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[ CAS No. 54060-30-9 ] {[proInfo.proName]}

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Chemical Structure| 54060-30-9
Chemical Structure| 54060-30-9
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Product Citations

Product Citations      Expand+

Wolfer, Jamison D ; Minkoff, Benjamin B ; Burch, Heather L , et al. DOI: PubMed ID:

Abstract: Protein footprinting is a useful method for studying protein higher order structure and conformational changes induced by interactions with various ligands via addition of covalent modifications onto the protein. Compared to other methods that provide single amino acid-level structural resolution, such as cryo-EM, X-ray diffraction, and NMR, mass spectrometry (MS)-based methods can be advantageous as they require lower protein amounts and purity. As with other MS-based proteomic methods, such as post-translational modification analysis, enrichment techniques have proven necessary for both optimal sensitivity and sequence coverage when analyzing highly complex proteomes. Currently used reagents for footprinting via covalent labeling, such as hydroxyl radicals and carbodiimide-based methods, do not yet have a suitable enrichment method, limiting their applicability to whole proteome analysis. Here, we report a method for enrichable covalent labeling built upon the GEE/EDC system commonly used to covalently label aspartic acid and glutamic acid residues. Novel labeling reagents containing alkynyl functionality can be "clicked" to any azido-containing molecule with copper-catalyzed azide?alkyne cycloaddition (CuAAC), allowing for enrichment or further labeling. Multiple azide- and alkyne-containing GEE-like molecules were tested, and the most efficient method was determined to be the EDC-facilitated coupling of glycine propargyl amide (GPA) to proteins. The pipeline we report includes clicking via CuAAC to a commercially available biotin-azide containing a photocleavable linker, followed by enrichment using a streptavidin resin and subsequent cleavage under ultraviolet light. The enrichment process was optimized through the screening of clickable amines, coupling reagents, and enrichment scaffolds and methods with pure model proteins and has also been applied to complex mixtures of proteins isolated from the model plant, Arabidopsis thaliana, suggesting that our method may ultimately be used to measure protein conformation on a proteomic scale.

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Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong , et al. DOI: PubMed ID:

Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

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Product Details of [ 54060-30-9 ]

CAS No. :54060-30-9 MDL No. :MFCD00014779
Formula : C8H7N Boiling Point : -
Linear Structure Formula :C6H4(CCH)(NH2) InChI Key :NNKQLUVBPJEUOR-UHFFFAOYSA-N
M.W : 117.15 Pubchem ID :104682
Synonyms :

Calculated chemistry of [ 54060-30-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.78
TPSA : 26.02 ?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) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.28
Log Po/w (WLOGP) : 1.34
Log Po/w (MLOGP) : 2.05
Log Po/w (SILICOS-IT) : 1.75
Consensus Log Po/w : 1.61

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.87
Solubility : 1.59 mg/ml ; 0.0136 mol/l
Class : Very soluble
Log S (Ali) : -1.43
Solubility : 4.39 mg/ml ; 0.0375 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.07
Solubility : 1.0 mg/ml ; 0.00855 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.27

Safety of [ 54060-30-9 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P240-P241-P242-P243-P261-P264-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501 UN#:1993
Hazard Statements:H225-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 54060-30-9 ]

* 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 [ 54060-30-9 ]

[ 54060-30-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 54060-30-9 ]
  • [ 119389-05-8 ]
  • N-(3-ethynylphenyl)-4'-phenylethynylphthalisoimide [ No CAS ]
  • [ 2387-23-7 ]
  • 2
  • [ 54060-30-9 ]
  • [ 119389-05-8 ]
  • N-(3-ethynylphenyl)-4'-phenylethynylphthalimide [ No CAS ]
  • 3
  • [ 1445-39-2 ]
  • [ 54060-30-9 ]
  • [ 857264-92-7 ]
YieldReaction ConditionsOperation in experiment
60% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 95℃; for 2h; 5-[(3-aminophenyl)ethynyl]pyrimidin-2-amine <strong>[1445-39-2]2-Amino-5-iodopyrimidine</strong> (2.21 g), bis(triphenylphosphine)palladium dichloride (350 mg) and copper(I) iodide (40 mg) were stirred in DMF (100 mL)-triethylamine (20 mL) and degassed with nitrogen for 10 min. 3-Ethynyl aniline (1.29 g) was added and the mixture heated to 95 C. for 2 hours. The solvent was evaporated and the residue was purified by trituration with DCM (20 mL) to give the title compound as a brown solid (1.25 g, 60%); 1H NMR (DMSO-d6) 5.21 (bs, 2H), 6.58-6.70 (m, 3H), 7.03-7.07 (m, 3H), 8.40 (s, 2H); MS m/e MH+211.
60% <strong>[1445-39-2]2-Amino-5-iodopyrimidine</strong> (2.21 g), bis (triphenylphosphine) palladium dichloride (350 mg) and copper (I) iodide (40 mg) were stirred in DMF (100 mL)- triethylamine (20 mL) and degassed with nitrogen for 10 min. 3-Ethynyl aniline (1.29 g) was added and the mixture heated to 95 C for 2 hours. The solvent was evaporated and the residue was purified by trituration with DCM (20 mL) to give the title compound as a brown solid (1.25 g, 60%); 'H NMR (DMSO-d6) 5.21 (bs, 2H), 6.58-6. 70 (m, 3H), 7.03-7. 07 (m, 3H), 8.40 (s, 2H); MS m/e MH+ 211.
  • 4
  • [ 54060-30-9 ]
  • [ 56844-12-3 ]
  • 6-bromo-N-(3-ethynylphenyl)thieno[2,3-d]pyrimidin-4-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In isopropyl alcohol; at 80℃; for 24h;Inert atmosphere; Compound 3 (300 mg, 1.20 mmol) was dissolved in i-PrOH (6 mL) under nitrogen atmosphere. 3-Ethynylaniline (169 mg, 1.44 mmol) was added, and the mixture was stirred at 80 C for 24 h. The reaction mixture was concentrated, and the residue triturated with Et2O (50 mL). Drying yielded 357 mg (0.974 mmol, 81%) of 1t·HCl as a beige solid, mp 208-210 C; HPLC purity: 96%, tR=27.6 min. 1H NMR (400 MHz, DMSO-d6) delta: 9.91 (s, 1H), 8.55 (s, 1H), 8.22 (s, 1H), 8.07 (s, 1H), 7.90-7.85 (m, 1H), 7.40 (t, J=8.0, 1H), 7.23-7.20 (m, 1H), 4.21 (s, 1H); 13C NMR (100 MHz, DMSO-d6) delta: 166.9, 153.4, 153.3, 139.3, 129.1, 126.6, 124.0, 123.0, 121.9, 121.8, 117.9, 111.2, 83.4, 80.7; IR (neat, cm-1): 3263, 3045, 2484, 1623, 1475, 1443, 1294, 892, 787, 762, 625; HRMS (APCI/ASAP, m/z): 329.9693 (calcd. C14H979BrN3S, 329.9701, [M+H]+).
  • 5
  • [ 54060-30-9 ]
  • [ 55496-69-0 ]
  • (3-ethynylphenyl)-(7-methoxy-6-nitroquinazolin-4-yl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In isopropyl alcohol; for 1h;Reflux; Step 1: N-(3-ethynylphenyl)-7-methoxy-6-nitroquinazoline-4-amine The <strong>[55496-69-0]4-chloro-7-methoxy-6-nitroquinazoline</strong> (1.00 g, 4.17 mmol) was added into a solution of 3-ethynylaniline (0.49 g, 4.17 mmol) in isopropanol (15 mL), refluxed with heating for 1 h. Once the reaction was complete, the solution was cooled and filtered, and the compound shown in the title (1.12 g, 84%) was obtained. 1H NMR (DMSO-d6): delta 11.08 (1H, br), 9.47 (1H, s), 8.89 (1H, s), 7.95 (1H, s), 7.79-7.82 (1H, m), 7.56 (1H, s), 7.47-7.52 (1H, m), 7.37-7.40 (1H, m), 4.27 (1H, s), 4.10 (3H, s).
  • 6
  • [ 54060-30-9 ]
  • [ 55496-69-0 ]
  • [ 1012057-52-1 ]
  • 7
  • [ 68500-37-8 ]
  • [ 54060-30-9 ]
  • N-(3-ethynylphenyl)-7-methoxyquinolin-4-amine [ No CAS ]
  • 8
  • [ 54060-30-9 ]
  • [ 150449-97-1 ]
  • [ 183321-26-8 ]
Reference: [1]ChemMedChem,2019
  • 9
  • [ 54060-30-9 ]
  • [ 364793-57-7 ]
  • 7-bromo-4-((3-ethynylphenyl)amino)quinoline-3-carbonitrile [ No CAS ]
Reference: [1]ChemMedChem,2019
  • 10
  • [ 32846-66-5 ]
  • [ 54060-30-9 ]
  • N1,N4-bis(3’-ethynylphenyl)cubane-1,4-dicarboxamide [ No CAS ]
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