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[ CAS No. 4760-34-3 ] {[proInfo.proName]}

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Chemical Structure| 4760-34-3
Chemical Structure| 4760-34-3
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Product Details of [ 4760-34-3 ]

CAS No. :4760-34-3 MDL No. :MFCD00192314
Formula : C7H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :RPKCLSMBVQLWIN-UHFFFAOYSA-N
M.W :122.17 Pubchem ID :78498
Synonyms :

Calculated chemistry of [ 4760-34-3 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.15
TPSA : 38.05 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) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.19
Log Po/w (XLOGP3) : 1.23
Log Po/w (WLOGP) : 1.13
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 0.81
Consensus Log Po/w : 1.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.8
Solubility : 1.94 mg/ml ; 0.0159 mol/l
Class : Very soluble
Log S (Ali) : -1.63
Solubility : 2.89 mg/ml ; 0.0236 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.43
Solubility : 0.454 mg/ml ; 0.00372 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 4760-34-3 ]

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

Application In Synthesis of [ 4760-34-3 ]

* 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 [ 4760-34-3 ]
  • Downstream synthetic route of [ 4760-34-3 ]

[ 4760-34-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 4760-34-3 ]
  • [ 20028-40-4 ]
Reference: [1] Patent: WO2018/172423, 2018, A1,
  • 2
  • [ 4760-34-3 ]
  • [ 459-73-4 ]
  • [ 20028-40-4 ]
Reference: [1] Journal of the Chemical Society, 1959, p. 2296
  • 3
  • [ 4760-34-3 ]
  • [ 3012-80-4 ]
Reference: [1] Patent: WO2011/150156, 2011, A2,
[2] Molecules, 2016, vol. 21, # 11,
  • 4
  • [ 87-69-4 ]
  • [ 4760-34-3 ]
  • [ 3012-80-4 ]
Reference: [1] Liebigs Annalen der Chemie, 1980, # 4, p. 542 - 556
  • 5
  • [ 4760-34-3 ]
  • [ 298-12-4 ]
  • [ 20572-01-4 ]
Reference: [1] Journal of the Chemical Society, 1923, vol. 123, p. 1082
  • 6
  • [ 372-09-8 ]
  • [ 4760-34-3 ]
  • [ 2735-62-8 ]
YieldReaction ConditionsOperation in experiment
14% at 165℃; for 2 h; A mixture of N-Methyl-benzene-1,2-diamine (250 mg,2.04 mmol) and cyanoacetic acid (348 mg, 4.09 mmol) in ethyleneglycol (10 mL) was heated at 165 °C for 2 h. TLC showed SM wasconsumed and formed a desired polar spot with major undesired.The reaction mixture was diluted with ethyl acetate. The organiclayer was washed with water followed by the brine washing. Thecombined organic solution was dried over sodium sulfate and thenconcentrated. The crude mass was purified by column chromatographyon silica, eluted with 1percent methanol in DCM to afford (1-Methyl-1H-benzoimidazol-2-yl)-acetonitrile (4) (50 mg, 14percent) aspink solid. 1HNMR (400 MHz, DMSO-d6): δ (ppm) = 7.62 (d, J = 7.72 Hz, 1H),7.54 (d, J = 8.04, 1H), 7.28-7.19 (m, 2H), 4.52 (s, 2H), 3.76 (s, 3H). MS(ESI): m/z calc. for C10H9N3: 171.08; found: 172.1[M + H]+.
Reference: [1] Journal of Photochemistry and Photobiology A: Chemistry, 2017, vol. 343, p. 7 - 16
  • 7
  • [ 4760-34-3 ]
  • [ 105-34-0 ]
  • [ 2735-62-8 ]
Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, p. 2339 - 2344
[2] Patent: TW2016/34463, 2016, A, . Location in patent: Paragraph 0090
  • 8
  • [ 4760-34-3 ]
  • [ 152628-03-0 ]
  • [ 152628-02-9 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 75 - 145℃;
Stage #2: With sodium hydroxide In water
Example 2; Variant 2; Methanesulphonic acid is heated to about 80° C. At a temperature of 75° C. to 85° C., 2-propyl-4-methyl-1H-benzimidazole-6-carboxylic acid is added. Then at 85° C. to 95° C. N-methyl-o-phenylene-diamine is added.The mixture is heated to110° C. to 130° C. and phosphorus pentoxide is metered in until an internal temperature of not more than 160° C. is reached. Then the mixture is stirred for 3 hours at a maximum temperature of 145° C. It is cooled to <100° C. and water is metered into the reaction mixture. 50percent sodium hydroxide solution is added at <100° C. until a pH of less than 3 is obtained.Finally, treatments with charcoal are carried out at <100° C.At a temperature of <80° C. isopropanol is added and the mixture is adjusted with sodium hydroxide solution to a pH between 4.5 and 7. The aqueous phase is separated off. In order to precipitate dimethyl-2'-propyl-2,5'-bi-1H-benzimidazole water is metered in, the contents of the apparatus are cooled to at least 40° C. for technical reasons and the product is isolated.Yield: 78-90percent of theoryHPLC purity: >99.5percent.
Reference: [1] Patent: US2011/190508, 2011, A1, . Location in patent: Page/Page column 2
[2] Journal of Chemical Research, 2010, # 2, p. 95 - 97
[3] Synthetic Communications, 2009, vol. 39, # 23, p. 4149 - 4157
[4] Patent: JP2015/160810, 2015, A, . Location in patent: Paragraph 0051; 0052
  • 9
  • [ 4760-34-3 ]
  • [ 152628-00-7 ]
  • [ 152628-02-9 ]
YieldReaction ConditionsOperation in experiment
62% at 150℃; for 12 h; A mixture of methyl 4-methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylate 2 (10 mmol) and N-methyl-o-phenylenediamine (10 mmol) in PPA (20 ml) were taken in a two necked flask fitted with a condenser and the reaction mixture was refluxed at 150 FontWeight="Bold" FontSize="10" °C for 12 h. After the completion of the reaction, the mixture was poured into water and the pH was adjusted to 9 using ammonium hydroxide. The mixture was extracted with ethyl acetate (50 mL x 3)and the combined organic phase was washed with brine (50 mL), dried over sodium sulphate and concentrated under vacuum. The crude mixture was purified by column chromatography using CHCl3-MeOH (9.3:0.7) to give the product 1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzo[d]imidazole (3). 1,7'-Dimethyl-2'-propyl-1H,3'H-2,5'-bibenzo[d]imidazole 3. Yield 62percent; m.p. 128-130 °C (lit 138-139 °C); IR (KBr): 3310 (N-H), 2928 (C-H), 1628 (C=C), 1284 (N-N) cm-1; 1H NMR (CDCl3, 400 MHz): δ 7.89 (s, 1H, Ar-H), FontWeight="Bold" FontSize="10" 7.62 (t, J=6.8 Hz, 2H, Ar-H), 7.31 (s, 1H, Ar-H), 7.24 (m, 2H, Ar-H), 5.57 (s, 1H, N-H), 3.92 (s, 3H, N-CH3), 3.16 (t, J=7.6 Hz, 2H, CH2), 2.66 (s, 3H, Ar–CH3), 1.94 (m, 2H, CH2), 1.12 (t, J=7.6Hz,3H, CH3); 13C NMR (CDCl3, 100M Hz): δ 153.3,151.4, 142.7, 139.3, 138.4, 136.4, 126.7, 124.1, 123.9, 123.0, 122.1, 119.5,111.2, 110.0, 31.9, 31.8, 21.6, 16.5, 13.9; MS (ESI): m/z 305 (M+1); Anal.Calcd for C19H20N4: C, 74.97; H, 6.22; N,18.41. Found: 75.05; H, 6.29; N, 18.49percent.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2589 - 2593
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