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[ CAS No. 54-96-6 ] {[proInfo.proName]}

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Chemical Structure| 54-96-6
Chemical Structure| 54-96-6
Structure of 54-96-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 54-96-6 ]

CAS No. :54-96-6 MDL No. :MFCD00006401
Formula : C5H7N3 Boiling Point : -
Linear Structure Formula :- InChI Key :OYTKINVCDFNREN-UHFFFAOYSA-N
M.W : 109.13 Pubchem ID :5918
Synonyms :
3,4-Diaminopyridine

Calculated chemistry of [ 54-96-6 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 33.05
TPSA : 64.93 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.57
Log Po/w (XLOGP3) : -0.51
Log Po/w (WLOGP) : 0.26
Log Po/w (MLOGP) : -0.86
Log Po/w (SILICOS-IT) : 0.01
Consensus Log Po/w : -0.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.75
Solubility : 19.4 mg/ml ; 0.178 mol/l
Class : Very soluble
Log S (Ali) : -0.39
Solubility : 44.9 mg/ml ; 0.412 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.24
Solubility : 6.25 mg/ml ; 0.0573 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 54-96-6 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P260-P264-P280-P284-P301+P310-P305+P351+P338 UN#:2811
Hazard Statements:H300+H330-H311-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 54-96-6 ]

* 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 [ 54-96-6 ]
  • Downstream synthetic route of [ 54-96-6 ]

[ 54-96-6 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 54-96-6 ]
  • [ 124-38-9 ]
  • [ 272-97-9 ]
Reference: [1] ChemCatChem, 2013, vol. 5, # 1, p. 117 - 120
[2] Patent: US2015/148535, 2015, A1, . Location in patent: Paragraph 0192; 0193
  • 2
  • [ 54-96-6 ]
  • [ 64-18-6 ]
  • [ 272-97-9 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 31, p. 9532 - 9533
[2] Journal of Natural Products, 2013, vol. 76, # 9, p. 1637 - 1646
[3] Journal of the Chemical Society, 1956, p. 4683
[4] Synlett, 2001, # 1, p. 73 - 74
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5023 - 5026
  • 3
  • [ 54-96-6 ]
  • [ 122-51-0 ]
  • [ 272-97-9 ]
Reference: [1] ChemMedChem, 2013, vol. 8, # 6, p. 985 - 993
[2] European Journal of Medicinal Chemistry, 2018, vol. 148, p. 384 - 396
  • 4
  • [ 54-96-6 ]
  • [ 89792-18-7 ]
  • [ 272-97-9 ]
Reference: [1] Patent: EP404797, 1995, B1,
  • 5
  • [ 54-96-6 ]
  • [ 68-12-2 ]
  • [ 272-97-9 ]
Reference: [1] New Journal of Chemistry, 2016, vol. 40, # 10, p. 8282 - 8287
  • 6
  • [ 54-96-6 ]
  • [ 50-00-0 ]
  • [ 272-97-9 ]
Reference: [1] Chemische Berichte, 1938, vol. 71, p. 2347,2358
  • 7
  • [ 54-96-6 ]
  • [ 2770-01-6 ]
Reference: [1] ChemMedChem, 2013, vol. 8, # 6, p. 985 - 993
[2] European Journal of Medicinal Chemistry, 2018, vol. 148, p. 384 - 396
  • 8
  • [ 54-96-6 ]
  • [ 3243-24-1 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 31, p. 9532 - 9533
  • 9
  • [ 1681-37-4 ]
  • [ 54-96-6 ]
YieldReaction ConditionsOperation in experiment
97% With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 10℃; for 24 h; The commercially available 3-nitropyridin-4-amine (50 g, 395 mmol) in the mixture of methanol (500 ml) and THF (500 ml) was hydrogenated with 10 percent Pd/C (5 g) as a catalyst at 10°C (1 atm) for 24 h. After uptake of (3 eq), the catalyst was filtered off and the filtrate was evaporated. 38 g of the title intermediate 8 was obtained, (Yield 97 percent).
Reference: [1] Journal of Heterocyclic Chemistry, 1999, vol. 36, # 5, p. 1143 - 1145
[2] Patent: WO2014/114776, 2014, A1, . Location in patent: Page/Page column 25
[3] Chemistry of Materials, 2016, vol. 28, # 7, p. 2058 - 2066
[4] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
[5] Chemische Berichte, 1926, vol. 59, p. 1210
[6] Justus Liebigs Annalen der Chemie, 1935, vol. 518, p. 274,287
[7] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5023 - 5026
[8] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6289 - 6304
[9] Patent: WO2017/168333, 2017, A1, . Location in patent: Page/Page column 16
  • 10
  • [ 33544-42-2 ]
  • [ 54-96-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
  • 11
  • [ 100306-70-5 ]
  • [ 54-96-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
  • 12
  • [ 626-64-2 ]
  • [ 54-96-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
[2] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
[3] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
  • 13
  • [ 94602-04-7 ]
  • [ 54-96-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
[2] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
[3] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
  • 14
  • [ 5435-54-1 ]
  • [ 54-96-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
[2] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
[3] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
  • 15
  • [ 5221-42-1 ]
  • [ 54-96-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1999, vol. 36, # 5, p. 1143 - 1145
  • 16
  • [ 79371-42-9 ]
  • [ 54-96-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1999, vol. 36, # 5, p. 1143 - 1145
  • 17
  • [ 504-24-5 ]
  • [ 54-96-6 ]
Reference: [1] Patent: WO2017/168333, 2017, A1,
  • 18
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  • [ 273-05-2 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride; sodium nitrite In water at 0℃; for 1 h; 3,4-diaminopyridine (2.0 g, 0.048 mol) was dissolved in a 2N hydrogen chloride aqueous solution (25 mL), cooled to 0 ° C, Sodium nitrite (1.9 g, 0.027 mol) was dissolved in distilled water (3 mL) and added slowly, And stirred for 1 hour. The resulting solid was filtered and washed with distilled water to give the title compound im-7-a (1.96 g, 89percent) as a yellow solid.
Reference: [1] Patent: KR101798840, 2017, B1, . Location in patent: Paragraph 0372-0375
[2] Tetrahedron Letters, 1997, vol. 38, # 50, p. 8607 - 8610
  • 19
  • [ 54-96-6 ]
  • [ 201230-82-2 ]
  • [ 7397-68-4 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, p. 1793 - 1800
[2] Phosphorus and Sulfur and the Related Elements, 1988, vol. 38, p. 137 - 148
  • 20
  • [ 54-96-6 ]
  • [ 57-13-6 ]
  • [ 7397-68-4 ]
Reference: [1] Patent: WO2007/61692, 2007, A2, . Location in patent: Page/Page column 117
[2] Patent: WO2007/61694, 2007, A2, . Location in patent: Page/Page column 113
[3] Patent: WO2006/31491, 2006, A2, . Location in patent: Page/Page column 80
[4] Patent: WO2008/153852, 2008, A1, . Location in patent: Page/Page column 77
  • 21
  • [ 54-96-6 ]
  • [ 530-62-1 ]
  • [ 7397-68-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 20, p. 8066 - 8096
  • 22
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  • [ 75115-28-5 ]
Reference: [1] Synthetic Communications, 2010, vol. 40, # 5, p. 697 - 708
  • 23
  • [ 54-96-6 ]
  • [ 221241-11-8 ]
YieldReaction ConditionsOperation in experiment
71% at 40 - 110℃; for 5 h; 0613] To the mixture of X-1 (10.0 g, 10 mmol) dissolved in HBr 48percent (200 mL), Br2 (12.5 mL, 13.4 mmol) was added dropwise under ice-water cooling bath, maintaining the temperature below 40° C. After that, the mixture was heated at 110° C. for 5 hrs. The reaction mixture was cooled to rt, filtered and washed with little water. The filter cake is basified to pH 78 with saturated aq. NaHCO3 and extracted with EtOAc (200 mL×3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to yield X-2 (17.2 g, 71percent yield). 1H NMR (DMSO-d6, 400 MHz) δ 7.95 (s, 1H), 5.20 (brs, 4H).
71% With hydrogen bromide; bromine In water at 40 - 110℃; for 5 h; Cooling with ice To the mixture of X-1 (10.0 g, 10 mmol) dissolved in HBr 48percent (200 mL), Br2 (12.5 mL, 13.4 mmol) was added dropwise under ice-water cooling bath, maintaining the temperature below 40°C. After that, the mixture was heated at 110°C for 5 hrs. The reaction mixture was cooled to rt, filtered and washed with little water. The filter cake is basified to pH 7--8 with saturated aq. NaHCO3 and extracted with EtOAc (200 mLx3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to yield X-2 (17.2 g, 71percent yield). ‘H NMR (DMSO-d6, 400 MHz) 5 7.95 (s, 1H), 5.20 (brs, 4H).
50% With hydrogen bromide; bromine In water at 100 - 135℃; for 5 h; The synthesis of 3,4-diamino-2,5-dibromopyridine was improved on the basis of the method reported in a literature [18]. The mixture of pyrido-3,4-diamine(2 g, 18.3 m mol) with an aqueous HBr (48percent, 30 ml) were prepared in a 250 ml three-neck round bottom flask with a magneton inside. After the mixture was heated to 100 deg.C, bromine(2.5 ml) was added dropwise, and the solution was stirred for 5 h at 135 deg.C. After the mixture was cooled to room temperature, an aqueous solution of Na2S2O3, an aqueous solution of Na2CO3, and distilled water were added in this order to get a yellow precipitate. Then the precipitate was separated by filtration and washed with distilled water three times. Recrystallization from the mixture solution of toluene: THF (v:v = 5:1) gave white flocculence solid, yielded: 50percent. 1H NMR (DMSO, 400 MHz, ppm): d=7.53 (s, 1H), 5.99 (s, 2H), 5.03 (s, 2H). 13C NMR (DMSO,101 MHz, ppm): d = 139.93, 139.13, 129.54, 126.67, 106.22 (seeFig. S1 in Supporting Informations)
30%
Stage #1: Reflux
Stage #2: at 80℃; for 16 h;
The mixture of 3,4-diaminopyridine (5.45 g, 50 mmol) with 48percent hydrobromic acid (24 mL) in a 50 mL flask was heated to reflux while stirring. After adding bromine (8 mL, 155.7 mmol) dropwise, the reaction mixture was heated for 16 h at 80 °C then cooled down to the room temperature. The mixture was filtered and washed with a saturated solution of Na2S2O3 (150 mL), NaHCO3 (150 mL) and finally water (150 mL). The residue was first purified by flash chromatography using PE (petroleum ether)/EA (ethyl acetate)=1:2 (v/v) as eluent and recrystallized in ethanol to give 4 g orange solid. (Yield: 30percent). 1H NMR (400 MHz, DMSO-d6, ppm): δ=7.53 (s, 1H), 5.99 (s, 2H), 5.05 (s, 2H); 13C NMR (100 MHz, DMSO-d6, ppm): δ=140.66, 140.45, 129.81, 128.30, 106.24.; HRMS (ESI, m/z): [M+H]+ calcd for (C5H5N3Br2), 264.8850; found, 264.8844.
25.5% for 5 h; Reflux In a three-neck 100 mL round-bottom flask, was added 3,4-diaminopyridine (1) (5.0 g, 45.2 mmol) with 9.3 mL of 48 percent hydrobromic acid. The resulting mixture was heated to reflux while stirring and bromine (7.6 mL, 148.5 mmol) was added dropwise. The reaction mixture was refluxed for 5 h and cooled to ambient temperature. The mixture was filtered and washed with a saturated solution of Na2S2O3 (100 mL),Na2CO3 (100 mL) and finally water (100 mL). To complete the neutralization process, the crude product was refluxed 30 min in a 10 percent solution of Na2CO3. The mixture was then filtered and washed with water. The brown-dark product wasfirst purified by column chromatography ethyl acetate/hexane(3:2) and by recrystallization from methanol to give compound 2 as an orange powder (3.1 g, 25.5 percent). 1HNMR(Acetone-d6, 300 MHz, δ/ppm): 7.65 (s, 1H), 5.54 (br, 2H),4.66 (br, 2H). 13C NMR (100 MHz, Acetone-d6, δ/ppm):140.66, 140.45, 129.81, 128.30, 106.24. EI-MS m/z: [M +H]+ Cacld for C5H5Br2N3: 264.88, Found: 264.70.

Reference: [1] Patent: US2014/94456, 2014, A1, . Location in patent: Paragraph 0612-0613; 0635-0636
[2] Patent: WO2015/153683, 2015, A1, . Location in patent: Paragraph 0360
[3] Chemistry of Materials, 2016, vol. 28, # 7, p. 2058 - 2066
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 12, p. 1822 - 1833
[5] RSC Advances, 2014, vol. 4, # 106, p. 61537 - 61547
[6] Electrochimica Acta, 2014, vol. 146, p. 231 - 241
[7] Tetrahedron, 2012, vol. 68, # 6, p. 1695 - 1703
[8] Angewandte Chemie - International Edition, 2010, vol. 49, # 43, p. 7992 - 7995
[9] Journal of Materials Chemistry, 2011, vol. 21, # 35, p. 13247 - 13255
[10] Tetrahedron, 2014, vol. 70, # 25, p. 3901 - 3908
[11] Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 732 - 742
[12] Journal of Fluorescence, 2016, vol. 26, # 3, p. 1045 - 1052
[13] Chemical Communications, 2017, vol. 53, # 76, p. 10576 - 10579
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  • [ 1007128-70-2 ]
Reference: [1] Patent: WO2015/153683, 2015, A1,
  • 25
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  • [ 333432-27-2 ]
Reference: [1] Journal of Materials Chemistry, 2011, vol. 21, # 35, p. 13247 - 13255
[2] RSC Advances, 2014, vol. 4, # 106, p. 61537 - 61547
  • 26
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  • [ 1590409-73-6 ]
Reference: [1] Patent: US2014/94456, 2014, A1,
[2] Patent: WO2015/153683, 2015, A1,
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