1733-76-2

Usage

Uses

Used in Pharmaceutical Industry:
1,5-bis(chloromethyl)naphthalene is used as a building block for the synthesis of various pharmaceutical compounds. Its reactivity allows for the formation of new chemical bonds, making it a valuable component in the development of new drugs.
Used in Dye Industry:
1,5-bis(chloromethyl)naphthalene is used as a starting material for the production of dyes. Its ability to participate in organic reactions enables the creation of a wide range of colored compounds for various applications.
Used in Polymer Industry:
1,5-bis(chloromethyl)naphthalene is used as a monomer in the synthesis of polymers. Its reactivity allows for the formation of long chains of repeating units, which can be used in the production of various types of plastics and other materials.
It is important to handle 1,5-bis(chloromethyl)naphthalene with care as it is toxic and can be harmful if ingested or inhaled. Additionally, it may have environmental implications, so proper disposal and handling procedures should be followed. Overall, 1,5-bis(chloromethyl)naphthalene is a versatile and valuable chemical compound used in various industries for the production of diverse organic compounds.

InChI:InChI=1/C12H10Cl2/c13-7-9-3-1-5-11-10(8-14)4-2-6-12(9)11/h1-6H,7-8H2

Synthetic route

formaldehyd (50-00-0) + naphthalene (91-20-3) → 1,4-bis(chloromethyl)naphthalene (6586-89-6) + 1,5-bis(chloromethyl)naphthalene (1733-76-2)

Conditions	Yield
With hydrogenchloride In water for 17h; Heating;	A 7% B n/a
With hydrogenchloride; phosphoric acid; acetic acid at 100℃;
With hydrogenchloride Einleiten von HCl;
With hydrogenchloride In water for 17h; Heating; Title compound not separated from byproducts;

formaldehyd (50-00-0) + naphthalene (91-20-3) → 1,5-bis(chloromethyl)naphthalene (1733-76-2)

Conditions	Yield
With hydrogenchloride Einleiten von HCl;

1,5-dimethylnaphthalene (571-61-9) → 1,5-bis(chloromethyl)naphthalene (1733-76-2)

Conditions	Yield
With chlorine at 170 - 190℃;

formaldehyd (50-00-0) + 1-Chloromethylnaphthalene (86-52-2) → 1,5-bis(chloromethyl)naphthalene (1733-76-2)

Conditions	Yield
With hydrogenchloride; phosphoric acid; acetic acid at 100℃;
With zinc(II) chloride; Petroleum ether Einleiten von HCl;

formaldehyd (50-00-0) + naphthalene (91-20-3) → 1,4-bis(chloromethyl)naphthalene (6586-89-6) + 1,5-bis(chloromethyl)naphthalene (1733-76-2) + 4,4'-bis(chloromethyl)-1,1'-methylenebisnaphthalene (121792-59-4)

Conditions	Yield
With hydrogenchloride; phosphoric acid; acetic acid In water at 105℃; for 17h;

hydrogenchloride (7647-01-0) + formaldehyd (50-00-0) + naphthalene (91-20-3) + water (7732-18-5) → 1,4-bis(chloromethyl)naphthalene (6586-89-6) + 1,5-bis(chloromethyl)naphthalene (1733-76-2) + 1-Chloromethylnaphthalene (86-52-2)

naphthalene (91-20-3) → 1,5-bis(chloromethyl)naphthalene (1733-76-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl; ZnCl2; petroleum ether 2: petroleum ether; ZnCl2 / Einleiten von HCl View Scheme

1,5-bis(chloromethyl)naphthalene (1733-76-2) + sodium cyanide (143-33-9) → 2,2'-(naphthalene-1,5-diyl)diacetonitrile (854817-67-7)

Conditions	Yield
With ethanol

1,5-bis(chloromethyl)naphthalene (1733-76-2) + potassium cyanide (151-50-8) → 2,2'-(naphthalene-1,5-diyl)diacetonitrile (854817-67-7)

Conditions	Yield
With ethanol

1,5-bis(chloromethyl)naphthalene (1733-76-2) → 1,5-dimethylnaphthalene (571-61-9)

Conditions	Yield
With Pd/SrCO3; ethanol; sodium ethanolate weiteres Reagens: Dioxan; Hydrogenolyse;
With hydrogenchloride; zinc

1,5-bis(chloromethyl)naphthalene (1733-76-2) → 1,5-bis(hydroxymethyl)naphthalene (54835-54-0)

Conditions	Yield
With sodium hydrogencarbonate
Multi-step reaction with 2 steps 2: aq.-ethanolic KOH View Scheme

1,5-bis(chloromethyl)naphthalene (1733-76-2) → 1,5-bis-aminomethyl-naphthalene (46263-19-8)

Conditions	Yield
With ammonia

1,5-bis(chloromethyl)naphthalene (1733-76-2) + potassium acetate (127-08-2) + acetic acid (64-19-7) → 1,5-bis-acetoxymethyl-naphthalene (32445-23-1)

1,5-bis(chloromethyl)naphthalene (1733-76-2) + potassium acrylate (10192-85-5) → Acrylic acid 5-acryloyloxymethyl-naphthalen-1-ylmethyl ester (53223-86-2)

Conditions	Yield
With hydroquinone In N,N-dimethyl-formamide

1,5-bis(chloromethyl)naphthalene (1733-76-2) + potassium methacrylate (6900-35-2) → 2-Methyl-acrylic acid 5-(2-methyl-acryloyloxymethyl)-naphthalen-1-ylmethyl ester (53223-87-3)

Conditions	Yield
With hydroquinone In N,N-dimethyl-formamide

hydrogenchloride (7647-01-0) + 1,5-bis(chloromethyl)naphthalene (1733-76-2) + zinc-powder → 1,5-dimethylnaphthalene (571-61-9)

1,5-bis(chloromethyl)naphthalene (1733-76-2) → naphthalene-1,5-dicarboxylic acid (7315-96-0)

Conditions	Yield
Multi-step reaction with 3 steps 2: aq.-ethanolic KOH 3: aqueous KMnO4 View Scheme

1,5-bis(chloromethyl)naphthalene (1733-76-2) → 2,2'-(naphthalene-1,5-diyl)diacetic acid (25178-67-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous ethanol 2: sulfuric acid; acetic acid; water View Scheme
Multi-step reaction with 2 steps 1: aqueous ethanol 2: sulfuric acid; acetic acid; water View Scheme

1,5-bis(chloromethyl)naphthalene (1733-76-2) → dimethyl naphthalene-1,5-diacetate (115414-91-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous ethanol 2: sulfuric acid; acetic acid; water 3: hydrogen chloride View Scheme
Multi-step reaction with 3 steps 1: aqueous ethanol 2: sulfuric acid; acetic acid; water 3: hydrogen chloride View Scheme

1,5-bis(chloromethyl)naphthalene (1733-76-2) → N,N'-naphthalene-1,5-diyldimethyl-bis-benzamide

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia 2: aqueous NaOH-solution View Scheme

1,4-bis(chloromethyl)naphthalene (6586-89-6) + 1,5-bis(chloromethyl)naphthalene (1733-76-2) → 1,4-bis[(3-ethyloxetan-3-yl)methoxymethyl]naphthalene (863394-98-3) + 1,5-bis[(3-ethyloxetan-3-yl)methoxymethyl]naphthalene (863394-99-4)

Conditions	Yield
Stage #1: 3-ethyl-3-(hydroxymethyl)oxetane With sodium hydroxide In toluene at 90℃; for 0.5h; Stage #2: 1,4-bis(chloromethyl)naphthalene; 1,5-bis(chloromethyl)naphthalene In toluene at 90℃; for 10.5h;

piperidine (110-89-4) + 1,5-bis(chloromethyl)naphthalene (1733-76-2) → 1,5-bis((piperidine-1-yl)methyl)naphthalene (1360606-97-8)

Conditions	Yield
In benzene for 6h; Reflux;

piperidine (110-89-4) + 1,5-bis(chloromethyl)naphthalene (1733-76-2) → 2Br(1-)*C46H80N2(2+)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene / 6 h / Reflux 2: ethanol / 12 h / Reflux View Scheme

1-methoxy-4-methylsulfanyl-benzene (1879-16-9) + 1,5-bis(chloromethyl)naphthalene (1733-76-2) → C28H30O2S2(2+)*2C24BF20(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 24 h / 25 °C 2: acetone / 24 h / 25 °C View Scheme

silver tetrafluoroborate (14104-20-2) + 1-methoxy-4-methylsulfanyl-benzene (1879-16-9) + 1,5-bis(chloromethyl)naphthalene (1733-76-2) → C28H30O2S2(2+)*2BF4(1-)

Conditions	Yield
In acetone at 25℃; for 24h;

Upstream product

• 50-00-0 formaldehyd 
• 91-20-3 naphthalene 
• 571-61-9 1,5-dimethylnaphthalene 
• 86-52-2 1-Chloromethylnaphthalene 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 

Downstream Products

• 571-61-9 1,5-dimethylnaphthalene 
• 7315-96-0 naphthalene-1,5-dicarboxylic acid 

Relevant academic research and scientific papers

Synthesis and Stability of Aryl Bis(nitrile oxides) with Potential as Curing Agents for Polysulfide Sealants

Several aromatic bis(nitrile oxides) have been prepared as potential curing agents for sealants produced from thiol-terminated polysulfide liquid polymers.All were obtained by dehydrohalogenation of α-halo oximes and the requisite aldehydes were synthesized from either the dimethyl derivatives or the chloromethylated hydrocarbons.The direct chloromethylation of naphthalene which offered a convenient route to the naphthalene-1,4- and 1,5-bis(carbonitrile oxides) was re-examined.Also prepared were naphthalene-2,6-bis(carbonitrile oxide), anthracene-9,10-bis(carbonitrile oxide) and 4,4'-sulfonylbisbenzonitrile dioxide.The course of the reaction between naphthalene-2,3-dicarbaldehyde and hydroxylamine was established and shown to differ from that involving phthalaldehyde.Stabilities of the nitrile oxides at -15 deg C, 4 deg C and 25 deg C were assessed by spectroscopic means.