[ CAS No. 16582-58-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Structure of 16582-58-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 16582-58-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 16582-58-4 ]

SDS Specification

Alternatived Products of [ 16582-58-4 ]

Product Details of [ 16582-58-4 ]

CAS No. :	16582-58-4	MDL No. :	MFCD00996639
Formula :	C₇H₅IN₂S	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	WMKLSFIAHMBOTP-UHFFFAOYSA-N
M.W :	276.10	Pubchem ID :	3524848
Synonyms :

Calculated chemistry of [ 16582-58-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.74
TPSA :	67.15 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	2.68
Log Po/w (WLOGP) :	2.49
Log Po/w (MLOGP) :	2.17
Log Po/w (SILICOS-IT) :	3.39
Consensus Log Po/w :	2.53

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.85
Solubility :	0.0394 mg/ml ; 0.000143 mol/l
Class :	Soluble
Log S (Ali) :	-3.74
Solubility :	0.05 mg/ml ; 0.000181 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.56
Solubility :	0.076 mg/ml ; 0.000275 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.35

Safety of [ 16582-58-4 ]

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

Application In Synthesis of [ 16582-58-4 ]

* 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 [ 16582-58-4 ]
Downstream synthetic route of [ 16582-58-4 ]

[ 16582-58-4 ] Synthesis Path-Upstream 1~7

1
[ 333-20-0 ]
[ 540-37-4 ]
[ 16582-58-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: at 20℃; Cooling with ice Stage #2: With ammonium hydroxide In water	General procedure: A mixture of 0.1 mol of 4-substituted aniline and 0.1 mol of Potassium thiocyanate (KCNS) in 100 ml glacial acetic acid (AcOH) was cooled in an ice bath and stirred for 10-20 min, and then 0.1 mol bromine in glacial acetic acid was added dropwise at such a rate to keep the temperature below 10 °C throughout the addition. The reaction mixture was stirred at room temperature for 2-4 h, the hydrobromide (HBr) salt thus separated out was filtered, washed with acetic acid, dried, dissolved in hot water and basified to pH 11.0 with ammonia solution (NH₄OH) and the resulting precipitate was filtered, washed with water and dried to get the desired product 3a-k. The progress of the reaction was monitored by Thin Layer Chromatography using toluene: acetone (8:2) solvent system.

Reference： [1] European Journal of Medicinal Chemistry, 2012, vol. 53, p. 41 - 51
[2] Heteroatom Chemistry, 2012, vol. 23, # 4, p. 399 - 410
[3] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 24 - 30
[4] Medicinal Chemistry, 2013, vol. 9, # 4, p. 596 - 607
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 23, p. 5561 - 5565

2
[ 18879-80-6 ]
[ 16582-58-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With bromine In chloroform for 6 h; Reflux	(0143) Chloroform suspension (7 ml) of 1-(4-iodophenyl)thiourea (889 mg, 3.19 mmol) was added with bromine (328 μl, 6.40 mmol), and heated to reflux and stirred for 6 hours. After the reaction was completed and the solvent was removed, the residue was added with dichloromethane and washed with saturated sodium bicarbonate solution and saturated sodium chloride solution. After the solution was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure, the resulting deposits were filtered to obtain 650 mg 2-amino-6-iodobenzothiazole in a yield of 73percent.

Reference： [1] Patent: US2016/2600, 2016, A1, . Location in patent: Paragraph 0143
[2] Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 122,127
[3] Journal of the Indian Chemical Society, 1931, vol. 8, p. 147,163
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 15, p. 2828 - 2843

3
[ 1147550-11-5 ]
[ 540-37-4 ]
[ 16582-58-4 ]

Reference： [1] European Journal of Organic Chemistry, 2011, # 31, p. 6206 - 6217

4
[ 540-37-4 ]
[ 16582-58-4 ]

Reference： [1] Medicinal Chemistry Research, 2013, vol. 22, # 1, p. 195 - 210
[2] Journal of Chemical Research, 2014, vol. 38, # 10, p. 611 - 616
[3] Patent: US2016/2600, 2016, A1,

5
[ 540-72-7 ]
[ 540-37-4 ]
[ 16582-58-4 ]

Reference： [1] Die Pharmazie, 1967, vol. 22, # 6, p. 229 - 233

6
[ 15192-76-4 ]
[ 540-37-4 ]
[ 16582-58-4 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1956, p. 1701

7
[ 67-66-3 ]
[ 18879-80-6 ]
[ 7726-95-6 ]
[ 16582-58-4 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 122,127
[2] Journal of the Indian Chemical Society, 1931, vol. 8, p. 147,163

[ 16582-58-4 ] Synthesis Path-Downstream 1~15

1
[ 16582-58-4 ]
[ 77-78-1 ]
6-iodo-3-methyl-2<i>H</i>-benzothiazol-2-one-imine [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1931,vol. 8,p. 147,163

2
[ 16582-58-4 ]
[ 74-88-4 ]
(6-iodo-3-methyl-3<i>H</i>-benzothiazol-2-ylidene)-nitroso-amine [ No CAS ]

Reference： [1]Journal of the Chemical Society,1935,p. 1755,1760

3
[ 16582-58-4 ]
[ 855282-75-6 ]

Reference： [1]Zhurnal Obshchei Khimii,1939,vol. 9,p. 409,411
Chemisches Zentralblatt,1940,vol. 111,p. 545

4
[ 540-72-7 ]
[ 540-37-4 ]
[ 16582-58-4 ]

Reference： [1]Pharmazie,1967,vol. 22,p. 229 - 233

5
[ 540-37-4 ]
p-chloro-benzenesulfonyl chloride [ No CAS ]
[ 16582-58-4 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2828 - 2843

6
[ 16582-58-4 ]
N-(4-chlorophenyl)-6-iodobenzo[d]thiazol-2-amine [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1935,vol. 54,p. 122,127

7
[ 16582-58-4 ]
4-(6-iodo-benzothiazol-2-ylamino)-benzonitrile [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1935,vol. 54,p. 122,127

Yield	Reaction Conditions	Operation in experiment
		Listed below are some typical examples of said 2-aminobenzothiazole compounds: ... 2-amino-6-methoxybenzothiazole 2-amino-6-ethoxybenzothiazole 2-amino-6-chlorobenzothiazole 2-amino-6-bromobenzothiazole 2-amino-6-iodobenzothiazole 2-amino-6-cyanobenzothiazole 2-amino-6-thiocyanobenzothiazole 2-amino-6-methylbenzothiazole ...

9
[ 16582-58-4 ]
[ 1262983-59-4 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 6206 - 6217

10
[ 16582-58-4 ]
[ 1352149-35-9 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 6206 - 6217

11
[ 16582-58-4 ]
[ 1352149-40-6 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 6206 - 6217

12
[ 16582-58-4 ]
C₁₆H₁₆IN₃O₅S [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 6206 - 6217

13
[ 1147550-11-5 ]
[ 540-37-4 ]
[ 16582-58-4 ]

Reference： [1],2020,vol. 10,p. 1401 - 1407
[2]European Journal of Organic Chemistry,2011,p. 6206 - 6217

14
[ 16582-58-4 ]
[ 1382132-16-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 53,p. 41 - 51

15
[ 16582-58-4 ]
[ 79-04-9 ]
[ 1372894-46-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; In benzene;Reflux;	General procedure: Chloroacetyl chloride (0.06 mol) was added dropwise to a mixture of the appropriate 2-amino-6-Substituted benzothiazole, 3a-k (0.05 mol) and K2CO3 (0.06 mol) in benzene (50 mL) at room temperature. The reaction mixture was refluxed for 6-12 h, then, after cooling to room temperature, it was slowly poured into 100 mL of ice water. A solid was formed thereafter. The precipitate was separated by filtration and washed successively with water. The product was dried under vacuum to obtain 4a-k. The progress of the reaction was monitored by Thin Layer Chromatography using toluene: acetone (8:2) solvent system.
	With potassium carbonate; In benzene;Reflux;	General procedure: Chloroacetyl chloride (0.06mol) was added dropwise to a mixture of the appropriate 2-amino-6-substituted benzothiazoles, 2a-k (0.05mol) and K2CO3 (0.06mol) in benzene (50mL) at room temperature. The reaction mixture was refluxed for 6-12h, then, after cooling to room temperature, it was slowly poured into 100mL of ice water. A solid was formed thereafter. The precipitate was separated by filtration and washed successively with water. The product was dried under vacuum to obtain 3a-k. The progress of the reaction was monitored by Thin Layer Chromatography using toluene:acetone (8:2) solvent system.
	With potassium carbonate; In benzene;Reflux;	General procedure: To 0.05 mol of each 2-amino-6-substituted benzothiazole derivative (3a-k) and 0.06 mol of anhydrous K2CO3 in 50 mL of benzene, 0.06 mol of chloroacetyl chloride (0.06 mol) was added dropwise at room temperature and mixture was allowed to reflux for 6 to 12 h. The reaction progress was monitored by TLC using toluene : acetone (V/V, 8:2) solvent system. After the completion of the reaction, the mixture was cooled and poured into crushed ice. A solid thus obtained was filtered, washed with water and dried on vacuum oven to get 4a-k [27].

With potassium carbonate; In benzene; at 20℃;Reflux;

General procedure: Chloroacetyl chloride (0.06 mol) was added dropwise to a mixture of the appropriate 2-amino-6-substituted benzothiazole, 3a-k (0.05 mol)and K2CO3 (0.06 mol) in benzene (50 mL) at room temperature. The reaction mixture was refluxed for 6 to 12 h, then, after cooling to room temperature, it was slowly poured into ice water (100 mL). The solid that formed was separated by filtration, washed successively with water, then dried under vacuum to obtain 4a-k.17-20 The progress of the reaction was monitored by TLC using toluene: acetone (8 : 2) solvent system.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 53,p. 41 - 51
[2]Medicinal Chemistry Research,2013,vol. 22,p. 195 - 210
[3]Heteroatom Chemistry,2012,vol. 23,p. 399 - 410
[4]European Journal of Medicinal Chemistry,2014,vol. 71,p. 24 - 30
[5]Medicinal Chemistry,2013,vol. 9,p. 596 - 607
[6]Journal of Chemical Research,2014,vol. 38,p. 611 - 616

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Isomers

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 ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? 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 ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

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P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
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P202	Do not handle until all safety precautions have been read and understood.
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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.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P265	Wash skin thouroughly after handling.
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P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
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P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
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.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
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.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
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
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
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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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.
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P501	Dispose of contents/container to ...
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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
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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
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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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
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H316	Causes mild skin irritation
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H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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[ CAS No. 16582-58-4 ] {[proInfo.proName]}

Quality Control of [ 16582-58-4 ]

Related Doc. of [ 16582-58-4 ]

Product Details of [ 16582-58-4 ]

Calculated chemistry of [ 16582-58-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 16582-58-4 ]

Application In Synthesis of [ 16582-58-4 ]

[ 16582-58-4 ] Synthesis Path-Upstream 1~7

[ 16582-58-4 ] Synthesis Path-Downstream 1~15

Technical Information

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry