Home Cart 0 Sign in  

[ CAS No. 622-88-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 622-88-8
Chemical Structure| 622-88-8
Structure of 622-88-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 622-88-8 ]

Related Doc. of [ 622-88-8 ]

Alternatived Products of [ 622-88-8 ]
Product Citations

Product Details of [ 622-88-8 ]

CAS No. :622-88-8 MDL No. :MFCD00012941
Formula : C6H8BrClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :RGGOWBBBHWTTRE-UHFFFAOYSA-N
M.W : 223.50 Pubchem ID :12157
Synonyms :

Calculated chemistry of [ 622-88-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.31
TPSA : 38.05 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) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.19
Log Po/w (WLOGP) : 2.35
Log Po/w (MLOGP) : 2.45
Log Po/w (SILICOS-IT) : 1.04
Consensus Log Po/w : 1.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.98
Solubility : 0.232 mg/ml ; 0.00104 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.533 mg/ml ; 0.00238 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.94
Solubility : 0.255 mg/ml ; 0.00114 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 622-88-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 622-88-8 ]

* 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 [ 622-88-8 ]
  • Downstream synthetic route of [ 622-88-8 ]

[ 622-88-8 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 188290-36-0 ]
  • [ 622-88-8 ]
  • [ 40133-22-0 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 40, p. 8055 - 8058
  • 2
  • [ 622-88-8 ]
  • [ 78-93-3 ]
  • [ 4583-55-5 ]
YieldReaction ConditionsOperation in experiment
80% at 80℃; for 96 h; Inert atmosphere A 500 ml_ three neck round bottomed flask equipped with a stir bar, thermocouple, heat mantle, and water condenser with nitrogen inlet was charged with 3-bromophenylhydrazine hydrochloride (19.84 g, 88.77 mmol) and isopropanol (240 ml_). 2-Butanone (8.0 ml_, 89.32 mmol) was added and the reaction was heated to 80 °C. After 4 days the reaction was allowed to cool to room temperature. The solvent was removed by rotary evaporation and the red residue dissolved in ethyl acetate (200 ml_). The organic layer was washed with 1 N hydrochloric acid (100 ml_) and saturated aqueous sodium bicarbonate (100 ml_). The organic layer was dried over magnesium sulfate, filtered, and concentrated by rotary evaporation to give 5- bromo-2,3-dimethyl-1 H-indole as a red solid (1 5.94 g, 71 .1 mmol, 80percent). 1 H NMR (400 MHz, CDCIs) δ 7.70 (s, 1 H), 7.59 - 7.55 (m, 1 H), 7.1 7 (dd, J = 8.5, 1 .9 Hz, 1 H), 7.1 1 (dd, J = 8.4, 0.6 Hz, 1 H), 2.35 (d, J = 0.8 Hz, 3H), 2.17 (q, J = 0.7 Hz, 3H). 13C NMR (1 01 MHz, CDCIs) δ 133.77, 132.10, 131 .27, 123.54, 120.61 , 1 12.26, 1 1 1 .35, 107.02, 1 1 .58, 8.35.
67% for 22 h; Reflux Following a published procedure (Gundersen, E. G. U.S. Patent App. Publ. US 2005/070592) 2-Butanone (0.11 mL, 1.278 mmol) was added to a solution of 4-bromophenylhydrazine hydrochloride (0.300 g, 1.342 mmol in EtOH (3.8 mL).
The mixture was heated to reflux for 22 h, concentrated in vacuo, and partitioned between EtOAc and 1N HCl.
The organic layer was washed with H2O and saturated aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated.
The crude residue was purified by chromatography (SiO2, 0-20percent EtOAc/Hexane) to afford the desired indole as a pink powder (200 mg, 67percent).
1H NMR (CDCl3, 500 MHz) δ 7.69 (br s, 1H), 7.55 (d, 1H, J=2.0 Hz), 7.15 (dd, 1H, J=2.0, 8.5 Hz), 7.09 (dd, 1H, J=0.5, 8.5 Hz), 2.34 (s, 3H), 2.15 (d, 3H, J=0.5 Hz)
ESI m/z 224.0 ([M+H]+, C10H11BrN requires 224.0)
Reference: [1] Heterocycles, 2007, vol. 72, p. 373 - 383
[2] Patent: WO2018/89181, 2018, A1, . Location in patent: Page/Page column 20
[3] Journal of the American Chemical Society, 2011, vol. 133, # 5, p. 1428 - 1437
[4] Patent: US9095571, 2015, B2, . Location in patent: Page/Page column 104
[5] Organic Letters, 2012, vol. 14, # 8, p. 2066 - 2069
  • 3
  • [ 622-88-8 ]
  • [ 108-94-1 ]
  • [ 1592-95-6 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 12, p. 3277 - 3280
[2] Tetrahedron Letters, 2018, vol. 59, # 22, p. 2145 - 2149
  • 4
  • [ 622-88-8 ]
  • [ 108-94-1 ]
  • [ 21865-50-9 ]
YieldReaction ConditionsOperation in experiment
82% for 8 h; Reflux General procedure: A substituted phenyl hydrazine. HCl (4.61 mmol) was added to the mixture of cyclohexanone (4.61 mmol) and acetic acid (15 ml) portion wise for 30 min. The mixture was then refluxed for 8 h and progress of reaction was monitored by thin layer chromatography. The reaction mixture was cooled and poured into crushed ice. The solid product was separated, filtered, dried and recrystallized from the methanol solvent.
74% for 7 h; Reflux To a solution of 4-bromophenylhydrazine hydrochloride (2.00 g, 8.95 mmol) inηOAc (13 ml) was added cyclohexanone (0.93 ml, 8.95 mmol). The resulting mixture was heated to reflux for 7 h and then cone, in vacuo. The crude product was dissolved in EtOAc (50 ml), washed with H2O, sat.NaHCO3, dried over MgSO4, filtered and cone, in vacuo. The crude product was purified by silica gel flash chromatography (EtOAc/hexane, 0-30percent) to give the title compound (brown solid, 1.63 g). The yield: 74.0percent.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 22, p. 2145 - 2149
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 41, p. 9868 - 9873
[3] Patent: WO2009/103022, 2009, A1, . Location in patent: Page/Page column 62
[4] Patent: WO2008/21745, 2008, A2, . Location in patent: Page/Page column 100
[5] Patent: WO2011/11186, 2011, A2, . Location in patent: Page/Page column 64
[6] Tetrahedron, 2017, vol. 73, # 45, p. 6436 - 6442
  • 5
  • [ 622-88-8 ]
  • [ 70070-32-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 892 - 913
  • 6
  • [ 617-35-6 ]
  • [ 622-88-8 ]
  • [ 103858-53-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 19, p. 3957 - 3960
  • 7
  • [ 622-88-8 ]
  • [ 123-06-8 ]
  • [ 5334-28-1 ]
Reference: [1] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 2, p. 352 - 358
[2] Patent: WO2007/62805, 2007, A1, . Location in patent: Page/Page column 51-52
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7451 - 7454
[4] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 6, p. 1425 - 1428
  • 8
  • [ 1191-99-7 ]
  • [ 622-88-8 ]
  • [ 32774-29-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 49, p. 12910 - 12914[2] Angew. Chem., 2013, vol. 125, # 49, p. 13148 - 13152,5
[3] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6710 - 6717
  • 9
  • [ 622-88-8 ]
  • [ 10075-48-6 ]
Reference: [1] Synthetic Communications, 1993, vol. 23, # 14, p. 2011 - 2017
  • 10
  • [ 622-88-8 ]
  • [ 135-19-3 ]
  • [ 1698-16-4 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1994, vol. 34, # 8, p. 697 - 706
  • 11
  • [ 110-86-1 ]
  • [ 622-88-8 ]
  • [ 63996-36-1 ]
  • [ 129013-83-8 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 54, p. 7124 - 7127
  • 12
  • [ 100-32-3 ]
  • [ 622-88-8 ]
  • [ 21969-12-0 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 6647 - 6655
  • 13
  • [ 622-88-8 ]
  • [ 108-24-7 ]
  • [ 14579-97-6 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 2, p. 437 - 441
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 47, p. 12426 - 12429[3] Angew. Chem., 2013, vol. 125, # 47, p. 12652 - 12656,4
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 29, p. 5469 - 5476
  • 14
  • [ 16511-38-9 ]
  • [ 622-88-8 ]
  • [ 142273-20-9 ]
YieldReaction ConditionsOperation in experiment
79.6%
Stage #1: at 70℃; for 3 h;
Stage #2: at 70℃; for 3 h;
Stage #3: With sodium acetate In water
Example 3; 9-Bromo-7,12-dihydroindolo[3,2-d][1]-benzazepin-6(5H)-one (Compound 1.2); To a suspension of 1 H-[1]benzazepin-2,5(3H, 4H) -dione (0.247 g, 1.3 mmol) in acetic acid (5 ml) was added 4-bromophenylhydrazine hydrochloride (0.532 g, 2.3 mmol) and sodium acetate (0.195 g, 2.3 mmol) and stirred under argon. The mixture was heated at 70°C for 3 hours, then cooled and concentrated sulfuric acid (0.5 ml) added, before heating at 70°C for a further 3 hours. The slurry was poured into 10percent sodium acetate aqueous solution (20 ml) and the precipitate filtered to give the title compound as a cream solid (0.367 g, yield 79.6percent), mp > 300°C; 1 H- NMR (DMSO- d6,300 MHz) : No. (ppm) = 11.82 (s; 1 H), 10.1 (s; 1H), 7.89 (d; 1H), 7.74 (dd; 1H), 7.41-7.36 (m; 2H), 7.30-7.21 (m; 3H), 3.51 (s; 2H).
Reference: [1] Patent: WO2005/107471, 2005, A1, . Location in patent: Page/Page column 21
  • 15
  • [ 41979-39-9 ]
  • [ 622-88-8 ]
  • [ 497261-38-8 ]
YieldReaction ConditionsOperation in experiment
39.3%
Stage #1: for 4 h; Heating / reflux
Stage #2: With hydrogenchloride In ethanol at 20℃; for 3 h; Heating / reflux
Stage #3: With sodium hydroxide In water
To a stirred solution of 4-bromophenylhydrazine hydrochloride (5.Og, 22.36 mmol) in ethanol (100 niL), piperidin-4-one hydrochloride (1.316g, 8.5984 mmol) was added and the mixture was heated to reflux. The reflux was maintained for 4 hours, then cooled to room temperature and dry hydrogen chloride gas was passed for 1 hour through the reaction mixture. The mixture was then again heated to reflux and maintained for 2h. After completion of reaction, ethanol was distilled off under vacuum and the residue was dissolved in water. The aqueous layer was neutralized with 2N sodium hydroxide solution and was extracted in dichloromethane (2 x 100 mL). The pH of the aqueous layer was then adjusted to 12.0 with 2N sodium hydroxide solution and the product was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude solid was washed with diethyl ether (50 mL) to obtain 8-bromo-2,3,4,5-tetrahydro-lH-pyrido[4,3-]indole (2.2g, 39.3percent) with purity 98.82percent by HPLC. 1HNMR (200 MHz, DMSO-d&6) δ: 2.7 (t, 2H, CH2), 3.0 (t, 2H, CH2), 3.8 (d, 2H, CH2), 7.05 (d, IH5 Ar-H), 7.2 (d, IH, Ar-H), 7.45 (s, IH, Ar-H), 10.97 (bs, IH, NH). m/e = 251 (M+HhI).To a solution of 8-bromo-2,3,4,5-tetrahydro-lH-pyrido[4,3-]indole (250mg, 0.991 mmol) in anhydrous DMF (10 mL) was added Example 7 (258mg, 1.194 mmol) and potassium carbonate (204mg, 1.401mmol) at room temperature. The reaction mixture was stirred at 100 0C for 6 hours. After completion, the reaction mixture was diluted with water and the compound was extracted with EtOAc. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue obtained was purified by column chromatography to obtain Example 33 (80mg, 21percent). HPLC: (RT =17.39min). 1H NMR (200 MHz, CDCl&3) ppm: 8.88 (s, 2H), 7.95 (bs, IH), 7.65-7.15 (m, 3H), 5.05 (s, 2H), 4.35 (m, 2H)3 3.88 (s, 3H), 2.93 (t, 2H, J= 5.4Hz); m/e = 387 (M+l).
Reference: [1] Patent: WO2006/88949, 2006, A1, . Location in patent: Page/Page column 113; 114
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 10183 - 10187
  • 16
  • [ 622-88-8 ]
  • [ 79099-07-3 ]
  • [ 497261-38-8 ]
Reference: [1] Helvetica Chimica Acta, 2012, vol. 95, # 2, p. 320 - 326
  • 17
  • [ 622-88-8 ]
  • [ 497261-38-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 145 - 155
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 622-88-8 ]

Aryls

Chemical Structure| 589-21-9

[ 589-21-9 ]

(4-Bromophenyl)hydrazine

Similarity: 0.97

Chemical Structure| 50709-33-6

[ 50709-33-6 ]

2-Bromophenylhydrazine hydrochloride

Similarity: 0.90

Chemical Structure| 62672-26-8

[ 62672-26-8 ]

(2,5-Dibromophenyl)hydrazine

Similarity: 0.88

Chemical Structure| 33786-90-2

[ 33786-90-2 ]

5-Bromobenzene-1,3-diamine

Similarity: 0.79

Chemical Structure| 626-40-4

[ 626-40-4 ]

3,5-Dibromoaniline

Similarity: 0.79

Bromides

Chemical Structure| 589-21-9

[ 589-21-9 ]

(4-Bromophenyl)hydrazine

Similarity: 0.97

Chemical Structure| 50709-33-6

[ 50709-33-6 ]

2-Bromophenylhydrazine hydrochloride

Similarity: 0.90

Chemical Structure| 62672-26-8

[ 62672-26-8 ]

(2,5-Dibromophenyl)hydrazine

Similarity: 0.88

Chemical Structure| 33786-90-2

[ 33786-90-2 ]

5-Bromobenzene-1,3-diamine

Similarity: 0.79

Chemical Structure| 626-40-4

[ 626-40-4 ]

3,5-Dibromoaniline

Similarity: 0.79

Amines

Chemical Structure| 589-21-9

[ 589-21-9 ]

(4-Bromophenyl)hydrazine

Similarity: 0.97

Chemical Structure| 50709-33-6

[ 50709-33-6 ]

2-Bromophenylhydrazine hydrochloride

Similarity: 0.90

Chemical Structure| 62672-26-8

[ 62672-26-8 ]

(2,5-Dibromophenyl)hydrazine

Similarity: 0.88

Chemical Structure| 33786-90-2

[ 33786-90-2 ]

5-Bromobenzene-1,3-diamine

Similarity: 0.79

Chemical Structure| 626-40-4

[ 626-40-4 ]

3,5-Dibromoaniline

Similarity: 0.79

Hydrazines

Chemical Structure| 589-21-9

[ 589-21-9 ]

(4-Bromophenyl)hydrazine

Similarity: 0.97

Chemical Structure| 50709-33-6

[ 50709-33-6 ]

2-Bromophenylhydrazine hydrochloride

Similarity: 0.90

Chemical Structure| 62672-26-8

[ 62672-26-8 ]

(2,5-Dibromophenyl)hydrazine

Similarity: 0.88

Chemical Structure| 214916-08-2

[ 214916-08-2 ]

(5-Bromo-2-fluorophenyl)hydrazine hydrochloride

Similarity: 0.73

Chemical Structure| 60481-35-8

[ 60481-35-8 ]

(2-Bromo-5-fluorophenyl)hydrazine hydrochloride

Similarity: 0.71