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[ CAS No. 149-30-4 ] {[proInfo.proName]}

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Chemical Structure| 149-30-4
Chemical Structure| 149-30-4
Structure of 149-30-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 149-30-4 ]

CAS No. :149-30-4 MDL No. :MFCD00005781
Formula : C7H5NS2 Boiling Point : -
Linear Structure Formula :- InChI Key :YXIWHUQXZSMYRE-UHFFFAOYSA-N
M.W : 167.25 Pubchem ID :697993
Synonyms :

Calculated chemistry of [ 149-30-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.01
TPSA : 76.12 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) : -5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 2.41
Log Po/w (WLOGP) : 2.96
Log Po/w (MLOGP) : 1.42
Log Po/w (SILICOS-IT) : 4.79
Consensus Log Po/w : 2.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.145 mg/ml ; 0.000868 mol/l
Class : Soluble
Log S (Ali) : -3.65
Solubility : 0.0374 mg/ml ; 0.000224 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.07
Solubility : 0.141 mg/ml ; 0.000845 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.23

Safety of [ 149-30-4 ]

Signal Word:Danger Class:9
Precautionary Statements:P201-P273-P280-P308+P313-P333+P313-P501 UN#:3077
Hazard Statements:H317-H350-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 149-30-4 ]

* 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 [ 149-30-4 ]
  • Downstream synthetic route of [ 149-30-4 ]

[ 149-30-4 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 149-30-4 ]
  • [ 615-21-4 ]
YieldReaction ConditionsOperation in experiment
73.5% With hydrazine hydrate In ethanol for 20 h; Reflux To a solution of MBT (10.0 mmol) in ethanol (30 mL), hydrazine hydrate (5 mL, 80.0 mmol) was added. The reaction mixture was refluxed for 20 h, after cooling to room temperature the precipitate was filtered off, washed with cold ethanol, and ether followed by recrystallization from ethanol. Colorless crystals (1.23 g, 73.5percent yield), m.p. 198-200 °C, lit mp 199-200 °C [15].
60% for 10 h; Reflux Equimolar solution of 2-mercaptobenzothiazole (0.01 mol) and hydrazine hydrate (0.01 mol) in methanol (20 mL) was refluxed on a steam bath for about 10 h. The obtained filtrate was washed with ice water. The product was dried and recrystallized from ethanol to yield the pure compound (yield 60percent, m.p. 201-205 °C).
Reference: [1] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 1, p. 67 - 74
[2] Journal of Chemical Crystallography, 2005, vol. 35, # 4, p. 293 - 296
[3] Indian Journal of Heterocyclic Chemistry, 2010, vol. 20, # 2, p. 163 - 166
[4] European Journal of Medicinal Chemistry, 2013, vol. 60, p. 503 - 511
[5] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 7, p. 654 - 657
[6] Journal of the Indian Chemical Society, 1983, vol. 60, p. 475 - 478
[7] Medicinal Chemistry Research, 2013, vol. 22, # 11, p. 5105 - 5111
[8] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 151, p. 480 - 489
[9] Journal of the Indian Chemical Society, 2006, vol. 83, # 12, p. 1263 - 1266
[10] Revue Roumaine de Chimie, 2008, vol. 53, # 10, p. 911 - 919
[11] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2011, vol. 79, # 5, p. 1418 - 1424
[12] Indian Journal of Heterocyclic Chemistry, 2012, vol. 22, # 1, p. 47 - 52
[13] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 3, p. 418 - 429
[14] Journal of the Chemical Society of Pakistan, 2016, vol. 38, # 2, p. 301 - 306
[15] Inorganica Chimica Acta, 2017, vol. 466, p. 625 - 631
[16] Journal of Molecular Structure, 2017, vol. 1149, p. 357 - 366
[17] Archiv der Pharmazie, 2018, vol. 351, # 3-4,
[18] Acta Poloniae Pharmaceutica - Drug Research, 2018, vol. 75, # 3, p. 625 - 636
[19] Asian Journal of Chemistry, 2018, vol. 30, # 12, p. 2608 - 2614
[20] Journal of Molecular Structure, 2019, vol. 1179, p. 65 - 75
  • 2
  • [ 149-30-4 ]
  • [ 615-21-4 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 355,361
  • 3
  • [ 149-30-4 ]
  • [ 2942-06-5 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[2] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
[3] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[4] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
  • 4
  • [ 149-30-4 ]
  • [ 615-20-3 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 20 - 25℃; for 0.25 h; Inert atmosphere
Stage #2: at 20 - 25℃; for 3 h; Inert atmosphere
General procedure: A mixture of the 2-mercaptobenzo[d]thiazole (>1 g, 1 equiv) and sul-furyl chloride (10 equiv) was stirred at 20–25 °C for 15 min. Next, H 2 O(2 equiv) was added and the mixture was stirred at 20–25 °C for anadditional 3 h. A sample was taken, quenched with MeCN/H 2 O (2:1)and analyzed by HPLC. After completion of the reaction, the mixturewas diluted with MeCN (5 volumes) and slowly quenched with H 2 O(20 volumes). The product precipitated from the aqueous solution.The solid was collected and washed with H 2 O. Drying under vacuumafforded the pure product. In the case of the liquid product 2-chloro-benzo[d]thiazole (13), the reaction mixture was extracted withEtOAc. The organic layer was then dried and concentrated to affordthe product as an oil.2-Chlorobenzo[d]thiazole (13)Yield: 3.30 g, 19.5 mmol (90percent); yellow oil.1 H NMR (400 MHz, DMSO-d 6 ): δ = 7.45–7.62 (m, 2 H), 7.96 (dd, J =8.07, 0.73 Hz, 1 H), 8.09 (dd, J = 7.89, 0.92 Hz, 1 H).13 C NMR (101 MHz, DMSO-d 6 ): δ = 122.81, 122.86, 126.49, 127.47,136.19, 150.91, 153.23. HRMS (ESI): m/z [M + H] + calcd for C 7 H 5 ClNS: 169.9831; found:169.9844.
36.1 g With hydrogenchloride; dihydrogen peroxide In water at 38℃; for 4 h; In a 500 ml reaction flask, 36.4 g of 2-mercaptobenzothiazole and 80 g of water were cast, 29.7 g of 30percent hydrochloric acid was added, the temperature was raised to 38 ° C,48.5g mass fraction of 20percent hydrogen peroxide was added dropwise, after the end of incubation was incubated dropwise to detect the bodyWhen the content of 2-mercaptobenzothiazole in the system is less than 0.2percent, hydrogen peroxide (about 4h)After the reaction was settled stratification,The upper oily liquid is 2 - chlorobenzothiazole crude,Finally, anhydrous 2 - chlorobenzothiazole dry crude product obtained2-Chlorobenzothiazole fine 36.1g.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 10, p. 2027 - 2032
[2] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 11, p. 3163 - 3173
[3] , 1965, vol. 1, p. 1702 - 1704[4] Zhurnal Organicheskoi Khimii, 1965, vol. 1, p. 1679 - 1682
[5] Synthetic Communications, 2007, vol. 37, # 12, p. 2039 - 2050
[6] Patent: CN107129484, 2017, A, . Location in patent: Paragraph 0019; 0014; 0015; 0016; 0017; 0018
  • 5
  • [ 149-30-4 ]
  • [ 615-20-3 ]
Reference: [1] Pharmaceutical Bulletin, 1953, vol. 1, p. 319,321
[2] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2813,2815[3] Chem. Zentralbl., 1938, vol. 109, # II, p. 3084
[4] Patent: US1757930, 1927, ,
[5] Patent: US1923957, 1929, ,
[6] Patent: US2043948, 1933, ,
[7] Journal of Organic Chemistry, 1937, vol. 2, p. 148,153
[8] Journal of the American Chemical Society, 1946, vol. 68, p. 1666
[9] Patent: US2469697, 1946, ,
[10] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 611
[11] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 611
  • 6
  • [ 149-30-4 ]
  • [ 615-20-3 ]
  • [ 4074-77-5 ]
Reference: [1] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2813,2815[2] Chem. Zentralbl., 1938, vol. 109, # II, p. 3084
  • 7
  • [ 149-30-4 ]
  • [ 1123-55-3 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[2] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
  • 8
  • [ 149-30-4 ]
  • [ 6285-57-0 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[2] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
[3] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[4] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
  • 9
  • [ 149-30-4 ]
  • [ 2407-11-6 ]
Reference: [1] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[2] Chem.Abstr., 1952, p. 112
[3] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2813,2815[4] Chem. Zentralbl., 1938, vol. 109, # II, p. 3084
[5] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[6] Chem.Abstr., 1952, p. 112
  • 10
  • [ 149-30-4 ]
  • [ 6973-51-9 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[2] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
  • 11
  • [ 149-30-4 ]
  • [ 101-83-7 ]
  • [ 4979-32-2 ]
YieldReaction ConditionsOperation in experiment
96.2%
Stage #1: at 50℃; for 2 h;
Stage #2: With hydrogenchloride In water at 35℃;
Stage #3: With sodium hypochlorite In water; toluene at 30℃; for 0.000555556 h;
(1) Disposing an M-Na salt solution: mixing 400 g of the promoter MBT with 360 g of a 32 wtpercent NaOH solution, and stirring at 50 ° C for 2 h to prepare an M-Na salt solution;A hydrochloric acid solution of cyclohexylamine was placed: 567 g of dicyclohexylamine was mixed with 376 g of industrial hydrochloric acid having a concentration of 31percent by weight.Adding 567 g of water and stirring at 35 ° C to obtain a hydrochloric acid solution of cyclohexylamine;(2) M-Na salt solution, dicyclohexylamine hydrochloric acid solution,Solvent toluene and sodium hypochlorite solution with 17percent effective chlorine content according to M-Na salt solution 69mL/min,Dihydrohexylamine hydrochloride solution 136mL / min,Toluene 130mL / min and sodium hypochlorite solution 49mL / min speed into the microchannel reactor for oxidation reaction, the reaction residence time is 2s, the reaction temperature is 30 ° C, the microchannel reactor is 4 reactors in series,The volume of each reactor was 3.2 mL, and the total volume of the reactor after the series was 12.8 mL;(4) Collecting the material flowing out of the reactor, and crystallization after stirring to a temperature of 5 ° C;The crude product is washed once with 200 mL of isopropyl alcohol aqueous solution and washed twice with 200 mL of water to obtain DCBS wet material. After drying, DCBS finished product can be obtained.The DCBS yield of this example was determined to be 96.2percent (based on the content of MBT), the purity of DCBS was 99.2percent by weight, and the appearance was a pale yellow powder. After the waste water was continuously distilled to recover isopropanol, the residual COD was 5900 ppm.
Reference: [1] Patent: CN108586383, 2018, A, . Location in patent: Paragraph 0069-0075; 0080; 0087; 0094; 0101
[2] Phosphorus and Sulfur and the Related Elements, 1988, vol. 35, p. 311 - 318
  • 12
  • [ 108-91-8 ]
  • [ 149-30-4 ]
  • [ 4979-32-2 ]
YieldReaction ConditionsOperation in experiment
61.2% at 45℃; General procedure: To a stirred solution of benzothiazole-2-thiol (1equiv) and cyclohexylamine (2.5equiv), the sodium hypochlorite solution was added slowly at 45°C. The completion of oxidation was confirmed by bluestone solution and KI starch solution. The reaction solution was cooled to room temperature and the precipitate was separated out. Then precipitate was washed by 9percent cyclohexylamine aqueous solution. Without further purification, the precipitate was filtered off to give the products.
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 423 - 430
  • 13
  • [ 149-30-4 ]
  • [ 101-83-7 ]
  • [ 7757-83-7 ]
  • [ 4979-32-2 ]
Reference: [1] Patent: EP314663, 1989, A1,
  • 14
  • [ 53078-85-6 ]
  • [ 149-30-4 ]
  • [ 21303-50-4 ]
Reference: [1] Patent: US2003/139390, 2003, A1,
  • 15
  • [ 149-30-4 ]
  • [ 120-78-5 ]
  • [ 4845-58-3 ]
Reference: [1] Patent: US4975448, 1990, A,
  • 16
  • [ 149-30-4 ]
  • [ 4845-58-3 ]
Reference: [1] Agricultural and Biological Chemistry, 1987, vol. 51, # 7, p. 1941 - 1946
[2] ChemMedChem, 2011, vol. 6, # 4, p. 654 - 666
  • 17
  • [ 80756-85-0 ]
  • [ 65872-41-5 ]
  • [ 149-30-4 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7259 - 7266
  • 18
  • [ 14814-09-6 ]
  • [ 120-78-5 ]
  • [ 149-30-4 ]
  • [ 56706-10-6 ]
Reference: [1] Patent: US5675014, 1997, A,
  • 19
  • [ 120-78-5 ]
  • [ 86299-47-0 ]
  • [ 89604-92-2 ]
  • [ 149-30-4 ]
Reference: [1] Research on Chemical Intermediates, 2013, vol. 39, # 2, p. 615 - 620
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