Product Name

  • Name

    9-(Chloromethyl)anthracene

  • EINECS 246-274-7
  • CAS No. 24463-19-2
  • Article Data22
  • CAS DataBase
  • Density 1.223 g/cm3
  • Solubility Soluble in chloroform. Insoluble in water.
  • Melting Point 138-140 °C(lit.)
  • Formula C15H11Cl
  • Boiling Point 402 °C at 760 mmHg
  • Molecular Weight 226.705
  • Flash Point 185 °C
  • Transport Information UN 3261 8/PG 2
  • Appearance yellow powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 24463-19-2 (9-(Chloromethyl)anthracene)
  • Hazard Symbols IrritantXi
  • Synonyms 9-(Chloromethyl)anthracene;9-Anthracenylmethyl chloride;NSC 241165;9-Chloromethylanthracene;9-(Chloromethyl)Anthracene;Anthracene, 9- (chloromethyl)-;
  • PSA 0.00000
  • LogP 4.73180

Synthetic route

anthracen-9-ylmethylene-hydrazine
7512-18-7

anthracen-9-ylmethylene-hydrazine

anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

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

9-hydroxymethylanthracene

anthracenylmethyl chloride
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%
9-methylanthracene
779-02-2

9-methylanthracene

A

anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

B

9-chloro-10-methylanthracene
19096-07-2

9-chloro-10-methylanthracene

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

9-(phenoxymethyl)anthracene

anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

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

9-anthracene aldehyde

anthracenylmethyl chloride
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
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

A

anthracenylmethyl chloride
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
anthracene
120-12-7

anthracene

anthracenylmethyl chloride
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
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

1-[(9-anthracenyl)methyl]-3-methylimidazolium 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%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

potassium cyanide
151-50-8

potassium cyanide

anthracen-9-yl-acetonitrile
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
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

2,8-dithia-5-aza-2,6-pyridinophane
771500-52-8

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

5-(9-anthracenylmethyl)-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%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

9-(azidomethyl)anthracene
195133-98-3

9-(azidomethyl)anthracene

Conditions
ConditionsYield
With sodium azide; tetrabutylammomium bromide In N,N-dimethyl-formamide at 79.84℃; for 1h;99%
With sodium azide; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20℃; Inert atmosphere;95%
With sodium azide In N,N-dimethyl-formamide at 20℃;95%
sodium cyanide
773837-37-9

sodium cyanide

anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

anthracen-9-yl-acetonitrile
2961-76-4

anthracen-9-yl-acetonitrile

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 55℃; for 4h; Inert atmosphere;99%
In N,N-dimethyl-formamide for 12h;93%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

1-t-Butoxycarbonylpiperazine
57260-71-6

1-t-Butoxycarbonylpiperazine

4-anthracen-9-ylmethylpiperazine-1-carboxylic acid tert-butyl ester
1419212-75-1

4-anthracen-9-ylmethylpiperazine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 18h; Reflux; Inert atmosphere;99%
With potassium carbonate In acetonitrile at 60℃;89%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

C20H26N2S2
109467-83-6

C20H26N2S2

C50H46N2S2

C50H46N2S2

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 47.5h; Inert atmosphere; Reflux;98.8%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

Cinchonin
118-10-5

Cinchonin

(2R,5R,1'S)-1-(9-anthracenyl)methyl-5-ethylene-2-[1-hydroxy-1-(quinol-4-yl)]methyl-1-azoniabicyclo[2.2.2]octane chloride

(2R,5R,1'S)-1-(9-anthracenyl)methyl-5-ethylene-2-[1-hydroxy-1-(quinol-4-yl)]methyl-1-azoniabicyclo[2.2.2]octane chloride

Conditions
ConditionsYield
In toluene at 110℃; for 2h;98%
In toluene Reflux;94%
In toluene for 24h; Heating;80%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

potassium phtalimide
1074-82-4

potassium phtalimide

N-(9-anthranylmethyl)phthalimide
94617-21-7

N-(9-anthranylmethyl)phthalimide

Conditions
ConditionsYield
With 18-crown-6 ether In toluene for 6h; Heating;98%
In N,N-dimethyl-formamide at 60℃; for 3h;
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

[3,5-bis[[3,5-bis[[3,5-bis(phenylmethoxy)phenyl]methoxy]phenyl]methoxy]phenyl]methyl alcohol
137472-16-3

[3,5-bis[[3,5-bis[[3,5-bis(phenylmethoxy)phenyl]methoxy]phenyl]methoxy]phenyl]methyl alcohol

9-[(3,5-bis{3,5-bis[3,5-bis(benzyloxy)benzyloxy]benzyloxy}benzyloxy)methyl]anthracene

9-[(3,5-bis{3,5-bis[3,5-bis(benzyloxy)benzyloxy]benzyloxy}benzyloxy)methyl]anthracene

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide In water; chlorobenzene at 60℃; for 72h;98%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

1,4,7-trithia-10-azacyclododecane
122011-96-5

1,4,7-trithia-10-azacyclododecane

1-(9-anthracenylmethyl)-1-aza-4,7,10-trithiacyclododecane
1219634-78-2

1-(9-anthracenylmethyl)-1-aza-4,7,10-trithiacyclododecane

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 168h; Inert atmosphere;98%
With triethylamine In tetrahydrofuran Inert atmosphere; Reflux;11.8%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

quinolin-4-yl((1S,2S,4S,5R)-5-vinyl-quinuclidin-2-yl)methanol
118-10-5, 485-70-1, 485-71-2, 550-54-9, 40134-63-2, 72402-55-2, 72402-56-3

quinolin-4-yl((1S,2S,4S,5R)-5-vinyl-quinuclidin-2-yl)methanol

(1S,2S,4S,5R)-1-(anthracen-9-ylmethyl)-2-(hydroxy(quinolin-4-yl)methyl)-5-vinyl-quinuclidin-1-ium chloride

(1S,2S,4S,5R)-1-(anthracen-9-ylmethyl)-2-(hydroxy(quinolin-4-yl)methyl)-5-vinyl-quinuclidin-1-ium chloride

Conditions
ConditionsYield
In toluene at 110℃; for 2h;98%
In toluene for 6h; Reflux; Inert atmosphere;970 mg
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

2,2'-iminobis[ethanol]
111-42-2

2,2'-iminobis[ethanol]

N-(anthracen-9-yl-methyl)bis(2-hydroxyethyl)amine
109297-66-7

N-(anthracen-9-yl-methyl)bis(2-hydroxyethyl)amine

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In chloroform; acetonitrile for 2.5h; Alkylation; Heating;97%
With potassium carbonate In toluene for 24h; Heating;62%
pentaethylene glycol
2615-15-8

pentaethylene glycol

anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

(9-anthracenylmethyl)hexaethylene glycol
327602-40-4

(9-anthracenylmethyl)hexaethylene glycol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 24h;97%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

C13H18N2

C13H18N2

1-(isobutyl)-3-(anthracen-9-ylmethyl)-5,6-dimethylbenzimidazolium chloride

1-(isobutyl)-3-(anthracen-9-ylmethyl)-5,6-dimethylbenzimidazolium chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere; Schlenk technique;97%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

N-(diphenylmethylene)glycine tert-butyl ester
81477-94-3

N-(diphenylmethylene)glycine tert-butyl ester

(S)-tert-butyl 3-(9-methylanthracenyl)-2-diphenylmethyleneaminopropanoate

(S)-tert-butyl 3-(9-methylanthracenyl)-2-diphenylmethyleneaminopropanoate

Conditions
ConditionsYield
With potassium hydroxide In chloroform; water; toluene at 0℃; for 0.5h;96%
With potassium hydroxide; 2,7-[bis((-)-hydrocinchonidine)methyl]naphthalene In chloroform; water; toluene at 0℃; for 2h;95%
With potassium hydroxide; O(9)-All-N-(2',3',4'-trifluorobenzyl)hydrocinchonidinium bromide In chloroform; water; toluene at -20℃; for 10h;95%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

allenyltributylstannane
53915-69-8

allenyltributylstannane

10-methylene-9-(propa-1,2-dienyl)-9,10-dihydroanthracene
1221432-97-8

10-methylene-9-(propa-1,2-dienyl)-9,10-dihydroanthracene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 20℃; for 12h; Inert atmosphere;96%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

1,3-Phenylenebis(methylene)selenocyanate
59395-13-0

1,3-Phenylenebis(methylene)selenocyanate

1,3-bis[(selenomethylanthryl)methyl]benzene

1,3-bis[(selenomethylanthryl)methyl]benzene

Conditions
ConditionsYield
Stage #1: 1,3-Phenylenebis(methylene)selenocyanate With sodium tetrahydroborate In tetrahydrofuran; ethanol for 1h; Reduction;
Stage #2: anthracenylmethyl chloride In tetrahydrofuran; ethanol for 24h; Alkylation;		95%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

[3,5-Bis-(3,5-bis-benzyloxy-benzyloxy)-phenyl]-methanol
129536-40-9

[3,5-Bis-(3,5-bis-benzyloxy-benzyloxy)-phenyl]-methanol

9-({3,5-bis[3,5-bis(benzyloxy)benzyloxy]benzyloxy}methyl)anthracene
496839-77-1

9-({3,5-bis[3,5-bis(benzyloxy)benzyloxy]benzyloxy}methyl)anthracene

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide In water; chlorobenzene at 60℃; for 72h;95%
With tetrabutylammomium bromide In water; chlorobenzene54%
Stage #1: [3,5-Bis-(3,5-bis-benzyloxy-benzyloxy)-phenyl]-methanol With sodium hydride In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: anthracenylmethyl chloride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid tert-butyl ester
709656-07-5

2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid tert-butyl ester

4-(anthracen-9-ylmethyl)-2-phenyl-1,3-oxazoline-4-carboxylic acid tert-butyl ester

4-(anthracen-9-ylmethyl)-2-phenyl-1,3-oxazoline-4-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide In toluene at 25℃; for 0.5h;95%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

3-Mercaptopropyltriethoxysilane
14814-09-6

3-Mercaptopropyltriethoxysilane

3-[(anthracen-10-yl)methylthio]propyltriethoxysilane
1239599-24-6

3-[(anthracen-10-yl)methylthio]propyltriethoxysilane

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 24h; Reflux;95%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

sodium acetate
127-09-3

sodium acetate

(anthracen-9-yl)methyl acetate
16430-32-3

(anthracen-9-yl)methyl acetate

Conditions
ConditionsYield
In ethanol at 50℃; for 6h;95%
phenyl selenocyanate
2179-79-5

phenyl selenocyanate

anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

9-anthrylmethyl phenyl selenide
78808-34-1

9-anthrylmethyl phenyl selenide

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 5h; Heating;94%
potassium cyanide

potassium cyanide

anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

anthracen-9-yl-acetonitrile
2961-76-4

anthracen-9-yl-acetonitrile

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 60℃; for 1h;94%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

(1R,5S)-1,8,8-trimethyl-4-(o-tolyl)-2,4-diazabicyclo[3.2.1]oct-2-ene

(1R,5S)-1,8,8-trimethyl-4-(o-tolyl)-2,4-diazabicyclo[3.2.1]oct-2-ene

(1R,5S)-2-(anthracen-9-ylmethyl)-1,8,8-trimethyl-4-(o-tolyl)-2,4-diazabicyclo[3.2.1]oct-2-en-2-ium chloride

(1R,5S)-2-(anthracen-9-ylmethyl)-1,8,8-trimethyl-4-(o-tolyl)-2,4-diazabicyclo[3.2.1]oct-2-en-2-ium chloride

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide; acetonitrile for 16h; Reflux; Schlenk technique;94%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

2,6-bis(selenocyanatomethyl)pyridine
85539-82-8

2,6-bis(selenocyanatomethyl)pyridine

2,6-bis[(selenomethylanthryl)methyl]pyridine

2,6-bis[(selenomethylanthryl)methyl]pyridine

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; ethanol for 24h; reductive alkylation;93%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

1-carbomethoxy-3,5-dihydroxybenzene
2150-44-9

1-carbomethoxy-3,5-dihydroxybenzene

methyl 3,5-bis(anthrylmethoxy)benzoate
540781-07-5

methyl 3,5-bis(anthrylmethoxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 3h;93%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

1-aza-4,10-dithia-7‐oxacyclododecane
24918-63-6

1-aza-4,10-dithia-7‐oxacyclododecane

1-(9-anthracenylmethyl)-1-aza-4,10-dithia-7-oxacyclododecane
1243242-53-6

1-(9-anthracenylmethyl)-1-aza-4,10-dithia-7-oxacyclododecane

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 168h; Inert atmosphere;93%

9-(Chloromethyl)anthracene 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.

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