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

,{[proInfo.pro_purity]}

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2D 3D

Chemical Structure| 622-88-8

Chemical Structure| 622-88-8

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Quality Control of [ 622-88-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 622-88-8 ]

SDS Specification

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 :	No data available
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 ?2

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 1~2

1
[ 188290-36-0 ]
[ 622-88-8 ]
[ 40133-22-0 ]

Reference： [1] Tetrahedron, 2002, vol. 58, # 40, p. 8055 - 8058

2
[ 16511-38-9 ]
[ 622-88-8 ]
[ 142273-20-9 ]

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).

Reference： [1] Patent: WO2005/107471, 2005, A1, . Location in patent: Page/Page column 21

[ 622-88-8 ] Synthesis Path-Downstream 1~11

1
[ 622-88-8 ]
[ 135-19-3 ]
[ 1698-16-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1994,vol. 34,p. 697 - 706

2
[ 16511-38-9 ]
[ 622-88-8 ]
[ 142273-20-9 ]

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).

Reference： [1]Patent: WO2005/107471,2005,A1 .Location in patent: Page/Page column 21

3
[ 622-88-8 ]
[ 765-87-7 ]
[ 59514-18-0 ]

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).

Reference： [1]Patent: WO2006/58088,2006,A2 .Location in patent: Page/Page column 54
[2]Patent: CN107739371,2018,A .Location in patent: Paragraph 0149; 0150
[3]Patent: WO2011/97496,2011,A1 .Location in patent: Page/Page column 98-99

4
[ 622-88-8 ]
[ 104618-32-8 ]
3-phthalimido-6-bromo-1,2,3,4-tetrahydrocarbazole [ No CAS ]

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).

Reference： [1]Patent: US5464864,1995,A
[2]Patent: EP603432,1994,A1

5
[ 1116-77-4 ]
[ 622-88-8 ]
[ 17274-65-6 ]

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).

Reference： [1]Patent: US2010/217013,2010,A1 .Location in patent: Page/Page column 6-7

6
[ 622-88-8 ]
[ 25602-68-0 ]
tert-butyl 2-bromo-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-11-carboxylate [ No CAS ]

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.

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 1522 - 1527

7
[ 622-88-8 ]
[ 27258-32-8 ]
[ 1610371-10-2 ]

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).

Reference： [1]Patent: WO2014/78608,2014,A1 .Location in patent: Paragraph 00346

8
[ 110-86-1 ]
[ 622-88-8 ]
[ 63996-36-1 ]
[ 129013-83-8 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 7124 - 7127

9
[ 622-88-8 ]
[ 70070-32-5 ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 892 - 913

10
[ 720-94-5 ]
[ 622-88-8 ]
1-(4-bromophenyl)-5-(p-tolyl)-3- (trifluoromethyl)-1H-pyrazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 2693 - 2699
[2]Journal of the American Chemical Society,2018,vol. 140,p. 8781 - 8787
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 14937 - 14941
Angew. Chem.,2017,vol. 129,p. 15133 - 15137,5

11
[ 4139-61-1 ]
[ 622-88-8 ]
[ 67-68-5 ]
2-bromo-9-bromo-6H-chromeno[4,3-b]quinolin-6-one [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 705 - 714

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Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

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P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
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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