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[ CAS No. 3218-49-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 3218-49-3
Chemical Structure| 3218-49-3
Chemical Structure| 3218-49-3
Structure of 3218-49-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3218-49-3 ]

CAS No. :3218-49-3 MDL No. :MFCD00001909
Formula : C8H5Cl2N Boiling Point : -
Linear Structure Formula :- InChI Key :QWZNCAFWRZZJMA-UHFFFAOYSA-N
M.W : 186.04 Pubchem ID :76690
Synonyms :

Calculated chemistry of [ 3218-49-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.98
TPSA : 23.79 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) : -5.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 3.28
Log Po/w (WLOGP) : 3.06
Log Po/w (MLOGP) : 2.94
Log Po/w (SILICOS-IT) : 3.4
Consensus Log Po/w : 2.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.4
Solubility : 0.0745 mg/ml ; 0.0004 mol/l
Class : Soluble
Log S (Ali) : -3.45
Solubility : 0.0653 mg/ml ; 0.000351 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.12
Solubility : 0.0141 mg/ml ; 0.0000757 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.35

Safety of [ 3218-49-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3218-49-3 ]

* 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 [ 3218-49-3 ]
  • Downstream synthetic route of [ 3218-49-3 ]

[ 3218-49-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 6011-14-9 ]
  • [ 151169-75-4 ]
  • [ 3218-49-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 2
  • [ 5807-30-7 ]
  • [ 55305-43-6 ]
  • [ 3218-49-3 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 7, p. 3530 - 3537
  • 3
  • [ 143-33-9 ]
  • [ 102-47-6 ]
  • [ 3218-49-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 8, p. 2632 - 2638
[2] Journal of Organic Chemistry, 1960, vol. 25, p. 2066 - 2067
[3] Phytochemistry (Elsevier), 1988, vol. 27, # l, p. 51 - 72
  • 4
  • [ 151-50-8 ]
  • [ 18880-04-1 ]
  • [ 3218-49-3 ]
Reference: [1] Journal of Organometallic Chemistry, 1996, vol. 507, # 1-2, p. 1 - 21
[2] Scientia Pharmaceutica, 2001, vol. 69, # 4, p. 329 - 350
[3] Patent: US2479295, 1946, ,
  • 5
  • [ 95-75-0 ]
  • [ 3218-49-3 ]
Reference: [1] Journal of Organometallic Chemistry, 1996, vol. 507, # 1-2, p. 1 - 21
  • 6
  • [ 102-47-6 ]
  • [ 3218-49-3 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2395
  • 7
  • [ 1805-32-9 ]
  • [ 3218-49-3 ]
Reference: [1] Scientia Pharmaceutica, 2001, vol. 69, # 4, p. 329 - 350
  • 8
  • [ 151-50-8 ]
  • [ 102-47-6 ]
  • [ 3218-49-3 ]
Reference: [1] Canadian Journal of Chemistry, 1960, vol. 38, p. 2042 - 2052
  • 9
  • [ 143-33-9 ]
  • [ 18880-04-1 ]
  • [ 3218-49-3 ]
Reference: [1] Il Farmaco; edizione scientifica, 1970, vol. 25, # 6, p. 409 - 421
  • 10
  • [ 3218-49-3 ]
  • [ 5807-30-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 11, p. 2241 - 2249
[2] Journal of Organic Chemistry, 1946, vol. 11, p. 636,638
[3] Phytochemistry (Elsevier), 1988, vol. 27, # l, p. 51 - 72
[4] Scientia Pharmaceutica, 2001, vol. 69, # 4, p. 329 - 350
[5] Patent: WO2006/23659, 2006, A2, . Location in patent: Page/Page column 21-22
[6] Patent: US4584293, 1986, A,
[7] Patent: US2007/43100, 2007, A1, . Location in patent: Page/Page column 9
  • 11
  • [ 3218-49-3 ]
  • [ 21581-45-3 ]
YieldReaction ConditionsOperation in experiment
92% With ammonia; hydrogen In ethanol; water for 6 h; Method A.
A solution of 3,4-dichlorophenylacetonitrile (3.001 g, 16.13 mmol) in ethanol (33 mL) and 29percent NH4OH (6.7 ml, 611.2 mg, 17.44 mmol) in the presence of Raney Ni (333 mg, 3.887 mmol) was stirred vigorously under H2 (1 atm) for 6 h.
The reaction mixture was filtered through Celite then the filtrate was concentrated under reduced pressure to give 2-(3,4-dichlorophenyl)ethylamine (2.82 g, 92percent) as a pale yellow oil. LC/MS ((10percent-99percent CH3CN (0.035percent TFA)/H2O (0.05percent TFA)), m/z: M+1 obs=190.3; tr=0.80 min.
85% With potassium borohydride; copper dichloride In water; isopropyl alcohol at 60℃; for 5 h; General procedure: General procedure for the reduction of nitrile by KBH4and CuCl2:To a 10 mL round-bottomed flask was added 2-(4-chlorophenyl)acetonitrile (0.1 5 g, 1 mmol), KBH4 (0.17 g, 3mmol), CuCl2 (0.03 g, 0.25 mmol) and 80 percent isopropanol (1.6mL isopropanol and 0.4 mL water). The reaction completed in8 h at 60 °C as evidenced by TLC (DCM:MeOH 10:1). Thereaction mixture was cooled to 25 °C and removed the solvent.Ethyl acetate (5 mL) was added to the residue, washed withwater (1 mL) and brine (1 mL). The organic layer were dried withanhydrous Na2SO4, filtered and evaporated in vacuo to affordthe crude product.
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877
[2] Patent: US2009/124655, 2009, A1, . Location in patent: Page/Page column 27-28
[3] Asian Journal of Chemistry, 2015, vol. 27, # 10, p. 3564 - 3566
[4] Gazzetta Chimica Italiana, 1956, vol. 86, p. 1054,1058
[5] Journal of Organic Chemistry, 1957, vol. 22, p. 1323,1325
[6] Canadian Journal of Chemistry, 1960, vol. 38, p. 2042 - 2052
[7] Journal of medicinal chemistry, 1973, vol. 16, # 2, p. 101 - 106
[8] Journal of Organic Chemistry, 1960, vol. 25, p. 2066 - 2067
[9] Patent: US2009/124655, 2009, A1, . Location in patent: Page/Page column 28
[10] Patent: DE1109700, 1959, ,
  • 12
  • [ 67-56-1 ]
  • [ 3218-49-3 ]
  • [ 6725-44-6 ]
Reference: [1] Patent: WO2012/75473, 2012, A1, . Location in patent: Page/Page column 64-65
[2] Patent: US2016/346249, 2016, A1, . Location in patent: Paragraph 0173
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