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Merck

790389

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
MDL number:
MFCD00467372
UNSPSC Code:
12352103
PubChem Substance ID:
329768210
NACRES:
NA.23

Product Name

Difluoro{2-[1-(3,5-dimethyl-2H-pyrrol-2-ylidene-N)ethyl]-3,5-dimethyl-1H-pyrrolato-N}boron, 99% (HPLC)

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

assay

99% (HPLC)

form

powder

mp

262-266 °C

fluorescence

λex 493 nm; λem 504 nm in methanol

Quality Level

100

Related Categories

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.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW4361
MKCS4112
MKCQ6701
MKCP4645
MKCL3473

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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
Sameh Rabhi et al.
PloS one, 11(2), e0148640-e0148640 (2016-02-13)
Leishmania, the causative agent of vector-borne diseases, known as leishmaniases, is an obligate intracellular parasite within mammalian hosts. The outcome of infection depends largely on the activation status of macrophages, the first line of mammalian defense and the major target
BODIPY dyes and their derivatives: syntheses and spectroscopic properties.
Loudet A and Burgess K
Chemical Reviews, 107(11), 4891-4932 (2007)
Inhibition of the acetyl lysine-binding pocket of bromodomain and extraterminal domain proteins interferes with adipogenesis.
Goupille O, et al.
Biochemical and Biophysical Research Communications, 472(4), 624-630 (2016)
Infused polymers for cell sheet release.
Juthani N, et al.
Scientific Reports, 6(11), 26109-26109 (2016)
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