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[ CAS No. 2516-40-7 ] {[proInfo.proName]}

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Chemical Structure| 2516-40-7
Chemical Structure| 2516-40-7
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Product Details of [ 2516-40-7 ]

CAS No. :2516-40-7 MDL No. :MFCD02681887
Formula : C7H4BrNS Boiling Point : -
Linear Structure Formula :- InChI Key :DRLMMVPCYXFPEP-UHFFFAOYSA-N
M.W :214.08 Pubchem ID :612040
Synonyms :

Calculated chemistry of [ 2516-40-7 ]

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 : 0.0
Molar Refractivity : 47.32
TPSA : 41.13 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) : -5.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 3.06
Log Po/w (MLOGP) : 2.27
Log Po/w (SILICOS-IT) : 3.87
Consensus Log Po/w : 2.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.7
Solubility : 0.0429 mg/ml ; 0.0002 mol/l
Class : Soluble
Log S (Ali) : -3.49
Solubility : 0.0698 mg/ml ; 0.000326 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.83
Solubility : 0.0317 mg/ml ; 0.000148 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.27

Safety of [ 2516-40-7 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H317-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2516-40-7 ]

* 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 [ 2516-40-7 ]
  • Downstream synthetic route of [ 2516-40-7 ]

[ 2516-40-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 1072-98-6 ]
  • [ 40473-01-6 ]
  • [ 2516-40-7 ]
Reference: [1] Patent: US4510148, 1985, A,
  • 2
  • [ 95-16-9 ]
  • [ 2516-40-7 ]
YieldReaction ConditionsOperation in experiment
93% With carbon tetrabromide; sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 3 h; Benzothiazole (1 mmol, 135.9 mg),Carbon tetrabromide (1.1 mmol, 364.8 mg) was placed in a 10 mL round bottom flask.Added 5 mL of N,N-dimethylformamide and sodium tert-butoxide (4.0 mmol, 384.4 mg).Stir at room temperature for 3 hours,TLC monitored the endpoint of the reaction.The mixture was poured into water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation to give the crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluent (volume ratio = 30:1).2-Bromobenzothiazole (light yellow oily liquid, 199 mg, yield 93percent) was obtained.
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 6, p. 886 - 890
[2] Patent: CN107501023, 2017, A, . Location in patent: Paragraph 0051; 0052
[3] Organic Letters, 2009, vol. 11, # 2, p. 421 - 423
[4] Journal of Organic Chemistry, 2009, vol. 74, # 21, p. 8309 - 8313
[5] European Journal of Organic Chemistry, 2013, # 9, p. 1644 - 1648
[6] Journal of Organometallic Chemistry, 2000, vol. 601, # 2, p. 233 - 236
[7] Tetrahedron Letters, 2003, vol. 44, # 47, p. 8535 - 8537
[8] Recueil des Travaux Chimiques des Pays-Bas, 1937, vol. 56, p. 699,706
  • 3
  • [ 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,
  • 4
  • [ 136-95-8 ]
  • [ 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,
  • 5
  • [ 934-34-9 ]
  • [ 2516-40-7 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 29, p. 4849 - 4851
  • 6
  • [ 1072-98-6 ]
  • [ 40473-01-6 ]
  • [ 2516-40-7 ]
Reference: [1] Patent: US4510148, 1985, A,
  • 7
  • [ 62-53-3 ]
  • [ 2516-40-7 ]
Reference: [1] Patent: CN103601698, 2016, B,
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