2-Anilino-3-chloro-1,4-naphthoquinone

Base Information

• Chemical Name: 2-Anilino-3-chloro-1,4-naphthoquinone
• CAS No.: 1090-16-0
• Molecular Formula: C16H10 Cl N O2
• Molecular Weight: 283.714
• Hs Code.: 2922399090
• NSC Number: 4285
• DSSTox Substance ID: DTXSID40148793
• Nikkaji Number: J236.138H
• Wikidata: Q83014414
• ChEMBL ID: CHEMBL155563
• Mol file: 1090-16-0.mol

Synonyms:1090-16-0;2-Anilino-3-chloro-1,4-naphthoquinone;2-chloro-3-(phenylamino)naphthalene-1,4-dione;2-anilino-3-chloronaphthalene-1,4-dione;1,4-NAPHTHOQUINONE, 2-ANILINO-3-CHLORO-;2-Chloro-3-(phenylamino)-1,4-naphthoquinone;NSC 4285;3-Anilino-2-chloro-1,4-naphthoquinone;BRN 1981676;C16H10ClNO2;MLS000588884;2-chloro-3-(phenylamino)-1,4-dihydronaphthalene-1,4-dione;SMR000212533;2-Chloro-3-phenylamino-[1,4]naphthoquinone;4-14-00-00405 (Beilstein Handbook Reference);NSC4285;cid_14161;CHEMBL155563;SCHEMBL6506683;BDBM68019;CIWCIDRTACZSAZ-UHFFFAOYSA-;DTXSID40148793;HMS2524F03;2-Anilino-3-chloronaphthoquinone #;NSC-4285;MFCD00010250;STK862428;AKOS001618279;SB82414;2-Anilino-2-Chloro-1,4-naphthoquinone;NCGC00246324-01;LS-95615;2-anilino-3-chloro-naphthalene-1,4-dione;CS-0329677;2-chloranyl-3-phenylazanyl-naphthalene-1,4-dione;11T-0643;7-chloro-5,8-dioxo-6-(phenylamino)naphthalen-1-yl;2-anilino-3-chloro-1,4-dihydronaphthalene-1,4-dione

Chemical Property of 2-Anilino-3-chloro-1,4-naphthoquinone

Chemical Property:

• Vapor Pressure: 2.21E-05mmHg at 25°C
• Boiling Point: 408.3°Cat760mmHg
• Flash Point: 200.7°C
• PSA: 46.17000
• Density: 1.39g/cm³
• LogP: 3.70110
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 283.0400063
• Heavy Atom Count: 20
• Complexity: 451

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Chloro-3-(phenylamino)-1,4-dihydronaphthalene-1,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC2=C(C(=O)C3=CC=CC=C3C2=O)Cl

Technology Process of 2-Anilino-3-chloro-1,4-naphthoquinone

There total 21 articles about 2-Anilino-3-chloro-1,4-naphthoquinone 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: 100.0%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + aniline (62-53-3) → 2-chloro-3-(phenylamino)naphthalene-1,4-dione (1090-16-0)

Guidance literature:

With water; at 50 ℃; for 0.25h;

DOI:10.1016/j.tetlet.2009.07.149

Reference yield: 88.0%

2-phenylimino-3,3-dichloro-2,3-dihydro-1,4-naphthoquinone (104307-23-5) → 2-chloro-3-(phenylamino)naphthalene-1,4-dione (1090-16-0)

Guidance literature:

With triethylamine; ethyl 2-cyanoacetate; In benzene; at 25 ℃; for 8h;

Reference yield: 87.0%

2-chloro-1,4-naphthoquinone (1010-60-2) + nitrobenzene (98-95-3,26969-40-4) → 2-chloro-3-(phenylamino)naphthalene-1,4-dione (1090-16-0)

Guidance literature:

With zinc(II) acetate dihydrate; acetic acid; zinc; In water; at 20 ℃; for 5h;

DOI:10.1055/s-0037-1610689

upstream raw materials:

2,3-Dichloro-1,4-naphthoquinone

ethanol

aniline

2-chloro-1,4-naphthoquinone

Downstream raw materials:

6-anilino-9-chloro-benzo[a]phenothiazin-5-one

6-anilino-9-ethoxy-benzo[a]phenothiazin-5-one

6-anilino-9-methyl-benzo[a]phenothiazin-5-one

6-anilino-9-fluoro-benzo[a]phenothiazin-5-one

Refernces

• 1、 Hodnett, Ernest M.,Wongwiechintana, Chinda,Dunn, William J.,Marrs, Pam. "Substituted 1,4-Naphthoquinones vs. the Ascitic Sarcoma 180 of Mice". . p. 570 - 574. Retrieved 1983.
• 2、 Rajalakshmi,Jayasudha,Ciattini, Samuele,Chelazzi, Laura,Elango, Kuppanagounder P.. "Crystallographic evidence for resonance assisted H-Bonding effect in selective colorimetric detection of cyanide by arylamino-naphthoquinones". . p. 259 - 268. Retrieved 2019.
• 3、 Ravichandiran, Palanisamy,Mas?yk, Maciej,Sheet, Sunirmal,Janeczko, Monika,Premnath, Dhanraj,Kim, Ae Rhan,Park, Byung-Hyun,Han, Myung-Kwan,Yoo, Dong Jin. "Synthesis and Antimicrobial Evaluation of 1,4-Naphthoquinone Derivatives as Potential Antibacterial Agents". . p. 589 - 600. Retrieved 2019.
• 4、 Leyva, Elisa,Baines, Kim M.,Espinosa-González, Claudia G.,López, Lluvia I.,Magaldi-Lara, Diego A.,Leyva, Socorro. "Synthesis of novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone". . p. 5248 - 5251. Retrieved 2015.
• 5、 Varricchio, Carmine,Beirne, Kathy,Aeschlimann, Pascale,Heard, Charles,Rozanowska, Malgorzata,Votruba, Marcela,Brancale, Andrea. "Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber's Hereditary Optic Neuropathy (LHON)". . p. 13638 - 13655. Retrieved 2020/11/30.