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Chemical Structure| 97483-77-7
Chemical Structure| 97483-77-7
Structure of 97483-77-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 97483-77-7 ]

CAS No. :97483-77-7 MDL No. :MFCD00234144
Formula : C6H3BrN2 Boiling Point : -
Linear Structure Formula :C5H3N(Br)(CN) InChI Key :DMSHUVBQFSNBBL-UHFFFAOYSA-N
M.W : 183.01 Pubchem ID :817154
Synonyms :
5-Bromo-pyridine-2-carbonitrile

Calculated chemistry of [ 97483-77-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.65
TPSA : 36.68 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) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.59
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 1.72
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 1.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.48
Solubility : 0.612 mg/ml ; 0.00334 mol/l
Class : Soluble
Log S (Ali) : -1.98
Solubility : 1.91 mg/ml ; 0.0104 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.199 mg/ml ; 0.00109 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 97483-77-7 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P261-P280-P301+P310-P305+P351+P338 UN#:2923
Hazard Statements:H301-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 97483-77-7 ]

* 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 [ 97483-77-7 ]
  • Downstream synthetic route of [ 97483-77-7 ]

[ 97483-77-7 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 97483-77-7 ]
  • [ 30766-11-1 ]
YieldReaction ConditionsOperation in experiment
64% With hydrogenchloride In waterReflux Preparation 245-Bromopyridine-2-carboxylic acidAdd 5-bromopicolinonitrile (1 g, 5.46 mmol) to concentrated HC1 (13.4 mL, 139.66 mmol) in a round bottomed flask. Heat the mixture to reflux with stirring overnight. Cool the mixture to room temperature. Filter the resulting white solid, washing with water. Dry the solid under reduced pressure to give 5-bromopyridine-2- carboxylic acid (0.707 g, 64percent) as a white solid. LC-ES/MS m/z 202 [M+H]+.
Reference: [1] Patent: WO2013/66640, 2013, A1, . Location in patent: Page/Page column 21
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 2074 - 2079
[3] Patent: WO2008/729, 2008, A1, . Location in patent: Page/Page column 74-75
[4] Patent: WO2005/14571, 2005, A1, . Location in patent: Page/Page column 23
[5] Patent: WO2005/14571, 2005, A1, . Location in patent: Page/Page column 27
[6] Patent: WO2005/40144, 2005, A1, . Location in patent: Page/Page column 12-13
[7] Patent: WO2006/40192, 2006, A1, . Location in patent: Page/Page column 39
[8] Patent: WO2006/29906, 2006, A1, . Location in patent: Page/Page column 16
  • 2
  • [ 97483-77-7 ]
  • [ 75754-04-0 ]
Reference: [1] Organic Letters, 2018,
  • 3
  • [ 97483-77-7 ]
  • [ 41960-47-8 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333
  • 4
  • [ 626-55-1 ]
  • [ 7677-24-9 ]
  • [ 55758-02-6 ]
  • [ 13958-98-0 ]
  • [ 97483-77-7 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14733 - 14737
  • 5
  • [ 2402-97-3 ]
  • [ 7677-24-9 ]
  • [ 55758-02-6 ]
  • [ 97483-77-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 565 - 571
[2] Patent: WO2010/30811, 2010, A2, . Location in patent: Page/Page column 77
[3] Patent: WO2009/55696, 2009, A1, . Location in patent: Page/Page column 90-91
  • 6
  • [ 626-55-1 ]
  • [ 7677-24-9 ]
  • [ 55758-02-6 ]
  • [ 13958-98-0 ]
  • [ 97483-77-7 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14733 - 14737
  • 7
  • [ 97483-77-7 ]
  • [ 31181-90-5 ]
YieldReaction ConditionsOperation in experiment
60% With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 4 h; To a stirred solution of 5-bromopicolinonitrile (0.5 g, 2.732 mmol, 1.0 eq) in tetrahydrofuran (10 mL) at -78 °C DIBAL (4 mL, 4.98 mmol, 1.5 eq) was added and reaction mixture was stirred for 4 h at -78 °C. The reaction mixture was monitored by TLC, and quenched with 2N HCI (2 mL) and extracted with dichloromethane (10 mL), dried over sodium sulphate and evaporated to provide fairly pure 5-bromopicolinaldehyde (0.3 g, ~ 60 percent) which was used to the next stage without further purification.
Reference: [1] Patent: WO2013/13815, 2013, A1, . Location in patent: Page/Page column 228
[2] Patent: US2010/222345, 2010, A1, . Location in patent: Page/Page column 96
[3] Patent: US2013/29962, 2013, A1, . Location in patent: Paragraph 1101
[4] Patent: WO2016/82930, 2016, A1, . Location in patent: Page/Page column 37
  • 8
  • [ 97483-77-7 ]
  • [ 88139-91-7 ]
Reference: [1] Patent: WO2013/13815, 2013, A1,
[2] Patent: US2013/29962, 2013, A1,
[3] Patent: WO2016/82930, 2016, A1,
  • 9
  • [ 75-16-1 ]
  • [ 97483-77-7 ]
  • [ 214701-49-2 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: at -20 - -10℃; for 3 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran at -40 - -35℃; for 0.166667 h;
Intermediate 10: 1-(5-Bromopyridin-2-yl)ethanone; see W098/46605; 5-Bromo-2-cyanopyridine (Markevitch, David Y.; Rapta, Miroslav; Hecker, Scott J. ; Renau, Thomas E. ; Synth. Commun.; 33; 19; 2003; 3285 - 3290) (8 g, 43.7 mmol) was dissolved in dry THF (200 mL) and cooled to - 20°C. Methylmagnesium bromide (43.7 mL, 3M) was added drop wise and the temperature was held between -20°C and -10°C for 3 hours. The reaction mixture was cooled to -40°C and conc. HCI (4.5 mL) in water (15 mL) was added dropwise. It was stirred for 10 minutes at -35°C and then poured into a beaker with potassium phosphate buffer (300 mL, 1M, pH 7), under stirring. Ethyl acetate (300 mL) was added and the organic phase was dried over sodium sulfate. Upon concentration at room temperature under reduced pressure to - 50 mL the product crystallized, 2.4 g, mp 112°C. The mother liquor was further concentrated and chromatographed on silica gel with dichloromethane/ ethylacetate (100:1) to give another 3.25 g product (65percent combined yield). 1H-NMR (DMSO-d6) No.: 2.60 (s, 3H) ; 7.88 (dd, 1H); 8.25 (dd, 1H); 8.86 (d, 1H).
65%
Stage #1: at -20 - -10℃; for 3 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran at -40 - -35℃; for 0.166667 h;
Stage #3: potassium phosphate buffer
Intermediate 10: 1-(5-Bromopyridin-2-yl)ethanone; See W098/46605; 5-Bromo-2-cyanopyridine (Markevitch, David Y. ; Rapta, Miroslav; Hecker, Scott J. ; Renau, Thomas E. ; Synth. Commun.; 33; 19; 2003; 3285 - 3290) (8 g, 43.7 mmol) was dissolved in dry THF (200 mL) and cooled to - 20°C. Methylmagnesium bromide (43.7 mL, 3M) was added drop wise and the temperature was held between -20°C and -10°C for 3 hours. The reaction mixture was cooled to -40°C and concentrated HCl (4.5 mL) in water (15 mL) was added dropwise. It was stirred for 10 minutes at -35°C and then poured into a beaker with potassium phosphate buffer (300 mL, 1M, pH 7), under stirring. Ethyl acetate (300 mL) was added and the organic phase was dried over sodium sulfate. Upon concentration at room temperature under reduced pressure to - 50 mL the product crystallized, 2.4 g, mp 112°C. The mother liquor was further concentrated and chromatographed on silica gel with dichloromethane/ ethylacetate (100:1) to give another 3.25 g product (65percent combined yield). (at)H-NMR (DMSO-d(at)) No.: 2.60 (s, 3H) ; 7.88 (dd, 1H) ; 8.25 (dd, 1H) ; 8.86 (d, 1H).
30%
Stage #1: at -20℃; for 3 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at -40℃;
5-Bromopicolinonitrile (5.4 g, 29.7 mmol) was dissolved in anhydrous THF (120 mL) and cooled to -200C. MeMgBr (35 mL, IM in Et2O) was added dropwise, and the reaction mixture was stirred at -200C for 3 h. The reaction mixture was cooled to -40 0C, and neutralized with cone. HCl. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with water. The aqueous layer was extracted with EtOAc. The combined organic phase was dried (Na2SO4) and evaporated under vacuum. The crude product was purified by column chromatography on silica gel (EtOAc - hexanes) to give l-(5-bromopyridin-2-yl)ethanone (1.9 g, 30percent yield).
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 20, p. 4868 - 4881
[2] Patent: WO2005/116022, 2005, A1, . Location in patent: Page/Page column 44
[3] Patent: WO2005/116023, 2005, A1, . Location in patent: Page/Page column 44-45
[4] Organic and Biomolecular Chemistry, 2015, vol. 13, # 36, p. 9418 - 9426
[5] Patent: WO2008/108988, 2008, A1, . Location in patent: Page/Page column 67
[6] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 22, p. 5909 - 5915
  • 10
  • [ 676-58-4 ]
  • [ 97483-77-7 ]
  • [ 214701-49-2 ]
Reference: [1] Patent: WO2008/91681, 2008, A2, . Location in patent: Page/Page column 239
[2] Patent: US2010/16298, 2010, A1, . Location in patent: Page/Page column 202
  • 11
  • [ 97483-77-7 ]
  • [ 77-78-1 ]
  • [ 380380-64-3 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With sodium azide; ammonium chloride In dimethyl sulfoxide at 95℃; for 4 h;
Stage #2: at 50℃; for 24 h;
Stage #3: for 3 h;
The 5 - bromo -2 - cyano pyridine (800g, 4.4 µM), dimethyl sulfoxide (4L) adding 20L in the bottle, addition of sodium azide (425.7g, 6 . 55 µM), ammonium chloride (350.3g, 6 . 55 µM), stirring, heated to 95 degrees, stirring 4 hours, cooling to room temperature.By adding sodium hydroxide (470g, 11.8 µM), dropping the dimethyl sulfate (665g, 5.3 µM), heating up to 50 degrees, stirring 24 hours, the reaction is finished, the addition of water (11L), centrifugal drying to obtain the crude product.The crude product by adding dilute hydrochloric acid, stirring 3 hours, filtration, the aqueous phase is 40percent of NaOH to adjust the PH=9 - 10, separating out 2 - methyl -5 - (5 - bromo pyridine -2 - yl) tetrazole, (792g, 3.3 µM), yield: 75percent.
Reference: [1] Patent: CN106699730, 2017, A, . Location in patent: Paragraph 0016; 0017; 0018; 0019; 0020; 0021
  • 12
  • [ 97483-77-7 ]
  • [ 380380-64-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 22, p. 5909 - 5915
[2] Patent: CN106432182, 2017, A,
[3] Patent: CN106432182, 2017, A,
[4] Patent: CN106432182, 2017, A,
[5] Patent: CN106432182, 2017, A,
[6] Patent: CN106432182, 2017, A,
[7] Patent: WO2008/108988, 2008, A1,
[8] Patent: WO2005/116023, 2005, A1, . Location in patent: Page/Page column 67
  • 13
  • [ 97483-77-7 ]
  • [ 380380-64-3 ]
  • [ 380380-63-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1027 - 1039
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 7, p. 1305 - 1313
[3] Patent: CN106146559, 2016, A,
[4] Patent: WO2005/116022, 2005, A1,
  • 14
  • [ 97483-77-7 ]
  • [ 137178-88-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 2074 - 2079
  • 15
  • [ 97483-77-7 ]
  • [ 73183-34-3 ]
  • [ 741709-63-7 ]
YieldReaction ConditionsOperation in experiment
46% With potassium acetate In dimethyl sulfoxide at 20 - 80℃; for 96 h; 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carbonitrile
Into a 250 mL RBF was added 3.0 g 5-Bromo-pyridine-2-carbonitrile (3.0 g, 16.39 mmol), Bis(pinacolato)diboron (4.58 g, 18.03 mmol), KOAc (5.47 g, 55.74 mmol), and DMSO (100 mL).
After degassing for 20 minutes, PdCl2dppf-CH2Cl2 (1.39 g, 1.64 mmol) was added and the solution was stirred for 24 hours at 80° C., and then room temperature for 3 days. 50 mL water was added and the product was extracted with ethyl acetate.
The combined organics were washed with brine, dried over Na2SO4 and concentrated.
The dark-colored residue was purified by FCC eluding with 20percent acetone/hexanes to give a red solid.
The solid was triturated with hexane to give 1.72 g (46percent) Int-26 as a light-pink solid.
Into a 250 mL round-bottomed flask was added 3.0 g of 5-bromo-pyridine-2-carbonitrile (3.0 g, 16.39 mmol), bis(piniacolato)diboron (4.58 g, 18.03 mmol), KOAc (5.47 g, 55.74 mmol), and DMSO (100 mL). After degassing for 20 minutes, PdCl2dppf-CH2Cl2 (1.39 g, 1.64 mmol) was added and the solution was stirred for 24 hours at 80° C., and then at room temperature for 3 days. 50 mL water was added and the product was extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4 and concentrated. The dark-colored residue was purified by flash column chromatography eluting with 20percent acetone/hexanes to give a red solid. The solid was triturated with hexane to give 1.72 g (46percent) of I-238 as a light-pink solid.
24% With potassium acetate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; Inert atmosphere [0450] To a solution of5-bromopicolinonitrile (1.00 g, 5.46mmol) in DMF (10 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (2.77 g, 10.9 mmol),Pd(OAc)2 (61.0mg, 0.273 mmol), PPh3 (285 mg, 1.09 mmol)and KOAc (1.61 g, 16.4 mol) under a nitrogen atmosphere.The resulting mixture was stirred at 80° C. overnight. Thereaction mixture was cooled tort and the solids were removedby filtration. The filtrate was concentrated under reducedpressure to obtain a residue, which was purified by flashcolunm chromatography on silica gel with EtOAc/petroleumether (1 :50 v/v) to obtain compound 1f as a white solid (300mg, 24percent yield). Mass Spectrum (LCMS, ESI pos.): Calcd.for C12H15BN20 2 : 231.1 (M+H). found: 231.1.
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 13, p. 5473 - 5494
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1277 - 1281
[3] Patent: US2009/136473, 2009, A1, . Location in patent: Page/Page column 36; 61
[4] Patent: US2014/364414, 2014, A1, . Location in patent: Paragraph 0438; 0449-0450
[5] Patent: WO2009/74812, 2009, A1, . Location in patent: Page/Page column 70
  • 16
  • [ 97483-77-7 ]
  • [ 856866-72-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1027 - 1039
  • 17
  • [ 97483-77-7 ]
  • [ 327056-62-2 ]
Reference: [1] Patent: WO2006/12374, 2006, A1, . Location in patent: Page/Page column 214
[2] Patent: US2003/225106, 2003, A1, . Location in patent: Page 95
  • 18
  • [ 97483-77-7 ]
  • [ 848141-14-0 ]
Reference: [1] Patent: WO2015/160654, 2015, A1,
[2] Patent: WO2017/58831, 2017, A1,
[3] Patent: WO2017/127375, 2017, A1,
  • 19
  • [ 97483-77-7 ]
  • [ 915720-71-7 ]
Reference: [1] Patent: WO2006/123113, 2006, A2,
  • 20
  • [ 97483-77-7 ]
  • [ 1056039-83-8 ]
Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 7, p. 1305 - 1313
[2] Patent: WO2008/108988, 2008, A1,
  • 21
  • [ 24424-99-5 ]
  • [ 97483-77-7 ]
  • [ 1188477-11-3 ]
YieldReaction ConditionsOperation in experiment
47% With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol at 0 - 15℃; for 3 h; To a mixture of 5- bromopicolinonitrile (3.0 g, 16.4 mmol) in MeOH (60 mL) was added di-tert-butyl dicarbonate (7.2 g, 32.8 mmol) and nickel chloride hexahydrate (0.33 g, 1.64 mmol). The mixture was cooled to 0°C, followed by portion wise addition of NaBH4 (4.3 g, 0.115 mol) over 2 hr. The mixture was stirred at 15°C for 1 hr then poured into ice- water (200 g) and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SC>4, and concentrated under reduced pressure. The residue was purified by flash column chromatography to give the desired product (2.2 g, 47percent yield) as a yellow solid. LC-MS: m/z 287,289 (M+H)+.
650 mg With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol at 0 - 20℃; for 14 h; Step 1
Preparation of (5-Bromo-pyridin-2-ylmethyl)-carbamic acid tert-butyl ester
To a solution of 5-Bromo-pyridine-2-carbonitrile (1.0 g, 5.46 mmol) in methanol (10 mL) at 0° C. is added NiCl2.6H2O (0.12 g, 0.54 mmol), Di-tert-butyl dicarbonate (2.38 g, 0.010 mmol) and NaBH4 (0.413 g, 0.010 mmol) at 0° C. then stirred at room temperature for 14 hours.
The reaction solvent is removed under reduced pressure and crude is diluted with water and ethyl acetate.
The organic layer was separated, dried over sodium sulphate and concentrated in vacuum.
The crude is purified by column chromatography eluting with 30percent ethyl acetate in hexane to afford the title compound (650 mg).
1H-NMR (400 MHz, CDCl3) δ: 1.44 (s, 9H), 4.37 (d, J=5.44 Hz, 2H), 5.41 (bs, 1H), 7.18 (d, J=8.28 Hz, 1H), 7.75-7.78 (dd, J1=8.32 Hz, J2=2.28 Hz, 1H), 8.57 (d, J=2.08 Hz, 1H). LC-MS (m/z): [M+H]=289.0.
1 g at 0 - 20℃; for 18 h; To a solution of 5-bromo-2-cyanopyridine (5.0 g, 27.32 mmol) in methanol (50 mL) at 0 °C were added nickel (II) chloride hexahydrate (649 mg, 27.32 mmol), di-tert-butyl dicarbonate (11.9 g, 54.64 mmol) and sodium borohydride (2.06 g, 54.64 mmol). The reaction mixture was stirred at RT for 18 h. The mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate and water. The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated. The residue thus obtained was purified by silica gel column chromatography to afford 1.0 g of the titled product. 1H NMR (300 MHz, CDCl3) δ 1.45 (s, 9H), 4.39 (d, = 5.4 Hz, 2H), 5.47 (br s, 1H), 7.21 (d, = 8.1 Hz, 1H), 7.79 (d, = 8.1 Hz, 1H), 8.59 (s, 1H); APCI-MS (m/z) 289 (M+H)+.
Reference: [1] Patent: WO2016/112088, 2016, A1, . Location in patent: Paragraph 0660
[2] Patent: US2013/237502, 2013, A1, . Location in patent: Paragraph 0367
[3] Patent: WO2018/42342, 2018, A1, . Location in patent: Page/Page column 53
  • 22
  • [ 1765-93-1 ]
  • [ 97483-77-7 ]
  • [ 914349-75-0 ]
Reference: [1] Chemical Research in Toxicology, 2014, vol. 27, # 12, p. 2052 - 2061
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 18, p. 4403 - 4407
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