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[ CAS No. 2687-25-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 2687-25-4
Chemical Structure| 2687-25-4
Chemical Structure| 2687-25-4
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Product Details of [ 2687-25-4 ]

CAS No. :2687-25-4 MDL No. :MFCD00011589
Formula : C7H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :AXNUJYHFQHQZBE-UHFFFAOYSA-N
M.W : 122.17 Pubchem ID :17593
Synonyms :

Calculated chemistry of [ 2687-25-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.22
TPSA : 52.04 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 : Yes
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 0.92
Log Po/w (WLOGP) : 1.18
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 0.87
Consensus Log Po/w : 1.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.67
Solubility : 2.61 mg/ml ; 0.0214 mol/l
Class : Very soluble
Log S (Ali) : -1.6
Solubility : 3.08 mg/ml ; 0.0252 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.02
Solubility : 1.17 mg/ml ; 0.00955 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 2687-25-4 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P270-P202-P201-P264-P280-P308+P313-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P302+P352+P312-P405 UN#:2811
Hazard Statements:H301-H312-H315-H319-H341 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2687-25-4 ]

* 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 [ 2687-25-4 ]
  • Downstream synthetic route of [ 2687-25-4 ]

[ 2687-25-4 ] Synthesis Path-Upstream   1~28

  • 1
  • [ 122-51-0 ]
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
YieldReaction ConditionsOperation in experiment
72% With iodine In acetonitrile at 20℃; EXAMPLE 17; N'-(3,4-Dimethoxybenzylidene)-3-(4-methyl-lH-benzo[d]imidazol-l- yl)propanehydrazide; [0523] (a) 4-Methyl-lH-benzo[d]imidazole: 3-Methylbenzene-l,2-diamine(400 mg, 3.27 mmol), triethylorthoformate (0.65 mL, 3.92 mmol) and I2 (83 mg, 0.327 mmol) were combined in MeCN (10 mL) and stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and washed with sat. aq. NaHCO3 and dried (Na2SO4). Purification on silica gel using EtOAc -hexane (0 to 80percent) gave the desired product (310 mg, 72percent).
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 7, p. 1154 - 1159
[2] Monatshefte fur Chemie, 2007, vol. 138, # 1, p. 89 - 94
[3] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 6, p. 1509 - 1512
[4] Patent: WO2010/132615, 2010, A1, . Location in patent: Page/Page column 113
  • 2
  • [ 4885-02-3 ]
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In tetrahydrofuran A.
4-Methyl-1H-benzimidazole
2,3 Diaminotoluene (675 mg, 5.53 mmol) was dissolved in 10 mL of dry tetrahydrofuran and triethylamine (0.77 mL, 5.53 mmol) was added.
The mixture was cooled to 0° C. and 1,1-dichloromethyl methyl ether (0.50 mL, 5.53 mmol) was added and the reaction was allowed to warm to room temperature.
After 20 hours, the reaction was quenched with sodium bicarbonate.
The aqueous phase was extracted with ethyl acetate, dried over magnesium sulfate, filtered and the solvent removed to yield 730 mg (100percent) of a brown solid.
Reference: [1] Patent: US5212177, 1993, A,
[2] Patent: US5374615, 1994, A,
  • 3
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide; formic acid In water Part B.
4-Methyl-1H-benzimidazole (Compound XVIII)
A mixture of 3-methyl-1,2-benzenediamine (11.9 g) and formic acid (150 mL) was heated at 70° C. for 15 minutes.
The solvent was removed under reduced pressure and the residual oil was stirred with water (100 mL) and sodium hydroxide solution (65 mL of 4.0 N) was added until the solution was just basic.
The precipitate was filtered off, washed with water, and air dried to give 11.6 g (90percent) of 4-methyl-1H-benzimidazole, mp 141°-145° C.
Reference: [1] Patent: US5273975, 1993, A,
  • 4
  • [ 1445-45-0 ]
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
Reference: [1] Journal of Fluorine Chemistry, 2010, vol. 131, # 12, p. 1377 - 1381
  • 5
  • [ 2687-25-4 ]
  • [ 149-73-5 ]
  • [ 4887-83-6 ]
Reference: [1] Journal of Fluorine Chemistry, 2010, vol. 131, # 12, p. 1377 - 1381
  • 6
  • [ 64-18-6 ]
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 1, p. 700 - 706
[2] Chemische Berichte, 1919, vol. 52, p. 1083
[3] Chemische Berichte, 1919, vol. 52, p. 1083
[4] Patent: US2006/211720, 2006, A1, . Location in patent: Page/Page column 79
  • 7
  • [ 20353-93-9 ]
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
Reference: [1] Synthetic Communications, 1986, vol. 16, # 3, p. 365 - 376
  • 8
  • [ 131543-46-9 ]
  • [ 2687-25-4 ]
  • [ 13708-12-8 ]
YieldReaction ConditionsOperation in experiment
98% With 10 wtpercent sulfated polyborate In neat (no solvent) at 100℃; for 0.05 h; Green chemistry General procedure: To a mixture of substituted o-phenylenediamines derivative(2.0 mmol) and 1,2-diketone / α-hydroxy ketone (2.0 mmol),was added sulfated polyborate (10 wtpercent). The reaction mixture was stirred at 100 °C in an oil bath. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature and quenched by water. The resultant product was filtered/extracted with EtOAc to get the product. Crude products were either recrystallized from ethanol or purified by column chromatography using silica as the stationary phase and EtOAc: pet. ether as mobile phase. The products obtained were known compounds and were identified by melting point and 1H and 13C NMR spectroscopy. The spectral data were compared with the literature values.
Reference: [1] Journal of Chemical Sciences, 2017, vol. 129, # 2, p. 141 - 148
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 357 - 364
[3] Organic Magnetic Resonance, 1980, vol. 14, # 4, p. 300 - 304
[4] Organic Process Research and Development, 2003, vol. 7, # 3, p. 318 - 323
  • 9
  • [ 517-21-5 ]
  • [ 2687-25-4 ]
  • [ 13708-12-8 ]
Reference: [1] Journal of the Chemical Society, 1953, p. 2816,2819
  • 10
  • [ 431-03-8 ]
  • [ 2687-25-4 ]
  • [ 62163-09-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 357 - 364
  • 11
  • [ 2687-25-4 ]
  • [ 2255-80-3 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 15, p. 6004 - 6017
[2] Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 629 - 633
[3] Journal of the American Chemical Society, 2015, vol. 137, # 2, p. 898 - 904
[4] Tetrahedron, 2016, vol. 72, # 23, p. 3232 - 3239
[5] Journal of Materials Chemistry C, 2014, vol. 2, # 40, p. 8515 - 8524
  • 12
  • [ 75-15-0 ]
  • [ 2687-25-4 ]
  • [ 27231-33-0 ]
Reference: [1] Agricultural and Biological Chemistry, 1987, vol. 51, # 7, p. 1941 - 1946
[2] Patent: US2007/10542, 2007, A1, . Location in patent: Page/Page column 77
  • 13
  • [ 140-89-6 ]
  • [ 2687-25-4 ]
  • [ 27231-33-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 6, p. 1517 - 1523
  • 14
  • [ 570-24-1 ]
  • [ 2687-25-4 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen In ethanol at 20℃; for 4 h; 4.0 g of 10 percent palladium-carbon catalyst (water content, 51.5 percent) was added to ethanol (200 ml) solution of 8.50 g (55.9 mmol) of 2-methyl-6-nitroaniline, and the resulting mixture was stirred under atmospheric pressure hydrogen at room temperature for 4 hours. The catalyst was removed through filtration, and the solvent was evaporated from the filtrate to obtain 6.64 g (97 percent) of a crude product of the entitled compound as a black crystal. This compound was directly used in the next reaction.1H-NMR(CDCl3)δ: 2.22(3H, s), 3.35-3.40(4H, m), 6.62-6.68(3H, m).
85.8% for 1 h; Reflux o-Diamines 5a and 5b were obtained following a standard reduction procedure [28]. Twenty-seven milliliters of concentrated HCl were added gradually, through a condenser, to a mixture of 10g (0.066mol) of 4-methyl-2-nitroaniline (4a) or 2-methyl-6-nitroaniline (4b) and 12g (0.1mol) of granulated Sn. During the addition of the acid the reaction mixture was vigorously stirred. After that, the reaction mixture was refluxed for 1h, cooled to room temperature and made alkaline with a solution of 20g of NaOH in 33mL of water. (0008) The reduction product of compound 4b, 3-methylbenzene-1,2-diamine (5b), was isolated from the reaction mixture by steam distillation. Compound 5b was “salted out” by saturating the distillate with NaCl and extracted with Et2O. Combined ethereal layers were dried over anhydrous MgSO4 and concentrated under reduced pressure. Since it was impossible to separate 4-methylbenzene-1,2-diamine (5a) by steam distillation, this diamine was directly “salted out” from the reaction mixture and extracted with Et2O. After the evaporation of the solvent, the crude 5a was purified by sublimation. The yield was 83.5percent (6.72g) and 85.8percent (6.92g) for compound 5a and 5b, respectively.
70%
Stage #1: With tin(ll) chloride In ethyl acetate for 6 h; Reflux
Stage #2: With water; sodium hydrogencarbonate In ethyl acetateCooling
To a stirred solution of 2-methyl-6-nitroaniline (0.3 g, 1.97 mmol) in ethyl acetate (10 mL), 1.7 g (11.84 mmol) of stannous chloride was added and the mixture was refluxed for 6 h. The reaction was cooled and added into ice water. The ethyl acetate layer was collected and repeatedly washed with sodium bicarbonate solution. The organic layer was concentrated under vacuum and the product was obtained as orange solid (0.17 g, 70percent). m.p. 52-55° C. 1H NMR (400 MHz, CDCl3, TMS) δ 6.64 (s, 3H), 3.4 (s, 4H), 2.20 (s, 3H).
Reference: [1] Patent: EP1479681, 2004, A1, . Location in patent: Page 110
[2] Polyhedron, 2016, vol. 105, p. 137 - 149
[3] Patent: US2012/130078, 2012, A1, . Location in patent: Page/Page column 6
[4] Heterocycles, 1997, vol. 45, # 5, p. 955 - 962
[5] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 543 - 548
[6] Justus Liebigs Annalen der Chemie, 1885, vol. 228, p. 243
[7] Chemische Berichte, 1919, vol. 52, p. 1083
[8] Journal of the Chemical Society, 1928, p. 355
[9] Tetrahedron, 1995, vol. 51, # 42, p. 11515 - 11530
[10] Journal of Organic Chemistry, 2005, vol. 70, # 15, p. 6004 - 6017
[11] Patent: US5273975, 1993, A,
[12] Patent: US4714764, 1987, A,
[13] Patent: US2007/10542, 2007, A1, . Location in patent: Page/Page column 77
[14] Patent: EP2653505, 2013, A1, . Location in patent: Paragraph 0179
[15] Organic Process Research and Development, 2003, vol. 7, # 3, p. 318 - 323
[16] Journal of Organic Chemistry, 2014, vol. 79, # 23, p. 11440 - 11453
[17] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6289 - 6304
  • 15
  • [ 16554-45-3 ]
  • [ 2687-25-4 ]
Reference: [1] Patent: JP5670893, 2015, B2, . Location in patent: Paragraph 0222; 0234; 0235
  • 16
  • [ 601-87-6 ]
  • [ 2687-25-4 ]
Reference: [1] Journal of Materials Chemistry C, 2014, vol. 2, # 40, p. 8515 - 8524
[2] Chemische Berichte, 1891, vol. 24, p. 564
[3] Synthetic Communications, 2007, vol. 37, # 19, p. 3455 - 3470
  • 17
  • [ 1457-92-7 ]
  • [ 2687-25-4 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 12, p. 2277 - 2279
  • 18
  • [ 823-40-5 ]
  • [ 95-80-7 ]
  • [ 115-11-7 ]
  • [ 2687-25-4 ]
Reference: [1] Patent: EP244778, 1991, B1,
[2] Patent: EP270031, 1988, A3,
[3] Patent: EP244778, 1987, A1,
[4] Patent: EP244778, 1987, A1,
  • 19
  • [ 75-13-8 ]
  • [ 95-80-7 ]
  • [ 2687-25-4 ]
Reference: [1] Patent: US4996359, 1991, A,
[2] Patent: EP391716, 1990, A1,
  • 20
  • [ 121-14-2 ]
  • [ 618-85-9 ]
  • [ 606-20-2 ]
  • [ 602-01-7 ]
  • [ 610-39-9 ]
  • [ 619-15-8 ]
  • [ 108-71-4 ]
  • [ 823-40-5 ]
  • [ 95-80-7 ]
  • [ 496-72-0 ]
  • [ 95-70-5 ]
  • [ 2687-25-4 ]
Reference: [1] Patent: EP1864969, 2007, A1, . Location in patent: Page/Page column 5; 6
  • 21
  • [ 120-66-1 ]
  • [ 2687-25-4 ]
Reference: [1] Chemische Berichte, 1919, vol. 52, p. 1083
[2] Polyhedron, 2016, vol. 105, p. 137 - 149
  • 22
  • [ 602-01-7 ]
  • [ 2687-25-4 ]
Reference: [1] Archiv der Pharmazie, 1989, vol. 322, # 8, p. 457 - 459
  • 23
  • [ 584-90-7 ]
  • [ 2687-25-4 ]
Reference: [1] Patent: CN104262166, 2016, B,
  • 24
  • [ 99-99-0 ]
  • [ 121-14-2 ]
  • [ 618-85-9 ]
  • [ 606-20-2 ]
  • [ 602-01-7 ]
  • [ 619-15-8 ]
  • [ 108-71-4 ]
  • [ 823-40-5 ]
  • [ 95-80-7 ]
  • [ 95-70-5 ]
  • [ 2687-25-4 ]
Reference: [1] Patent: US6359177, 2002, B1, . Location in patent: Page column 7
  • 25
  • [ 570-24-1 ]
  • [ 10034-85-2 ]
  • [ 2687-25-4 ]
Reference: [1] Chemische Berichte, 1919, vol. 52, p. 1083
  • 26
  • [ 530-62-1 ]
  • [ 2687-25-4 ]
  • [ 15965-57-8 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 28, p. 8836 - 8844
  • 27
  • [ 2687-25-4 ]
  • [ 15965-57-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1071 - 1074
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 15, p. 7188 - 7211
  • 28
  • [ 2687-25-4 ]
  • [ 1071224-34-4 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 2, p. 898 - 904
[2] Journal of Materials Chemistry C, 2014, vol. 2, # 40, p. 8515 - 8524
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