[ CAS No. 19983-44-9 ] {[proInfo.proName]}

Name: 19983-44-9|6-Nitrobenzo[b]thiophene 1,1-dioxide|98%
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3d Animation Molecule Structure of 19983-44-9

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Quality Control of [ 19983-44-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 19983-44-9 ]

SDS Specification

Alternatived Products of [ 19983-44-9 ]

Product Details of [ 19983-44-9 ]

CAS No. :	19983-44-9	MDL No. :
Formula :	C₈H₅NO₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZRRGOUHITGRLBA-UHFFFAOYSA-N
M.W :	211.19	Pubchem ID :	2779853
Synonyms :	STAT3 Inhibitor V	Chemical Name :	6-Nitrobenzo[b]thiophene 1,1-dioxide

Calculated chemistry of [ 19983-44-9 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.53
TPSA :	88.34 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.96
Log Po/w (XLOGP3) :	0.71
Log Po/w (WLOGP) :	2.32
Log Po/w (MLOGP) :	1.1
Log Po/w (SILICOS-IT) :	-0.84
Consensus Log Po/w :	0.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.85
Solubility :	3.0 mg/ml ; 0.0142 mol/l
Class :	Very soluble
Log S (Ali) :	-2.14
Solubility :	1.52 mg/ml ; 0.00719 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.79
Solubility :	3.4 mg/ml ; 0.0161 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.96

Safety of [ 19983-44-9 ]

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

Application In Synthesis of [ 19983-44-9 ]

* 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 [ 19983-44-9 ]
Downstream synthetic route of [ 19983-44-9 ]

[ 19983-44-9 ] Synthesis Path-Upstream 1~8

1
[ 19983-44-9 ]
[ 20503-40-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 963 - 968
[2] Journal of the Chemical Society, 1955, p. 1565,1568

2
[ 825-44-5 ]
[ 19983-44-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	at 0℃; for 0.5 h;	Reference Example 118 6-Nitro-1-benzothiophene 1,1-dioxide Nitric acid (10 mL) was slowly added to sulfuric acid (10 mL) at 0°C, and the mixture was stirred at the same temperature for 10 min. To this solution was slowly added 1-benzothiophene 1,1-dioxide (3.99 g) at 0°C, and the mixture was further stirred at the same temperature for 30 min. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed twice with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound as a pale-yellow solid (yield 4.26 g, 84percent). ¹H-NMR (CDCl₃)δ: 7.00 (1H, d, J=6.9 Hz), 7.33 (1H, dd, J=1.2, 6.9 Hz), 7.58 (1H, d, J=8.4 Hz), 8.47 (1H, dd, J=1.8, 8.4 Hz), 8.55-8.57 (1H, m).

Reference： [1] Patent: WO2006/36024, 2006, A1, . Location in patent: Page/Page column 154-155
[2] Patent: EP2336107, 2015, B1, . Location in patent: Paragraph 0292
[3] Journal of the Chemical Society, 1948, p. 1615,1617
[4] Journal of the Chemical Society, 1957, p. 826,830
[5] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 963 - 968
[6] Patent: EP1803709, 2007, A1,

3
[ 858819-40-6 ]
[ 19983-44-9 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 5939,5943

4
[ 857473-99-5 ]
[ 19983-44-9 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 5939,5943

5
[ 850855-54-8 ]
[ 19983-44-9 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 5939,5943

6
[ 51956-01-5 ]
[ 19983-44-9 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 5939,5943

7
[ 95-15-8 ]
[ 19983-44-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 963 - 968
[2] Patent: EP2336107, 2015, B1,

8
[ 825-44-5 ]
[ 7697-37-2 ]
[ 19983-44-9 ]
[ 22952-26-7 ]

Reference： [1] Journal of the Chemical Society, 1948, p. 1615,1617

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P234	Keep only in original container.
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Code	Phrase
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P321
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P337	If eye irritation persists:
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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
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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P370	In case of fire:
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P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
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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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
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.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
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Yield	Reaction Conditions	Operation in experiment
75%	With palladium 10% on activated carbon; hydrogen; In methanol; ethanol; for 12.0h;	Reference Example 119 2,3-Dihydro-1-benzothiophene-6-amine 1,1-dioxide To a suspension of <strong>[19983-44-9]6-nitro-1-benzothiophene 1,1-dioxide</strong> (2.02 g) in ethanol (200 mL) and methanol (60 mL) was added 10% palladium carbon (50% containing water, 265 mg), and the mixture was stirred under a hydrogen atmosphere for 12 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound as a white solid (yield 1.31 g, 75%). 1H-NMR (CDCl3)delta: 3.25 (2H, t, J=6.9 Hz), 3.44-3.49 (2H, m), 3.93 (2H, brs), 6.84-6.87 (1H, m), 6.94-6.95 (1H, m), 7.12 (1H, d, J=8.1 Hz).
	palladium-carbon; In methanol; ethanol;	Reference Example 119 2,3-Dihydro-1-benzothiophene-6-amine 1,1-dioxide To a suspension of <strong>[19983-44-9]6-nitro-1-benzothiophene 1,1-dioxide</strong> (2.02 g) in ethanol (200 mL) and methanol (60 mL) was added 10% palladium carbon (50% containing water, 265 mg), and the mixture was stirred under a hydrogen atmosphere for 12 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound as a white solid (yield 1.31 g, 75%). 1H-NMR (CDCl3)delta: 3.25 (2H, t, J=6.9 Hz), 3.44-3.49 (2H, m), 3.93 (2H, brs), 6.84-6.87 (1H, m), 6.94-6.95 (1H, m), 7.12 (1H, d, J=8.1 Hz).
	With hydrogen; acetic acid;palladium 10% on activated carbon; In ethyl acetate;	A solution of <strong>[19983-44-9]6-nitro-1-benzothiophene 1,1-dioxide</strong> (1.04 g) in acetic acid (50 ml) and ethyl acetate (50 ml) was hydrogenated(10% palladium on carbon (130 mg, 50% wet). The catalyst was removed by filtration and washed with ethyl acetate. The filtrate and washings were evaporated under reduced pressure to give the title compound (1.1g). LCMS RT=1. 50 min

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

Yield	Reaction Conditions	Operation in experiment
84%	With sulfuric acid; nitric acid; for 0.5h;	Reference Example 118 6-Nitro-1-benzothiophene 1,1-dioxide Nitric acid (10 mL) was slowly added to sulfuric acid (10 mL) at 0C, and the mixture was stirred at the same temperature for 10 min. To this solution was slowly added 1-benzothiophene 1,1-dioxide (3.99 g) at 0C, and the mixture was further stirred at the same temperature for 30 min. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed twice with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound as a pale-yellow solid (yield 4.26 g, 84%). 1H-NMR (CDCl3)delta: 7.00 (1H, d, J=6.9 Hz), 7.33 (1H, dd, J=1.2, 6.9 Hz), 7.58 (1H, d, J=8.4 Hz), 8.47 (1H, dd, J=1.8, 8.4 Hz), 8.55-8.57 (1H, m).
	With sulfuric acid; nitric acid;	Reference Example 118 6-Nitro-1-benzothiophene 1,1-dioxide Nitric acid (10 mL) was slowly added to sulfuric acid (10 mL) at 0C, and the mixture was stirred at the same temperature for 10 min. To this solution was slowly added 1-benzothiophene 1,1-dioxide (3.99 g) at 0C, and the mixture was further stirred at the same temperature for 30 min. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed twice with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound as a pale-yellow solid (yield 4.26 g, 84%). 1H-NMR (CDCl3)delta: 7.00 (1H, d, J=6.9 Hz), 7.33 (1H, dd, J=1.2, 6.9 Hz), 7.58 (1H, d, J=8.4 Hz), 8.47 (1H, dd, J=1.8, 8.4 Hz), 8.55-8.57 (1H, m).

[ CAS No. 19983-44-9 ] {[proInfo.proName]}

Quality Control of [ 19983-44-9 ]

Related Doc. of [ 19983-44-9 ]

Product Details of [ 19983-44-9 ]

Calculated chemistry of [ 19983-44-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 19983-44-9 ]

Application In Synthesis of [ 19983-44-9 ]

[ 19983-44-9 ] Synthesis Path-Upstream 1~8

[ 19983-44-9 ] Synthesis Path-Downstream 1~68

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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