Squarylium dye III

Base Information

• Chemical Name: Squarylium dye III
• CAS No.: 43134-09-4
• Molecular Formula: C₂₀H₂₀N₂O₂
• Molecular Weight: 320.391
• Hs Code.: 2922499990
• European Community (EC) Number: 625-525-8
• DSSTox Substance ID: DTXSID60401337
• Nikkaji Number: J1.840.162B,J638.731D
• NSC Number: 125878
• Wikidata: Q27123342
• Mol file: 43134-09-4.mol

Synonyms:Squarylium dye III;43134-09-4;13458-60-1;1,3-Bis[4-(dimethylamino)phenyl]-2,4-dihydroxycyclobutenediylium dihydroxide, bis(inner salt);1,3-BIS(4-DIMETHYLAMINO-PHENYL)-2-OXO-CYCLOBUTEYYLIUM-4-OLAT;2-[4-(dimethylamino)phenyl]-4-(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-3-oxocyclobuten-1-olate;F0712-0056;CHEBI:52272;DTXSID60401337;MFCD00142504;NSC125878;AKOS002785142;NSC-125878;CS-0433679;Q27123342;1,3-Bis[4-(dimethylamino)phenyl]-2,4-dihydroxycyclobutenediylium dihydroxide, bis(inner salt), Dye content 90 %;2-(4-(dimethylamino)phenyl)-4-(4-(dimethyliminio)cyclohexa-2,5-dien-1-ylidene)-3-oxocyclobut-1-enolate;2-[4-(dimethylamino)phenyl]-4-[4-(dimethyliminio)cyclohexa-2,5-dien-1-ylidene]-3-oxocyclobut-1-en-1-olate

Chemical Property of Squarylium dye III

Chemical Property:

• Melting Point: >300 °C(lit.)
• PSA: 46.38000
• LogP: 2.61260
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 320.152477885
• Heavy Atom Count: 24
• Complexity: 613

Purity/Quality:

98% ^*data from raw suppliers

1-(4-DIMETHYLAMINO-PHENYL)-3-(4-DIMETHYLIMMONIUM-CYCLOHEXA- 2,5-DIEN-1-YLIDENE)-2-OXO-CYCLOBUTEN-4-OLATE 95.00% ^*data from reagent suppliers

Safty Information:

• 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(=[N+](C)C)C=C3)C2=O)[O-]

Technology Process of Squarylium dye III

There total 6 articles about Squarylium dye III 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: 60.0%

N,N-dimethyl-aniline (121-69-7,77733-26-7) + squaric acid (2892-51-5) → bis[4-(dimethylamino)phenyl]squaraine (43134-09-4,13458-60-1)

Guidance literature:

In toluene; butan-1-ol; for 8h; Heating;

Reference yield: 52.0%

N,N-dimethyl-aniline (121-69-7,77733-26-7) + squaric acid (2892-51-5) → 1,3-bis[4-(dimethylamino)phenyl]-2,4-dihydroxycyclobutenediylium dihydroxide bis(inner salt) (43134-09-4)

Guidance literature:

In butan-1-ol; benzene; Heating;

DOI:10.1039/f19827801847

Reference yield: 46.0%

3-(4-(N,N-dimethylamino)phenyl)-4-hydroxycyclobut-3-ene-1,2-dione (107885-39-2) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → bis[4-(dimethylamino)phenyl]squaraine (43134-09-4,13458-60-1)

Guidance literature:

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

upstream raw materials:

di-n-propyl squarate

N,N-dimethyl-aniline

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

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

Downstream raw materials:

bis<4-(dimethylamino)phenyl>squaraine radical cation

Refernces

• 1、 Chun, Hye W.,Jung, Daewoong,Kim, Jae Keon,Kim, Jong H.,Lee, Junyeop,Lee, Woosung,Noh, Ha Lim,Oh, Byeong M.,Park, Young Ki,Zheng, Jian. "Chromogenic detection of hydrogen sulfide using squarylium-based chemosensors". . . Retrieved 2020/05/25.
• 2、 Law, Kock-Yee,Bailey, F. Court. "Squaraine chemistry. A new approach to symmetrical and unsymmetrical photoconductive squaraines. Characterization and solid state properties of these materials". . p. 494 - 505. Retrieved 2007/10/02.