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[ CAS No. 84459-33-6 ] {[proInfo.proName]}

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Chemical Structure| 84459-33-6
Chemical Structure| 84459-33-6
Structure of 84459-33-6 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

William E. Meador ; Eric Y. Lin ; Irene Lim , et al. DOI: PubMed ID:

Abstract: In vivo fluorescence imaging in the shortwave infrared (SWIR, 1,000-1,700 nm) and extended SWIR (ESWIR, 1,700-2,700 nm) regions has tremendous potential for diagnostic imaging. Although image contrast has been shown to improve as longer wavelengths are accessed, the design and synthesis of organic fluorophores that emit in these regions is challenging. Here we synthesize a series of silicon-RosIndolizine (SiRos) fluorophores that exhibit peak emission wavelengths from 1,300-1,700 nm and emission onsets of 1,800-2,200 nm. We characterize the fluorophores photophysically (both steady-state and time-resolved), electrochemically and computationally using time-dependent density functional theory. Using two of the fluorophores (SiRos1300 and SiRos1550), we formulate nanoemulsions and use them for general systemic circulatory SWIR fluorescence imaging of the in mice. These studies resulted in high-resolution SWIR images with well-defined vasculature visible throughout the entire circulatory system. This SiRos scaffold establishes design principles for generating long-wavelength emitting SWIR and ESWIR fluorophores.

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Product Details of [ 84459-33-6 ]

CAS No. :84459-33-6 MDL No. :MFCD09056792
Formula : C7H4BrClO Boiling Point : No data available
Linear Structure Formula :- InChI Key :AJOAHIKYBSZIEV-UHFFFAOYSA-N
M.W : 219.46 Pubchem ID :13154710
Synonyms :

Calculated chemistry of [ 84459-33-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.54
TPSA : 17.07 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 3.29
Log Po/w (WLOGP) : 2.92
Log Po/w (MLOGP) : 2.79
Log Po/w (SILICOS-IT) : 3.3
Consensus Log Po/w : 2.85

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.65
Solubility : 0.049 mg/ml ; 0.000223 mol/l
Class : Soluble
Log S (Ali) : -3.32
Solubility : 0.104 mg/ml ; 0.000475 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.82
Solubility : 0.0331 mg/ml ; 0.000151 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 84459-33-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 84459-33-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 84459-33-6 ]

[ 84459-33-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 4341-24-6 ]
  • [ 3325-11-9 ]
  • [ 84459-33-6 ]
  • 3-chloro-12-methyl-12,13-dihydroquinolino[4,3,2-mn][1,2,3]triazolo[4,5,1-de]acridin-14(11H)-one [ No CAS ]
  • 2
  • [ 201230-82-2 ]
  • [ 5900-59-4 ]
  • [ 84459-33-6 ]
  • 2,9-dichloro-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione [ No CAS ]
  • 3
  • [ 110-91-8 ]
  • [ 871231-45-7 ]
  • [ 84459-33-6 ]
  • 6-chloro-9-morpholino-9H-fluoren-3-ol [ No CAS ]
  • 6-chloro-9-morpholino-9H-fluoren-1-ol [ No CAS ]
  • 4
  • [ 871231-45-7 ]
  • [ 84459-33-6 ]
  • 6-chloro-9H-fluorene-3,9-diol [ No CAS ]
  • 5
  • [ 27139-97-5 ]
  • [ 84459-33-6 ]
  • 6
  • [ 32566-01-1 ]
  • [ 84459-33-6 ]
  • C21H14BrClN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; at 70℃; for 10h;Inert atmosphere; Schlenk technique; General procedure: To a schlenk tube (15 mL) containing a solution of <strong>[32566-01-1]2-(1H-indol-2-yl)aniline</strong> 3a (0.4 mmol) in DMSO (2 mL) was added 2-bromobenzaldehyde 4 (0.44 mmol) under nitrogen atmosphere.Then, the reaction mixture was stirred at 70C for 10 h until <strong>[32566-01-1]2-(1H-indol-2-yl)aniline</strong> 3a was consumed completely. Next, Pd(PPh3)2Cl2(0.02 mmol), [(t-Bu)3PH]BF4 (0.06 mmol) and Et3N (1.2 mmol) wereadded into the above reaction system under CO (1 atm) atmo-sphere. After being stirred at 120C for 5 h, the resulting mixturewas quenched with NH4Cl and extracted with ethyl acetate. Thecombined organic layer was washed with H2O and brine, and thendried over anhydrous Na2SO4. The solvent was removed underreduced pressure and the residue was puried by column chro-matography on silica gel (petroleum ether/ethyl acetate 5:1) toafford the corresponding indolo[1,2-c]isoindolo[2,1-a]quinazolin-5(16aH)-one 2.
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Technical Information

? Alkyl Halide Occurrence ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Julia-Kocienski Olefination ? Kinetics of Alkyl Halides ? Knoevenagel Condensation ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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