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[ CAS No. 41939-61-1 ] {[proInfo.proName]}

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Chemical Structure| 41939-61-1
Chemical Structure| 41939-61-1
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Product Details of [ 41939-61-1 ]

CAS No. :41939-61-1 MDL No. :MFCD00156607
Formula : C7H9N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :MNIKERWISBANET-UHFFFAOYSA-N
M.W : 167.17 Pubchem ID :3420025
Synonyms :

Calculated chemistry of [ 41939-61-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.97
TPSA : 83.87 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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.06
Log Po/w (XLOGP3) : 1.55
Log Po/w (WLOGP) : 1.04
Log Po/w (MLOGP) : 0.05
Log Po/w (SILICOS-IT) : -1.36
Consensus Log Po/w : 0.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.09
Solubility : 1.36 mg/ml ; 0.00811 mol/l
Class : Soluble
Log S (Ali) : -2.92
Solubility : 0.201 mg/ml ; 0.0012 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.85
Solubility : 2.36 mg/ml ; 0.0141 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 41939-61-1 ]

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 [ 41939-61-1 ]

* 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 [ 41939-61-1 ]
  • Downstream synthetic route of [ 41939-61-1 ]

[ 41939-61-1 ] Synthesis Path-Upstream   1~11

  • 1
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  • [ 10394-38-4 ]
Reference: [1] Journal of Pharmacy and Pharmacology, 1951, vol. 3, p. 420,424
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YieldReaction ConditionsOperation in experiment
95% With formic acid; triethylamine In acetonitrile at -15℃; for 3 h; Reflux Step 2: Pd/C (10percent) was added to a solution of (2,4-dinitrophenyl)methylamine 1 (12.14 g, 60.9 mmol) in acetonitrile (35 mL) and triethylamine (36.4 mL). The mixture was cooled to - 15 0C and then formic acid (11.1 mL) in acetonitrile (35 mL) was added. The mixture was refluxed for 3 h and then filtered. The solvent was evaporated under reduced pressure to yield the products 2 as red liquid in over 95percent yield.
68% With sodium sulfide nonahydrate; sulfur In ethanol; water at 100℃; for 2 h; To a solution of 1-chloro-2,4-dinitrobenzene in tetrahydrofuran was added methylamine in portions. After stirring for 1 h at RT N-methyl-2,4-dinitroaniline precipitate from solution. The precipitate was filtered off, washed with water and cold ethanol. Than the a suspension of crude N-methyl-2,4-dinitroaniline in ethanol was added to solution of sodium sulphide nonahydrate and powder sulphur in water and heated to 100° C for 2 h. Diluting the reaction mixture a cooling it to 0° C lead to precipitation of crude product. After filtration and washing with water and cold ethanol the title compound was obtained (6.6 g, 68 percent) as dark red precipitate. Spectral data were in agreement with literature. Russ. J. Gen. Chem. 2006, 76, No 6, 1282-1287
68% With sodium sulphide nonohydrate; sulfur In ethanol; water at 100℃; for 2 h; To a solution of 1 -chloro-2,4-dinitrobenzene in tetrahydrofuran was added methylamine in portions. After stirring for 1 h at RT N-methyl-2,4-dmitroaniline precipitate from solution. The precipitate was filtered off, washed with water and cold ethanol. Than the a suspension of crude N-methyl-2,4-dinitroaniline in ethanol was added to solution of sodium sulphide nonahydrate and powder sulphur in water and heated to 100° C for 2 h. Diluting the reaction mixture a cooling it to 0° C lead to precipitation of crude product. After filtration and washing with water and cold ethanol the title compound was obtained (6.6 g, 68 percent) as dark red precipitate. Spectral data were in agreement with literature. Russ. J. Gen. Chem. 2006, 76, No 6, 1282-1287
59% With formic acid; triethylamine In acetonitrile at -15 - 80℃; for 4.5 h; Step: 22bSynthesis of N'-Methyl-^nitro-benzene- -diamine.Procedure:TEA (5.64g, 0.0404mol) and Pd-C (0.108g) was added to a solution of 1 -Chloro-2,4- dinitro-benzene (2g, O.OlOlmol) in CH3CN. The flask was chilled to -15 °C , formic acid (2.07ml, 0.0505mol) was added and was maintained at -15 °C for 5mins. The flask was stirred at RT for 4.5 hrs followed by heating at 80°C for lOmins. The reaction was monitored by the TLC (50percent EtOAc in hexane). The resulting reaction mixture was filtered, the residue was washed with MeOH and the filtrate was concentrated, purified by columnchromatography (using silica gel of mesh size of 60-120, 12percent EtOAc in hexane as eluant) to afford lg (59percent yield) of N1 -Methyl -4-nitro-benzene-l,2-diamine.

Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 16, p. 2567 - 2571
[2] Patent: WO2010/85377, 2010, A2, . Location in patent: Page/Page column 41
[3] Journal of the Indian Chemical Society, 1988, vol. 65, # 8, p. 567 - 570
[4] Patent: EP2769723, 2014, A1, . Location in patent: Paragraph 0160-0161
[5] Patent: WO2014/128206, 2014, A1, . Location in patent: Page/Page column 51
[6] Patent: WO2012/59932, 2012, A1, . Location in patent: Page/Page column 163
[7] Chemische Berichte, 1923, vol. 56, p. 110
[8] Journal of the Chemical Society, 1930, p. 1409,1413
[9] Journal of the Chemical Society, 1929, p. 2266
[10] Patent: WO2012/59935, 2012, A1, . Location in patent: Page/Page column 26
[11] Patent: US2013/217888, 2013, A1, . Location in patent: Paragraph 0160-0162
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  • [ 108-01-0 ]
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YieldReaction ConditionsOperation in experiment
92%
Stage #1: at 90℃; for 3 h;
Stage #2: With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide); water; ethyl acetate
A solution of fluoride 247 (5.41g, 34.7 mmol) in DMF (40mL) was treated with 40percent w/w solution of MeNH2 in water (lOmL, 128 mmol). The mixture stirred at 90 OC for 3h, diluted with EtOAc, washed with saturated aqueous NaHCO3. Organic phase was dried over MgS04, evaporated and the residue was purified by flash chromatography (eluent 50percent EtOAc in CH2CI2) to afford compound 248 (5.31g, 92percent yield).'H NMR: (CDCI3) 6 (ppm): 7.75 (dd, J = 2.6, 8.8 Hz, 1H), 7.53 (d, J = 2.6 Hz, 1H), 6.45 (d, J = 8.8 Hz, 1H), 4.24 (bs, 3H), 2.91 (s, 3H). LRMS: (calcd.) 167.2 ; (found) 168.1 (MH) +.
Reference: [1] Patent: WO2005/92899, 2005, A1, . Location in patent: Page/Page column 151-152
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  • [ 593-51-1 ]
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YieldReaction ConditionsOperation in experiment
86%
Stage #1: at 20℃; for 14 h;
Stage #2: With potassium hydroxide In ethanol; water at 60℃;
2-flouro-5-nitroaniline (468 mg, 3.00 mmol) and methylamine hydrochloride (486 mg, 9.00 mmol) were dissolved in 15 mL EtOH and stirred at room temperature for 10 min. An aqueous solution of potassium hydroxide (1.009 g, 18.0 mmol) in 5 mL H20 was introduced and the mixture was stirred at reflux at 60 °C overnight. Then poured into water (100 mL) and precipitate formed was extracted with ethyl acetate (3 >< 30 mL). The organic extracts were dried over Na2S04 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel, using ethyl acetate/hexane (2: 1) as eluent, and gave N'-methyM-nitrobenzene-l^-diamine as red solid (429 mg, 86 percent); 1H NMR (400 MHz, DMSO) δ 7.56 (dd, J= 8.8, 2.7 Hz, 1H), 7.41 (d, J= 2.7 Hz, 1H), 6.43 (d, J= 8.9 Hz, 1H), 6.12 (s 1H), 5.08 (s, 2H), 2.85 (s, 3H); 13C NMR (101 MHz, DMSO) δ 144.09, 136.99, 134.89, 116.46, 107.42, 106.94, 30.12; LRMS (ESI): calcd for: C7H9N3O2 [M+H]+ = 168.2, obsd [M+H]+ = 168.
Reference: [1] Patent: WO2015/171951, 2015, A1, . Location in patent: Paragraph 0047; 0068
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YieldReaction ConditionsOperation in experiment
94.4% With sodium hydroxide; sodium bicarbonate In methanol; water (b)
2-Amino-4-nitro-N-methylaniline
71 Parts of 2,4-dinitro-N-methylaniline and 53 parts of sodium hydrogen carbonate are stirred in 144 parts of methanol.
The yellow suspension is heated in the course of 20 minutes to 40° C.
Simultaneously, 81.9 parts of 60percent sodium sulphide are dissolved in 144 parts of water of approx.
40° C and 1.2 parts of 30percent sodium hydroxide solution are added to the resultant solution.
The turbid yellow solution is filtered.
The clear yellow filtrate is added dropwise in the course of 2 hours to the suspension of 2,4-dinitro-N-methylaniline.
An exothermic reaction occurs during the dropwise addition.
The contents of the flask turn dark in colour.
The new suspension is heated in the course of 1 hour to 70° C and stirred for 15 minutes at this temperature (reflux).
Then 144 parts of methanol are distilled off.
The residue is cooled to 25° C and 50 parts of ice are added.
After suction filtration at 8° C, the filter cake is washed three times with 160 parts of water and dried in vacuo at 60° C, affording 56.8 parts of 2-amino-4-nitro-N-methylaniline (94.4percent of theory).
The melting point of the product is 177°-178° C.
Analysis: Calculated: C 50.29; H 5.43; N 25.14percent. Found: C 50.0; H 5.4; N 25.0percent.
Reference: [1] Patent: US4138568, 1979, A,
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Reference: [1] Patent: US6114532, 2000, A,
[2] Patent: US6200976, 2001, B1,
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  • [ 369-36-8 ]
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Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 41, p. 7303 - 7306
[2] Patent: WO2003/74515, 2003, A1, . Location in patent: Page/Page column 59; 102
[3] Patent: EP2311825, 2015, B1, . Location in patent: Paragraph 0189; 0190
[4] Patent: WO2008/67644, 2008, A1, . Location in patent: Page/Page column 46
  • 8
  • [ 97-00-7 ]
  • [ 41939-61-1 ]
Reference: [1] Patent: WO2012/59935, 2012, A1,
[2] Patent: WO2012/59932, 2012, A1,
[3] Patent: EP2769723, 2014, A1,
[4] Patent: WO2014/128206, 2014, A1,
[5] Patent: WO2010/85377, 2010, A2,
  • 9
  • [ 6283-25-6 ]
  • [ 74-89-5 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 775 - 780
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  • [ 2044-88-4 ]
  • [ 2784-96-5 ]
  • [ 41939-61-1 ]
Reference: [1] Chemische Berichte, 1895, vol. 28, p. 1716
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  • [ 41939-61-1 ]
  • [ 3543-75-7 ]
Reference: [1] Patent: WO2012/59935, 2012, A1,
[2] Patent: US2013/217888, 2013, A1,
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