[ CAS No. 532-55-8 ] {[proInfo.proName]}

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Quality Control of [ 532-55-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 532-55-8 ]

Product Details of [ 532-55-8 ]

CAS No. :	532-55-8	MDL No. :	MFCD00004815
Formula :	C₈H₅NOS	Boiling Point :	-
Linear Structure Formula :	C₆H₅CO(NCS)	InChI Key :	CPEKAXYCDKETEN-UHFFFAOYSA-N
M.W :	163.20	Pubchem ID :	68284
Synonyms :

Safety of [ 532-55-8 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P261-P264-P270-P272-P280-P301+P310-P302+P352-P305+P351+P338-P310-P321-P330-P333+P313-P363-P405-P501	UN#:	2922
Hazard Statements:	H301-H317-H318	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 532-55-8 ]

* 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 [ 532-55-8 ]
Downstream synthetic route of [ 532-55-8 ]

[ 532-55-8 ] Synthesis Path-Upstream 1~1

1
[ 1824-81-3 ]
[ 532-55-8 ]
[ 96938-51-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	for 3 h; Reflux	To the solution of benzylisothiocyanate (83.0 g, 509.3 mmol) in acetone (700mL) was added compound 6-methylpyridin-2 -amine (50 g, 463.0mmol) in acetone (600 ml) dropwise, then the reaction mixture was stirred at reflux for 3h. The reaction mixture was poured on to crushed ice, then filtered and washed with water, water/MeOH (1 : 1) and MeOH to give l-benzoyl-3-(6- methylpyridin-2-yl)thiourea as a yellow solid (100.1 g, yield 80percent). To a solution of 1-benzoyl-3-(6-methylpyridin-2-yl)thiourea (60 g,221.4 mmol) in THF ( 1000 ml) was added 2N NaOH (243.5ml), then heated at reflux for 3 h. Cooled to RT and filtered to give (6-methylpyridin-2- yl)thiourea as a white solid (34.1 g, yield 92percent). A mixture of (6-methylpyridin-2-yl)thiourea (13.2 g, 79.16 mmol) and 2-bromo-l-(4-bromophenyl)ethan-l-one (22 g, 79.16 mmol) in ethanol (300 mL) was stirred at reflux for 3h, then concentrated and purified with silica gel column to give N-[4-(4-bromophenyl)-l,3-thiazol-2-yl]-6-methylpyridin-2-amine as a yellow solid (14.3 g,53percent). A solution of N-[4-(4-bromophenyl)-l,3-thiazol-2-yl]-6-methylpyridin-2-amine (5 g. 14.5mmol), Bis(pinacolato)diboron (4.8 g, 18.8mmol), Pd(dppf)2Ci2 (1.2 mg, 1.5mmol) and AcOK (4.3 g, 43.3mmol) in dioxane (100ml) was heated to 80 under 2 overnight. The mixture was evaporated to give (6-methyl-N-{4-[4-(tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-l,3-thiazol-2-yl}pyridin-2-amine). Coupling (200mg) with 2-dimethylamino-4- bromopyridine under standard conditions gave 33 mg from 200 mg of, yellow solid, 17 percent yield.

Reference： [1] Patent: WO2013/33037, 2013, A2, . Location in patent: Paragraph 0752
[2] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 1, p. 137 - 140
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 3081 - 3085
[4] Patent: WO2005/95345, 2005, A2, . Location in patent: Page/Page column 41
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 634 - 639
[6] ChemMedChem, 2013, vol. 8, # 5, p. 847 - 857
[7] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6385 - 6397
[8] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 8, p. 1366 - 1377

[ 532-55-8 ] Synthesis Path-Downstream 1~14

1
[ 32202-61-2 ]
[ 532-55-8 ]
[ 40507-75-3 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Benzoylchloride was added drop wise to a stirred solution of NH4SCN inacetone and stirred at 50°C for 2 hours. Next, a solution of substitutednaphthylamines in acetone was added drop wise, and the mixture wasstirred at 50oC for 24 hours. The reaction mixture was diluted withwater; the precipitated crystals collected by filtration and washedwith water. The crystals were then suspended in 2M NaOH (50 ml),refluxed for 1 hour, and poured into cold water and filtered. The crudecrystals of the resulting thiourea were dissolved in acetic acid, towhich benzyl trimethylammonium tribromide was added and allowedto react overnight. Ethyl ether (Et2O) was added and the precipitate ofthe resulting product-HBr salt was collected by filtration and washedwith Et2O. The salt was then treated with 1M NaOH to liberate thefree base, which was recrystallized in methanol.

Reference： [1]Arzneimittel-Forschung/Drug Research,1980,vol. 30,p. 1733 - 1737
[2]Journal of Organic Chemistry,2010,vol. 75,p. 2092 - 2095
[3]Molecular Pharmacology,2014,vol. 86,p. 342 - 357

2
[ 538-28-3 ]
[ 532-55-8 ]
[ 116719-71-2 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 269 - 271

3
[ 538-28-3 ]
[ 532-55-8 ]
[ 116719-68-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 269 - 271

4
[ 120-35-4 ]
[ 532-55-8 ]
3-[3-(3-Nitrophenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 254 4-Methoxy-3-[3-(3-nitro-phenyl)-thioureido]-N-phenyl-benzamide The title compound has been made using the procedure of Example 60, but using 3-amino-4-methoxy-N-phenyl benzamide and benzoyl isothiocyanate as starting materials, which are commercially available from Aldrich; m.p. 217-219 C.

Reference： [1]Patent: US6268387,2001,B1

5
[ 120-35-4 ]
[ 532-55-8 ]
4-Methoxy-N-phenyl-3-(3-benzoyl-thioureido)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 67 4-Methoxy-N-phenyl-3-(3-benzoyl-thioureido)-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.243 g, 1.0 mmol) and benzoyl isothiocyanate (0.171 g, 1.04 mmol) to afford the product (0.371 g); m.p. 219-222 C. CI Mass Spectrum: [M+H+]+=406. Calculated for C22H19N3O3S: C, 65.17; H, 4.72; N, 10.36. Found: C, 64.98; H, 4.57; N, 10.26.

Reference： [1]Patent: US6268387,2001,B1

6
[ 20358-03-6 ]
[ 532-55-8 ]
[ 1223564-51-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331

7
[ 16582-59-5 ]
[ 532-55-8 ]
[ 1537865-67-0 ]

Reference： [1]Turkish Journal of Chemistry,2013,vol. 37,p. 909 - 916

8
[ 16582-59-5 ]
[ 532-55-8 ]
[ 1537865-78-3 ]

Reference： [1]Turkish Journal of Chemistry,2013,vol. 37,p. 909 - 916

9
[ 39150-45-3 ]
[ 532-55-8 ]
N-((2,6-dibromo-4-sulfamoylphenyl)carbamothioyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone; for 2.0h;Reflux;	General procedure: A solution of acyl chloride (5mmol) and potassium thiocyanate (5.5mmol) in acetone (20mL) was reacted under reflux for 1h. Aromatic amine (5mmol) was added and the mixture was stirred under reflux for 2h. The reaction mixture was cooled to room temperature. The precipitate was filtered, washed with water and recrystallized from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 229 - 236

10
[ 16618-68-1 ]
[ 532-55-8 ]
N-((3-bromo-5-methoxyphenyl)carbamothioyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In acetone; at 20℃; for 1h;	To a solution of <strong>[16618-68-1]3-bromo-5-methoxyaniline</strong> (5.0 g, 25 mmol) stirred in acetone (100 mL) at room temperature, benzoyl isothiocyanate (3.95 mL, 27.2 mmol) was added. The reaction mixture was stirred for 1 hour before the acetone was removed by evaporation. The crude residue obtained was washed with hexanes and collected by filtration to give N-((3-bromo-5-ethoxyphenyl)carbamothioyl)benzamide as a yellow solid (8.0 g, 89 %). LC (Method B): 2.351 min. MS (APCI): calcd for Ci5Hi4BrN202S [M+H]+ m/z 365.0, 367.0, found 365.0, 367.0. 1H NMR (DMSO-d6, 400 MHz) 5 ppm 12.57 (br s, 1H), 11.64 (br s, 1H), 7.98 (d, J = 7.4 Hz, 2H), 7.67 (t, J = 7.4 Hz, 1H), 7.60 (br s, 1H), 7.55 (t, J = 7.8 Hz, 2H), 7.34 (br s, 1H), 7.08 (t, J = 2.0 Hz, 1H), 3.79 (s, 3H).

Reference： [1]Patent: WO2016/138199,2016,A1 .Location in patent: Paragraph 0084

11
[ 886372-63-0 ]
[ 532-55-8 ]
N-((5-fluoro-6-methoxypyridin-3-yl)carbamothioyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In acetone; at 20℃; for 3h;	To a solution of <strong>[886372-63-0]5-fluoro-6-methoxypyridin-3-amine</strong> (0.100 g, 0.704 mmol) in acetone (1 mL) was added dropwise benzoyl isothiocyanate (0. 104 mL, 0.774 mmol). The reaction mixture was all owed to stir at room temperature for 3 h. The reaction mixture was diluted with water and EtOAc. The layers were separated and the organic layer was washed with brine, dried with sodium sulfate, and concentrated under reduced pressure to yield Intermediate 1-21 A (0.215 g, 0.704 mmol, 100 % yield): 1H NMR (400MHz, CDCl3) delta 12,48 (brs, 1H), 9.12 (br s, 1 H), 8,06 (d, 2.0 Hz, 1H ). 8.01 (dd, J=10.8, 2,2 Hz, 1H), 7.91 (d, J=1.1Hz, 1 H), 7.89 (d, J = 1 .5 Hz, 1H), 7.71-7.65 (m, 1H), 7.60-7.54 (m, 2H), 4,06 (s, 3H), LC-MS: method H, RT = 1.18 rnin. MS (ESI) m/z: 306.1 (M+H)+.
100%	In acetone; at 20℃; for 3h;	To a solution of <strong>[886372-63-0]5-fluoro-6-methoxypyridin-3-amine</strong> (0.100 g, 0.704 mmol) in acetone (1 mL) was added dropwise benzoyl isothiocyanate (0.104 mL, 0.774 mmol). The reaction mixture was allowed to stir at room temperature for 3 h. The reaction mixture was diluted with water and EtOAc. The layers were separated and the organiclayer was washed with brine, dried with sodium sulfate, and concentrated under reduced pressure to yield Intermediate I-17A (0.215 g, 0.704 mmol, 100 % yield): ?H NMR (400MHz, CHLOROFORM-d) 12.48 (br. s., 1H), 9.12 (br. s., 1H), 8.06 (d, J2.0 Hz, 1H), 8.01 (dd,J=10.8, 2.2 Hz, 1H), 7.91 (d,J=1.1 Hz, 1H), 7.89 (d,J1.5 Hz, 1H),7.71-7.65 (m, 1H), 7.60-7.54 (m, 2H), 4.06 (s, 3H). LC-MS: method H, RT = 1.18 mm,MS (ESI) m/z: 306.1 (M+H).

Reference： [1]Patent: WO2018/13770,2018,A1 .Location in patent: Page/Page column 77
[2]Patent: WO2018/13774,2018,A1 .Location in patent: Page/Page column 142

12
[ 89283-92-1 ]
[ 532-55-8 ]
N-[7-bromo-[1,3]thiazolo[4,5-c]pyridin-2-yl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In acetone; at 50℃; for 16.0h;	To a solution of <strong>[89283-92-1]5-bromo-4-chloropyridin-3-amine</strong> (2.97 g, 14.3 mmol) in acetone(64 mL) was added benzoyl isothiocyanate (4.47 g, 27.4 mmol) at roomtemperature. The resulting mixture was stirred for 16 h at 50°C. When the reactionwas done, the solids were collected by filtration to yield N-[7-bromo-[1 ,3]thiazolo[4,5-c]pyridin-2-yl]benzamide as a yellow solid (3.36 g, 70percent). MS: m/z= 333.8 [M+H].

Reference： [1]Patent: WO2019/25099,2019,A1 .Location in patent: Page/Page column 142

13
[ 7321-93-9 ]
[ 532-55-8 ]
C₁₃H₉Cl₂N₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In acetone; at 60℃; for 3h;	A solution of commercially available <strong>[7321-93-9]4,6-dichloropyridin-3-amine</strong> (8.0 g, 49.07 mmol) and benzoyl isothiocyanate (7.3 ml_, 53.98 mmol) in acetone (120 ml_) was stirred at 60 C for 3 hours. The reaction was monitored by the TLC. The solvent was evaporated and the solid was filtered, washed with n-hexane (100 ml.) and dried to give the desired product as an off-white solid (14.0 g, 87%). (0683) MS: 328.0 (M+H)+. (0684) 1H-NMR (400 MHz, DMSO- 6) d =12.39 (s, 1 H), 12.02 (s, 1 H), 8.74 (s, 1 H), 7.98-7.99 (m, 3H), 7.67-7.68 (m, 1 H), 7.56 (t, J = 7.60 Hz, 2H).

Reference： [1]Patent: WO2019/134978,2019,A1 .Location in patent: Page/Page column 109

14
[ 57772-50-6 ]
[ 532-55-8 ]
C₁₆H₁₆N₂O₂S [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 380 - 396

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• Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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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
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

[ CAS No. 532-55-8 ] {[proInfo.proName]}

Quality Control of [ 532-55-8 ]

Related Doc. of [ 532-55-8 ]

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[ 532-55-8 ] Synthesis Path-Upstream 1~1

[ 532-55-8 ] Synthesis Path-Downstream 1~14

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