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24463-19-2

Basic Information
CAS No.: 24463-19-2
Name: 9-(Chloromethyl)anthracene
Article Data: 22
Molecular Structure:
Molecular Structure of 24463-19-2 (9-(Chloromethyl)anthracene)
Formula: C15H11Cl
Molecular Weight: 226.705
Synonyms: 9-(Chloromethyl)anthracene;9-Anthracenylmethyl chloride;NSC 241165;9-Chloromethylanthracene;9-(Chloromethyl)Anthracene;Anthracene, 9- (chloromethyl)-;
EINECS: 246-274-7
Density: 1.223 g/cm3
Melting Point: 138-140 °C(lit.)
Boiling Point: 402 °C at 760 mmHg
Flash Point: 185 °C
Solubility: Soluble in chloroform. Insoluble in water.
Appearance: yellow powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information: UN 3261 8/PG 2
PSA: 0.00000
LogP: 4.73180
Synthetic route
7512-18-7

anthracen-9-ylmethylene-hydrazine

24463-19-2

anthracenylmethyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃;98%
1468-95-7

9-hydroxymethylanthracene

24463-19-2

anthracenylmethyl chloride

Conditions
ConditionsYield
With thionyl chloride In 1,4-dioxane for 5h; Heating;95%
With thionyl chloride In dichloromethane for 2h; Substitution; Heating;87.9%
With thionyl chloride In tetrahydrofuran for 5h; Reflux; Inert atmosphere;85%
779-02-2

9-methylanthracene

A

24463-19-2

anthracenylmethyl chloride

B

19096-07-2

9-chloro-10-methylanthracene

Conditions
ConditionsYield
With hydrogenchloride In tetrachloromethane for 1h; Chlorination; Heating;A 9%
B 32%
16430-34-5

9-(phenoxymethyl)anthracene

24463-19-2

anthracenylmethyl chloride

Conditions
ConditionsYield
With dichloromethane Substitution; laser-jet photolysis;100 % Spectr.
642-31-9

9-anthracene aldehyde

24463-19-2

anthracenylmethyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Magnesium / 1.) Ether, 2.) THF, 40 deg C, 30 min
2: Thionyl chloride / benzene / 3 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: Sodium borohydride / methanol; H2O / 1.) 50 deg C, 2.) RT, 1.5 h
2: Thionyl chloride / benzene / 3 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: LiAlH4; diethyl ether
2: benzene; PCl5
View Scheme
Stage #1: 9-anthracene aldehyde With methanol; sodium tetrahydroborate at 0℃;
Stage #2: With thionyl chloride In dichloromethane at 0℃;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; ethanol / 2 h / 40 °C
2: thionyl chloride / tetrahydrofuran / 5 h / Reflux; Inert atmosphere
View Scheme
642-31-9

9-anthracene aldehyde

A

24463-19-2

anthracenylmethyl chloride

B

H2O-dioxane mixtures

H2O-dioxane mixtures

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4
2: HCl
View Scheme
Multi-step reaction with 2 steps
1: aq. NaBH4
2: SOCl2
View Scheme
120-12-7

anthracene

24463-19-2

anthracenylmethyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: trichlorophosphate / 80 °C
2.1: sodium tetrahydroborate; methanol / 0 °C
2.2: 0 °C
View Scheme
Multi-step reaction with 3 steps
1: trichlorophosphate / chlorobenzene / 2 h / Schlenk technique; Inert atmosphere; Reflux
2: sodium tetrahydroborate; ethanol / 2 h / 40 °C
3: thionyl chloride / tetrahydrofuran / 5 h / Reflux; Inert atmosphere
View Scheme
616-47-7

1-methyl-1H-imidazole

24463-19-2

anthracenylmethyl chloride

61865-02-9

1-[(9-anthracenyl)methyl]-3-methylimidazolium chloride

Conditions
ConditionsYield
In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;100%
In acetonitrile for 48h; Inert atmosphere; Darkness; Reflux;92%
24463-19-2

anthracenylmethyl chloride

151-50-8

potassium cyanide

2961-76-4

anthracen-9-yl-acetonitrile

Conditions
ConditionsYield
In acetonitrile for 2h; Heating;99%
In acetonitrile for 2h; Heating / reflux;98%
In dimethyl sulfoxide
24463-19-2

anthracenylmethyl chloride

771500-52-8

2,8-dithia-5-aza-2,6-pyridinophane

5-(9-anthracenylmethyl)-2,8-dithia-5-aza-2,6-pyridinophane

Conditions
ConditionsYield
With potassium carbonate In dichloromethane for 24h; Heating;99%
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Specification

The Anthracene,9-(chloromethyl)-, with the CAS registry number 24463-19-2 and EINECS registry number 246-274-7, has the systematic name of 9-(chloromethyl)anthracene. It is a kind of yellow powder, and should be stored in a sealed container to protect from strong oxidant and alkali. And the molecular formula of this chemical is C15H11Cl.

The physical properties of Anthracene,9-(chloromethyl)- are as following: (1)ACD/LogP: 4.95; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.95; (4)ACD/LogD (pH 7.4): 4.95; (5)ACD/BCF (pH 5.5): 3393.94; (6)ACD/BCF (pH 7.4): 3393.94; (7)ACD/KOC (pH 5.5): 11718.5; (8)ACD/KOC (pH 7.4): 11718.5; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.7; (14)Molar Refractivity: 71.7 cm3; (15)Molar Volume: 185.3 cm3; (16)Polarizability: 28.42×10-24cm3; (17)Surface Tension: 48.9 dyne/cm; (18)Density: 1.223 g/cm3; (19)Flash Point: 185 °C; (20)Enthalpy of Vaporization: 62.77 kJ/mol; (21)Boiling Point: 402 °C at 760 mmHg; (22)Vapour Pressure: 2.63E-06 mmHg at 25°C. 

Uses of Anthracene,9-(chloromethyl)-: It can react with pyridine to produce N-(9-anthracenylmethyl)pyridinium chloride. And the yield is about 90%. 

Anthracene,9-(chloromethyl)- can react with pyridine to produce N-(9-anthracenylmethyl)pyridinium chloride

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: ClCc2c3c(cc1c2cccc1)cccc3
(2)InChI: InChI=1/C15H11Cl/c16-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)15/h1-9H,10H2
(3)InChIKey: PCVRSXXPGXRVEZ-UHFFFAOYAH

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intravenous 2267ug/kg (2.267mg/kg)   Cancer Research. Vol. 36, Pg. 2423, 1976.