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[ CAS No. 533-30-2 ]

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Chemical Structure| 533-30-2
Chemical Structure| 533-30-2
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CAS No. :533-30-2 MDL No. :MFCD00015461
Formula : C7H6N2S Boiling Point : 323.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :150.20 g/mol Pubchem ID :68288
Synonyms :

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

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[ 533-30-2 ] Synthesis Path-Upstream   1~18

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Reference: [1] Patent: US6573264, 2003, B1,
[2] Patent: US2003/216409, 2003, A1,
[3] Patent: US6849632, 2005, B2,
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YieldReaction ConditionsOperation in experiment
88% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; General procedure: A mixture of compounds 1–4 (6.13 mmol) in ethanol (30 mL) was treated with 10percent Pd/C (20 wt. percentof 1–4) and subjected overnight to 50 psi H2 (g) in a Parr hydrogenation apparatus. The reaction mixture was filtered and concentrated in vacuo. Pure products 1M–4M were obtained via flash chromatography by eluting with a gradient of 30percent–40percent EtOAc/hexanes.
72% at 20℃; To a solution of 6-nitrobenzothiazole (3.8 g, 0.02mol) in 40 ml 2N HCl was added SnCl2 (15.9 g, O.Omol), and the mixture was stirred at room temperature overnight. The reaction mixture was treated with concentrated NH4OH to pH 11 and extracted with ethyl acetate (3 x 150ml). The combined organic phase was concentrated under reduced pressure. The residue was purified (silica gel chromatography) to give benzo[d]thiazol-6-amine (3g, 72percent).
55 %Chromat. With carbon monoxide; water In tetrahydrofuran at 125℃; for 24 h; Inert atmosphere; Autoclave General procedure: Into a reaction glass vial fitted with a magnetic stirring bar anda septum cap penetrated with a syringe needle was added theCo3O4/NGrC-catalyst (2 molpercent, 3 wtpercent Co-phenanthroline oncarbon, 20 mg) followed by the nitro arene (0.5 mmol), theinternal standard (hexadecane, 100 μL), THF (2 mL), and H2O(200 μL). The reaction vial was then placed into a 300 mL autoclave.The autoclave was flushed twice with nitrogen, pressurized with CO at 30 bar pressure. Finally, the autoclave was usedat 60 bar by adding nitrogen and placed into an aluminiumblock, which was preheated at 125 °C. After 24 h the autoclavewas placed into a water bath and cooled to r.t. Finally, theremaining gas was discharged, and the samples were removedfrom the autoclave, diluted with EtOAc and analyzed by GC. Todetermine the yield of isolated products, the general procedurewas scaled up by the factor of two, and no internal standard wasadded. After the reaction was completed, the catalyst was filteredoff, and the filtrate was concentrated and purified by silicagel column chromatography (n-heptane–EtOAc mixtures) togive the corresponding anilines.
Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 11-12, p. 1834 - 1840
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 19, p. 7002 - 7007
[3] Synthesis, 2005, # 4, p. 600 - 604
[4] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 8726 - 8736
[5] Molecules, 2014, vol. 19, # 1, p. 925 - 939
[6] ACS Catalysis, 2015, vol. 5, # 3, p. 1526 - 1529
[7] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2131 - 2137
[8] Arkivoc, 2010, vol. 2010, # 11, p. 265 - 290
[9] Journal of Medicinal Chemistry, 2009, vol. 52, # 22, p. 7090 - 7102
[10] Patent: WO2010/91310, 2010, A1, . Location in patent: Page/Page column 103
[11] Synthesis, 2006, # 19, p. 3316 - 3340
[12] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2358 - 2361
[13] Journal of Organic Chemistry, 2014, vol. 79, # 19, p. 9433 - 9439
[14] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[15] Chem.Abstr., 1951, p. 609
[16] Bulletin de la Societe Chimique de France, 1949, p. 103,111
[17] Journal of the Chemical Society, 1949, p. 355,361
[18] Journal of the Chemical Society, 1949, p. 355,361
[19] Journal of the Chemical Society, 1949, p. 355,361
[20] Patent: US5677321, 1997, A,
[21] Chemistry - A European Journal, 2011, vol. 17, # 21, p. 5903 - 5907
[22] Phytochemistry, 2012, vol. 74, p. 159 - 165
[23] Nature Chemistry, 2013, vol. 5, # 6, p. 537 - 543
[24] Chemical Communications, 2013, vol. 49, # 80, p. 9089 - 9091
[25] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00154
[26] Patent: US2014/357651, 2014, A1, . Location in patent: Paragraph 0498
[27] Synlett, 2015, vol. 26, # 3, p. 313 - 317
[28] Green Chemistry, 2015, vol. 17, # 2, p. 898 - 902
[29] Patent: US9174994, 2015, B2, . Location in patent: Page/Page column 126
[30] Bulletin of the Korean Chemical Society, 2016, vol. 37, # 8, p. 1320 - 1325
[31] Applied Catalysis A: General, 2018, vol. 559, p. 127 - 137
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Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 1, p. 82 - 86
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Reference: [1] Bulletin de la Societe Chimique de France, 1949, p. 103,111
[2] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[3] Chem.Abstr., 1951, p. 609
[4] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 8726 - 8736
[5] Phytochemistry, 2012, vol. 74, p. 159 - 165
[6] Patent: WO2014/151147, 2014, A1,
[7] Patent: US2014/357651, 2014, A1,
[8] Patent: US9174994, 2015, B2,
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Reference: [1] RSC Advances, 2014, vol. 4, # 100, p. 56957 - 56960
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2358 - 2361
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Reference: [1] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[2] Chem.Abstr., 1951, p. 609
[3] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[4] Chem.Abstr., 1951, p. 609
[5] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[6] Chem.Abstr., 1951, p. 609
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Reference: [1] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[2] Chem.Abstr., 1951, p. 609
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Reference: [1] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[2] Chem.Abstr., 1951, p. 609
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Reference: [1] Dissertation <Berlin 1883>, S. 58,
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YieldReaction ConditionsOperation in experiment
29%
Stage #1: With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 65℃; for 0.166667 h;
Stage #2: at 65℃; for 0.583333 h;
Add anhydrous copper (II) bromide (1.79 g, 7.99 mmol), tert-butyl nitrite (1.2 mL, 9.98 mmol) and anhydrous acetonitrile (20 mL) to a round bottom flask fitted with a reflux condenser and an addition funnel. Heat at 65 C for 10 min. Add a solution of benzothiazol-6-ylamine (Lancaster; 1 g, 6.66 mmol) in acetonitrile (10 mL) over a period of 5 min via addition funnel. Stir at 65 C for 30 min. Cool to room temperature, pour into 20percent aqueous hydrochloric acid (100 mL), and extract with ether (2 x 100 mL). Wash the organic layer with 20percent aqueous hydrochloric acid. Dry the organic phase with sodium sulfate, filter, evaporate and chromatograph (10percent ethyl acetate/90percent hexanes) to give the title product (0.4 g, 29percent) as a pale yellow solid. MS (ESI) M/E 215 (M+1).
0.26 g
Stage #1: With hydrogen bromide; sodium nitrite In water at 0 - 20℃; for 0.5 h;
Stage #2: With hydrogenchloride; copper(I) bromide In water at 0 - 60℃; for 1.5 h;
[0408] A solution of sodium nitrite (0.147 g, 2.1 mmol) in water (1.0 mL) was slowly added to a suspension of 6-aminobenzothiazole (0.30 g, 2.0 mmol) in HBr (48percent in water, 3 mL) at 0 °C and then the mixture was stirred at roomtemperature for 30 min. The formed solution was then slowly added to a solution of copper (I) bromide (0.435 g, 3.0mmol) in HCl (conc., 5 mL) at 0 °C. After the addition, the mixture was stirred at 60 °C for 1.5 h. Cooled down, and thereaction mixture was basified with excess ammonia and extracted with diethyl ether. The combined extract was washedwith water, brine, dried and concentrated. The 6-bromobenzothiazole (0.26 g) was obtained by Combiflash and thenconverted to the final compound using procedures analogous to those for example 1, MS(ESI): (M+H)+ = 413.1
Reference: [1] Organic Letters, 2007, vol. 9, # 18, p. 3623 - 3625
[2] Patent: WO2004/50659, 2004, A1, . Location in patent: Page 49-50
[3] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00154
[4] Patent: US2014/357651, 2014, A1, . Location in patent: Paragraph 0498
[5] Patent: US9174994, 2015, B2, . Location in patent: Page/Page column 126
[6] Patent: EP1622569, 2015, B1, . Location in patent: Paragraph 0408
[7] Patent: WO2018/160878, 2018, A1, . Location in patent: Page/Page column 298
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YieldReaction ConditionsOperation in experiment
80% With bromine In chloroform for 0.25 h; To a solution of benzo[d]thiazol-6-amine (100 mg, 0.67mmol) in 6 ml CHCl3 was added Br2 (42 mg, 0.27mmol) in CHCI3 (10ml) dropwise about 15 min. The mixture was concentrated under reduced pressure, and the residue was crystallized from DCM:MeOH (5: 1) to give 7-bromobenzo[d]thiazol-6-amine (80mg, 80percent).
75% With bromine In chloroform at 0℃; for 1 h; A mixture of benzo[djthiazol-6-amine (2-17, 1 g, 6.6 mmol) and Br2 (1.06 g, 6.6 mmol) in CHC13 (5 mL) was stirred at 0 °C for 1 h. Upon reaction completion, the resulting mixture was concentrated under reduced pressure to provide intermediate 2-18 (yellow solid, 1.2 g, 75percent yield). LCMS (m/z): 229 [M + HI .
67% at 20℃; for 1 h; Step A: 7-bromo-benzothiazol-6-ylamineTo a solution of benzothiazol-6-ylamine (6.4 g, 42.6 mmol) in glacial acetic acid (40 mL) was added bromine (2.18 mL) in glacial acetic acid (10 mL) dropwise. The reaction mixture was stirred at RT for 1 h. Water (160 mL) was added to the reaction mixture and the solid formed was extracted with ethyl acetate (3 x 40 mL). The combined organic fractions were washed with saturated aqueous sodium bicarbonate solution (200 mL), water (100 mL), and brine (20 mL), dried over anhydrous sodium sulfate, and concentrated. Purification of the residue by column chromatography (20percent ethyl acetate: hexanes) afforded 6.5 g (67percent) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCI3): δ 4.31 (br. s, 2H), 7.02 (d, J=8.4 Hz, 1 H), 7.92 (d, J=8.4 Hz, 1 H), 8.80 (s, 1 H).
34 mmol, 80% With bromine In acetic acid; ethyl acetate 7-Bromo-6-aminobenzothiazole
To a solution of 6-aminobenzothiazole (16 g, 107 mmol) in 100 mL of AcOH was added Br2 (2.0 mL, 43 mmol) dropwise and the resulting reaction mixture was stirred for 1 h at 25° C.
Reaction mixture was concentrated in vacuo, yielding a yellow solid which was dissolved in EtOAc and washed with aq. NaHCO3.
Organic layer was dried over Na2 SO4 and concentrated in vacuo, yielding an oil which was subjected to column chromatography (10-50percent EtOAc/n-Hexane) to obtain 7.8 g (34 mmol, 80percent) of the desired product.

Reference: [1] Patent: WO2010/91310, 2010, A1, . Location in patent: Page/Page column 103
[2] Patent: WO2016/161145, 2016, A1, . Location in patent: Paragraph 00693
[3] Patent: WO2011/100502, 2011, A1, . Location in patent: Page/Page column 55
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 18, p. 5919 - 5923
[5] Journal of the Chemical Society, 1949, p. 355,361
[6] Patent: US5677321, 1997, A,
[7] Journal of Molecular Structure, 2010, vol. 975, # 1-3, p. 115 - 127
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 18, p. 5919 - 5923
[2] Patent: WO2016/161145, 2016, A1,
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Reference: [1] Journal of Molecular Catalysis A: Chemical, 2010, vol. 328, # 1-2, p. 99 - 107
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YieldReaction ConditionsOperation in experiment
34 mmol, 80% With chlorine In acetic acid; ethyl acetate 7-Chloro-6-aminobenzothiazole
To a solution of 6-aminobenzothiazole (2.0 g, 13.4 mmol) in 100 mL of AcOH was added a solution of Cl2 saturated AcOH and the resulting reaction mixture was stirred for 1 h at 25° C.
Reaction mixture was concentrated in vacuo, yielding a yellow solid which was dissolved in EtOAc and washed with aq. NaHCO3.
Organic layer was dried over Na2 SO4 and concentrated in vacuo, yielding an oil which was subjected to column chromatography (10-50percent EtOAc/n-Hexane) to obtain 7.8 g (34 mmol, 80percent) of the desired product.
Reference: [1] Patent: US5677321, 1997, A,
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  • [ 181124-40-3 ]
Reference: [1] Patent: EP1803709, 2007, A1,
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  • [ 654070-00-5 ]
YieldReaction ConditionsOperation in experiment
68.5%
Stage #1: at 20℃; for 0.5 h;
Stage #2: With potassium iodide In water at 70℃; for 0.5 h;
General procedure: To a mixture of concd H2SO4 (45 mL) and NaNO2 (3.04 g, 44 mmol) warmed to 70 °C for 15 min then cooled to 40 °C, 6-aminobenzothiazole 1a (6.0 g, 40 mmol) or 6-amino-2-methylbenzothiazole 1b (6.57 g, 40 mmol) in acetic acid (80 mL) was added and stirred at rt for 30 min. A stirred solution of KI (7.32 g, 44 mmol) in water (70 mL) was heated to 70 °C, and the previously prepared diazonium salt was added. After 30 min the reaction mixture was poured onto ice and the obtained crude product was filtered off, washed with water, and dissolved in dichloromethane. The dichloromethane solution was treated with 10percent Na2S2O3, washed with water, and dried. The solvent was concentrated, and the residue purified by chromatography (silica gel/dichloromethane).
Reference: [1] Tetrahedron, 2011, vol. 67, # 15, p. 2760 - 2767
[2] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 8726 - 8736
[3] Heterocycles, 2006, vol. 68, # 9, p. 1909 - 1916
[4] Journal of Molecular Structure, 2010, vol. 975, # 1-3, p. 115 - 127
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Reference: [1] Patent: US2014/357651, 2014, A1,
[2] Patent: WO2014/151147, 2014, A1,
[3] Patent: US9174994, 2015, B2,
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