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Chemical Structure| 136-95-8
Chemical Structure| 136-95-8
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Product Details of [ 136-95-8 ]

CAS No. :136-95-8 MDL No. :MFCD00005785
Formula : C7H6N2S Boiling Point : -
Linear Structure Formula :- InChI Key :UHGULLIUJBCTEF-UHFFFAOYSA-N
M.W :150.20 Pubchem ID :8706
Synonyms :
Benzo[d]thiazol-2-amine

Calculated chemistry of [ 136-95-8 ]

Physicochemical Properties

Num. heavy atoms : 10
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 : 44.02
TPSA : 67.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 1.59
Log Po/w (WLOGP) : 1.89
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.547 mg/ml ; 0.00364 mol/l
Class : Soluble
Log S (Ali) : -2.61
Solubility : 0.368 mg/ml ; 0.00245 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.384 mg/ml ; 0.00256 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 136-95-8 ]

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

Application In Synthesis of [ 136-95-8 ]

* 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 [ 136-95-8 ]
  • Downstream synthetic route of [ 136-95-8 ]

[ 136-95-8 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 136-95-8 ]
  • [ 615-21-4 ]
YieldReaction ConditionsOperation in experiment
90% at 140℃; Representative procedure for the synthesis of compound 32 To a solution of hydrazine hydrate (1 equiv) in ethylene glycol at 5 °C, conc. HCl (2 mL) was added drop wise with stirring, followed by addition of 2-amino benzothiazole (1 equiv). The reaction mixture was refluxed for 2-3 h and then cooled to the room temperature. The resulting solid formed was filtered, washed with water and recrystallized from ethanol to afford compound 32. 2-hydrazinylbenzo[d]thiazole (32) White colour crystals, yield: 90percent, mp: 200e202 C; 1H NMR(DMSO-d6, 400 MHz): d 4.84 (2H, s), 6.85e7.65 (4H, m), 8.62 (1H, s);ESI-MS (m/z): 166 (MH).
79% With hydrazine hydrate; hydrazinium sulfate In ethylene glycol at 140℃; for 2 h; Inert atmosphere 2.2.1
Synthesis of 2-hydrazinobenzothiazole (I)
Into a three necked round bottomed flask 2-aminobenzothiazole (0.15 mol, 22.5 g), ethylene glycol (100 ml), hydrazine monohydrate (0.30 mol, 14.6 ml) and hydrazinium sulphate (0.15 mol, 19.5 g) were added and the mixture was refluxed at 140 °C for 2 h under nitrogen atmosphere.
The product was poured into a beaker and let to cool to room temperature.
Water (40 mL) was added to the crystallized product, the mixture was stirred and filtered by vacuum.
The crystals were recrystallized from ethanol, filtered and air dried.
Yield 79.0percent. m.p. 201-203 °C (lit.
Yield 60.6percent, m.p. 198-199 °C)
[32]
.
IR (KBr) 3326 cm-1 (N-H); 3210 cm-1 (double band, NH2); 3031 cm-1 (Ar. C-H); 1650 cm-1, 1599 cm-1, 1561 cm-1 (C=C, C=N).
1H NMR (d6-DMSO) 8.88 (s, NH), 7.61-6.92 (m, Ar-CH), 4.91 (s, NH2).
Reference: [1] Helvetica Chimica Acta, 1980, vol. 63, # 3, p. 682 - 692
[2] European Journal of Medicinal Chemistry, 2015, vol. 103, p. 418 - 428
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025
[4] Medicinal Chemistry Research, 2012, vol. 21, # 9, p. 2428 - 2442
[5] Journal of Molecular Structure, 2014, vol. 1060, # 1, p. 215 - 222
[6] Journal of Chemical Research, 2005, # 8, p. 526 - 529
[7] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 649 - 652
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
[9] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 113, p. 325 - 331
[10] Combinatorial Chemistry and High Throughput Screening, 2013, vol. 16, # 3, p. 244 - 247
[11] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1327 - 1341
[12] Monatshefte fur Chemie, 2017, vol. 148, # 6, p. 1057 - 1067
[13] Phosphorus, Sulfur and Silicon and the Related Elements, 2017, vol. 192, # 5, p. 565 - 569
[14] Patent: CN107973807, 2018, A, . Location in patent: Paragraph 0020
[15] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 11, p. 2507 - 2515
[16] International Journal of Pharmacy and Pharmaceutical Sciences, 2018, vol. 10, # 10, p. 57 - 61
  • 2
  • [ 136-95-8 ]
  • [ 2644-70-4 ]
  • [ 615-21-4 ]
Reference: [1] Patent: US3937714, 1976, A,
  • 3
  • [ 136-95-8 ]
  • [ 615-21-4 ]
  • [ 1141-88-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2068,2070; engl. Ausg. S. 2036, 2037
  • 4
  • [ 136-95-8 ]
  • [ 7803-57-8 ]
  • [ 615-21-4 ]
  • [ 1141-88-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2068,2070; engl. Ausg. S. 2036, 2037
  • 5
  • [ 136-95-8 ]
  • [ 2942-06-5 ]
Reference: [1] Gazzetta Chimica Italiana, 1964, vol. 94, p. 435 - 443
  • 6
  • [ 136-95-8 ]
  • [ 615-20-3 ]
Reference: [1] Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, # 9, p. 1561 - 1562
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 14, p. 5275 - 5284
[3] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14622 - 14626
[4] Organic Process Research and Development, 2017, vol. 21, # 1, p. 44 - 51
[5] Organic and Biomolecular Chemistry, 2013, vol. 11, # 7, p. 1103 - 1108
[6] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2813,2815[7] Chem. Zentralbl., 1938, vol. 109, # II, p. 3084
[8] Journal of the Chemical Society, 1930, p. 2190,2209
[9] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025
[10] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
  • 7
  • [ 136-95-8 ]
  • [ 67-66-3 ]
  • [ 95-16-9 ]
  • [ 615-20-3 ]
  • [ 34263-66-6 ]
  • [ 2602-85-9 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1980, # 12, p. 4935 - 4953
[2] Journal of Chemical Research, Miniprint, 1980, # 12, p. 4935 - 4953
  • 8
  • [ 136-95-8 ]
  • [ 2516-40-7 ]
YieldReaction ConditionsOperation in experiment
71% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at -5 - 5℃; for 6 h; 2.2 g (0.012 mol) of copper bromide was added to 20 mL of acetonitrile, cooled to -5 ° C in an ice-salt bath, and 1.75 mL of t-butyl nitrite was slowly added dropwise. After completion of the dropwise addition, reaction was carried out at 0-5 ° C for 30 min. Further, 1.5 g (0. Olmol) of 2-aminobenzothiazole was added,The reaction was carried out for 6 hours. The insoluble matter was filtered off and the filtrate was concentrated to give 1.7 g of a pale yellow solid in a yield of 71.0percent
57% With tert.-butylnitrite; copper(I) bromide In acetonitrile at 60℃; for 1 h; General procedure: To a stirred suspension of CuBr (1.57 g, 10.9 mmol) in MeCN (25 ml) was added tBuONO (1.63 ml, 13.7 mmol) and the mixture was stirred at 60 °C for 10 min. Then 2-amino-6-methylbenzothiazole (14b) (1.50 g, 9.13 mmol) was added to the mixture, and the reaction mixture was stirred at 60 °C for 1 h. After cooled to room temperature, the mixture was poured into 1 N HCl. The resulting precipitate was dissolved into EtOAc, washed with 1 N HCl, brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (7:1, v/v) as eluent to give the title compound (703 mg, 34percent) as a brown oil.
56.1% With tert.-butylnitrite; copper(ll) bromide In acetonitrile for 0.5 h; To a solution of copper (II) bromide (134mg, 0.600 mmol) in Acetonitrile (1 mL) was added benzo[d]thiazol-2-amine (100mg, 0.666 mmol) at room temperature. t-Butylnitrite (0.106 mL, 0.800 mmol) was then added. Bubbling immediately observed. After30 mm, diluted with EtOAc and washed with 1.0 M HC1 followed by brine. The organic phase was concentrated and purified by ISCO flash chromatography (0-5percent EtOAc/Hex over 20 mm, 24 g silica gel cartridge — product at 2.5percent) to afford Intermediate 256A (80 mg, 0.374 mmol, 56.1percent yield) as a pink oil. LC-MS: Method H, RT = 1.16 mm, MS(ESI) m/z: 214.0, 216.0 (M+H). ‘H NIVIR (4001V11{z, CHLOROFORM-d) 8.00 (d, J=8.1 Hz, 1H), 7.82 (d, J=7.9 Hz, 1H), 7.53-7.37 (m, 2H).
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14622 - 14626
[2] Tetrahedron, 2010, vol. 66, # 37, p. 7418 - 7422
[3] Patent: CN103601698, 2016, B, . Location in patent: Paragraph 0076; 0085; 0086
[4] Organic Letters, 2015, vol. 17, # 15, p. 3722 - 3725
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 3, p. 1201 - 1212
[6] Patent: WO2018/13774, 2018, A1, . Location in patent: Page/Page column 680
[7] Patent: US4510148, 1985, A,
  • 9
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  • [ 7787-70-4 ]
  • [ 2516-40-7 ]
YieldReaction ConditionsOperation in experiment
57% With tert.-butylnitrite In hydrogenchloride; hexane; ethyl acetate; acetonitrile (Step 1)
Synthesis of 2-bromobenzothiazole
Copper (I) bromide (1.93 g, 13.5 mmol) was suspended in acetonitrile (30 ml).
To the resulting suspension was added tert-butyl nitrite (2.00 ml, 16.8 mmol) and the mixture was stirred at 60OEC for 15 minutes.
To the reaction mixture was added 2-aminobenzothiazole (1.68 g, 11.2 mmol) and the mixture was stirred at 60OEC for 1 hour.
After cooling, the reaction mixture was poured in 1N HCl, followed by extraction with ethyl acetate.
The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent.
The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ ethyl acetate (7:1, v/v) eluate fractions, 2-bromobenzothiazole (1.36 g, 57percent) was obtained as a brown oil.
1H-NMR (CDCl3) δ: 7.39-7.51 (m, 2H), 7.77-7.82 (m, 1H), 7.94-8.00 (m, 1H).
Reference: [1] Patent: EP1346982, 2003, A1,
  • 10
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  • [ 95-24-9 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 493
  • 11
  • [ 136-95-8 ]
  • [ 80945-86-4 ]
Reference: [1] Journal of the Indian Chemical Society, 1933, vol. 10, p. 563,568
  • 12
  • [ 136-95-8 ]
  • [ 15864-32-1 ]
Reference: [1] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 3, p. 496 - 501
[2] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 1668,1673[3] Chem. Zentralbl., 1937, vol. 108, # II, p. 3604
[4] Journal of the Indian Chemical Society, 1933, vol. 10, p. 563,568
[5] Journal of the Chemical Society, 1930, p. 125,145
  • 13
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  • [ 15864-32-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1882, vol. 212, p. 327
[2] Chemische Berichte, 1903, vol. 36, p. 3128[3] Chemische Berichte, 1901, vol. 34, p. 3136
  • 14
  • [ 136-95-8 ]
  • [ 22913-24-2 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 20, p. 5334 - 5337,4
  • 15
  • [ 13534-89-9 ]
  • [ 136-95-8 ]
  • [ 261-96-1 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2012, vol. 48, # 9, p. 1420 - 1422[2] Khim. Geterotsikl. Soedin., 2012, vol. 48, # 9, p. 1521 - 1524,3
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  • [ 6285-57-0 ]
Reference: [1] Helvetica Chimica Acta, 1980, vol. 63, # 3, p. 682 - 692
[2] Chinese Chemical Letters, 2010, vol. 21, # 5, p. 554 - 557
[3] Journal of the Chemical Society, 1930, p. 2190,2209
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6206 - 6209
  • 17
  • [ 136-95-8 ]
  • [ 625-58-1 ]
  • [ 6285-57-0 ]
Reference: [1] Pubbl. Ist. Chim. ind. Univ. Bologna, 1943, # 4, p. 3
  • 18
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  • [ 625-58-1 ]
  • [ 7664-93-9 ]
  • [ 6285-57-0 ]
Reference: [1] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1944, vol. 5, p. 11,14, 16, 18
[2] Gazzetta Chimica Italiana, 1948, vol. 78, p. 462,467, 469
  • 19
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  • [ 7697-37-2 ]
  • [ 6285-57-0 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 2190,2209
  • 20
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  • [ 2407-11-6 ]
Reference: [1] Chinese Chemical Letters, 2010, vol. 21, # 5, p. 554 - 557
  • 21
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  • [ 1123-99-5 ]
YieldReaction ConditionsOperation in experiment
84.7% With toluene-4-sulfonic acid; potassium iodide; sodium nitrite In water; acetonitrile at 0 - 20℃; To a solution of 2-aminobenzothiazole (6) (3.75g, 25mol) and p-TsOH (15g, 75mmol) in acetonitrile (100ml) was added a mixture solution of KI (10.5g, 65mmol) and NaNO2 (3.5g, 50mol) in water (15ml) at 0°C. The reaction solution was stirred at 0°C for 2h, and then at RTovernight. To the reaction solution was added around 350ml of water, adjust the solution pH to 8-9 with NaHCO3 and added Na2S2O3, filtered and the solid was washed to give brown solid 5.52g (yield 84.7percent). TLC: Rf: 0.6 (hexane/ethyl acetate=6/1). MS (ESI) m/z 262 (M++H);1HNMR (CDCl3, 300MHz) δ 8.06 (1H, dd, J1=7.5Hz, J2=1.8Hz), 7.87 (1H, dd, J1=6.9Hz,J2=1.5Hz), 7.50~7.38 (2H, m).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 320 - 323
[2] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14622 - 14626
[3] Tetrahedron Letters, 2009, vol. 50, # 52, p. 7263 - 7267
[4] Synthesis, 2007, # 1, p. 81 - 84
[5] Gazzetta Chimica Italiana, 1964, vol. 94, p. 435 - 443
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1979, p. 433 - 435
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