2-Naphthoyl chloride

Base Information

• Chemical Name: 2-Naphthoyl chloride
• CAS No.: 2243-83-6
• Molecular Formula: C11H7ClO
• Molecular Weight: 190.629
• Hs Code.: 2916.39
• European Community (EC) Number: 218-822-5
• NSC Number: 9842
• DSSTox Substance ID: DTXSID3062287
• Nikkaji Number: J95.582E
• Wikidata: Q72493650
• Mol file: 2243-83-6.mol

Synonyms:2-naphthoyl chloride;2-naphthoyl chloride, 3H-labeled

Chemical Property of 2-Naphthoyl chloride

Chemical Property:

• Appearance/Colour: off white to yellow solid
• Vapor Pressure: 0.000726mmHg at 25°C
• Melting Point: 50-52 °C(lit.)
• Refractive Index: 1.644
• Boiling Point: 307.4 °C at 760 mmHg
• Flash Point: 141.2 °C
• PSA: 17.07000
• Density: 1.271 g/cm³
• LogP: 3.21880
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: soluble in Toluene
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 190.0185425
• Heavy Atom Count: 13
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

2-Naphthoyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)C(=O)Cl
• Uses: 2-Naphthoyl Chloride can be used for anticancer and antiinflammatory agents. 2-Naphthoyl chloride has been used in:preparation of amide derivatives of the amphetamine enantiomerssynthesis of 7-dimethylamino-2-methyl-3-naphthamido-phenothiazinium saltmodification of self-assembled monolayer formed on silica surface from ((((aminoethyl)amino)-methyl)phenethyl)trimethoxysilane

Technology Process of 2-Naphthoyl chloride

There total 10 articles about 2-Naphthoyl chloride 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: 94.0%

N,N-dimethyl-2-naphthylcarboxamide (13577-85-0) → 2-naphthaloyl chloride (2243-83-6)

Guidance literature:

With iodine; N,N-dimethyl-formamide; phosphorus trichloride; In 1,2-dichloro-ethane; at 100 ℃; for 12h; Schlenk technique; Sealed tube;

DOI:10.1002/ejoc.202100630

Reference yield: 91.0%

methyl 2-naphthyl ketone (93-08-3) → 2-naphthaloyl chloride (2243-83-6)

Guidance literature:

methyl 2-naphthyl ketone; With pyridine; disulfur dichloride; In chlorobenzene; at 20 ℃; for 2h;

With sulfuryl dichloride; In chlorobenzene; at 20 - 132 ℃; for 15.5h; Reagent/catalyst; Temperature;

Reference yield: 90.0%

methyl naphthalene-2-carboxylate (2459-25-8) → 2-naphthaloyl chloride (2243-83-6)

Guidance literature:

With iodine; phosphorus trichloride; at 160 ℃; for 48h; Schlenk technique; Sealed tube;

DOI:10.1002/ejoc.202100630

upstream raw materials:

2-naphthalenecarbonitrile

2-naphthalenesulfonic acid sodium salt

methyl 2-naphthyl ketone

2-naphthoic acid tert-butyl ester

Downstream raw materials:

2-(diazoacetyl)naphthalene

(2,5-dimethyl-[3]furyl)-[2]naphthyl ketone

O-(Naphthoyl-⁽²⁾)-all-trans-retinol

N-(4-methylphenyl)-2-naphthamide

Refernces

• 1、 Nikitas, Nikolaos F.,Apostolopoulou, Mary K.,Skolia, Elpida,Tsoukaki, Anna,Kokotos, Christoforos G.. "Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters". supporting information. p. 7915 - 7922. Retrieved 2021/05/03.
• 2、 Wu, Xiaofang,Zhou, Lei,Yang, Ruoqi,Guo, Fengzhe,Tang, Zi-Long,Xiao, Jing. "A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides". . p. 301 - 304. Retrieved 2020/01/29.