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[ CAS No. 3843-97-8 ] {[proInfo.proName]}

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Chemical Structure| 3843-97-8
Chemical Structure| 3843-97-8
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Product Details of [ 3843-97-8 ]

CAS No. :3843-97-8 MDL No. :MFCD20694404
Formula : C8H10ClN Boiling Point : -
Linear Structure Formula :- InChI Key :GXMFLLVURQXDPD-UHFFFAOYSA-N
M.W : 155.62 Pubchem ID :12465045
Synonyms :

Calculated chemistry of [ 3843-97-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.63
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) : -5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.99
Log Po/w (XLOGP3) : 2.67
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 2.72
Log Po/w (SILICOS-IT) : 2.54
Consensus Log Po/w : 2.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.86
Solubility : 0.212 mg/ml ; 0.00136 mol/l
Class : Soluble
Log S (Ali) : -2.87
Solubility : 0.211 mg/ml ; 0.00135 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.43
Solubility : 0.0577 mg/ml ; 0.000371 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 3843-97-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3843-97-8 ]

* 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 [ 3843-97-8 ]
  • Downstream synthetic route of [ 3843-97-8 ]

[ 3843-97-8 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 2001-16-3 ]
  • [ 3843-97-8 ]
YieldReaction ConditionsOperation in experiment
100% With iron(III) chloride; amino aminoalcohol In methanol at 20 - 80℃; for 5 h; Sealed tube Step 3:ο a mixture of 4-chloro-l-ethyl-2-nitrobenzene (0.9 g, 4.9 mmol), iron (III) chloride (0.13 g, 0.49 mmol), and charcoal (80 mg, 6.6 mmol) in methanol (17 ml) was added hydrazine hydrate (0.95 ml, 20 mmol) in methanol (7 ml). The reaction mixture was stirred at rt as gas was evolved. When gas evolution ceased, the vial was sealed and heated at 80 deg C for 5 h (**pressure builds over time and vial needed to be vented frequently). The mixture was cooled to rt and filtered through celite washing with methanol, concentrated, and purified by silica gel chromatography (gradient 0 to 50percent EtOAc/hexanes). The product, aniline 4, is a light yellow oil (quant.); 1H NMR (400 MHz, DMSO-d6) δ 6.86 (dd, = 8.0, 0.7 Hz, 1H), 6.59 (d, = 2.2 Hz, 1H), 6.44 (dd, 7 = 8.0, 2.2 Hz, 1H), 5.11 (s, 2H), 2.43 - 2.31 (m, 2H), 1.06 (t, J = 7.5 Hz, 3H).
97% With iron(III) chloride; hydrazine hydrate In methanol for 13 h; Reflux Step 3 : 5-Chloro-2-ethylanilineA solution of hydrazine hydrate (6.95 mL, 134.7 mmol) in MeOH (50 mL) was added dropwise to a solution of 4- chloro-1-ethyl-2-nitrobenzene (6.25 g, 33.7 mmol) in MeOH (120 mL), in the presence of iron(lll) chloride (547 mg, 3.4 mmol) and activated charcoal (547 mg), and the reaction mixture was stirred under reflux for 13 h. The solids were filtered over celite, the filtrate concentrated and purified by flash chromatography (hexane:AcOEt 9:1) to obtain the title compound as a light-pink oil (5.09 g, 97percent).1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (t, J =7.51 Hz, 3 H), 2.39 (q, J =7.49 Hz, 2 H), 5.13 (s, 2 H), 6.47 (dd, J =8.06, 2.20 Hz, 1 H), 6.62 (d, J =2.20 Hz, 1 H), 6.89 (d, J =8.06 Hz, 1 H).
97% With iron(III) chloride; hydrazine hydrate In methanol for 13 h; Reflux Step 3: 5-Chloro-2-ethylanilineA solution of hydrazine hydrate (6.95 mL, 134.7 mmol) in methanol (50 mL) was added drop wise to a solution of 4- chloro-1-ethyl-2-nitrobenzene (6.25 g, 33.7 mmol) in methanol (120 mL), in the presence of iron (III) chloride (547 mg, 3.4 mmol) and activated charcoal (547 mg) and the reaction mixture was stirred under reflux for 13 h. The solids were filtered over celite, the filtrate concentrated and purified by flash chromatography (hexane/EtOAc 9/1) to obtain the title compound as a light-pink oil (5.09 g, 97percent).1H NMR (400 MHz, DMSO- /6) δ ppm 1.09 (t, J=7.51 Hz, 3 H), 2.39 (q, J=7A9 Hz, 2 H), 5.13 (s, 2 H), 6.47 (dd, J=8.06, 2.20 Hz, 1 H), 6.62 (d, J=2.20 Hz, 1 H), 6.89 (d, J=8.06 Hz, 1 H).
97% With iron(III) chloride; hydrazine hydrate In methanol for 14 h; Reflux Step 3: 5’Chloro.2.ethylenlllne A solution of hydrazine hydrate (6.95 itt, 134.7 mmd) In methand (50 nt) was added drop wise to a sdudon of 4-chloro-1-ethyl-2-nlb’cbenzene (6.25 g, 33.7 mmd) In methanol (120 nt), In the presence of Iron (Ill) chloride (547mg,3Ammd)andacdedcftm&(M7mg)andthereadionmbcbirewasstirredunderrefiuxtrl4h.Thesolidswere removed by filtration through Celite, the titrate concentrated and purified by flash chromatography(hexanelEtOAc WI) to obtain the dUe compound as a light-pink 01(5.099,97percent).1H NMR (400 MHz, DM8O.) 86.89 (d, J= 8.0 Hz, IH), 6.62 (d, J= 22Hz, IH), 6.47 (dd, J=2.2, 8.0 Hz, IH), 5.12(s, 2H), 2.39 (q, J= 7.5 Hz, 2H), 1.09 (t, J= 7.4Hz, 3H).
97% With iron(III) chloride; pyrographite; hydrazine hydrate In methanol for 13 h; Reflux Step 3:
5-Chloro-2-ethylaniline
A solution of hydrazine hydrate (6.95 mL, 134.7 mmol) in MeOH (50 mL) was added dropwise to a solution of 4-chloro-1-ethyl-2-nitrobenzene (6.25 g, 33.7 mmol) in MeOH (120 mL), in the presence of iron(III) chloride (547 mg, 3.4 mmol) and activated charcoal (547 mg), and the reaction mixture was stirred under reflux for 13 h.
The solids were filtered over celite, the filtrate concentrated and purified by flash chromatography (hexane:AcOEt 9:1) to obtain the title compound as a light-pink oil (5.09 g, 97percent).
1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (t, J=7.51 Hz, 3H), 2.39 (q, J=7.49 Hz, 2H), 5.13 (s, 2H), 6.47 (dd, J=8.06, 2.20 Hz, 1H), 6.62 (d, J=2.20 Hz, 1H), 6.89 (d, J=8.06 Hz, 1H).

Reference: [1] Patent: WO2016/106331, 2016, A1, . Location in patent: Paragraph 0222
[2] Patent: WO2012/139930, 2012, A1, . Location in patent: Page/Page column 72
[3] Patent: WO2012/143248, 2012, A1, . Location in patent: Page/Page column 24
[4] Patent: WO2014/19908, 2014, A2, . Location in patent: Page/Page column 33
[5] Patent: US2014/51708, 2014, A1, . Location in patent: Paragraph 0722; 0723
[6] Journal of Organic Chemistry, 1957, vol. 22, p. 639,641
[7] Patent: US2012/15962, 2012, A1, . Location in patent: Page/Page column 75
[8] Patent: CN104163764, 2016, B, . Location in patent: Paragraph 0050-0053
[9] Patent: WO2017/223202, 2017, A1, . Location in patent: Paragraph 0119
  • 2
  • [ 589-16-2 ]
  • [ 3843-97-8 ]
Reference: [1] Patent: US2012/15962, 2012, A1,
[2] Patent: WO2012/139930, 2012, A1,
[3] Patent: WO2012/143248, 2012, A1,
[4] Patent: WO2014/19908, 2014, A2,
[5] Patent: US2014/51708, 2014, A1,
[6] Patent: WO2016/106331, 2016, A1,
[7] Patent: WO2017/223202, 2017, A1,
  • 3
  • [ 51529-96-5 ]
  • [ 3843-97-8 ]
Reference: [1] Patent: US2012/15962, 2012, A1,
[2] Patent: WO2012/139930, 2012, A1,
[3] Patent: WO2012/143248, 2012, A1,
[4] Patent: WO2014/19908, 2014, A2,
[5] Patent: US2014/51708, 2014, A1,
[6] Patent: WO2016/106331, 2016, A1,
[7] Patent: WO2017/223202, 2017, A1,
  • 4
  • [ 5805-89-0 ]
  • [ 3843-97-8 ]
Reference: [1] Patent: US2012/15962, 2012, A1,
  • 5
  • [ 3663-34-1 ]
  • [ 3843-97-8 ]
Reference: [1] Patent: US2012/15962, 2012, A1,
  • 6
  • [ 622-98-0 ]
  • [ 3843-97-8 ]
Reference: [1] Journal of Organic Chemistry, 1957, vol. 22, p. 639,641
  • 7
  • [ 74-85-1 ]
  • [ 108-42-9 ]
  • [ 3843-97-8 ]
Reference: [1] Angewandte Chemie, 1957, vol. 69, p. 124,126
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