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

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Limited Quantity USD 15-60
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Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
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Chemical Structure| 54060-30-9
Chemical Structure| 54060-30-9
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Product Citations

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 :- 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 Ų

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.

  • Upstream synthesis route of [ 54060-30-9 ]
  • Downstream synthetic route of [ 54060-30-9 ]

[ 54060-30-9 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 24424-99-5 ]
  • [ 54060-30-9 ]
  • [ 185619-66-3 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: at 70℃;
Stage #2: at 20℃; for 1 h;
Step a) (3-Ethynyl-phenyl)-carbamic acid tert-butyl ester
A solution of 3-ethynyl-phenylamine (25.0 g, 213 mmol) and di-tert-butyldicarbonate (93.1 g, 427 mmol) in THF (427 mL) was heated at 70° C. overnight.
The reaction was cooled to room temperature and then 3-dimethylamino-1-propylamine (32.1 g, 320 mmol) was added and allowed to stir at room temperature for 1 h.
The reaction was concentrated and taken in diethyl ether, washed with 1N HCl, brine, sodium bicarbonate, brine and dried over sodium sulfate and concentrated in vacuo to provide the title compound (45.0 g, 97percent), characterized by NMR and mass spectral analyses.
92% for 48 h; 3-aminophenylacetylene (10.5 mL) and di-tertbutyldicarbonate (44.0 g) in THF (250 mL) were stirred for 48 hours, concentrated in vacuo, dissolved in DCM, washed with water and concentrated in vacuo. Purification by flash chromatography on silica using 0-50percent DCM in isohexane as eluent gave the title compound as a yellow oil (20.0 g, 92percent); 'HNMR (CDC13) 1.52 (s, 9H), 3.04 (s, 1H), 6.45 (s, br, 1H), 7.15 (d, 1H), 7.23 (t, 1H), 7.35 (d, 1H), 7.52 (s, 1H) ; MS m/e (M-CH3) H+ 203.
90% Reflux Di-tert-butyl dicarbonate(123 ml,531 mmol)was added to a stirred solution of 3-ethynylaniline(56.6 g,483 mmol)in THF(300 mL). The mixture was heated to reflux for overnight. Themixture was then cooled to ambient temperature and taken up in ethyl acetate(500 mL)and washedsequentia11y with IN aqueous HCl(200 mL),saturated aqueous Na2C03(200 mL)and brine(200 mL).The organic layer was dried over Na2S04,concentrated in vacuo,and purified by silica gel columnchromatography(eluted with 15percent EtOac/PE)to give tert-butyl (3-ethynylphenyl)carbamate(94 g,435mmol,90percent yield). LCMS(Method f,Table 7)Rt=l.80 min; MS m/z = 162 [M-t-Bu+H+].
72% With triethylamine In tetrahydrofuran at 55℃; Example 459(S)-tert-butyl (3-[5-([methyl(oxo)phenyl-λ6-sulfanylidene]amino}carbonyl)pyridin-3- yl] ethynyl} phenyl)carbamate.Step 1 tert-butyl 3-ethynylphenylcarbamateA dry 25mL flask was charged with 3-ethynyl-phenylamine (0.100 g, 0.855 mmol) and THF (5 mL) was added. Di-tert-butyl dicarbonate (0.242 g, 1.11 mmol) was added to the THF solution followed by NEt3 (0.23mL, 1.71 mmol). The mixture was allowed to stir at 55 0C after which it was cooled to room temperature and extracted twice with EtOAc (-10 mL), water (-10 mL) and saturated aqueous NaHCO3. The combined organic extracts were dried over anhydrous Na2SO4(S) and then concentrated to give the title compound (0.13 g, 0.67 mmol, 72percent).

Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 20, p. 4232 - 4235
[2] Patent: US2009/48320, 2009, A1, . Location in patent: Page/Page column 39-40
[3] Patent: WO2005/60970, 2005, A1, . Location in patent: Page/Page column 148
[4] Patent: WO2017/210471, 2017, A1, . Location in patent: Paragraph 001146; 001147
[5] Patent: WO2008/61236, 2008, A2, . Location in patent: Page/Page column 71
[6] Patent: US2004/167188, 2004, A1,
[7] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4370 - 4373
[8] Patent: US2004/214870, 2004, A1, . Location in patent: Page 19
[9] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 678 - 688
  • 2
  • [ 54060-30-9 ]
  • [ 24608-52-4 ]
  • [ 185619-66-3 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 15, p. 8282 - 8289
  • 3
  • [ 54060-30-9 ]
  • [ 183322-18-1 ]
  • [ 179688-29-0 ]
  • [ 183319-69-9 ]
Reference: [1] Patent: WO2011/76813, 2011, A1, . Location in patent: Page/Page column 19
[2] Patent: EP2348020, 2011, A1, . Location in patent: Page/Page column 11
  • 4
  • [ 54060-30-9 ]
  • [ 55496-69-0 ]
  • [ 1012057-52-1 ]
Reference: [1] Patent: US2016/214964, 2016, A1,
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