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Chemistry
Heterocyclic Building Blocks
Benzimidazoles
2-Cyclopropyl-1H-benzimidazole
Chemistry
Heterocyclic Building Blocks
Benzimidazoles

[ CAS No. 16405-79-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 16405-79-1
Chemical Structure| 16405-79-1
Structure of 16405-79-1 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 16405-79-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 16405-79-1 ]

SDS Specification
Alternatived Products of [ 16405-79-1 ]

Product Details of [ 16405-79-1 ]

CAS No. :16405-79-1 MDL No. :MFCD01859172
Formula : C10H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :ACQZKAMBZDAMRZ-UHFFFAOYSA-N
M.W : 158.20 Pubchem ID :1084419
Synonyms :

Calculated chemistry of [ 16405-79-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.3
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.56
TPSA : 28.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 2.15
Log Po/w (WLOGP) : 2.38
Log Po/w (MLOGP) : 1.94
Log Po/w (SILICOS-IT) : 3.04
Consensus Log Po/w : 2.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.66
Solubility : 0.343 mg/ml ; 0.00217 mol/l
Class : Soluble
Log S (Ali) : -2.38
Solubility : 0.653 mg/ml ; 0.00413 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.5
Solubility : 0.0504 mg/ml ; 0.000318 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 16405-79-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16405-79-1 ]

* 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.

  • Downstream synthetic route of [ 16405-79-1 ]

[ 16405-79-1 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 765-43-5 ]
  • [ 95-54-5 ]
  • [ 16405-79-1 ]
Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 975,982
  • 2
  • [ 95-54-5 ]
  • [ 1759-53-1 ]
  • [ 16405-79-1 ]
Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 7739 - 7755
[2]European Journal of Organic Chemistry,2000,p. 1229 - 1233
[3]Journal of the American Chemical Society,1951,vol. 73,p. 975,982
  • 3
  • [ 623-73-4 ]
  • [ 16405-79-1 ]
  • [ 97968-81-5 ]
Reference： [1]Archiv der Pharmazie,1985,vol. 318,p. 393 - 399
  • 4
  • [ 51-17-2 ]
  • [ 1759-53-1 ]
  • [ 16405-79-1 ]
Reference： [1]Archiv der Pharmazie,1985,vol. 318,p. 393 - 399
  • 6
  • [ 16405-79-1 ]
  • [ 77-78-1 ]
  • 2-cyclopropyl-1,3-dimethylbenzimidazolium tetrafluoroborate [ No CAS ]
Reference： [1]European Journal of Organic Chemistry,2000,p. 1229 - 1233
  • 7
  • [ 16405-79-1 ]
  • [ 97968-85-9 ]
Reference： [1]Archiv der Pharmazie,1985,vol. 318,p. 393 - 399
  • 8
  • [ 16405-79-1 ]
  • (2-Cyclopropyl-benzoimidazol-1-yl)-acetyl chloride [ No CAS ]
Reference： [1]Archiv der Pharmazie,1985,vol. 318,p. 393 - 399
  • 9
  • [ 16405-79-1 ]
  • (2-Cyclopropyl-1-benzimidazolyl)-N,N-diethylacetamide [ No CAS ]
Reference： [1]Archiv der Pharmazie,1985,vol. 318,p. 393 - 399
  • 10
  • [ 615-28-1 ]
  • [ 1759-53-1 ]
  • [ 16405-79-1 ]
YieldReaction ConditionsOperation in experiment
13% (13a) 2-cyclopropanecarboxylic acid (4 g, 52 mmol) was treated with phenylenediamine bis-hydrochloride (1 eq) and polyphosphosphoric acid (52 mL) and heated to 160 C. for 6 h. The reaction was cooled to 0 C. and diluted with water, then basified with NaOH (50% aqueous) until pH>10. The solution was extracted with ethyl acetate, dried (MgSO4), filtered and concentrated, purified by flash chromatography (100% ethyl acetate) giving 2-cyclopropylbenzimidazole (1.1 g, 13%). MS found: (M+H)+=159.
13% (70a) Cyclopropanecarboxylic acid (4 g, 52 mmol) was treated with phenylenediamine bis-hydrochloride (1 eq) and polyphosphosphoric acid (52 mL) and heated to 160 C. for 6 h. The reaction was cooled to 0 C. and diluted with water, then basified with NaOH (50% aqueous) until pH>10. The solution was extracted with ethyl acetate, dried (MgSO4), filtered and concentrated, purified by flash chromatography (100% ethyl acetate) giving 2-cyclopropylbenzimidazole (1.1 g, 13%). MS found: (M+H)+=159.
Reference： [1]Patent: US2003/87882,2003,A1
[2]Patent: US2003/139388,2003,A1
  • 11
  • [ 16405-79-1 ]
  • [ 2417-72-3 ]
  • C19H18N2O2 [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1577 - 1582
  • 12
  • [ 614-76-6 ]
  • [ 57297-29-7 ]
  • [ 16405-79-1 ]
Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7841 - 7844
  • 13
  • [ 16405-79-1 ]
  • [ 1248473-37-1 ]
Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 5120 - 5123
  • 14
  • [ 16405-79-1 ]
  • [ 54104-43-7 ]
Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 5120 - 5123
  • 15
  • [ 16405-79-1 ]
  • 2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole hydrobromide [ No CAS ]
Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 5120 - 5123
  • 16
  • [ 16405-79-1 ]
  • 2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole hydroiodide [ No CAS ]
Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 5120 - 5123
  • 17
  • [ 16405-79-1 ]
  • [ 1257295-02-5 ]
  • [ 1257378-54-3 ]
Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7686 - 7695
  • 18
  • [ 1342132-54-0 ]
  • [ 16405-79-1 ]
Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13964 - 13967
  • 19
  • [ 62-53-3 ]
  • [ 16405-79-1 ]
Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13964 - 13967
  • 20
  • [ 95-54-5 ]
  • [ 1489-69-6 ]
  • [ 16405-79-1 ]
Reference： [1]Green Chemistry,2012,vol. 14,p. 3273 - 3276
  • 21
  • [ 95-54-5 ]
  • [ 2516-47-4 ]
  • [ 16405-79-1 ]
Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1025 - 1032
  • 22
  • [ 16405-79-1 ]
  • 1-methyl-2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)-1H-benzo[d]imidazole [ No CAS ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 13127 - 13131
  • 23
  • [ 16405-79-1 ]
  • potasium trifluoro[2-(1-methyl-1H-benzo[d]imidazol-2-yl)cyclopropyl]borate [ No CAS ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 13127 - 13131
  • 24
  • [ 16405-79-1 ]
  • 1-methyl-2-(2-phenylcyclopropyl)-1H-benzo[d]imidazole [ No CAS ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 13127 - 13131
  • 25
  • [ 16405-79-1 ]
  • 2-[2-(4-methoxyphenyl)cyclopropyl]-1-methyl-1H-benzo[d]imidazole [ No CAS ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 13127 - 13131
  • 26
  • [ 16405-79-1 ]
  • methyl 4-[2-(1-methyl-1H-benzo[d]imidazol-2-yl)cyclopropyl]benzoate [ No CAS ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 13127 - 13131
  • 27
  • [ 16405-79-1 ]
  • 1-methyl-2-(2-(2-methylprop-1-en-1-yl)cyclopropyl)-1H-benzo[d]imidazole [ No CAS ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 13127 - 13131
  • 28
  • [ 16405-79-1 ]
  • [ 74-88-4 ]
  • 2-cyclopropyl-1-methyl-1H-benzo[d]imidazole [ No CAS ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 13127 - 13131
[2]Chemical Communications,2017,vol. 53,p. 9281 - 9284
  • 29
  • [ 16405-79-1 ]
  • 2-[3-(triethylsilyl)propyl]-1-methyl-1H-benzimidazole [ No CAS ]
Reference： [1]Chemical Communications,2017,vol. 53,p. 9281 - 9284
  • 30
  • [ 95-54-5 ]
  • [ 24922-02-9 ]
  • [ 16405-79-1 ]
Reference： [1]Green Chemistry,2017,vol. 19,p. 5818 - 5830
  • 31
  • [ 16405-79-1 ]
  • (R)-((2-Chloro-6-(3-methylmorpholino)pyrimidin-4-yl)imino)dimethyl-λ6-sulfanone [ No CAS ]
  • (R)-((2-(2-cyclopropyl-1H-benzo[d]imidazol-1-yl)-6-(3-methylmorpholino)pyrimidin-4-yl)imino)dimethyl-λ6-sulfanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; In 1,4-dioxane; at 150℃; for 1h;Inert atmosphere; Sealed tube; Microwave irradiation; (R)-((2-(2-cyclopropyl-1H-benzo[d]imidazol-1-yl)-6-(3-methylmorpholino)-pyrimidin-4-yl)imino)dimethyl-lambda6-sulfanone A reaction vial was charged with Int. D (120 mg, 0.39 mmol), <strong>[16405-79-1]2-cyclopropyl-1H-benzo[d]imidazole</strong> (94 mg, 0.59 mmol), Pd2dba3 (18 mg, 0.02 mmol), XPhos (16 mg, 0.04 mmol), Cs2CO3 (380 mg, 1.17 mmol) and dioxane (6 mL). The vial was purged with N2 for 2 min., sealed and heated to 150 C. for 1 h in a microwave reactor. The reaction mixture was cooled to RT, filtered through CELITE, and concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC (Mobile phase: A=10 mM NH4HCO3/H2O, B=MeCN; Gradient: B=40-70%; 15 min; Column: Agela C18, 10 mum, 150 A, 21.2 mm*250 mm) to afford the title compound (83.0 mg, 50% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) delta 8.10 (dd, J=6.8, 2.3 Hz, 1H), 7.53 (dd, J=6.5, 2.2 Hz, 1H), 7.24-7.14 (m, 2H), 5.93 (s, 1H), 4.36 (s, 1H), 3.94 (dd, J=16.4, 8.5 Hz, 2H), 3.72 (d, J=11.4 Hz, 1H), 3.61 (dd, J=11.4, 2.9 Hz, 1H), 3.50-3.44 (m, 1H), 3.42 (s, 6H), 3.17 (td, J=13.0, 3.9 Hz, 1H), 3.09-3.01 (m, 1H), 1.21 (d, J=6.7 Hz, 3H), 1.17-1.11 (m, 2H), 1.09-1.02 (m, 2H); MS (ES+) C18H22N6O2S requires: 426, found: 427 [M+H]+.
Reference： [1]Patent: US2019/16713,2019,A1 .Location in patent: Paragraph 0956-0959
  • 32
  • [ 2516-33-8 ]
  • [ 88-74-4 ]
  • [ 16405-79-1 ]
Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 12111 - 12119

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