Structure of 622-88-8
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CAS No. : | 622-88-8 |
Formula : | C6H8BrClN2 |
M.W : | 223.50 |
SMILES Code : | NNC1=CC=C(Br)C=C1.[H]Cl |
MDL No. : | MFCD00012941 |
InChI Key : | RGGOWBBBHWTTRE-UHFFFAOYSA-N |
Pubchem ID : | 12157 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 |
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 ? Topological Polar Surface Area: Calculated from |
38.05 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.19 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.35 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.45 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.04 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.61 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.98 |
Solubility | 0.232 mg/ml ; 0.00104 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.62 |
Solubility | 0.533 mg/ml ; 0.00238 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.94 |
Solubility | 0.255 mg/ml ; 0.00114 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.11 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.64 |
* 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.
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.6% | 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 70C for 3 hours, then cooled and concentrated sulfuric acid (0.5 ml) added, before heating at 70C for a further 3 hours. The slurry was poured into 10% sodium acetate aqueous solution (20 ml) and the precipitate filtered to give the title compound as a cream solid (0.367 g, yield 79.6%), mp > 300C; 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With hydrogenchloride; In methanol; water; acetic acid; at 20 - 60℃; | 4-bromophenylhydrazine hydrochloride in a solution of methanol (MeOH, 250 mL) is added to a solution of 1 ,2-cyclohexanedione (10.03 g, 89 mmol) in a mixture of AcOH (225 mL) and con. HCl (80 mL) at 6O0C over a period of 1.5 h. After the addition, the reaction mixture is stirred at room temperature overnight. The precipitated solid is filtered, washed with MeOH and dried. On evaporation, the filtrate yields a residue, which on washing with MeOH, gives additional product. The combined yield is 8.75 g (74%). ES-MS: 264.03 (MH)+ |
56% | With hydrogenchloride; acetic acid; In methanol; water; at 60℃; | 4-Bromophenylhydrazine hydrochloride (10 mmol, 2235 mg) was dissolved in 25 mL of methanol and stirred to completely dissolve, and 1,2-cyclohexanedione (20 mmol, 2243 mg) was dissolved in 40 mL of glacial acetic acid and added to 13 mL. Concentrated HCl was stirred at 60C. A 4-bromophenylhydrazine hydrochloride solution in methanol was slowly added dropwise thereto using a constant pressure dropping funnel. The reaction was maintained overnight at 60C. TLC monitored the reaction.After completion, the solvent was evaporated and dissolved with EA (20 mL). The pH was adjusted to 8-9 with sat. NaHCO3 and then EA (2 x 20 mL) was added.The combined organic phases were extracted, washed with saturated brine, dried over anhydrous Na 2 SO 4 , and the solvent was distilled off under reduced pressure with methanol and dichloromethan.Recrystallization of the alkane gave the intermediate 6-bromo-2,3,4,9-tetrahydro-1H-indazole-1-one (1.48 g, yield 56%). |
22% | With hydrogenchloride; acetic acid; In methanol; at 20 - 60℃; for 12h; | Example 316-Bromo-9H-carbazol-l-olIntermediate 31a6-Bromo-2,3,4,9-tetrahydro-lH-carbazol-l-4-Bromophenyl hydrazine hydrochloride (0.3 g, 1.3 mmol) in MeOH (3 mL) was heated to 60 C and 1, 2-cyclohexanedione (0.16 g, 1.4 mmol), dissolved in AcOH (4 mL) and cone. HCI (1.5 mL) were added while maintaining the temperature at 60 C. After the addition was completed, the reaction mixture was cooled to room temperature and stirred for 12 h during time a solid precipitated out. The mixture was basified with aq NaHC03 and extracted with EtOAc (3 x 25 mL). The combined organic extracts were washed with water, dried over Na S04 and concentrated in vacuo to give the crude product which was purified by column chromatography to give the title compound as a pale yellow solid (0.080 g, 22%). 1H NMR (500 MHz, CDC13, delta in ppm) 8.8 (bs, 1H), 7.8 (s, 1H), 7.43 (dd, J= 10.0, 2.0 Hz, 1H), 7.24 (d, J= 9.5 Hz, 1H), 2.98 (t, J= 8.0 Hz, 2H), 2.63 (t, J= 8.0 Hz, 2H), 2.24 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In butan-1-ol; | EXAMPLE 4 3-Amino-6-bromo-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-bromophenylhydrazine hydrochloride (4.0 g, 18.1 mmol) with 4-phthalimido-cyclohexanone (4.39 g, 18.1 mmol) in refluxing n-butanol for 20 min, followed by cooling, filtration, and evaporation of the filtrate to dryness yielded 3-phthalimido-6-bromo-1,2,3,4-tetrahydrocarbazole as an orange solid (7.45 g). | |
In butan-1-ol; | Example 4 3-Amino-6-bromo-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-bromophenylhydrazine hydrochloride (4.0g, 18.1 mmol) with 4-phthalimido-cyclohexanone (4.39g, 18.1 mmol) in refluxing n-butanol for 20 min, followed by cooling, filtration, and evaporation of the filtrate to dryness yielded 3-phthalimido-6-bromo-1,2,3,4-tetrahydrocarbazole as an orange solid (7.45g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 2Preparation of 2-(5-bromo-1H-indol-3-yl)-N,N-dimethylethanamine (IV) 8.3 g of 4-dimethylaminobutanal diethylacetal (Tech grade from Aldrich) was added to a solution of 11.3 g of the product from Example 1 in a mixture of acetic acid (110 mL) and water (5 mL) and the resulting mixture was refluxed for 4 h. The mixture was cooled and evaporated in vacuum. The residue was dissolved in 100 mL of water and the pH was adjusted to 89 by saturated sodium bicarbonate, then extracted with 5×50 mL of dichloromethane. The combined organics were concentrated in vacuo and the residue was eluted through a silica column using DCM/EtOH/NH4OH (30:8:1) as eluant to give 3.0 g of the desired product as a pale yellow oil.1H NMR (DMSO-d6, delta): 2.53 (s, 6H, NMe2), 2.93 (s, 4H, CH2CH2), 7.16 (d, 1H, Ar), 7.26 (s, 1H, Ar), 7.33 (d, 1H, Ar), 7.75 (s, 1H, Ar), 11.20 (s, 1H, NH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | General procedure: 4.2.1. tert-Butyl 2-bromo-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-11-carboxylate 2. A slurry of 4-bromophenyl hydrazine hydrochloride (124.0 g, 554.8 mmol) and <strong>[25602-68-0]nortropinone hydrochloride</strong> (89.7 g, 554.8 mmol) in ethanol (900 mL) was heated at reflux for 4 h. The reaction mixture was cooled to room temperature and concentrated hydrochloric acid (650 mL) was added; again the reaction mixture was refluxed for a further 65 h. The reaction mixture was concentrated in vacuo to give a brown oil, which was diluted with 2-propanol (900 mL), water (450 mL), basified with potassium carbonate (214 g, 1.5 mol) at 0 °C prior to the addition of di-tert-butyl dicarbonate (181.6 g, 832.0 mmol). The reaction mixture was stirred at 0 °C for 6 h then diluted with water (1.5 L) and extracted with dichloromethane (2 x 2 L). The extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was diluted with dichloromethane, stored overnight in a refrigerator and filtered. The filter cake was rinsed with cold dichloromethane, and dried in vacuo to afford 2 (55.4 g, 26percent) as a gray solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 21h;Inert atmosphere; | [00346] 55A. 3-((2-(4-bromophenyl)hydrazono)methyl)-l-methyl-lH-pyrazole: To a solution of (4-bromophenyl)hydrazine hydrochloride (1 150 mg, 5.04 mmol) and 1- methyl-lH-pyrazole-3-carbaldehyde (580 mg, 5.00 mmol) in DMF (5.1 mL) was added triethylamine (0.84 mL, 6.00 mmol). The mixture was stirred at rt under argon for 21 h, water (9 mL) was added and stirring was continued for 1 h. The solid that resulted was filtered, rinsed with water (5 mL) and dissolved in CH2C12 (120 mL). The CH2C12 solution was dried (Na2S04) and concentrated to provide 55A (1400 mg, 5.02 mmol, 100 percent yield) as a yellowish solid: lH NMR (400MHz, CDC13) d 7.76 (s, 1H), 7.63 (s, 1H), 7.34 (m, 3H), 6.97 (d, J= 8.8 Hz, 2H), 3.91 (s, 3H). |
Tags: 622-88-8 synthesis path| 622-88-8 SDS| 622-88-8 COA| 622-88-8 purity| 622-88-8 application| 622-88-8 NMR| 622-88-8 COA| 622-88-8 structure
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H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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