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[ CAS No. 5198-80-1 ]

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2D
Chemical Structure| 5198-80-1
Chemical Structure| 5198-80-1
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Product Details of [ 5198-80-1 ]

CAS No. :5198-80-1MDL No. :MFCD04115726
Formula : C4H2BrNOS Boiling Point : 264.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :192.03Pubchem ID :17750433
Synonyms :

Computed Properties of [ 5198-80-1 ]

TPSA : 58.2 H-Bond Acceptor Count : 3
XLogP3 : 1.8 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 5198-80-1 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H317-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5198-80-1 ]

  • Upstream synthesis route of [ 5198-80-1 ]
  • Downstream synthetic route of [ 5198-80-1 ]

[ 5198-80-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 5198-80-1 ]
  • [ 5198-86-7 ]
Reference: [1] Patent: WO2008/57336, 2008, A2, . Location in patent: Page/Page column 39
  • 2
  • [ 5198-86-7 ]
  • [ 5198-80-1 ]
YieldReaction ConditionsOperation in experiment
92% With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -75 - 10℃; for 3 h; A solution of 0.22 mol of dimethyl sulfoxide in 50 mL of dichloromethane was added dropwise to a solution of 0.11 mol of oxalyl chloride in 200 mL of dichloromethane in a temperature range of –75 to –65°C. The mixture was stirred for 0.5 h, and then a solution of 0.1 mol of 11 in 100 mL of dichloromethane was added dropwise at –75 to –65°C. The mixture was stirred for an additional 2 h, and then 0.5 mol of triethylamine was added dropwise at –75 to –65°C. After the temperature of the reaction mixture was raised to –10°C for 1 h, the mixture was poured into a solution of 0.4 mol of sodium bicarbonate in 400 mL of water, stirred for 0.5 h and extracted with dichloromethane. The organic layer was dried with sodium sulfate, the solvent was removed at a reduced pressure, and the residue was chromatographed.
81% With Dess-Martin periodane In dichloromethane at 20℃; for 2 h; Into a 250-mL round-bottom flask, was placed (2-bromothiazol-4-yl)methanol (10 g, 51.53 mmol), DCM (100 mL) and Dess-Martin reagent (24 g, 56.60 mmol). The resulting solution was stirred for 2 h at RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:50 to 1:20). This resulted in 8 g (81percent) of the title compound as yellow oil. MS-ESI: 193.9, 191.9 (M+1).
Reference: [1] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 2766 - 2775[2] Zh. Obshch. Khim., 2017, vol. 87, # 12, p. 1947 - 1956,10
[3] Patent: WO2017/184624, 2017, A1, . Location in patent: Page/Page column 185; 186
  • 3
  • [ 100367-77-9 ]
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Reference: [1] Tetrahedron Asymmetry, 1998, vol. 9, # 8, p. 1395 - 1407
[2] Patent: WO2007/65669, 2007, A1, . Location in patent: Page/Page column 30
[3] European Journal of Organic Chemistry, 2008, # 16, p. 2701 - 2704
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 92 - 96
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  • [ 888314-10-1 ]
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Reference: [1] Patent: US2015/18328, 2015, A1, . Location in patent: Paragraph 1248
[2] Patent: WO2015/3640, 2015, A1, . Location in patent: Page/Page column 273; 274
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