1-(Chloromethyl)naphthalene

Base Information

• Chemical Name: 1-(Chloromethyl)naphthalene
• CAS No.: 86-52-2
• Molecular Formula: C11H9Cl
• Molecular Weight: 176.645
• Hs Code.: 29036990
• European Community (EC) Number: 201-678-2,252-469-8
• NSC Number: 8473
• UNII: KD3RZ3R8C4
• DSSTox Substance ID: DTXSID5058939
• Nikkaji Number: J32.568F
• Wikidata: Q63395890
• Mol file: 86-52-2.mol

Synonyms:1-chloromethylnaphthalene;1-Cl-me-naphthalene;1-CMN

Chemical Property of 1-(Chloromethyl)naphthalene

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 0.00339mmHg at 25°C
• Melting Point: 32 °C(lit.)
• Refractive Index: n20/D 1.635(lit.)
• Boiling Point: 291.5 °C at 760 mmHg
• Flash Point: 129.9 °C
• PSA: 0.00000
• Density: 1.167 g/cm³
• LogP: 3.57860
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 176.0392780
• Heavy Atom Count: 12
• Complexity: 144

Purity/Quality:

99% ^*data from raw suppliers

1-(Chloromethyl)naphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xn
• Hazard Codes: C,Xn
• Statements: 21/22-34-36/37/38-36-20/21/22
• Safety Statements: 26-36/37/39-45-60-20-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Naphthalenes
• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2CCl
• Uses: 1-(Chloromethyl)naphthalene is a key material for synthesis dye pigment and as fluorescent brightening agent. It is employed in synthetic resin and medicine. Palladium-catalyzed nucleophilic dearomatization of chloromethyl naphthalene derivatives produce ortho- or para-substituted carbocycles in satisfactory to excellent yields.

Technology Process of 1-(Chloromethyl)naphthalene

There total 30 articles about 1-(Chloromethyl)naphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.4%

1-naphthalene methanol (4780-79-4) → 1-Chloromethylnaphthalene (86-52-2)

Guidance literature:

With thionyl chloride; In toluene; for 12h;

DOI:10.1021/ol034060w

Reference yield: 92.0%

1-(dimethoxymethyl)naphthalene (33250-32-7) → 1-Chloromethylnaphthalene (86-52-2)

Guidance literature:

With triethylsilane; acetyl chloride; tin(ll) chloride; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1246/bcsj.64.1410

Reference yield: 92.0%

naphthalen-1-yl-acetyl chloride (5121-00-6) → 1-Chloromethylnaphthalene (86-52-2)

Guidance literature:

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;

DOI:10.1021/acs.orglett.7b02024

upstream raw materials:

N-chloro-succinimide

1-Methylnaphthalene

formaldehyd

naphthalene

Downstream raw materials:

1-naphthalen-1-ylmethyl-piperazine

1-[1]naphthylmethyl-pyridinium; chloride

1-naphthaldehyde

5,5-dimethyl-2-naphthalen-1-ylmethyl-cyclohexane-1,3-dione

Refernces

Heterocyclic steroids - part X: Total synthesis of 12,15-bisthia-1,3,5(10),6,8,13(14)-gonahexaen-17-one

10.1016/0039-128X(81)90038-6

The research focuses on the total synthesis of 12,15-bisthia-1,3,5(10),6,8,13(14)-gonahexaen-17-one (III), a heterocyclic steroid compound. The study aims to explore the influence of sulfur at position '12' of the steroid nucleus on biological activity, building on previous work on 3-deoxy-12-thiaequilenin and 12-thiaequilenin methyl ether. The synthesis involves a series of chemical reactions starting with 1-chloromethylnaphthalene (IV), which is treated with thioglycollic acid in sodium hydroxide to form l-naphthylmethyl-thioacetic acid (V). This compound is then cyclodehydrated with phosphorus pentoxide to yield 1-oxo-3-thia-1,2,3,4-tetrahydrophenanthrene (VI). Further reactions with thioglycollic acid and p-toluenesulfonic acid (PTS) lead to the formation of (3-thia-3,4-dihydrophenanthren-1-yl)thioacetic acid (VII), which is cyclodehydrated again to obtain the target compound (III).