Bis(dithiarsolanyl)-bis(sulfobutyl) Cyanine 3

Base Information

• Chemical Name: Bis(dithiarsolanyl)-bis(sulfobutyl) Cyanine 3
• CAS No.: 946135-47-3
• Molecular Formula: C₃₅H₄₆As₂N₂O₆S₆
• Molecular Weight: 932.999
• Mol file: 946135-47-3.mol

Synonyms:Bis(dithiarsolanyl)-bis(sulfobutyl) Cyanine 3;5-(1,3,2-Dithiarsolan-2-yl)-2-[3-[5-(1,3,2-dithiarsolan-2-yl)-1,3-dihydro-3,3-diMethyl-1-(4-sulfobutyl)-2H-indol-2-ylidene]-1-propen-1-yl]-3,3-diMethyl-1-(4-sulfobutyl)-3H-indoliuM Inner Salt;AsCy3

Chemical Property of Bis(dithiarsolanyl)-bis(sulfobutyl) Cyanine 3

Chemical Property:

• PSA: 235.78000
• LogP: 7.82990

Purity/Quality:

Bis(dithiarsolanyl)-bis(sulfobutyl)Cyanine3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A red Cy3-based biarsenical fluorescent probe targeted to a complementary binding peptide. AsCy3 has good photostability, low pH sensitivity, high absorbance, and good quantum yield. This new probe provides a FRET partner to biarsenical dye FlAsH, making this discovery an important step toward a whole toolkit of colored probes directed to different small peptide motifs.

Technology Process of Bis(dithiarsolanyl)-bis(sulfobutyl) Cyanine 3

There total 3 articles about Bis(dithiarsolanyl)-bis(sulfobutyl) Cyanine 3 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: 81.0%

3-((3,3-dimethyl-1-(4-sulfobutyl)indolin-2-ylidene)prop-1-enyl)-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium + ethane-1,2-dithiol (540-63-6) → 3-((5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethyl-1-(4-sulfobutyl)indolin-2-ylidene)prop-1-enyl)-5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium (946135-47-3)

Guidance literature:

3-((3,3-dimethyl-1-(4-sulfobutyl)indolin-2-ylidene)prop-1-enyl)-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium; With trifluoroacetic acid; mercury(II) oxide; at 20 ℃;

With arsenic trichloride; N-ethyl-N,N-diisopropylamine; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 8h;

ethane-1,2-dithiol; In 1-methyl-pyrrolidin-2-one; phosphate buffer; pH=7; Further stages.;

DOI:10.1021/ja070003c

Reference yield:

2,3,3-trimethylindoleniune (1640-39-7) → 3-((5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethyl-1-(4-sulfobutyl)indolin-2-ylidene)prop-1-enyl)-5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium (946135-47-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 69 percent / 1,2-dichloro-benzene / 12 h / 120 °C

2.1: 90 percent / Ac₂O; AcOH / 12 h / 120 °C

3.1: trifluoroacetic acid; HgO / 20 °C

3.2: AsCl₃; iPr₂NEt / Pd(OAc)2 / 1-methyl-pyrrolidin-2-one / 8 h / 20 °C

3.3: 81 percent / 1-methyl-pyrrolidin-2-one; aq. phosphate buffer / pH 7

With acetic anhydride; acetic acid; trifluoroacetic acid; mercury(II) oxide; In 1,2-dichloro-benzene;

DOI:10.1021/ja070003c

Reference yield:

4-(2,3,3-trimethyl-3H-indolium-1-yl)butane-1-sulfonate (54136-26-4) → 3-((5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethyl-1-(4-sulfobutyl)indolin-2-ylidene)prop-1-enyl)-5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium (946135-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / Ac₂O; AcOH / 12 h / 120 °C

2.1: trifluoroacetic acid; HgO / 20 °C

2.2: AsCl₃; iPr₂NEt / Pd(OAc)2 / 1-methyl-pyrrolidin-2-one / 8 h / 20 °C

2.3: 81 percent / 1-methyl-pyrrolidin-2-one; aq. phosphate buffer / pH 7

With acetic anhydride; acetic acid; trifluoroacetic acid; mercury(II) oxide;

DOI:10.1021/ja070003c

upstream raw materials:

ethane-1,2-dithiol

2,3,3-trimethylindoleniune

4-(2,3,3-trimethyl-3H-indolium-1-yl)butane-1-sulfonate