4,4-DIFLUORO-1,3,5,7,8-PENTAMETHYL-4-BORA-3A,4A-DIAZA-S-INDACENE

Base Information

• Chemical Name: 4,4-DIFLUORO-1,3,5,7,8-PENTAMETHYL-4-BORA-3A,4A-DIAZA-S-INDACENE
• CAS No.: 121207-31-6
• Molecular Formula: C14H17 B F2 N2
• Molecular Weight: 262.11
• Hs Code.: 29349990
• Mol file: 121207-31-6.mol

Synonyms:Boron,[2-[1-(3,5-dimethyl-2H-pyrrol-2-ylidene)ethyl]-3,5-dimethyl-1H-pyrrolato-N1,N2]difluoro-,(T-4)-; 1H-Pyrrole,2-[1-(3,5-dimethyl-2H-pyrrol-2-ylidene)ethyl]-3,5-dimethyl-, boron complex;4,4-Difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene; BODIPY493/503; PM 546; PMPBF2; Pyrromethene 546

Chemical Property of 4,4-DIFLUORO-1,3,5,7,8-PENTAMETHYL-4-BORA-3A,4A-DIAZA-S-INDACENE

Chemical Property:

• Melting Point: 257°C(lit.)
• PSA: 13.32000
• LogP: 2.82650
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

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

Pyrromethene546 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Pyrromethene 546 is a hydrophobic compound that adsorbed strongly to the PDMS (poly(dimethylsiloxane)), indicating the hydrophobicity of the channel walls is clearly problematic for CZE analysis of hydrophobic analytes.

Technology Process of 4,4-DIFLUORO-1,3,5,7,8-PENTAMETHYL-4-BORA-3A,4A-DIAZA-S-INDACENE

There total 17 articles about 4,4-DIFLUORO-1,3,5,7,8-PENTAMETHYL-4-BORA-3A,4A-DIAZA-S-INDACENE 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: 97.0%

10-chloro-5,5-difluoro-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide (1414345-95-1) + tetramethylstannane (594-27-4) → 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene (121207-31-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 5h; Inert atmosphere; Reflux;

DOI:10.1002/chem.201304310

Reference yield: 72.0%

2,4-dimethyl-1H-pyrrole (625-82-1) + trifluoroborane diethyl ether (109-63-7) + acetyl chloride (75-36-5) → 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene (121207-31-6)

Guidance literature:

With N(CH₂CH₃)3; In dichloromethane; addn. of acetyl chloride to pyrrole deriv. in CH2Cl2 at room temp. over 30 min, refluxing for 1 h, cooling, addn. to hexane, evapn., dissolving in CH2Cl2, addn. of amine deriv., stirring for 10 min at room temp., addn. of boron compd., stirring for 1 h; washing with aq. satd. soln. of Na2CO3, drying over Na2SO4, evapn., chromy. (silica, n-pentane/CH2Cl2 (1:1)), evapn., recrystn. (CH2Cl2/methanol), NMR and MS;

DOI:10.1021/ja2010219

Reference yield: 70.0%

2,4-dimethyl-1H-pyrrole (625-82-1) + boron trifluoride diethyl etherate (109-63-7) + acetyl chloride (75-36-5) → 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene (121207-31-6)

Guidance literature:

2,4-dimethyl-1H-pyrrole; acetyl chloride; In dichloromethane; at 20 ℃; for 1.5h;

boron trifluoride diethyl etherate; With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/c9dt00094a

upstream raw materials:

tetrabutyl ammonium fluoride

3,5,3',5',6-pentamethyldipyrrin hydrochloride

2,4-dimethyl-1H-pyrrole

trifluoroborane diethyl ether

Downstream raw materials:

5,5-difluoro-2-iodo-1,3,7,9,10-pentamethyl-5H-5λ⁴,6λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

5,5-difluoro-2,8-diiodo-1,3,7,9,10-pentamethyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

C₂₃H₂₃BF₂N₂O

C₂₂H₂₀BF₂N₃O₂

Refernces

• 1、 Donnelly, Joanna L.,Offenbartl-Stiegert, Daniel,Marín-Beloqui, José M.,Rizzello, Loris,Battaglia, Guiseppe,Clarke, Tracey M.,Howorka, Stefan,Wilden, Jonathan D.. "Exploring the Relationship between BODIPY Structure and Spectroscopic Properties to Design Fluorophores for Bioimaging". . p. 863 - 872. Retrieved 2020.
• 2、 Musser, Andrew J.,Neelakandan, Prakash P.,Richter, Johannes M.,Mori, Hirotaka,Friend, Richard H.,Nitschke, Jonathan R.. "Excitation Energy Delocalization and Transfer to Guests within MII4L6 Cage Frameworks". . p. 12050 - 12059. Retrieved 2017.
• 3、 Mu, Huiying,Miki, Koji,Kubo, Takuya,Otsuka, Koji,Ohe, Kouichi. "Substitutedmeso-vinyl-BODIPY as thiol-selective fluorogenic probes for sensing unfolded proteins in the endoplasmic reticulum". . p. 1818 - 1821. Retrieved 2021.
• 4、 Hudnall, Todd W.,Gabbai, Francois P.. "A BODIPY boronium cation for the sensing of fluoride ions". . p. 4596 - 4597. Retrieved 2008.
• 5、 -. "A photosensitizer molecule and its application in improving tumor retention time to enhance large-volume tumor treatment". Paragraph 0040-0043. . Retrieved 2022/01/08.