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[ CAS No. 78667-04-6 ] {[proInfo.proName]}

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Chemical Structure| 78667-04-6
Chemical Structure| 78667-04-6
Structure of 78667-04-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 78667-04-6 ]

CAS No. :78667-04-6 MDL No. :MFCD00234118
Formula : C5H8Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :JDIPKQBKSBWIKU-UHFFFAOYSA-N
M.W : 167.04 Pubchem ID :2795406
Synonyms :

Calculated chemistry of [ 78667-04-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.22
TPSA : 17.82 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) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.24
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 0.67
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 1.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.0
Solubility : 1.66 mg/ml ; 0.00996 mol/l
Class : Soluble
Log S (Ali) : -1.21
Solubility : 10.2 mg/ml ; 0.0614 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.78
Solubility : 2.77 mg/ml ; 0.0166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 78667-04-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 78667-04-6 ]

* 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 [ 78667-04-6 ]
  • Downstream synthetic route of [ 78667-04-6 ]

[ 78667-04-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 17334-08-6 ]
  • [ 78667-04-6 ]
YieldReaction ConditionsOperation in experiment
95% With thionyl chloride In diethyl ether; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran Synthesis of 2-(Chloromethyl)-1-methyl-1H-imidazole Hydrochloride (BB7)
To a solution of (BB6) (35.5 g, 316.96 mmol) in DCM (1500 mL) was added SOCl2 (330 mL, 4436 mmol) at 0° C.
The reaction was warmed to ambient temperature and stirred for 5 h.
The reaction mixture was concentrated, the residue was washed with DCM (2*500 mL), followed by Et2O (2*200 mL) to obtain (BB7) (50 g, 95percent) as an off-white solid. Rf: 0.4 (EtOAc).
1H NMR (400 MHz, DMSO-d6): δ 7.76 (1H, app d), 7.70 (1H, app d), 5.17 (2H, s), 3.87 (3H, s); ink 131 (MH)+.
88% Cooling with ice; Reflux 1-Methyl-2-hydroxymethyl imidazole (15.0 g, 134 mmol) was added, with shaking and exclusion of moisture, over a period of 15 min to ice cooled thionyl dichloride (24.6 mL, 30 g, 0.25 mol). The reactants were then heated under reflux for 15 min. The cooled solution was evaporated under reduced pressure followed by recrystallization from ethanol (25 mL) and dried under high vacuum to give 2-(chloromethy1)-1-methyl-1H-imidazole hydrochloride as brown crystals. Yield: 15.1g, 88percent. 1H NMR (CDCl3) δ ppm: 7.79 (s, 1H), 7.70 (s, 1H), 5.2 (s, 2H), 3.86 (s, 3H). 3C NMR (CD3OD) δ ppm: 142.05, 124.7, 119.08, 33.9, 31.4. TOF-MS m/z: 131.0384 (M+H+, 100percent). Molecular formula of cation, C5H7N2Cl, calculated m/z of cation: 131.04 (M+H+)
78%
Stage #1: at 0℃; for 0.5 h; Reflux; Inert atmosphere
Stage #2: With hydrogenchloride In water
This compound was synthesised using a modified procedure described in literature.6 1-Methyl-2-hydroxymethyl imidazole (6.500 g, 58.000 mmol) was added in small portions to SOCl2 (12.7 mL, 174 mol) at 0 °C. The mixture was heated under reflux for 30 min. After cooling, the solution was concentrated under reduced pressure followed by recrystallization from ethanol (17 mL) to afford 2-(chloromethy1)-1-methyl-1H-imidazole hydrochloride. Yellow crystals; 7.580g, yield: 78percent. The NMR spectrum was according to literature.6 1H NMR (CDCl3) δ = 7.79 (d, 1H, J = 1.9 Hz; ImH), 7.70 (d, 1H, J = 1.9 Hz; ImH), 5.20 (s, 2H; CH2Cl), 3.86 ppm (s, 3H; NCH3).
Reference: [1] Patent: US2012/322722, 2012, A1,
[2] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5308 - 5310
[3] Tetrahedron, 1996, vol. 52, # 48, p. 15171 - 15188
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 19, p. 2291 - 2302
[5] Tetrahedron Letters, 2013, vol. 54, # 45, p. 6087 - 6089
[6] Organic and Biomolecular Chemistry, 2009, vol. 7, # 2, p. 229 - 231
[7] Patent: US6646122, 2003, B1, . Location in patent: Page/Page column 10
[8] Patent: EP1422228, 2004, A1, . Location in patent: Page 228
[9] Patent: EP1724263, 2006, A1, . Location in patent: Page/Page column 29
  • 2
  • [ 13750-81-7 ]
  • [ 78667-04-6 ]
Reference: [1] Tetrahedron, 1996, vol. 52, # 48, p. 15171 - 15188
[2] Patent: US2012/322722, 2012, A1,
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