1,3-Bis[4-(dimethylamino)-2-hydroxyphenyl]-2,4-dihydroxycyclobutenediylium dihydroxide, bis(inner salt)

Base Information

• Chemical Name: 1,3-Bis[4-(dimethylamino)-2-hydroxyphenyl]-2,4-dihydroxycyclobutenediylium dihydroxide, bis(inner salt)
• CAS No.: 63842-83-1
• Molecular Formula: C20H20N2O4
• Molecular Weight: 352.39
• European Community (EC) Number: 624-210-2
• Mol file: 63842-83-1.mol

Synonyms:1,3-Bis[4-(dimethylamino)-2-hydroxyphenyl]-2,4-dihydroxycyclobutenediylium dihydroxide, bis(inner salt)

Chemical Property of 1,3-Bis[4-(dimethylamino)-2-hydroxyphenyl]-2,4-dihydroxycyclobutenediylium dihydroxide, bis(inner salt)

Chemical Property:

• Melting Point: >300oC(lit.)
• PSA: 81.08000
• LogP: 2.19100
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 352.14230712
• Heavy Atom Count: 26
• Complexity: 771

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC(=C(C=C1)C2=C(C(=C3C=CC(=CC3=O)N(C)C)C2=O)O)O
• Isomeric SMILES: CN(C)C1=CC(=C(C=C1)C2=C(/C(=C\3/C=CC(=CC3=O)N(C)C)/C2=O)O)O

Technology Process of 1,3-Bis[4-(dimethylamino)-2-hydroxyphenyl]-2,4-dihydroxycyclobutenediylium dihydroxide, bis(inner salt)

There total 3 articles about 1,3-Bis[4-(dimethylamino)-2-hydroxyphenyl]-2,4-dihydroxycyclobutenediylium dihydroxide, bis(inner salt) 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: 92.0%

squaric acid (2892-51-5) + 3-Dimethylaminophenol (99-07-0) → bis<4-(dimethylamino)-2-hydroxyphenyl>squaraine (63842-83-1)

Guidance literature:

In toluene; butan-1-ol; for 12h; Reflux;

DOI:10.1016/j.saa.2020.118457

Reference yield: 85.0%

3,4-dibutoxy-3-cyclobutene-1,2-dione (2892-62-8) + 3-Dimethylaminophenol (99-07-0) → bis<4-(dimethylamino)-2-hydroxyphenyl>squaraine (63842-83-1)

Guidance literature:

With sulfuric acid; water; In butan-1-ol; at 125 - 130 ℃;

Reference yield: 52.0%

3-(4-(N,N-dimethylamino)phenyl)-4-hydroxycyclobut-3-ene-1,2-dione (107885-39-2) + 3-Dimethylaminophenol (99-07-0) → bis<4-(dimethylamino)-2-hydroxyphenyl>squaraine (63842-83-1)

Guidance literature:

With Tributyl orthoformate; In N,N-dimethyl-formamide; isopropyl alcohol; for 3h; Heating;

upstream raw materials:

3-(4-(N,N-dimethylamino)phenyl)-4-hydroxycyclobut-3-ene-1,2-dione

3-Dimethylaminophenol

3,4-dibutoxy-3-cyclobutene-1,2-dione

squaric acid

Refernces

• 1、 McKerrow, Andrew J.,Buncel, Erwin,Kazmaier, Peter M.. "Aggregation of squaraine dyes: Structure-property relationships and solvent effects". . p. 1605 - 1615. Retrieved 2007/10/02.
• 2、 Law, Kock-Yee,Bailey, F. Court. "Squaraine chemistry. Synthesis of bis(4-dimethylaminophenyl)squaraine from dialkyl squarates. Mechanism and scope of the synthesis". . p. 2267 - 2273. Retrieved 2007/10/02.