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[ CAS No. 625-82-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 625-82-1
Chemical Structure| 625-82-1
Chemical Structure| 625-82-1
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Product Details of [ 625-82-1 ]

CAS No. :625-82-1 MDL No. :MFCD00192088
Formula : C6H9N Boiling Point : -
Linear Structure Formula :- InChI Key :MFFMQGGZCLEMCI-UHFFFAOYSA-N
M.W : 95.14 Pubchem ID :39539
Synonyms :

Calculated chemistry of [ 625-82-1 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 30.72
TPSA : 15.79 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.55
Log Po/w (XLOGP3) : 1.48
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 0.84
Log Po/w (SILICOS-IT) : 2.35
Consensus Log Po/w : 1.57

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.89
Solubility : 1.22 mg/ml ; 0.0129 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 3.63 mg/ml ; 0.0381 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.483 mg/ml ; 0.00508 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 625-82-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 625-82-1 ]

* 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 [ 625-82-1 ]
  • Downstream synthetic route of [ 625-82-1 ]

[ 625-82-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 625-82-1 ]
  • [ 2199-58-8 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: at 0℃; for 0.333333 h;
Stage #2: at 0℃; for 0.5 h; Heating / reflux
Stage #3: With sodium acetate In 1,2-dichloro-ethane for 0.333333 h; Heating / reflux
A.
2-formyl-3,5-dimethylpyrrole
To dimethylformamide (4.5 mL, 57.8 mmol) under argon at 0° C. was added phosphorus oxychloride (57.8 mmol) dropwise over 5 min.
The cooling bath was removed and after 15 min. 1,2-dichloroethane (15 mL) was added.
The reaction mixture was again cooled to 0° C. and a solution of 2,4-dimethylpyrrole (52.6 mmol) in 1,2-dichloroethane (15 mL) was added dropwise over 15 min.
The reaction was heated to reflux for 15 min, and then cooled to rt.
A solution of sodium acetate (24 g) in water (75 mL) was added slowly to the reaction mixture and the resulting mixture was again heated to reflux for 20 min.
After the reaction mixture was cooled to rt it was diluted with CH2Cl2, and the aqueous phase was washed with CH2Cl2 (2*50 mL).
The combined organic fractions were washed with saturated NaHCO3, dried (Na2SO4), and concentrated in vacuo.
The crude material was purified by chromatography on silica gel eluding with 10percent ethyl acetate in hexane to provide 5.2 g (80percent) of the desired compound 2-formyl-3,5-dimethylpyrrole. [M+H]+=124.1, [M-H]-=122.0
Reference: [1] Patent: US6982265, 2006, B1, . Location in patent: Page/Page column 28
[2] Gazzetta Chimica Italiana, 1934, vol. 64, p. 778,782
  • 2
  • [ 625-82-1 ]
  • [ 68-12-2 ]
  • [ 2199-58-8 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: at 0 - 20℃; Inert atmosphere
Stage #2: at 0 - 40℃; Inert atmosphere
POCl3 (1.00mL, 11 mmol) was added dropwise at 0°C to DMF (20mL) and the resulting mixture was stirred for 5min. The solution was then stirred at rt for 30min before being cooled back down to 0°C. The solution was then treated with 3,5-dimethyl-1H-pyrrole (1.0mL, 10mmol). The resulting mixture was allowed to warm up to rt, and then heated to 40°C until completion as indicated by TLC analysis (18h). The reaction was then cooled down to rt and diluted with EtOAc (30mL). The resulting solution was washed with H2O (8×50mL), brine (3×50mL), dried (Na2SO4) and concentrated in vacuo to afford the crude as a dark brown solid. Column chromatography (silica gel, 50percent Et2O/petroleum ether) afforded (1.1g, 82percent) of the desired pyrrole carbaldehyde 8 as an off white solid. 1H NMR (CDCl3, 400MHz) δ: 10.14 (1H, br s), 9.49 (1H, s), 5.89 (1H, s), 2.32 (3H, s), 2.30 (3H, s). 13C NMR (CDCl3, 100MHz) δ: 176.0, 138.5, 134.8, 128.8, 112.1, 13.2, 10.5.
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 21, p. 4829 - 4841
[2] Chemical Communications, 2008, # 40, p. 4933 - 4935
[3] Tetrahedron, 2013, vol. 69, # 39, p. 8527 - 8533
[4] Russian Journal of General Chemistry, 2010, vol. 80, # 11, p. 2374 - 2381
[5] Russian Journal of General Chemistry, 2013, vol. 83, # 8, p. 1571 - 1579[6] Zh. Obshch. Khim., 2013, vol. 83, # 8, p. 1342 - 1350,9
  • 3
  • [ 625-82-1 ]
  • [ 75-34-3 ]
  • [ 2199-58-8 ]
Reference: [1] Patent: US6147106, 2000, A,
  • 4
  • [ 625-82-1 ]
  • [ 127-09-3 ]
  • [ 2199-58-8 ]
Reference: [1] Dalton Transactions, 2012, vol. 41, # 34, p. 10199 - 10210
  • 5
  • [ 625-82-1 ]
  • [ 74-90-8 ]
  • [ 2199-58-8 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1949[2] Chemische Berichte, 1923, vol. 56, p. 520,523
[3] Chemische Berichte, 1922, vol. 55, p. 1949[4] Chemische Berichte, 1923, vol. 56, p. 520,523
[5] Journal of the American Chemical Society, 1941, vol. 63, p. 1829,1831
  • 6
  • [ 625-82-1 ]
  • [ 68-12-2 ]
  • [ 2199-58-8 ]
  • [ 2199-61-3 ]
Reference: [1] Rend.Accad.Bologna, 1956, vol. <11>3, p. 16,22
  • 7
  • [ 625-82-1 ]
  • [ 77287-34-4 ]
  • [ 2199-58-8 ]
Reference: [1] Bulet.Soc.Chim.Romania, 1929, vol. 11, p. 135,138
  • 8
  • [ 625-82-1 ]
  • [ 149-73-5 ]
  • [ 2199-58-8 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 35, p. 11327 - 11334
  • 9
  • [ 625-82-1 ]
  • [ 68-12-2 ]
  • [ 10025-87-3 ]
  • [ 2199-58-8 ]
  • [ 2199-61-3 ]
Reference: [1] Rend. Accad. Bologna, 1956, vol. <11> 3, p. 16,22
  • 10
  • [ 625-82-1 ]
  • [ 773-64-8 ]
  • [ 885434-70-8 ]
YieldReaction ConditionsOperation in experiment
58% With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 16 h; To a solution of 2,4-dimethyl-lH-pyrrole (24 mg, 0.25 mmol) and mesitylsulfonyl chloride (218 mg, 1.0 mmol) in 5 mL of THF was added 60percent NaH (40 mg, 1.0 mmol) at 0 °C. The resulting mixture was stirred at r.t. for 16 h. The solution was diluted with EtOAc (50 mL), washed with 1 N HC1 (aq.) (10 mL) and brine (10 mL). The organic layer was dried over anhydrous Na2S04 and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hexane/EtOAc = 10/1) to give the desired product as a pale red solid (40 mg, 58percent). H NMR (600 MHz, CDC13) δ 7.01 (s, 1H), 6.95 (s, 2H), 5.77 (s, 1H), 2.49 (s, 6H), 2.31 (s, 3H), 2.00 (s, 3H), 1.99 (s, 3H). 13C NMR (150 MHz, CDCI3) δ 143.8, 140.2, 133.8, 132.2, 130.2, 119.7, 119.2, 114.5, 23.4, 21.1, 12.6, 11.8.
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 952 - 962
[2] Patent: WO2013/119931, 2013, A1, . Location in patent: Paragraph 0201
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