[ CAS No. 216394-05-7 ] {[proInfo.proName]}

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Quality Control of [ 216394-05-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 216394-05-7 ]

Product Details of [ 216394-05-7 ]

CAS No. :	216394-05-7	MDL No. :	MFCD01318107
Formula :	C₅H₂BrCl₂NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	TURGMVYIESHZBE-UHFFFAOYSA-N
M.W :	290.95	Pubchem ID :	2793626
Synonyms :

Safety of [ 216394-05-7 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P303+P361+P353-P210-P402+P404-P501-P260-P301+P330+P331-P305+P351+P338	UN#:	3261
Hazard Statements:	H302-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 216394-05-7 ]

* 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.

Downstream synthetic route of [ 216394-05-7 ]

[ 216394-05-7 ] Synthesis Path-Downstream 1~9

1
[ 134003-84-2 ]
[ 216394-05-7 ]
[ 1001407-42-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3627 - 3644

2
[ 70125-16-5 ]
[ 216394-05-7 ]
[ 1146771-34-7 ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 1378 - 1388

3
[ 247582-62-3 ]
[ 216394-05-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 2-Amino-3-bromopyridine-5-sulphonic Acid With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Stage #2: With phosphorus pentachloride; trichlorophosphate at 75 - 125℃;	199.1 A cooled (0 0C) solution of θ-amino-S-bromopyridine-S-sulfonic acid (12.65 g; 50.00 mmol) in HCI (60 ml; 5 N solution in water) was treated carefully with a solution of sodium nitrite (3.80 g; 55.0 mmol) in water (15 ml) and stirred at 0 0C for 1 hour. The solvents were evaporated and the residue was dried under high vacuum for 2 days, then treated with phosphorus pentachloride (15.00 g; 72 mmol) and phosphorus oxide chloride (0.50 ml; 5.5 mmol). The solid mixture was heated at 125 0C to give a refluxing solution. After heating at 75 0C for 3 hours, the solution was cooled and carefully poured on crushed ice. EtOAc was added and the phases separated. The organic phase was washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to give the title compound as a brown oil (14.91 g, quantitative yield), which was used without purification.
100%	Stage #1: 2-Amino-3-bromopyridine-5-sulphonic Acid With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Stage #2: With phosphorus pentachloride In trichlorophosphate at 75℃; for 3h;
26.58 g	Stage #1: 2-Amino-3-bromopyridine-5-sulphonic Acid With hydrogenchloride; sodium nitrite In water at 0 - 25℃; for 1.5h; Cooling with ice; Stage #2: With phosphorus pentachloride; trichlorophosphate at 125℃; for 3h;	5.1. Pyridine 2-ethoxy-5-(4-ethylpiperazin-1-ylsulphonyl)-3-carboxylic acid (3a) (iii) A solution of sodium nitrite (7.6 g, 110.0 mmol) in water (30 mL) was added dropwise to an ice-cooled solution of the bromo sulphonic acid (25.3 g, 100.0 mmol) in 20% aqueous hydrochloric acid (115 mL), so as to maintain the temperature below 6 °C. The reaction was stirred for 30 min at 0 °C and for a further 1 h at room temperature. The reaction mixture was evaporated under reduced pressure and the residue dried under vacuum at 70 °C for 72 h. A mixture of this solid, phosphorus pentachloride (30.0 g, 144.0 mmol) and phosphorus oxychloride (1 mL, 10.8 mmol) was heated at 125 °C for 3 h, and then cooled. The reaction mixture was poured onto ice (100 g) and the resulting solid filtered, and washed with water. The product was dissolved in dichloromethane, dried (MgSO4), and evaporated under reduced pressure to afford pyridine-3-bromo-2-chloro-5-sulphonyl chloride as a yellow solid (26.58 g). 1H NMR (CDCl3) δ: 8.46 (s, 1H), 8.92 (s, 1H).

Reference： [1]Current Patent Assignee: MERCK KGAA - WO2010/92043, 2010, A1 Location in patent: Page/Page column 145-146
[2]Crosignani, Stefano; Prêtre, Adeline; Jorand-Lebrun, Catherine; Fraboulet, Gaële; Seenisamy, Jeyaprakashnarayanan; Augustine, John Kallikat; Missotten, Marc; Humbert, Yves; Cleva, Christophe; Abla, Nada; Daff, Hamina; Schott, Olivier; Schneider, Manfred; Burgat-Charvillon, Fabienne; Rivron, Delphine; Hamernig, Ingrid; Arrighi, Jean-François; Gaudet, Marilène; Zimmerli, Simone C.; Juillard, Pierre; Johnson, Zoe [Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7299 - 7317]
[3]Location in patent: experimental part Rawson, David J.; Ballard, Stephen; Barber, Christopher; Barker, Laura; Beaumont, Kevin; Bunnage, Mark; Cole, Susan; Corless, Martin; Denton, Stephen; Ellis, David; Floc'H, Marion; Foster, Laura; Gosset, James; Holmwood, Frances; Lane, Charlotte; Leahy, David; Mathias, John; Maw, Graham; Million, William; Poinsard, Cedric; Price, Jenny; Russel, Rachel; Street, Stephen; Watson, Lesa [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 498 - 509]

4
[ 16250-08-1 ]
[ 216394-05-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509

5
[ 808770-39-0 ]
[ 216394-05-7 ]
5-bromo-6-chloro-N-(6-chloro-4-methoxypyridazin-3-yl)pyridine-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	Stage #1: 6-chloro-4-methoxypyridazin-3-amine With sodium hydride In 1,2-dimethoxyethane for 0.0833333h; Stage #2: 5-bromo-6-chloropyridine-3-sulfonyl chloride In 1,2-dimethoxyethane for 1h;	5-bromo-6-chloro-N-(6-chloro-4-methoxypyridazin-3-yl)pyridine-3-sulfonamide Toa suspension of 6-chloro-4-methoxypyridazin-3-amine (3.00g, 18.8 mmol) in drydimethoxyethane (60 mL) was added sodium hydride (752 mg, 60%, 18.8 mmol) andthe mixture stirred 5 mins. 5-bromo-6-chloropyridine-3-sulfonyl chloride (4.92g, 16.9 mmol) was then added and the mixture stirred 1 hr. EtOAc was added (100mL) followed by water (15 mL) and the phases were separated. The aqueous phasewas then acidified (1M HC1) resulting in a white emulsion. More EtOAc (50 mL)was added.The phases were separated and the organic phase was washed with brine(15 mL), dried ( a2S04), the mixture filtered and thefiltrate evaporated to dryness to afford an off white solid containing thetitle compound (1.03g, 13%); m/z=412.7, 414.7 (MH)+.

Reference： [1]Current Patent Assignee: ACTIVE BIOTECH AB - WO2014/184234, 2014, A1 Location in patent: Page/Page column 74

6
[ 33631-09-3 ]
[ 216394-05-7 ]
5-bromo-6-chloro-N-(4-hydroxypyridin-3-yl)pyridine-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%		A mixture of <strong>[33631-09-3]3-amino-4-methoxypyridine</strong> (124 mg, 1.0 mmol) and 5-bromo-6-chloro- pyridine-3-sulfonyl chloride (291 mg, 1.0 mmol) was heated at 130C for 2 h. 2M HC1 in EtOH (200 mu) was added to the warm mixture to complete hydrolysis of the methoxy group and heated at 130C for one additional hour. The mixture was allowed to cool to 60C and MeOH (2 mL) was added. After stirring for 0.5 h at 60C, the decanted solution was allowed to pass through an NH2-column, eluted with acetone/MeOH (1 :0 to 1 : 1) and fractions containing product were evaporated. The residue was chromato graphed on silica (EtOAc/(MeOH/HOAc/H20 3:3 :2) 40:1 , 20:1 , 10:1), evaporated and dried in vacuum to afford 5-bromo-6-chloro-N-(4-hydroxypyridin-3-yl)pyridine-3-sulfonamide (70 mg, 19%).

Reference： [1]Patent: WO2014/184234,2014,A1 .Location in patent: Page/Page column 130; 131

7
[ 101084-20-2 ]
[ 216394-05-7 ]
5-bromo-N-(5-bromo-4-hydroxypyridin-3-yl)-6-methoxypyridine-3-sulfonamide [ No CAS ]

Reference： [1]Patent: WO2014/184234,2014,A1

8
[ 101084-20-2 ]
[ 216394-05-7 ]
C₁₀H₆Br₂ClN₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[101084-20-2]3-amino-5-bromopyridin-4-ol</strong> (250 mg, 0.926 mmol) in pyridine (3 mL) at 80C was added a crystal of DMAP, and the solution stirred at this temperature for 10 min. Then 5-bromo-6-chloropyridine-3-sulfonyl chloride (269 mg, 0.926 mmol) was added in portions over 3 min. The mixture was stirred for 1 hr at this temperature then the pyridine was evaporated. The residue was suspended in MeOH (10 mL), methanolic sodium methoxide solution added via syringe (5.4M, 1.2 mL, 6.5 mmol) and the mixture heated at 75C for 3h. The solvent was evaporated and the residue acidified with 0.5M HC1. EtOAc (50 mL) was added, the phases were separated and the organic phase was washed with brine (20 mL), dried (Na2SC>4), the mixture filtered and the filtrate evaporated to dryness to afford a red solid which was purified by automated reverse- phase HPLC (low pH method) to afford the title compound as a pink solid (10 mg, 2%).

Reference： [1]Patent: WO2014/184234,2014,A1 .Location in patent: Page/Page column 145

9
[ 216394-05-7 ]
[ 1196153-82-8 ]
[ 1638200-93-7 ]

Yield	Reaction Conditions	Operation in experiment
12%	With pyridine; dmap at 0 - 20℃; for 1h;	128 5-bromo-6-chloro-N-[4-hydroxy-6-(trifluoromethyl)pyridiii-3-yl]pyridine-3- sulfonamide To a stirred solution of 5-amino-2-(trifiuoromethyl)pyridin-4-ol (130 mg, 0.73 mmol) and N,N-dimethylpyridin-4-amine (4.4 mg, 0.036 mmol) in pyridine (1.5 mL) at 0°C was added 5-bromo-6-chloropyridine-3-sulfonyl chloride (220 mg, 0.759 mmol). The reaction mixture was stirred at room temperture for 1 hr. More 5-bromo-6-chloropyridine-3- sulfonyl chloride (26 mg, 0.091 mmol) was added and stirring continued for a further 1 hr. The pH was adjusted to 3 with 1 M HC1, the mixture extracted with EtOAc (3x 1 OmL) and the organics combined, dried (MgSC^), filtered and the filtrate concentrated to dryness. The crude material was purified by automated reverse phase HPLC (low pH method) to yield the title compound as an off white solid (36 mg, 12%).

Reference： [1]Current Patent Assignee: ACTIVE BIOTECH AB - WO2014/184234, 2014, A1 Location in patent: Page/Page column 162

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P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
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Prevention
Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P251	Pressurized container: Do not pierce or burn, even after use.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
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Code	Phrase
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P304	IF INHALED:
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P306	IF ON CLOTHING:
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P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
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P411 + P235	Keep cool.
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Physical hazards
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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
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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
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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
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H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
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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

[ CAS No. 216394-05-7 ] {[proInfo.proName]}

Quality Control of [ 216394-05-7 ]

Related Doc. of [ 216394-05-7 ]

Product Details of [ 216394-05-7 ]

Safety of [ 216394-05-7 ]

Application In Synthesis of [ 216394-05-7 ]

[ 216394-05-7 ] Synthesis Path-Downstream 1~9

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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