1-Aminoanthraquinone-2-carboxylic acid

Base Information

• Chemical Name: 1-Aminoanthraquinone-2-carboxylic acid
• CAS No.: 82-24-6
• Molecular Formula: C15H9 N O4
• Molecular Weight: 267.241
• European Community (EC) Number: 201-406-2
• NSC Number: 39940,9026
• UNII: 413N4ED0PF
• DSSTox Substance ID: DTXSID9058866
• Nikkaji Number: J52.254F
• Wikidata: Q27258389
• ChEMBL ID: CHEMBL1565911
• Mol file: 82-24-6.mol

Synonyms:82-24-6;1-amino-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid;1-AMINOANTHRAQUINONE-2-CARBOXYLIC ACID;1-Amino-2-carboxyanthraquinone;1-amino-9,10-dioxoanthracene-2-carboxylic acid;2-Anthraquinonecarboxylic acid, 1-amino-;2-Anthracenecarboxylic acid, 1-amino-9,10-dihydro-9,10-dioxo-;1-Amino-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid;EINECS 201-406-2;1-Amino-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylic acid;NSC 39940;BRN 2219360;UNII-413N4ED0PF;MLS000713412;413N4ED0PF;NSC-9026;NSC-39940;l-Aminoanthraquinone-2-carboxylic acid;SMR000272893;1-Amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid;4-14-00-02591 (Beilstein Handbook Reference);2-Anthroic acid, 1-amino-9,10-dihydro-9,10-dioxo-;2-Anthracenecarboxylic acid, 9,10-dihydro-1-amino-9,10-dioxo-;NSC9026;Maybridge1_002350;cid_6701;REGID_for_CID_6701;DivK1c_001102;SCHEMBL2839419;CHEMBL1565911;DTXSID9058866;BDBM55794;HMS548C18;1-Amino-9,10-dioxo-9,10-dihydroanthracene-2-carboxylicacid;HMS2640G22;NSC39940;STK793124;AKOS000593025;1-Amino-2-anthraquinonecarboxylic acid;1-amino-anthraquinone-2-carboxylic acid;CDS1_000062;NCGC00245081-01;5306-09-2;LS-20277;CS-0220974;FT-0747817;EN300-08029;1-amino-9,10-dioxo-2-anthracenecarboxylic acid;AB00079716-01;1-amino-9,10-diketo-anthracene-2-carboxylic acid;1-amino-9,10-dioxo-anthracene-2-carboxylic acid;1-AMINOANTHRAQUINONE-2-CARBOXYLIC ACID [MI];W-109295;Q27258389;Z56759396;F0433-0500;1-amino-9,10-dihydro-9,10-dioxoanthracen-2-carboxylsyre;1-azanyl-9,10-bis(oxidanylidene)anthracene-2-carboxylic acid

Chemical Property of 1-Aminoanthraquinone-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 4.22E-14mmHg at 25°C
• Melting Point: 291°C
• Refractive Index: 1.6231 (estimate)
• Boiling Point: 575.9°C at 760 mmHg
• Flash Point: 302.1°C
• PSA: 97.46000
• Density: 1.2671 (rough estimate)
• LogP: 2.32360
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 267.05315777
• Heavy Atom Count: 20
• Complexity: 461

Purity/Quality:

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

1-Amino-9,10-dioxo-9,10-dihydroanthracene-2-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)C(=O)O)N

Technology Process of 1-Aminoanthraquinone-2-carboxylic acid

There total 34 articles about 1-Aminoanthraquinone-2-carboxylic acid 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: 99.0%

1-nitroanthraquinone-2-carboxylic acid (128-67-6) → 1-aminoanthraquinone-2-carboxylic acid (82-24-6)

Guidance literature:

With sodium tetrahydroborate; ammonia; In water; at 20 ℃; for 4h;

DOI:10.3390/molecules25071672

Reference yield: 93.6%

1-amino-2-hydroxymethyl-9,10-dioxo-9,10-dihydroanthracene (24094-44-8) → 1-aminoanthraquinone-2-carboxylic acid (82-24-6)

Guidance literature:

With pyridine; potassium permanganate; sodium carbonate; In water; at 70 ℃;

DOI:10.3762/bjoc.11.253

Reference yield: 32.0%

1-nitroanthraquinone-2-carboxylic acid (128-67-6) + 3-amino-5-methylpyrazole (31230-17-8) → 1-aminoanthraquinone-2-carboxylic acid (82-24-6) + 1-amino-9,10-anthracenedione (82-45-1) + 2-methylpyrazolo-<5,1-b>naphtho<2,3-h>quinazoline-5,10,13-trione

Guidance literature:

With sodium carbonate; In sulfolane; at 150 ℃; for 4h;

DOI:10.1007/BF00531475

upstream raw materials:

1-nitro-2-methylanthraquinone

2-bromomethyl-1-nitro-anthraquinone

1-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid

1-amino-9,10-dioxo-9,10-dihydro-anthracene-2-carbonitrile

Downstream raw materials:

3,4-Phthaloyl-isatosaeureanhydrid

1-amino-2-anthraquinonecarbonyl chloride

1-Amino-4-bromoanthraquinone-2-carboxylic acid

1-amino-4-nitroanthraquinone-2-carboxylic acid

Refernces

• 1、 Chen, Tinggui,Feng, Liheng,Guan, Yingying,Guo, Fang,Li, Yuying,Liu, Yaoming,Ma, Kaiqing,Su, Qiang,Wang, Zhuanhua,Zhang, Liwei,Zhou, Yuzhi. "Novel anthraquinone compounds inhibit colon cancer cell proliferation via the reactive oxygen species/JNK pathway". . . Retrieved 2020/04/10.
• 2、 Malik, Enas M.,Baqi, Younis,Müller, Christa E.. "Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - Precursors for dyes and drugs". . p. 2326 - 2333. Retrieved 2016/02/12.