12086 - 12090
[4] Angew. Chem., 2013, vol. 125, # 46, p. 12308 - 12312,5
[5] RSC Advances, 2015, vol. 5, # 90, p. 73951 - 73957

9,10-Bis(chloromethyl)anthracene(10387-13-0)Related Product Information

• Anthracene
• 2-Chloro-5-chloromethylpyridine
• 4-(Chloromethyl)benzoic acid
• Chloromethyltrimethylsilane
• tert-Butyldimethylsilyl chloride
• 4-Vinylbenzyl chloride
• 9,10-DIMETHYLANTHRACENE
• 1-CHLOROMETHYL-4-METHYLNAPHTHALENE
• 9-(Chloromethyl)anthracene
• 9-METHYLANTHRACENE
• 1-Chloromethyl naphthalene
• alpha,alpha'-Dichloro-p-xylene
• Chloromethyl methyl ether
• 1,4-DIMETHYLNAPHTHALENE
• 1,4-BISCHLOROMETHYL-NAPHTHALENE
• 9,10-Bis(chloromethyl)anthracene