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[ CAS No. 83741-35-9 ] {[proInfo.proName]}

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Chemical Structure| 83741-35-9
Chemical Structure| 83741-35-9
Structure of 83741-35-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 83741-35-9 ]

CAS No. :83741-35-9 MDL No. :MFCD09754164
Formula : C7H5BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :MUQFMGBYYAOIJK-UHFFFAOYSA-N
M.W : 197.03 Pubchem ID :11252584
Synonyms :

Calculated chemistry of [ 83741-35-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.79
TPSA : 28.68 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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 2.18
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 1.75
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.156 mg/ml ; 0.000793 mol/l
Class : Soluble
Log S (Ali) : -2.42
Solubility : 0.757 mg/ml ; 0.00384 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0337 mg/ml ; 0.000171 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 83741-35-9 ]

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

Application In Synthesis of [ 83741-35-9 ]

* 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 [ 83741-35-9 ]
  • Downstream synthetic route of [ 83741-35-9 ]

[ 83741-35-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 64-18-6 ]
  • [ 1575-36-6 ]
  • [ 83741-35-9 ]
YieldReaction ConditionsOperation in experiment
97% at 100℃; for 2 h; A solution of 3-bromobenzene-1,2-diamine (2-21, 400 mg, 2.15 mmol) in HCOOH (5 mL) was stirred at 100 °C for 2 h. Upon reaction completion, the resulting mixture was concentrated under reduced pressure to provide intermediate 2-22 (yellow solid, 410 mg, 97percent yield). LCMS (m/z): 197 [M + HI .
95% for 2 h; Reflux step 2: A mixture of 3-bromobenzene-l,2-diamine (1.5 g, 8 mmol) in formic acid (10 mL) was heated at reflux for 2 h. The reaction mixture was concentrated in vacuo. To the residue was added a satd. aq. solution of NaHC03 and mixture was extracted with EtOAc. The combined extracts was dried (MgSO i), filtered, and evaporated in vacuo to afford 4-bromo-lH-benzo[d]imidazole as a gray solid (1.5 g, 95percent). MS (ESI): m/z = 197 [M+l]+.
94%
Stage #1: at 100℃; for 1 h;
Stage #2: With sodium hydroxide In water
Step 2: 4-Bromo-lH-benzimidazole; A solution of l,2-diamino-3-bromobenzene (2.00 g, 10.7 mmol) in formic acid (10 mL) was stirred at 1000C for 1 hour. The pΗ of the mixture was adjusted to 14 by the addition of 4 M sodium hydroxide solution, precipitating the product as a solid. This was separated by filtration, washed with water and air- dried affording the product as an off-white solid. A further crop of equally pure material precipitated from the filtrate upon standing at room temperature for a few days. Total yield = 1.98 g, 94percent. 1H NMR (500 MHz, ds-DMSO): δ 12.83 (1 H, s), 8.30 (1 H, s), 7.58 (1 H, d, J = 7.9 Hz), 7.41 (1 H, d, J = 7.1 Hz), 7.14 (1 H, t, J = 7.8 Hz); m/z (ES+) 197, 199 [MH+].
94%
Stage #1: at 100℃; for 1 h;
Step 2: 4-Bromo-lH-benzimidazole; A solution of l,2-diamino-3-bromobenzene (2.00 g, 10.7 mmol) in formic acid (10 mL) was stirred at 1000C for 1 hour. The pΗ of the mixture was adjusted to 14 by the addition of 4M sodium hydroxide solution, precipitating the product as a solid. This was separated by filtration, washed with water and air- dried affording the product as an off-white solid. A further crop of equally pure material precipitated from the filtrate upon standing at room temperature for a few days. Total yield = 1.98 g, 94percent. 1H NMR (500 MHz, DMSO): δ 12.83 (1 H, s), 8.30 (1 H, s), 7.58 (1 H, d, J 7.9 Hz), 7.41 (1 H, d, J 7.1 Hz), 7.14 (1 H, t, J 7.8 Hz); m/z (ES+) 197, 199 [MH+].
83% at 100℃; for 1 h; A solution of 1,2-diamino-3-bromobenzene (750 mg, 4.0 mmol) in formic acid (4 mL) was heated at 100 °C for 1 h. The mixture was allowed to cool to room temperature, then was basified (pH - 14) by the addition of 4 N sodium hydroxide solution. The product 4-bromo-lH-benzimidazole precipitated as an off-white solid, and was separated by filtration, washed with water and dried in a drying pistol under vacuum at 50 °C (654 mg, 83percent). m/z (ES+) 197, 199 [MH]+.
1.65 g at 100℃; for 1 h; A mixture of 3-bromobenzene-l,2-diamine (2 g, 10.7 mmol) in HCOOH was stirred at 100°C for 1 h. The mixture was cooled and concentrated in vacuo and diluted with ethyl acetate and aq. NaHC03. The mixture was extracted further with ethyl acetate and the combined organic layers dried and concentrated to give the crude product which was purified by column chromatography to obtain the desired product (1.65 g, Yield 80percent). LCMS (m/z): 197.0 (M+l).

Reference: [1] Patent: WO2016/161145, 2016, A1, . Location in patent: Paragraph 00697
[2] Patent: WO2013/26914, 2013, A1, . Location in patent: Page/Page column 108
[3] Patent: WO2006/59149, 2006, A1, . Location in patent: Page/Page column 41
[4] Patent: WO2006/97766, 2006, A1, . Location in patent: Page/Page column 23
[5] Patent: WO2006/21805, 2006, A1, . Location in patent: Page/Page column 76
[6] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1953, vol. 11, p. 42
[7] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00420
  • 2
  • [ 1575-36-6 ]
  • [ 122-51-0 ]
  • [ 83741-35-9 ]
YieldReaction ConditionsOperation in experiment
4.9 g With toluene-4-sulfonic acid In tetrahydrofuran at 60℃; for 0.333333 h; Inert atmosphere To a stirring dark suspension of 3-bromo-l,2-benzenediamine (Combi-Blocks, Inc. 4.7 g, 25.1 mmol) and 4- methylbenzene sulfonic acid, monohydrate (0.048 g, 0.251 mmol) in THF (40 mL) at 20 °C under argon was added triethyl orthoformate (Sigma- Aldrich, St. Louis MO, 4.18 mL, 25.1 mmol) dropwise over a period of 5 min. The reaction was stirred for 10 min then heated to 60 °C for 20 min. The reaction was then cooled and concentrated under reduced pressure. The resulting dark solid was then triturated with diethyl ether (50 mL) and dried under reduced pressure to afford 4-bromo-lH-benzo[d]imidazole (4.9 g) as dark solid.
Reference: [1] Patent: WO2013/173382, 2013, A1, . Location in patent: Page/Page column 199
  • 3
  • [ 64-18-6 ]
  • [ 7138-15-0 ]
  • [ 16712-16-6 ]
  • [ 83741-35-9 ]
Reference: [1] Patent: WO2013/26914, 2013, A1, . Location in patent: Page/Page column 128
  • 4
  • [ 59255-95-7 ]
  • [ 83741-35-9 ]
Reference: [1] Patent: WO2013/26914, 2013, A1,
  • 5
  • [ 7138-15-0 ]
  • [ 83741-35-9 ]
Reference: [1] Patent: WO2014/100695, 2014, A1,
  • 6
  • [ 19613-76-4 ]
  • [ 83741-35-9 ]
Reference: [1] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1953, vol. 11, p. 42
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