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[ CAS No. 81167-60-4 ] {[proInfo.proName]}

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Type HazMat fee for 500 gram (Estimated)
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Limited Quantity USD 15-60
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3d Animation Molecule Structure of 81167-60-4
Chemical Structure| 81167-60-4
Chemical Structure| 81167-60-4
Structure of 81167-60-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 81167-60-4 ]

CAS No. :81167-60-4 MDL No. :MFCD12131129
Formula : C9H12ClN Boiling Point : -
Linear Structure Formula :- InChI Key :UGGNULHQVUWRGQ-UHFFFAOYSA-N
M.W : 169.65 Pubchem ID :57345981
Synonyms :

Calculated chemistry of [ 81167-60-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.44
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.52
TPSA : 12.89 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) : -4.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 3.49
Log Po/w (WLOGP) : 3.03
Log Po/w (MLOGP) : 2.37
Log Po/w (SILICOS-IT) : 3.09
Consensus Log Po/w : 2.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.43
Solubility : 0.0633 mg/ml ; 0.000373 mol/l
Class : Soluble
Log S (Ali) : -3.44
Solubility : 0.0611 mg/ml ; 0.00036 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.85
Solubility : 0.0242 mg/ml ; 0.000143 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.63

Safety of [ 81167-60-4 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P201-P202-P260-P262-P264-P270-P271-P272-P273-P280-P261-P301+P330+P331-P302+P352-P304+P340-P305+P351+P338-P312-P330-P333+P313-P337+P313-P361-P363-P403+P233-P501 UN#:2810
Hazard Statements:H302-H311+H331-H315-H318-H335-H373-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 81167-60-4 ]

* 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 [ 81167-60-4 ]
  • Downstream synthetic route of [ 81167-60-4 ]

[ 81167-60-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 81167-60-4 ]
  • [ 72914-19-3 ]
YieldReaction ConditionsOperation in experiment
90% With manganese; nickel(II) bromide trihydrate In N,N-dimethyl-formamide at 20 - 60℃; for 20 h; Inert atmosphere General procedure: On the benchtop, a 50 mL round-bottomed flask equipped with a inch Teflon coated magnetic stir bar was charged with NiBr2·3H2O(401 mg, 1.47 mmol) and DMF (20.0 mL). The vessel was stopperedwith a rubber septum and heated to 60 °C until a green homogeneoussolution resulted (approx. 20 min). Once homogeneity wasachieved, the vessel was removed from the heat and allowed to coolto r.t. Once at r.t., 4-tert-butyl-2-chloropyridine (2a; 4.99 g, 29.4mmol) and Mn powder (–325 mesh, 3.30 g, 60.0 mmol) were added,and the vessel was resealed with the septum, purged with argon, andheated again to 60 °C for the duration of the reaction. Reactionprogress was monitored by GC analysis of aliquots of the crude reactionmixture. In general, the reaction turns very dark brown orblack in color when complete, and the color change is a reliable indicatorfor the reaction endpoint. Upon completion, the reactionmixture was cooled to r.t., diluted with Et2O (80 mL), and filteredthrough a short pad of Celite (approx. 2 in × 2 in × 2 in) that hadbeen wetted with Et2O to remove metal salts. The reaction vesselwas washed with Et2O (2 × 40 mL) and the washings were thenpassed through the filter. The combined filtrates were transferred toa separatory funnel and washed with aq 1 M NaOH (200 mL). Abrown emulsion formed in the separatory funnel during the workupthat slowly separated. Care was taken to keep the brown emulsion with the organics. Once separated, the aqueous layer was extractedwith additional Et2O (3 × 150 mL). The combined organic extracts and brown emulsion were washed with brine (500 mL). Again carewas taken to keep the brown emulsion with the organics. The organicswere dried with copious amounts of MgSO4. The solid dryingagent was removed by filtration, ground into a fine powder, andwashed with additional Et2O (3 × 150 mL). The filtrate was evaporated to dryness to give 3a (3.57 g) as faintly yellow crystals in 90percentyield. This material was judged analytically pure by NMR and combustion analysis. If necessary the product can be further purified bysublimation (140 °C/300 mtorr).
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 22, p. 3099 - 3102
  • 2
  • [ 81167-60-4 ]
  • [ 50488-34-1 ]
YieldReaction ConditionsOperation in experiment
80% for 48 h; Reflux Compound L4-2 (3 g, 17.6 mmol) and trimethylsilyl bromide (7 ml, 53.05 mmol) were placed in a reaction flask, and 50 ml of propionitrile was then added to the reaction flask to obtain a mixture. The mixture was heated under reflux for reaction for 24 hours, and was allowed to cool to 20° C., followed by further addition of trimethylsilyl bromide (7 ml, 53.05 mmol) to the reaction flask. Next, the contents in the reaction flask were further heated under reflux for another 24 hours, and then the temperature was slowly reduced to 20° C. Thereafter, the reaction flask was vacuum pumped to remove the solvents from the contents in the reaction flask, a sodium carbonate aqueous solution was added to the reaction flask for neutralization, and the contents in the reaction flask were extracted using ethyl acetate to collect a first organic layer. The first organic layer was dehydrated using sodium sulfate (Na2SO4), and was washed several times with ethyl acetate and with a saturated sodium chloride aqueous solution to collect a second organic layer. The second organic layer was dehydrated using sodium sulfate (Na2SO4) to obtain a crude product. The crude product was subjected to column chromatography (SiO2, ethyl acetate:n-hexane=1:6), thereby obtaining a yellow oil (3 g, 80percent yield). (0082) The spectrum analysis for the yellow oil is: 1H NMR (400 MHz, CDCl3): δ 8.22 (d, J=5.2 Hz, 1H), 7.41 (s, 1H), 7.20 (dd, J=5.2 Hz, 1.6 Hz, 1H), 1.26 (s, 9H). The yellow oil was confirmed to be Compound L4-3 having a chemical structure represented by
Reference: [1] Patent: US9219237, 2015, B1, . Location in patent: Page/Page column 13
  • 3
  • [ 23569-17-7 ]
  • [ 81167-60-4 ]
YieldReaction ConditionsOperation in experiment
72% for 24 h; Reflux Compound L4-1 (5 g, 33.07 mmol) was placed in a two-neck flask. The two-neck flask was cooled in an ice bath, and 25 ml of phosphoryl chloride (POCl3) was slowly added to the two-neck flask to obtain a mixture. The mixture was heated under reflux for 24 hours for reaction. Thereafter, the temperature was slowly reduced to 20° C., the solvent was removed from the mixture by vacuum pumping, a sodium carbonate aqueous solution was added to the two-neck flask for neutralization, and the contents in the two-neck flask were extracted using ethyl acetate to collect an organic layer. The organic layer was dehydrated using sodium sulfate (Na2SO4) to obtain a crude product. The crude product was subjected to column chromatography (SiO2, ethyl acetate:n-hexane=1:6), thereby obtaining a transparent liquid (4 g, 72percent yield). (0079) The spectrum analysis for the transparent liquid is: 1H-NMR (400 MHz, CDCl3): δ 8.27 (d, J=5.3 Hz, 1H), 7.28 (s, 1H), 7.19 (dd, J=5.2 Hz, 1.6 Hz, 1H), 1.29 (s, 9H). The transparent liquid was confirmed to be Compound L4-2 having a chemical structure represented by
Reference: [1] Organometallics, 2011, vol. 30, # 24, p. 6751 - 6765
[2] Synthesis (Germany), 2013, vol. 45, # 22, p. 3099 - 3102
[3] Patent: US9219237, 2015, B1, . Location in patent: Page/Page column 13
[4] Patent: WO2012/41476, 2012, A1, . Location in patent: Page/Page column 52
[5] Inorganica Chimica Acta, 2012, vol. 383, p. 316 - 319
[6] Inorganic Chemistry, 2012, vol. 51, # 4, p. 2263 - 2271
[7] Patent: EP2441755, 2012, A1, . Location in patent: Paragraph 0159
[8] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12321 - 12324[9] Angew. Chem., 2016, vol. 128, p. 12509 - 12512,4
[10] Patent: JP2017/39654, 2017, A, . Location in patent: Paragraph 0160; 0161
  • 4
  • [ 3978-81-2 ]
  • [ 81167-60-4 ]
Reference: [1] Patent: WO2012/41476, 2012, A1,
[2] Patent: EP2441755, 2012, A1,
[3] Synthesis (Germany), 2013, vol. 45, # 22, p. 3099 - 3102
[4] Patent: US9219237, 2015, B1,
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12321 - 12324[6] Angew. Chem., 2016, vol. 128, p. 12509 - 12512,4
[7] Patent: JP2017/39654, 2017, A,
  • 5
  • [ 109-09-1 ]
  • [ 38442-51-2 ]
  • [ 81167-60-4 ]
  • [ 97691-23-1 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 18, p. 3423 - 3425
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