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[ CAS No. 24006-09-5 ] {[proInfo.proName]}

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Chemical Structure| 24006-09-5
Chemical Structure| 24006-09-5
Structure of 24006-09-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 24006-09-5 ]

CAS No. :24006-09-5 MDL No. :MFCD00052268
Formula : C9H15ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 186.68 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 24006-09-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 55.51
TPSA : 38.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.05
Log Po/w (WLOGP) : 2.51
Log Po/w (MLOGP) : 2.64
Log Po/w (SILICOS-IT) : 1.71
Consensus Log Po/w : 1.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.22
Solubility : 0.112 mg/ml ; 0.000599 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.057 mg/ml ; 0.000305 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.23
Solubility : 0.109 mg/ml ; 0.000585 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.36

Safety of [ 24006-09-5 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P301+P310+P330-P405-P501 UN#:2811
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 24006-09-5 ]

* 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 [ 24006-09-5 ]
  • Downstream synthetic route of [ 24006-09-5 ]

[ 24006-09-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 88-05-1 ]
  • [ 24006-09-5 ]
YieldReaction ConditionsOperation in experiment
54%
Stage #1: With hydrogenchloride In water at -5℃; for 0.75 - 0.833333 h;
Stage #2: With sodium nitrite In water for 1 - 1.25 h;
A 3.0 L, 3-neck round bottom flask equipped with a mechanical stirrer and an addition funnel was charged with concentrated hydrochloric acid (0.125 L) and deionized water ( 0.100 L ). The solution was cooled to -5 0C in an ice/salt water bath, and 2,4,6-trimethylaniline (70 niL, 0.50 mol, 1.0 equiv.) was added dropwise over 30 minutes; during this time a white precipitate formed. The mixture was stirred for an additional 15-20 minutes before 52.5 mL of a 9.5 M aq. solution of sodium nitrite (70 mL, 0.50 mol, 1.0 equiv. ) was added dropwise over 30^45 minutes. The resulting brown solution was allowed to stir for 30 minutes before a 3.3 M solution of stannous chloride dihydrate in 1 : 1 concentrated HChH2O (0.455 L, 1.5 mol, 2.5 equiv.) was added over 4 hours with vigorous stirring. (Upon addition of the stannous chloride solution a thick light orange slurry had formed which sometimes caused seizure of the mechanical stirrer. Addition small amounts of deionized water helped to facilitate stirring again.) The mixture was allowed to warm to room temperature and stirred vigorously for 16 hours. The mixture was cooled to 0 0C for 1 hour before filtering through a fine porosity glass fritted buchner funnel, and the collected orange solid washed with brine and diethyl ether. This orange solid was added to a 2-L round-bottom charged with 10 M NaOH(aq) (1.0 L) and diethyl ether (0.700 L) and cooled to -5 0C. Once nearly all of the solid had dissolved (ca. 1 h), the organic layer was removed, and the aqueous layer extracted with diethyl ether (2 x 0.400 L). The combined organic fractions were dried over Na2SO4, filtered into a flame-dried 2.0 L round-bottom flask, placed under an atmosphere of N2(g), cooled to 0 0C, and treated with 4 M HCl in 1 ,4-dioxane (0.125 L). A white precipitate formed, was collected by vacuum filtration, washed with diethyl ether, and recrystalized from 200 proof EtOH to afford the title compound (50 g, 0.27 mol, 54percent) as a white powder. 1H NMR (400 MHz, DMSO) δ 9.57 (3H, s, br, NH, varies), 6.89 (s, 2H), 2.33 (s, 6H), 2.21 (s, 3H); 13C NMR (100 MHz, DMSO) δ 138.06, 136.20, 135.01, 129.17, 20.54, 17.95; IR <n="56"/>(thin film) v 3294, 3002, 2964, 2911, 2680, 1564, 1513, 1481, 852, 825, 753 cm"1; HRESI+/TOF-MS calcd for C9Hi5N2+ [M]+ 151.1230, found 134.0921 for aniline anion radical (134.0975).
45%
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℃;
General procedure: 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.
Reference: [1] Patent: WO2007/124494, 2007, A2, . Location in patent: Page/Page column 54-55
[2] Tetrahedron, 2016, vol. 72, # 17, p. 2186 - 2195
[3] Organic Syntheses, 2010, vol. 87, p. 362 - 376
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