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[ CAS No. 2538-61-6 ] {[proInfo.proName]}

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Chemical Structure| 2538-61-6
Chemical Structure| 2538-61-6
Structure of 2538-61-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2538-61-6 ]

CAS No. :2538-61-6 MDL No. :MFCD01861265
Formula : C8H13ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :GQKQMDUOOZVZFD-UHFFFAOYSA-N
M.W : 172.66 Pubchem ID :12405010
Synonyms :

Calculated chemistry of [ 2538-61-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 49.43
TPSA : 38.05 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.69
Log Po/w (WLOGP) : -1.49
Log Po/w (MLOGP) : 2.34
Log Po/w (SILICOS-IT) : 1.25
Consensus Log Po/w : 0.96

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.197 mg/ml ; 0.00114 mol/l
Class : Soluble
Log S (Ali) : -3.14
Solubility : 0.125 mg/ml ; 0.000722 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.83
Solubility : 0.254 mg/ml ; 0.00147 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.15

Safety of [ 2538-61-6 ]

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

Application In Synthesis of [ 2538-61-6 ]

* 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.

  • Upstream synthesis route of [ 2538-61-6 ]
  • Downstream synthetic route of [ 2538-61-6 ]

[ 2538-61-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 85518-80-5 ]
  • [ 2538-61-6 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride; tin(ll) chloride In water at 0 - 20℃; for 6.41667 h; To a cold (0° C.) solution of 2,6-dimethylaniline (5.0 g, 41.3 mmol) in 50percent aqueous HCl (45 mL), was added slowly under stirring a cold (0° C.) solution of NaNO2 (2.85 g, 41.3 mmol) in water (22.5 mL). The temperature was closely monitored during the addition and was not allowed to exceed 5° C. Upon completion of the addition, the bright orange solution containing the diazonium salt intermediate was stirred at the same temperature for 20 min. A mixture of SnCl2 (11.0 g, 57.8 mmol) in conc HCl (30 mL) was added to the reaction mixture at 0° C. over a period of 5 min. The reaction mixture was then warmed to rt and stirred for 6 h. The precipitate was collected by filtration and washed with a small volume of cold water. Drying in vacuo afforded the title compound as a white amorphous solid (7.00 g, 98percent). The product was used in the next step without further purification. ES-MS m/z 137.0 (MH+); HPLC RT (min) 1.09.
Reference: [1] Patent: US2005/192294, 2005, A1, . Location in patent: Page/Page column 10
  • 2
  • [ 87-62-7 ]
  • [ 2538-61-6 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: With hydrogenchloride; sodium nitrite In water at -4 - 0℃; for 0.5 h;
Stage #2: With hydrogenchloride; tin(II) chloride hydrate In water at 20℃;
Stage #3: With sodium hydroxide In water at 15℃;
To a mixture of concentrated HCl (50 mL) and water (40 mL) was added 2,6-dimethylaniline (24.2 g, 0.2 mol) under vigorous stirring. The resulting mixture was cooled to −4 °C, and a solution of NaNO2 (15.2 g, 0.22 mol) in water (30 mL) was added dropwise to maintain temperature below 0 °C. After addition of the sodium nitrite solution, the reaction mixture was stirred for 30 min. A solution of stannous dichloride hydrate (112.8 g, 0.5 mol) in 160 mL of 6 mol/L hydrochloric acid was added over a period of 1.5 h, during which the temperature of the reaction mixture was maintained below 5 °C. The yellowish slurry was allowed to stand overnight at room temperature and stirring was continued for another 22 h. And then the mixture was cooled by ice-water for 1 h. The pale yellow tin complex salt was collected by filtration, dried on the funnel and washed with brine (50 mL), and ether (2×50 mL). The dry complex salt was stirred in water (100 mL), and slurry was stirred vigorously while it was treated with 10 mol/L NaOH (100 mL). The temperature of the mixture was maintained below 15 °C. The crude hydrazine was extracted from the mixture with ether (2×200 mL), and the etheral solution was washed with water (200 mL) and dried over Na2SO4. The dried etheral solution was diluted with ether to 500 mL. The diluted solution was treated with 4.8 mol/L HCl in 1,4-dioxane (50 mL) until precipitation of the hydrazine hydrochloride was complete. The filtered hydrochloride was washed with ether (50 mL), dried over Na2SO4, and recrystallized from ethanol to afford 2,6-dimethylphenylhydrazine hydrochloride salt as colorless crystals 21.9 g in 63percent yield. 4.2.1. 2,6-Dimethylphenylhydrazine hydrochloride salt. Colorless crystals, mp 210–212 °C dec (Lit.15 211 °C dec), 1H NMR (300 MHz, DMSO-d6) δ: 2.39 (s, 6H), 6.71 (br s, 1H), 7.08 (s, 3H), 9.82 (s, 3H). 13C NMR (50 MHz, DMSO-d6) δ: 140.6, 134.9, 128.6, 126.9, 18.0.
Reference: [1] Chinese Journal of Chemistry, 2012, vol. 30, # 4, p. 919 - 923
[2] Tetrahedron, 2016, vol. 72, # 17, p. 2186 - 2195
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