Home Cart 0 Sign in  
X

[ CAS No. 58533-15-6 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 58533-15-6
Chemical Structure| 58533-15-6
Chemical Structure| 58533-15-6
Structure of 58533-15-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Quality Control of [ 58533-15-6 ]

Related Doc. of [ 58533-15-6 ]

Alternatived Products of [ 58533-15-6 ]

Product Details of [ 58533-15-6 ]

CAS No. :58533-15-6 MDL No. :MFCD00769822
Formula : C9H9ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :IROJYPSJGGDBCD-UHFFFAOYSA-N
M.W :180.63 g/mol Pubchem ID :3744796
Synonyms :

Calculated chemistry of [ 58533-15-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.81
TPSA : 17.82 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) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 2.7
Log Po/w (WLOGP) : 2.71
Log Po/w (MLOGP) : 2.21
Log Po/w (SILICOS-IT) : 2.38
Consensus Log Po/w : 2.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.15
Solubility : 0.128 mg/ml ; 0.000708 mol/l
Class : Soluble
Log S (Ali) : -2.73
Solubility : 0.339 mg/ml ; 0.00187 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.49
Solubility : 0.0582 mg/ml ; 0.000322 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 58533-15-6 ]

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 [ 58533-15-6 ]

* 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 [ 58533-15-6 ]
  • Downstream synthetic route of [ 58533-15-6 ]

[ 58533-15-6 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 4857-06-1 ]
  • [ 74-96-4 ]
  • [ 58533-15-6 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1 h;
Stage #2: at 20℃;
General procedure: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 °C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 °C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.
Reference: [1] Zeitschrift fur Anorganische und Allgemeine Chemie, 2013, vol. 639, # 14, p. 2450 - 2454
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 417 - 422
[3] European Journal of Medicinal Chemistry, 2010, vol. 45, # 3, p. 909 - 914
  • 2
  • [ 4857-06-1 ]
  • [ 75-03-6 ]
  • [ 58533-15-6 ]
YieldReaction ConditionsOperation in experiment
61% With NaH In N,N-dimethyl-formamide; mineral oil Step 1) Preparation of 2-Chloro-1-ethylbenzimidazole
To a cooled (0° C.) stirred suspension of NaH (60percent dispersion in mineral oil; 7.08 g, 0.118 mol) in DMF (100 mL) was added 2-chlorobenzimidazole (15.00 g, 0.098 mol).
The mixture was warmed to room temperature and stirred for 1 hour.
Ethyl iodide (18.40 g, 0.118 mol) was added and stirring was continued for 3 hours.
The mixture was poured onto the ice water and the resulting off-white solid was collected by filtration to give 10.0 g (61percent) of product m.p. 48°-50° C.
NMR (DMSO-d6, 300 MHz): δ1.3 (t, J=8.6 Hz, 3H), 4.28 (q, J=8.6 Hz, 2H), 7.25 (m, 2H), 7.60 (m, 2H).
Reference: [1] Patent: US5149700, 1992, A,
[2] Patent: KR2018/36412, 2018, A, . Location in patent: Paragraph 0103; 0107-0108
  • 3
  • [ 10045-45-1 ]
  • [ 58533-15-6 ]
YieldReaction ConditionsOperation in experiment
77% With hydrogenchloride In dichloromethane; trichlorophosphate A.
2-chloro-1-ethylbenzimidazole
1-Ethyl-2-benzimidazolinone (100 g, 0.62 mol) was dissolved in phosphorus oxychloride (475 mL) with stirring and heated to reflux temperature.
Hydrogen chloride gas was passed into the refluxing solution for 4 h.
Excess phosphorous oxychloride was removed on a rotary evaporator at 70° C.
The residue was poured into a stirred mixture of aqueous potassium carbonate solution and methylene chloride.
The mixture was basified with 50percent sodium hydroxide solution and the methylene chloride layer was separated, dried (Na2 SO4), concentrated, and distilled to obtain 86 g (77percent) of oil, bp 110°-115° C./2-0.3 mmHg, which crystallized on standing; mp 50°-52° C.
Reference: [1] Patent: US5106857, 1992, A,
  • 4
  • [ 4857-06-1 ]
  • [ 64-67-5 ]
  • [ 58533-15-6 ]
Reference: [1] Asian Journal of Chemistry, 2012, vol. 24, # 12, p. 5756 - 5758,3
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 9, p. 1210 - 1213
  • 5
  • [ 4857-06-1 ]
  • [ 623-81-4 ]
  • [ 58533-15-6 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 6, p. 829 - 832
  • 6
  • [ 10045-45-1 ]
  • [ 58533-15-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 20, p. 2709 - 2712
  • 7
  • [ 23838-73-5 ]
  • [ 58533-15-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 20, p. 2709 - 2712
Historical Records

Related Functional Groups of
[ 58533-15-6 ]

Chlorides

Chemical Structure| 3705-87-1

[ 3705-87-1 ]

2-Chloro-1-isopropyl-1H-benzo[d]imidazole

Similarity: 0.96

Chemical Structure| 40019-65-6

[ 40019-65-6 ]

2-(2-Chloro-1H-benzo[d]imidazol-1-yl)ethanol

Similarity: 0.93

Chemical Structure| 43181-78-8

[ 43181-78-8 ]

1-Benzyl-2-chloro-1H-benzo[d]imidazole

Similarity: 0.89

Chemical Structure| 87233-54-3

[ 87233-54-3 ]

2-Chloro-1-(2-ethoxyethyl)-1H-benzo[d]imidazole

Similarity: 0.86

Chemical Structure| 1849-02-1

[ 1849-02-1 ]

2-Chloro-1-methyl-1H-benzo[d]imidazole

Similarity: 0.86

Related Parent Nucleus of
[ 58533-15-6 ]

Benzimidazoles

Chemical Structure| 3705-87-1

[ 3705-87-1 ]

2-Chloro-1-isopropyl-1H-benzo[d]imidazole

Similarity: 0.96

Chemical Structure| 40019-65-6

[ 40019-65-6 ]

2-(2-Chloro-1H-benzo[d]imidazol-1-yl)ethanol

Similarity: 0.93

Chemical Structure| 43181-78-8

[ 43181-78-8 ]

1-Benzyl-2-chloro-1H-benzo[d]imidazole

Similarity: 0.89

Chemical Structure| 87233-54-3

[ 87233-54-3 ]

2-Chloro-1-(2-ethoxyethyl)-1H-benzo[d]imidazole

Similarity: 0.86

Chemical Structure| 1849-02-1

[ 1849-02-1 ]

2-Chloro-1-methyl-1H-benzo[d]imidazole

Similarity: 0.86