Product Name

  • Name

    1-Chloromethyl naphthalene

  • EINECS 201-678-2
  • CAS No. 86-52-2
  • Article Data74
  • CAS DataBase
  • Density 1.167 g/cm3
  • Solubility Insoluble in water.
  • Melting Point 32 °C(lit.)
  • Formula C11H9Cl
  • Boiling Point 291.5 °C at 760 mmHg
  • Molecular Weight 176.645
  • Flash Point 129.9 °C
  • Transport Information UN 3261 8/PG 2
  • Appearance Solid
  • Safety 26-36/37/39-45-60-20-27
  • Risk Codes 21/22-34-36/37/38-36-20/21/22
  • Molecular Structure Molecular Structure of 86-52-2 (1-Chloromethyl naphthalene)
  • Hazard Symbols CorrosiveC, HarmfulXn
  • Synonyms 1-(Chloromethyl)naphthalene;1-Naphthalenylmethyl chloride;1-Naphthalylmethyl chloride;1-Naphthylmethylchloride;a-(Chloromethyl)naphthalene;a-Naphthylmethyl chloride;
  • PSA 0.00000
  • LogP 3.57860

Synthetic route

1-naphthalene methanol
4780-79-4

1-naphthalene methanol

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With thionyl chloride In toluene for 12h;98%
With thionyl chloride In chloroform at 5 - 30℃;98.4%
With pyridine; thionyl chloride In diethyl ether at -5 - 25℃; for 12h;98%
1-(dimethoxymethyl)naphthalene
33250-32-7

1-(dimethoxymethyl)naphthalene

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With triethylsilane; acetyl chloride; tin(ll) chloride In dichloromethane at 0℃; for 2h;92%
naphthalen-1-yl-acetyl chloride
5121-00-6

naphthalen-1-yl-acetyl chloride

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With bis(tri-ortho-tolylphosphine)palladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In toluene at 130℃; for 20h; Inert atmosphere; Glovebox;92%
1-naphthalene methanol
4780-79-4

1-naphthalene methanol

Benzotrichlorid
98-07-7

Benzotrichlorid

A

benzylidene dichloride
98-87-3

benzylidene dichloride

B

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With TOP; phenylsilane In neat (no solvent) at 100℃; for 24h; Appel Halogenation; Inert atmosphere;A n/a
B 81%
1-tributylstannyl-methylnaphthalene
113688-53-2

1-tributylstannyl-methylnaphthalene

A

1-naphthalenecarboxylic acid
86-55-5

1-naphthalenecarboxylic acid

B

1-naphthalene methanol
4780-79-4

1-naphthalene methanol

C

1-naphthaldehyde
66-77-3

1-naphthaldehyde

D

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With C2H2Cl2F3O2V; oxygen In tert-butyl alcohol at 50℃; for 24h;A 38%
B n/a
C 58%
D n/a
With C2H2Cl2F3O2V; oxygen In tert-butyl alcohol at 50℃; for 24h;A 28%
B 5%
C 58%
D 4%
formaldehyd
50-00-0

formaldehyd

naphthalene
91-20-3

naphthalene

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With hydrogenchloride; phosphoric acid; acetic acid In water for 6h; Reflux;56%
With hydrogenchloride; zinc(II) chloride; Petroleum ether
With hydrogenchloride at 60 - 65℃;
1-Methylnaphthalene
90-12-0

1-Methylnaphthalene

A

4-chloro-1-methyl-naphthalene
17075-39-7

4-chloro-1-methyl-naphthalene

B

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With N-chloro-succinimide; barium(II) chloride at 102℃; under 2625.26 Torr; for 0.0666667h; Microwave irradiation; Darkness; chemoselective reaction;A 45%
B 18%
With aluminum oxide; iron(III) chloride Irradiation; Title compound not separated from byproducts;
With aluminum oxide; iron(III) chloride Irradiation; Title compound not separated from byproducts;
dichloromethane
75-09-2

dichloromethane

(naphthalene-1,8-diyl)dilithium
61767-59-7

(naphthalene-1,8-diyl)dilithium

A

naphthalene
91-20-3

naphthalene

C

(E)-1,2-bis(1-naphthyl)ethene
1233-36-9

(E)-1,2-bis(1-naphthyl)ethene

D

1H-Cyclobutanaphthalene
24973-91-9

1H-Cyclobutanaphthalene

E

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

F

acenaphthylene
208-96-8

acenaphthylene

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In diethyl ether at -100 - -60℃; Product distribution; Mechanism; var. of temp., further with CD2Cl2;A 42%
B n/a
C n/a
D 21%
E n/a
F n/a
tetrachloromethane
56-23-5

tetrachloromethane

1-Methylnaphthalene
90-12-0

1-Methylnaphthalene

A

bis-chloromethylnaphthalene
17180-26-6

bis-chloromethylnaphthalene

B

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
at 250℃; under 52505.3 Torr; for 7h; Inert atmosphere;A 37%
B 36%
1-Methylnaphthalene
90-12-0

1-Methylnaphthalene

A

bis-chloromethylnaphthalene
17180-26-6

bis-chloromethylnaphthalene

B

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With tetrachloromethane at 250℃; for 7h; Inert atmosphere; Autoclave;A 37%
B 36%
1-Methylnaphthalene
90-12-0

1-Methylnaphthalene

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With N-chloro-succinimide; N-hydroxyphthalimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 80℃; for 3h; Time; Sealed tube; Inert atmosphere;16%
With N-hydroxyphthalimide; carbon tetrabromide; trichloroisocyanuric acid; copper(II) acetate monohydrate In dichloromethane at 25℃; for 21h;15%
With chlorine at 260℃;
With chlorine
With sodium hypochlorite; tetrabutyl-ammonium chloride In dichloromethane at 20℃; for 12h; Catalytic behavior; Inert atmosphere; Sealed tube;20 %Chromat.
N-chloro-succinimide
128-09-6

N-chloro-succinimide

1-Methylnaphthalene
90-12-0

1-Methylnaphthalene

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With chlorobenzene unter Einwirkung von UV-Licht;
naphthalene
91-20-3

naphthalene

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With hydrogenchloride; formaldehyd; arsenic trichloride
With hydrogenchloride; formaldehyd; arsenic(III) trioxide
naphthalene
91-20-3

naphthalene

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With acetic acid at 65℃;
naphthalene
91-20-3

naphthalene

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With hydrogenchloride; formaldehyd; acetic acid
naphthalene
91-20-3

naphthalene

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With diethyl ether; tin(IV) chloride
naphthalene
91-20-3

naphthalene

chloromethyl isocyanate
7093-91-6

chloromethyl isocyanate

A

2-naphthylmethylisocyanate
191855-57-9

2-naphthylmethylisocyanate

B

1-isocyanatomethyl-naphthalene
61924-27-4

1-isocyanatomethyl-naphthalene

C

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

D

1-chloromethylnaphthalene
2506-41-4

1-chloromethylnaphthalene

Conditions
ConditionsYield
With iron(III) chloride at 140 - 150℃; for 2h;A 10 % Spectr.
B 85 % Spectr.
C n/a
D n/a
With iron(III) chloride at 40 - 150℃; for 2h;A 10 % Spectr.
B 85 % Spectr.
C n/a
D n/a
1-(diazomethyl)naphthalene
10378-55-9

1-(diazomethyl)naphthalene

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With 1,1,2-Trichloro-1,2,2-trifluoroethane Irradiation;
di-α-menaphthyl ether

di-α-menaphthyl ether

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With phosphorus pentachloride
N-α-menaphthyl-benzamide

N-α-menaphthyl-benzamide

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With phosphorus pentachloride Destillieren des Reaktionsgemisches im Vakuum;
N.N-di-α-menaphthyl-benzamide

N.N-di-α-menaphthyl-benzamide

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With phosphorus pentachloride Destillieren des Reaktionsgemisches im Vakuum;
formaldehyd
50-00-0

formaldehyd

naphthalene
91-20-3

naphthalene

(E)-3-Ureido-but-2-enoic acid ethyl ester
5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

petroleum ether

petroleum ether

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

naphthalene
91-20-3

naphthalene

diethyl ether
60-29-7

diethyl ether

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

tin (II)-chloride

tin (II)-chloride

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

hydrogenchloride
7647-01-0

hydrogenchloride

formaldehyd
50-00-0

formaldehyd

naphthalene
91-20-3

naphthalene

water
7732-18-5

water

A

1,4-bis(chloromethyl)naphthalene
6586-89-6

1,4-bis(chloromethyl)naphthalene

B

1,5-bis(chloromethyl)naphthalene
1733-76-2

1,5-bis(chloromethyl)naphthalene

C

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

bis(α-naphthylmethyl) ether
35310-62-4

bis(α-naphthylmethyl) ether

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

1-naphthalene methanol
4780-79-4

1-naphthalene methanol

A

bis(α-naphthylmethyl) ether
35310-62-4

bis(α-naphthylmethyl) ether

B

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With hydrogenchloride In water at 120℃; under 5171.62 Torr; for 0.25h; Flow reactor;A n/a
B 90 %Spectr.
1-phenyl-pent-4-yn-2-ol

1-phenyl-pent-4-yn-2-ol

A

(naphtalen-1-yl)methyl iodide
24471-54-3

(naphtalen-1-yl)methyl iodide

B

4-(iodomethylene)-1,2,3,4-tetrahydronaphthalen-2-ol

4-(iodomethylene)-1,2,3,4-tetrahydronaphthalen-2-ol

C

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
With Iodine monochloride In dichloromethane at 20℃; Inert atmosphere;
naphth-1-yl acetic acid
86-87-3

naphth-1-yl acetic acid

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride; N,N-dimethyl-formamide / 4 h
2: bis(tri-ortho-tolylphosphine)palladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 20 h / 130 °C / Inert atmosphere; Glovebox
View Scheme
1-naphthaldehyde
66-77-3

1-naphthaldehyde

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / 0.5 h / 0 °C
2: pyridine; thionyl chloride / diethyl ether / 12 h / -5 - 25 °C
View Scheme
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

triethyl phosphite
122-52-1

triethyl phosphite

diethyl 1-naphthylmethylphosphonate
53575-08-9

diethyl 1-naphthylmethylphosphonate

Conditions
ConditionsYield
at 160℃; for 7h; Reflux;100%
at 150℃;
(N-benzoyl-anilino)-phenyl-acetonitrile
14062-91-0

(N-benzoyl-anilino)-phenyl-acetonitrile

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

N-(1-Cyano-2-naphthalen-1-yl-1-phenyl-ethyl)-N-phenyl-benzamide
72867-71-1

N-(1-Cyano-2-naphthalen-1-yl-1-phenyl-ethyl)-N-phenyl-benzamide

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 96h;100%
2-<(tetrahydrofur-2-yl)methyl>propanedionate de dimethyle
139157-65-6, 139157-66-7

2-<(tetrahydrofur-2-yl)methyl>propanedionate de dimethyle

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

2-<(naphth-1-yl)methyl>-2-<(tetrahydrofur-2-yl)methyl>propanedioate de dimethyle
139157-68-9

2-<(naphth-1-yl)methyl>-2-<(tetrahydrofur-2-yl)methyl>propanedioate de dimethyle

Conditions
ConditionsYield
With sodium methylate; carbonic acid dimethyl ester for 42h; Heating;100%
2-<(tetrahydrofur-2-yl)methyl>propanedionate de dimethyle
139157-65-6, 139157-66-7

2-<(tetrahydrofur-2-yl)methyl>propanedionate de dimethyle

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

2-<(naphth-1-yl)methyl>-2-<(tetrahydrofur-2-yl)methyl>propanedioate de dimethyle
139157-67-8

2-<(naphth-1-yl)methyl>-2-<(tetrahydrofur-2-yl)methyl>propanedioate de dimethyle

Conditions
ConditionsYield
With sodium methylate; carbonic acid dimethyl ester for 42h; Heating;100%
O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)
439694-11-8

O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)

propylene sulphide
1072-43-1

propylene sulphide

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

polymer, three-armed star-shaped, Mn 11900 Da, Mw/Mn 1.14; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene

polymer, three-armed star-shaped, Mn 11900 Da, Mw/Mn 1.14; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene

Conditions
ConditionsYield
Stage #1: O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate) With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at -78℃; for 0.5h;
Stage #2: propylene sulphide In N,N-dimethyl-formamide at 0℃; for 2h;
Stage #3: 1-Chloromethylnaphthalene With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;
100%
O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)
439694-11-8

O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)

propylene sulphide
1072-43-1

propylene sulphide

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

polymer, three-armed star-shaped, Mn 15500 Da, Mw/Mn 1.17; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene

polymer, three-armed star-shaped, Mn 15500 Da, Mw/Mn 1.17; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene

Conditions
ConditionsYield
Stage #1: O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate) With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at -78℃; for 0.5h;
Stage #2: propylene sulphide In N,N-dimethyl-formamide at 0℃; for 2h;
Stage #3: 1-Chloromethylnaphthalene With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;
100%
methyldiethoxyphosphine
15715-41-0

methyldiethoxyphosphine

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

C14H17O2P
936366-26-6

C14H17O2P

Conditions
ConditionsYield
for 2.5h; Heating;100%
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

C22H24N2O
685127-04-2

C22H24N2O

Conditions
ConditionsYield
Stage #1: N-tert-butyl-3-methylpyridine-2-carboxamide With n-butyllithium; sodium bromide In tetrahydrofuran; hexane at -40℃; for 0.5h;
Stage #2: 1-Chloromethylnaphthalene In tetrahydrofuran; hexane at -40℃; for 1.5h;
100%
4-nitro-aniline
100-01-6

4-nitro-aniline

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

bis(naphthalen-1-ylmethyl)(4-nitrophenyl)amine
1032373-74-2

bis(naphthalen-1-ylmethyl)(4-nitrophenyl)amine

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;100%
4-nitro-phenol
100-02-7

4-nitro-phenol

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

1-(4-nitrophenoxymethyl)naphthalene
115720-21-3

1-(4-nitrophenoxymethyl)naphthalene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h;99.1%
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

1,2-di(1-naphthyl)ethane
15374-45-5

1,2-di(1-naphthyl)ethane

Conditions
ConditionsYield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; zinc In tetrahydrofuran at 23 - 25℃; for 5h; Irradiation; Inert atmosphere;99%
With magnesium In tetrahydrofuran at 20℃; for 2.5h; Reflux;96%
With copper(I) bromide In water at 20℃; for 0.416667h; under air;88%
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

1-(azidomethyl)naphthalene
55210-79-2

1-(azidomethyl)naphthalene

Conditions
ConditionsYield
With sodium azide In acetonitrile for 16h; Reflux;99%
With sodium azide In dimethyl sulfoxide91%
With sodium azide In dimethyl sulfoxide91%
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

N-(4-biphenylcarbonyl)-5-aminofluorescein

N-(4-biphenylcarbonyl)-5-aminofluorescein

3'-O-(1-naphthyl)methyl-5-aminofluorescein

3'-O-(1-naphthyl)methyl-5-aminofluorescein

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 4h; Ambient temperature;99%
1H-imidazole
288-32-4

1H-imidazole

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

1-(naphthalen-1-ylmethyl)-1H-imidazole
72459-37-1

1-(naphthalen-1-ylmethyl)-1H-imidazole

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran Heating;99%
With potassium carbonate In acetonitrile Reflux;90%
Stage #1: 1H-imidazole With sodium hydride In 1,2-dimethoxyethane at 0℃; for 0.75h;
Stage #2: 1-Chloromethylnaphthalene In 1,2-dimethoxyethane at 20℃; for 4h; Further stages.;
In dichloromethane
Stage #1: 1H-imidazole With sodium hydride In 1,4-dioxane at 90℃; for 1h;
Stage #2: 1-Chloromethylnaphthalene In 1,4-dioxane at 90℃; for 22h;
O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)
439694-11-8

O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)

propylene sulphide
1072-43-1

propylene sulphide

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

polymer, three-armed star-shaped, Mn 8500 Da, Mw/Mn 1.06; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene

polymer, three-armed star-shaped, Mn 8500 Da, Mw/Mn 1.06; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene

Conditions
ConditionsYield
Stage #1: O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate) With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at -78℃; for 0.5h;
Stage #2: propylene sulphide In N,N-dimethyl-formamide at 0℃; for 2h;
Stage #3: 1-Chloromethylnaphthalene With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;
99%
potassium phtalimide
1074-82-4

potassium phtalimide

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

2-[(1-naphthyl)methyl]-1H-isoindole-1,3(2H)-dione
6968-09-8

2-[(1-naphthyl)methyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
In DMF (N,N-dimethyl-formamide) at 100℃;99%
In N,N-dimethyl-formamide99%
In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere;
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

(E)-3-phenyl-2-propenyl 1-naphthylmethyl ether
98977-56-1

(E)-3-phenyl-2-propenyl 1-naphthylmethyl ether

Conditions
ConditionsYield
Stage #1: (2E)-3-phenyl-2-propen-1-ol With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: 1-Chloromethylnaphthalene In tetrahydrofuran at 20℃; for 24h;
99%
(S)-4-benzyl-1-(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazole
1353761-69-9

(S)-4-benzyl-1-(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazole

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

(S)-4-benzyl-1-(2,6-diisopropylphenyl)-3-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazol-3-ium chloride
1450713-41-3

(S)-4-benzyl-1-(2,6-diisopropylphenyl)-3-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazol-3-ium chloride

Conditions
ConditionsYield
In acetonitrile at 110℃; for 5h;99%
N-formyldiethylamine
617-84-5

N-formyldiethylamine

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

1-<(N,N-diethylamino)methyl>naphthalene
35693-45-9

1-<(N,N-diethylamino)methyl>naphthalene

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;99%
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;85%
t-butyl malonate
541-16-2

t-butyl malonate

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

di-t-butyl (1-naphthylmethyl)malonate
188822-17-5

di-t-butyl (1-naphthylmethyl)malonate

Conditions
ConditionsYield
In tetrahydrofuran; ethyl acetate98.4%
triphenylphosphine
603-35-0

triphenylphosphine

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

1-naphthylmethyltriphenylphosphonium chloride
23277-00-1

1-naphthylmethyltriphenylphosphonium chloride

Conditions
ConditionsYield
In toluene Reflux;98%
In acetonitrile for 8h; Heating;94%
In N,N-dimethyl-formamide for 5h; Heating;91%
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

trimethylamine
75-50-3

trimethylamine

N,N,N-trimethyl-1-(naphthalene-1-yl)methanaminium chloride
1930-16-1

N,N,N-trimethyl-1-(naphthalene-1-yl)methanaminium chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60℃; for 12h;98%
In ethanol80%
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

(naphth-1-yl)methylamine
118-31-0

(naphth-1-yl)methylamine

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 3h;98%
With ammonia fluess. Ammoniak;
With hydrogenchloride; hexamethylenetetramine 1) CH2Cl2, 12 h, 2) ethanol; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 10 h / 20 °C / Inert atmosphere
2: hydrazine hydrate / ethanol / 4 h / Inert atmosphere; Reflux
View Scheme
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

1-Methylnaphthalene
90-12-0

1-Methylnaphthalene

Conditions
ConditionsYield
With potassium formate; PdCl22 In benzene at 60℃; for 4h;98%
With potassium formate; PdCl22 In benzene at 60℃; for 4h; Product distribution; further catalyst, reagent; solid or aqueous solution of reagent;98%
With sodium tetrahydroborate; water In methanol at 20℃; for 0.333333h;94%
O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)
439694-11-8

O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)

propylene sulphide
1072-43-1

propylene sulphide

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

polymer, three-armed star-shaped, Mn 5700 Da, Mw/Mn 1.10; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene

polymer, three-armed star-shaped, Mn 5700 Da, Mw/Mn 1.10; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene

Conditions
ConditionsYield
Stage #1: O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate) With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at -78℃; for 0.5h;
Stage #2: propylene sulphide In N,N-dimethyl-formamide at 0℃; for 2h;
Stage #3: 1-Chloromethylnaphthalene With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;
98%
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

2-Amino-5-nitrophenol
121-88-0

2-Amino-5-nitrophenol

2-(α-naphthylmethoxy)-4-nitroaniline
930797-61-8

2-(α-naphthylmethoxy)-4-nitroaniline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;98%
(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol
22323-82-6

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

(R)-1-O-(1-naphthylmethyl)glycerol
868635-31-8

(R)-1-O-(1-naphthylmethyl)glycerol

Conditions
ConditionsYield
Stage #1: (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol; 1-Chloromethylnaphthalene With potassium hydroxide In 1,4-dioxane; toluene for 2h; Heating;
Stage #2: With acetic acid at 20℃; for 6h; Further stages.;
98%
Stage #1: (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol; 1-Chloromethylnaphthalene With potassium hydroxide In 1,4-dioxane; toluene at 120℃; for 2h;
Stage #2: With water; acetic acid at 20℃; for 6h;
98%
carbon disulfide
75-15-0

carbon disulfide

1-amino-2-propene
107-11-9

1-amino-2-propene

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

2-(naphthalen-1-yl)methyl N-allylcarbamodithioate
1448156-38-4

2-(naphthalen-1-yl)methyl N-allylcarbamodithioate

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 3h;98%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

4-(naphthalene-1-ylmethyl)morpholine
2862-82-0

4-(naphthalene-1-ylmethyl)morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;98%
With potassium hydroxide In water at 80℃; for 3h; Temperature; Green chemistry;87%

1-Chloromethyl naphthalene Chemical Properties

Molecular Structure of 1-Chloromethyl naphthalene (CAS NO.86-52-2):

IUPAC Name: 1-(chloromethyl)naphthalene 
Empirical Formula: C11H9Cl
Molecular Weight: 176.6422
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: 0Å2
Index of Refraction: 1.63
Molar Refractivity: 53.86 cm3
Molar Volume: 151.2 cm3
Surface Tension: 42.5 dyne/cm
Density: 1.167 g/cm3
Flash Point: 129.9 °C
Enthalpy of Vaporization: 50.97 kJ/mol
Boiling Point: 291.5 °C at 760 mmHg
Vapour Pressure: 0.00339 mmHg at 25°C
EINECS: 201-678-2
Melting point: 32 °C(lit.)
Storage temp: Refrigerator
InChI
InChI=1/C11H9Cl/c12-8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2
Smiles
c12c(cccc1CCl)cccc2
Product Categories: Naphthalene derivatives; API intermediates; Naphthalene series

1-Chloromethyl naphthalene Toxicity Data With Reference

1.    

orl-rat LD50:890 mg/kg

    IHFCAY    Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. 6 (1967),1.
2.    

skn-rbt LD50:2000 mg/kg

    IHFCAY    Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. 6 (1967),1.

1-Chloromethyl naphthalene Consensus Reports

Reported in EPA TSCA Inventory.

1-Chloromethyl naphthalene Safety Profile

Moderately toxic by ingestion and skin contact. See also CHLORINATED HYDROCARBONS, AROMATIC. Combustible when exposed to heat or flame. To fight fire, use dry chemical, spray or mist, CO2. When heated to decomposition it emits toxic fumes of Cl.
The Hazard Codes of 1-Chloromethyl naphthalene (CAS NO.86-52-2):  C, Xn
HazardClass: 8
The Risk Statements information:
34:  Causes burns 
20/21:  Harmful by inhalation and in contact with skin 
20/21/22:  Harmful by inhalation, in contact with skin and if swallowed 
36/37/38:  Irritating to eyes, respiratory system and skin 
The Safety Statements information:
20:  When using, do not eat or drink 
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
27:  Take off immediately all contaminated clothing 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
60:  This material and/or its container must be disposed of as hazardous waste 
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
RIDADR: UN 3261 8/PG 2
WGK Germany: 3

1-Chloromethyl naphthalene Specification

  1-Chloromethyl naphthalene , with CAS number of 86-52-2, can be called 1-(Chloromethyl)naphthalene ; 1-Naphthalenylmethyl chloride ; 1-Naphthylmethylchloride ; a-Naphthylmethyl chloride .

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