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[ CAS No. 131747-63-2 ] {[proInfo.proName]}

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Chemical Structure| 131747-63-2
Chemical Structure| 131747-63-2
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Product Citations

Product Citations

Meador, William E ; Saucier, Matthew A ; Tucker, Max R , et al. DOI:

Abstract: Shortwave infrared (SWIR, 1000-1700 nm) and extended SWIR (ESWIR, 1700-2700 nm) absorbing materials are valuable for applications including fluorescence based biological imaging, photodetectors, and light emitting diodes. Currently, ESWIR absorbing materials are largely dominated by inorganic semiconductors which are often costly both in raw materials and manufacturing processes used to produce them. The development of ESWIR absorbing organic molecules is thus of interest due to the tunability, solution processability, and low cost of organic materials compared to their inorganic counterparts. Herein, through the combination of heterocyclic indolizine donors and an antiaromatic fluorene core, a series of organic chromophores with absorption maxima ranging from 1470-2088 nm (0.84-0.59 eV) and absorption onsets ranging from 1693-2596 nm (0.73-0.48 eV) are designed and synthesized. The photophysical and electrochemical properties of these chromophores, referred to as FluIndz herein, are described via absorption spectroscopy in 17 solvents, cyclic voltammetry, solution photostability, and transient absorption spectroscopy. Molecular orbital energies, predicted electronic transitions, and antiaromaticity are compared to higher energy absorbing chromophores using density functional theory. The presence of thermally accessible diradical states is demonstrated using density functional theory and EPR spectroscopy, while XRD crystallography confirms structural connectivity and existence as a single molecule. Overall, the FluIndz chromophore scaffold exhibits a rational means to access organic chromophores with extremely narrow optical gaps.

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Product Details of [ 131747-63-2 ]

CAS No. :131747-63-2 MDL No. :MFCD08690697
Formula : C6H4BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :CKVQWOKUEZYWRQ-UHFFFAOYSA-N
M.W : 186.01 Pubchem ID :14761472
Synonyms :
Chemical Name :4-Bromopicolinaldehyde

Calculated chemistry of [ 131747-63-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.32
TPSA : 29.96 ?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) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : 1.34
Log Po/w (WLOGP) : 1.66
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 2.2
Consensus Log Po/w : 1.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.26
Solubility : 1.01 mg/ml ; 0.00544 mol/l
Class : Soluble
Log S (Ali) : -1.57
Solubility : 5.0 mg/ml ; 0.0269 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.83
Solubility : 0.278 mg/ml ; 0.00149 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 131747-63-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 131747-63-2 ]

* 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 [ 131747-63-2 ]

[ 131747-63-2 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 131747-45-0 ]
  • [ 131747-63-2 ]
YieldReaction ConditionsOperation in experiment
100% With manganese(IV) oxide; In chloroform; for 0.75h;Reflux; Example 29i 4-Bromopicolinaldehyde Manganese(IV) oxide (22.19 g, 255.29 mmol) was added to a solution of (4-bromopyridin-2-yl)methanol (4.00 g, 21.27 mmol) in chloroform (80 mL) and the reaction mixture was stirred under reflux for 45 min. After the mixture had cooled to room temperature the solids were removed by filtration through a pad of Celite.(R).. The solvent was removed in vacuo and the residue (3.96 g, quant.) was used without further purification in the next step. 1H NMR (500 MHz, DMSO-d6) delta ppm 9.97 (s, 1H) 8.80 (d, 1H) 7.98 (d, 1H) 7.88 (dd, 1 H); MS (APCI+): m/z 186, 188 [M+H]+.
75% With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -65 - -60℃; for 1.5h;Inert atmosphere; Under the protection of nitrogen,Add 3L DCM to the 5L three-neck bottle to cool down.240g of oxalyl chloride was added dropwise during cooling;At -60 ° C,295.6 g of Dimethyl sulfoxide (DMSO) was added dropwise to the reaction solution.Keep warm for 30min;At -60 ° C,237.5 g of Cpd 3 was added dropwise to the reaction solution.The reaction was carried out at -65 ° C for 1 hour;At this temperature, 3.5 eq of triethylamine (TEA) was added dropwise.After the solution was allowed to stand, the plate was measured.Through the column, the product 4-bromopyridine-2-carbaldehyde is obtained.(Cpd 4) 177.2g,The yield was 75percent.
Description 5: 4-Bromo-2-pyridinecarbaldehyde (D5); To a solution of the oxalyl chloride (0.364 mL, 4.09 mmol) in dry DCM (30 mL) at -780C was added DMSO (0.634 mL, 8.93 mmol) in dry DCM (5 mL) dropwise. The mixture was stirred at this temperature under argon atmosphere for 10 minutes <n="29"/>before a solution of (4-bromo-2-pyridinyl)methanol (D4) (700 mg, 3.72 mmol) in dry DCM (15 ml.) was added dropwise. After circa 30 minutes, triethylamine (2.6 mL, 18.6 mmol) was added and the cooling bath was removed. The reaction mixture was allowed to stir at room temperature for 1 h after which water was added and it was extracted 3 times with DCM. The combined organics were dried over MgSO4. The crude material (700 mg) was purified by flash chromatography (Biotage SP4, 25+M column) with a gradient of EtOAc in hexane to afford 425 mg (61 percent) of the desired product D5.1H-NMR (CDCI3): delta 7.70 (1 H, dd), 8.12 (1 H1 d), 8.61 (1 H, d), 10.05 (1 H, s); Description 5 - alternative procedure: 4-Bromo-2-pyridinecarbaldehyde (D5); To a solution of oxalyl chloride (13.2 mL, 0.149 mol) in dry dichloromethane (1 L) at - 78 0C under argon was added a solution of DMSO (23 mL, 0.324 mol) in dry dichloromethane (180 mL) dropwise over 20 minutes. The mixture was stirred at -78 0C under argon for 15 minutes and then a solution of (4-bromo-2-pyridinyl)methanol (D4) (25.4 g, 0.135 mol) in dry dichloromethane (500 mL) was added dropwise over 30 minutes. The resulting white suspension was stirred at -78 CC for 40-45 minutes and then triethylamine (95 mL, 0.676 mol) was added dropwise over 15 minutes. After stirring at -78 0C for 15 minutes, the mixture was allowed to reach room temperature over -1.5 h and then poured into water (400 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3x, ~1 L total solvent). The combined organic layers were washed with brine (20OmL), dried over MgSO4 and concentrated. The crude material was purified by flash chromatography on silica gel with a gradient of 0 to 30 percent ethyl acetate in hexane to afford 20.5 g (82percent) of the desired product D5, with NMR data consistent with those previously obtained.
  • 2
  • [ 54527-68-3 ]
  • [ 131747-63-2 ]
  • [ 14205-39-1 ]
  • [ 131747-73-4 ]
  • 3
  • [ 131747-63-2 ]
  • [ 1576-35-8 ]
  • [ 192642-79-8 ]
  • 4
  • [ 128796-39-4 ]
  • [ 131747-63-2 ]
  • [ 1005189-47-8 ]
YieldReaction ConditionsOperation in experiment
60% With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 130℃; for 0.25 - 0.333333h;Microwave irradiation;Product distribution / selectivity; Description 6: 4-[4-(Trifluoromethyl)phenyl]-2-pyridinecarbaldehyde (D6); A mixture of 4-trifluoromethylphenylboronic acid (644 mg, 3.39 mmol), 4-bromo-2- pyridinecarbaldehyde (D5) (420 mg, 2.26 mmol) and 2M Na2CO3 (4 mL, 7.91 mmol) in dimethoxyethane (12 mL) was degassed for 5-10 minutes in an ultrasonic bath <n="30"/>under a flow of argon. Pd(dppf)CI2 (92 mg, 0.113 mmol) was added and the resulting mixture was heated with stirring at 130 0C for 10 minutes in a microwave reactor. TLC (EtOAc/hexane 1:1) after 10 minutes showed the reaction went to completion . The mixture was filtered through a pad of celite, washed with EtOAc and concentrated to afford 1 g of crude material which was purified by flash chromatography (Biotage SP4, 40+S column) with a gradient 0 to 50percent of EtOAc in hexane to yield 340 mg (60percent) of desired product D6.1H-NMR (CDCI3): delta 7.76 (1 H, m), 7.81 (4H, s), 8.2 (1 H, s), 8.89 (1 H, d), 10.18 (1 H, s)
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 90℃; for 18.25h;Product distribution / selectivity; Description 6 - alternative procedure: 4-[4-(Trifluoromethyl)phenyl]-2- pyridinecarboxaldehyde. (D6); A mixture of <strong>[131747-63-2]4-bromo-2-pyridinecarboxaldehyde</strong> (D5) (18.33 g, 98.5 mmol), 4-trifluoromethylphenylboronic acid (20.6 g, 108.4 mmol) and sodium bicarbonate(41.4 g, 492.7 mmol) in toluene (550 ml_) and water (55 mL) was degassed with argon for 15 minutes. To this suspension under argon was added tetrakis(triphenylphosphine) palladium(O) (3.42 g, 2.96 mmol) in one portion and the reaction was heated to 90 0C for 18 h. After cooling the solvent was evaporated and the residue suspended in ethyl acetate (1 L). This was filtered and the filter cake washed with ethyl acetate (4 chi 100 mL). The combined organics were evaporated to afford a yellow solid which was purified by flash chromatography (Biotage Flash 75L, silica gel, 3:1 --> 2:1 40-60 petroleum ether / ethyl acetate) to afford the title compound as a yellow solid (22.46 g) (D6), with NMR data consistent with those previously obtained.LC-MS: [MH+] = 252, C13H8F3NO requires 251.
  • 5
  • [ 17704-74-4 ]
  • [ 131747-63-2 ]
  • C10H12BrN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; In 1,2-dichloro-ethane; at 20℃; for 18h;Molecular sieve; Description 11 : lambda/2-[(4-Bromo-2-pyridinyl)methyl]-2-methylalaninamide (D11); To a solution of <strong>[131747-63-2]4-bromo-2-pyridinecarbaldehyde</strong> (4 g, 21.5 mmol) (D5) in DCE (160 mL) was added 2-methylalaninamide hydrochloride (D2) (4.47 g, 32.25 mmol),NaOAc (2.65 g, 32.25 mmol) and 4 A molecular sieves (activated in the vacuum oven at 70 0C for 1 day, 20 g) and the resulting mixture was stirred under argon at room temperature. The imine formation was checked by 1H-NMR and after 18 h,NaBH(OAc)3 (6.84 g, 32.25 mmol) and acetic acid (1.94 mL, 32.25 mmol) were added. After stirring for 6 h a NMR sample showed reduction of the imine; saturated aqueous sodium bicarbonate solution (110 mL) was added slowly and the solution was stirred at room temperature for 1 hour after which it was filtered through a pad ofCelite, washed with DCM (100 mL) and the organic layer was separated. The aqueous phase was extracted with DCM (50 mL) and the combined organics were washed with brine (50 mL), dried over MgSO4 and concentrated to afford 5.4 g of <n="33"/>crude material. This was purified by flash chromatography using the Biotage SP4 (40+M silica cartridge), eluting with a gradient of 0 to 10percent MeOH in DCM to yield 5.4 g of the title compound D11.NMR deltaH (CDCI3): 1.43 (6H, s), 1.95 (1 H, broad s), 3.84 (2H, s), 5.36 (1H, broad s), 7.37 (1 H, dd, J = 5.2, 1.6 Hz), 7.47 (1 H, d, J = 1.6 Hz), 7.48 (1 H, broad s), 8.39 (1 H, d, J = 5.2 Hz).LC-MS: MH+ = 272/274, C10H14BrN3O requires 271/273.
  • 6
  • [ 110-89-4 ]
  • [ 131747-63-2 ]
  • [ 956593-44-5 ]
  • 10
  • [ 131747-63-2 ]
  • 5-Piperidin-1-yl-[1,2,3]triazolo[1,5-a]pyridine [ No CAS ]
  • 11
  • [ 131747-63-2 ]
  • 4-([1,2,3]triazolo[1,5-a]pyridin-5-yl)morpholine [ No CAS ]
  • 12
  • [ 131747-63-2 ]
  • 5-(4-Methoxy-phenoxy)-[1,2,3]triazolo[1,5-a]pyridine [ No CAS ]
  • 13
  • [ 192642-94-7 ]
  • [ 131747-63-2 ]
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