4-Chloro-1,8-naphthalic anhydride

Base Information

• Chemical Name: 4-Chloro-1,8-naphthalic anhydride
• CAS No.: 4053-08-1
• Molecular Formula: C12H5ClO3
• Molecular Weight: 232.623
• Hs Code.: Oral rat LD50: 3460 mg/kg
• European Community (EC) Number: 223-760-7
• UNII: 3TK8N66ETU
• DSSTox Substance ID: DTXSID1063279
• Nikkaji Number: J40.511F
• Wikidata: Q72455580
• ChEMBL ID: CHEMBL2323370
• Mol file: 4053-08-1.mol

Synonyms:4-Chloro-1,8-naphthalic anhydride;4053-08-1;6-Chlorobenzo[de]isochromene-1,3-dione;4-Chloronaphthalic anhydride;6-Chloro-1H,3H-benzo[de]isochromene-1,3-dione;4-Chloronapthalic anhydride;4-Chloronaphthalene-1,8-dicarboxylic anhydride;CHEMBL2323370;6-Chloronaphtho[1,8,8a-c,d]pyran-1,3-dione;EINECS 223-760-7;1H,3H-Naphtho(1,8-cd)pyran-1,3-dione, 6-chloro-;8-chloro-3-oxatricyclo[7.3.1.0]trideca-1(13),5,7,9,11-pentaene-2,4-dione;8-chloro-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione;6-Chloro-1H,3H-naphtho(1,8-cd)pyran-1,3-dione;1H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-chloro-;6-Chloro-1H,3H-naphtho[1,8-cd]pyran-1,3-dione;3TK8N66ETU;SCHEMBL212889;DTXSID1063279;Naphthalic anhydride, 4-chloro-;BDBM50426877;MFCD00006928;STL483080;AKOS003238974;FS-1789;SB40609;AC-11206;LS-95514;CS-0049951;FT-0617977;Naphthalic anhydride, 4-chloro- (7CI,8CI);4-chloro-1,8-naphthalenedicarboxylic anhydride;P16623;6-chloro-1H,3H-benzo[de]isochromene-1 ,3-dione;A825156;AH-034/32464018;6-Chloro-1H,3H-benzo[de]isochromene-1,3-dione #;W-106346;4-Chloro-1,8-naphthalic anhydride, >=95.0% (T);8-chloro-3-oxatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene-2,4-dione

Chemical Property of 4-Chloro-1,8-naphthalic anhydride

Chemical Property:

• Appearance/Colour: beige to brown powder
• Vapor Pressure: 2.53E-08mmHg at 25°C
• Melting Point: 202-206 °C (dec.)
• Refractive Index: 1.715
• Boiling Point: 450.9 °C at 760 mmHg
• Flash Point: 208.3 °C
• PSA: 43.37000
• Density: 1.565 g/cm³
• LogP: 2.80380
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: DMSO (Sparingly), Methanol (Slightly, Sonicated)
• Water Solubility.: Hydrolyzes in water.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 231.9927217
• Heavy Atom Count: 16
• Complexity: 341

Purity/Quality:

99% ^*data from raw suppliers

4-Chloro-1,8-naphthalicAnhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=CC3=C2C(=C1)C(=O)OC3=O)Cl
• Uses: 4-Chloro-1,8-naphthalic anhydride is used in dyes and pigments. It is also used in agrochemical, pharmaceutical.

Technology Process of 4-Chloro-1,8-naphthalic anhydride

There total 10 articles about 4-Chloro-1,8-naphthalic anhydride 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: 93.0%

5-chloroacenaphthene (5209-33-6) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Guidance literature:

With copper(II) acetate dihydrate; manganese(II) acetate dihydrate; oxygen; acetic acid; potassium bromide; at 100 ℃;

DOI:10.1021/op0100448

Reference yield: 82.0%

1,8-Naphthalic anhydride (81-84-5) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Guidance literature:

With sodium hydroxide; phosphoric acid; chlorine; for 3h; Ambient temperature;

DOI:10.1021/je00054a038

Reference yield:

5-Chloracenaphthen-2-ol (31996-05-1) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / diethyl ether

2: Na₂Cr₂O₇, AcOH

With hydrogenchloride; sodium dichromate; acetic acid; In diethyl ether;

upstream raw materials:

5-chloroacenaphthene

4-chloro-naphthalene-1,8-dicarboxylic acid

acenaphthene

1,8-Naphthalic anhydride

Downstream raw materials:

3-hydroxy-1,8-naphthalic acid anhydride

4-chloro-N-(4-carboxyphenylmethyl)-1,8-naphthalimide

4-(4-chloro-naphthalimidyl-methyl)benzoic acid ethyl ester

4-((2-aminophenyl)thio)-1,8-naphthalic anhydride

Refernces

• 1、 Bukharkina, Tatiana V.,Grechishkina, Olga S.,Digurov, Nikolai G.,Kon'kov, Ivan I.. "Catalytic oxidation of acenaphthene and its derivatives in acetic acid". . p. 394 - 400. Retrieved 2013/09/06.