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790389

Sigma-Aldrich

Difluoro{2-[1-(3,5-dimethyl-2H-pyrrol-2-ylidene-N)ethyl]-3,5-dimethyl-1H-pyrrolato-N}boron

99% (HPLC)

Synonym(s):

1,3,5,7,8-Pentamethyl-4,4-difluorro-4-bora-3a,4a-diaza-s-indacene, 2-[1-(3,5-Dimethyl-2H-pyrrol-2-ylidene)ethyl]-3,,5-dimethyl-1H-pyrrole, boron complex, 4,4-Difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene, BODIPY 493/503, PM 546, PMPBF2, Pyrromethene 546, [[2-[1-(3,5-Dimethyl-2H-pyrrol-2-ylidene)ethyl]-3,5-dimethyl-1H-pyrrolato-N1,N2]difluoro]boron

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About This Item

Empirical Formula (Hill Notation):
C14H17BF2N2
CAS Number:
121207-31-6
Molecular Weight:
262.11
UNSPSC Code:
12352103
PubChem Substance ID:
329768210
NACRES:
NA.23

Quality Level

100

Assay

99% (HPLC)

form

powder

mp

262-266 °C

fluorescence

λex 493 nm; λem 504 nm in methanol

SMILES string

CC(C1=C(C)C=C(C)N1B(F)2F)=C3[N]2=C(C)C=C3C

InChI

1S/C14H17BF2N2/c1-8-6-10(3)18-13(8)12(5)14-9(2)7-11(4)19(14)15(18,16)17/h6-7H,1-5H3

InChI key

DRJHPEGNOPSARR-UHFFFAOYSA-N

Related Categories

General description

Difluoro{2-(1-(3,5-dimethyl-2H-pyrrol-2-ylidene-N)ethyl)-3,5-dimethyl-1H-pyrrolato-N}boron is an organoboron composed of dipyrromethene with a boron in the center. It is a fluorescent dye with a high quantum yield and an ability to absorb small molecules with sharp peaks in the ultraviolet region.

Application

BODIPY can be infused in silicon oil to impart fluorescence which can be used in light microscopy for cell sheets. It can be used in labelling of mouse pre-adipocyte 3t3-L1 cells. It may also be used in combination with bipyridine copper based complex which can be used in the sensing of nitrogen oxide(NOx) in air and living cells.
BODIPY laser dyes are used to generate fluorescent conjugates of proteins, nucleotides, oligonucleotides and dextrans, and to prepare fluorescent enzyme substrates, fatty acids, phospholipids, lipopolysaccharides, receptor ligands and polystyrene microspheres.
Also used for solid-state dye laser devices and organic solar cells.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Loudet A and Burgess K
Chemical Reviews, 107(11), 4891-4932 (2007)
Iyappan Ramachandiran et al.
Scientific reports, 8(1), 1154-1154 (2018-01-20)
Protein phosphorylation is an important post-translational modification that can regulate the protein function. The current knowledge on the phosphorylation status of plant oil body (OB) proteins is inadequate. This present study identifies the distinct physiological substrates of Arabidopsis serine/threonine/tyrosine protein
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Cells, 8(12) (2019-12-15)
Anti-angiogenic therapy triggers metabolic alterations in experimental and human tumors, the best characterized being exacerbated glycolysis and lactate production. By using both Liquid Chromatography-Mass Spectrometry (LC-MS) and Nuclear Magnetic Resonance (NMR) analysis, we found that treatment of ovarian cancer xenografts
A Boron Dipyrromethene (BODIPY)-Based CuII-Bipyridine Complex for Highly Selective NO Detection.
Juarez LA, et al.
Chemistry?A European Journal , 21(44), 15486-15490 (2015)
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