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[ CAS No. 118-29-6 ] {[proInfo.proName]}

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Chemical Structure| 118-29-6
Chemical Structure| 118-29-6
Structure of 118-29-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 118-29-6 ]

CAS No. :118-29-6 MDL No. :MFCD00005899
Formula : C9H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :MNSGOOCAMMSKGI-UHFFFAOYSA-N
M.W : 177.16 Pubchem ID :8354
Synonyms :
Chemical Name :2-(Hydroxymethyl)isoindoline-1,3-dione

Calculated chemistry of [ 118-29-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.88
TPSA : 57.61 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) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.27
Log Po/w (XLOGP3) : 1.45
Log Po/w (WLOGP) : -0.15
Log Po/w (MLOGP) : 0.72
Log Po/w (SILICOS-IT) : 0.77
Consensus Log Po/w : 0.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.32 mg/ml ; 0.00746 mol/l
Class : Soluble
Log S (Ali) : -2.27
Solubility : 0.961 mg/ml ; 0.00542 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.89
Solubility : 2.28 mg/ml ; 0.0129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.3

Safety of [ 118-29-6 ]

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 [ 118-29-6 ]

* 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 [ 118-29-6 ]
  • Downstream synthetic route of [ 118-29-6 ]

[ 118-29-6 ] Synthesis Path-Upstream   1~22

  • 1
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  • [ 5332-26-3 ]
Reference: [1] Organic Syntheses, 1987, vol. 65, p. 119 - 119
[2] Tetrahedron Letters, 1992, vol. 33, # 1, p. 77 - 80
[3] Journal of the American Chemical Society, 1997, vol. 119, # 35, p. 8177 - 8190
[4] Chemische Berichte, 1908, vol. 41, p. 248
[5] Journal of the American Chemical Society, 1922, vol. 44, p. 823
[6] Journal of Organic Chemistry, 1958, vol. 23, p. 815,818
[7] Journal of Organic Chemistry, 1950, vol. 15, p. 1253
[8] Revue Roumaine de Chimie, 2010, vol. 55, # 9, p. 559 - 564
  • 2
  • [ 7647-01-0 ]
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  • [ 10035-10-6 ]
  • [ 5332-26-3 ]
Reference: [1] Chemische Berichte, 1908, vol. 41, p. 248
  • 3
  • [ 136918-14-4 ]
  • [ 50-00-0 ]
  • [ 118-29-6 ]
YieldReaction ConditionsOperation in experiment
96% for 1.5 h; Reflux A mixture of   phthalimide (41.14 g, 0.30 mol) and distilled   water (100 mL) was stirred for 10 min at room temperature. After addition of   formaldehyde solution (40percent, 27 mL, 0.36 mol), the resulting solution was refluxed for 1.5 h. After cooling to 0–5 °C, the resulting precipitate was collected by filtration, washed with cold water (0–5 °C, 200 mL) and dried in air to give the corresponding   N-hydroxymethylphthalimide (51.01 g, 96percent yield).(0010)A solution of   thionyl chloride (23.0 mL, 37.7 g, 0.32 mol) in   dichloromethane (50 mL) was slowly added to a mixture of the resulting   N-hydroxymethylphthalimide and dichloromethane (550 mL) and N,N-dimethylformamide (350 mL) during 30 min at room temperature with stirring. The resulting mixture was further stirred for 2 h at room temperature. After cooling to 0 °C,   water (200 mL) was added slowly. And the solution was neutralized to pH 6.7–7.0 by using saturated   aqueous NaHCO3 solution. The organic layer was separated and then was dried over anhydrous magnesium sulfate. After evaporation of the solvent under the reduced pressure, the residue was washed with n-hexane (100 mL) to give   N-chloromethylphthalimide (51.4 g, 93percent yield).(0011)   N-Chloromethylphthalimide (51.0 g, 0.26 mol) was dissolved in   acetone (500 mL) and   potassium O-ethyl xanthate (43.9 g, 274 mmol) was added portionwise in an ice water bath under stirring. The resulting solution was further stirred for 10 h at room temperature. After removal of the solvent, the residue was dissolved in   dichloromethane. The resulting solution was washed with water and dried over sodium sulfate. After removal of the solvent under the reduced pressure, pale yellow solid was obtained and recrystallized from ethyl acetate to afford the xanthate   1 as colorless crystals 67.2 g, 92percent yield, mp: 99–100 °C. Lit.20 mp: 94–95 °C. 1H NMR (CDCl3, 400 MHz) (δ, ppm) 1.47 (t, J=7.1 Hz, 3H, CH3), 4.68 (q, J=7.1 Hz, 2H, CH2), 5.34 (s, 2H, CH2), 7.75 (dd, J=5.5, 3.1 Hz, 2H, ArH), 7.88 (dd, J=5.5, 3.1 Hz, 2H, ArH). 13C NMR (CDCl3, 100 MHz) (δ, ppm) 13.7, 41.2, 70.5, 123.6, 131.8, 134.4, 166.6, 210.2.
75% With potassium carbonate In water for 2.33333 h; Heating; Reflux The titled compound was prepared according to the method described in the literature 15. A mixture of phthalimide (0.1 mol), formalin (0.25 mol) and anhydrous potassium carbonate (1 g) was dissolved in water (50 mL) by heating on a water bath for 5 min. The resultant solution was stirred for 15 min and then refluxed on a sand-bath for 2 h. On cooling, a solid separated out which was filtered off and washed repeatedly with ice-cold water. The solid thus obtained, was dried and recrystallized from ethanol. A colorless needle was obtained. m.p., 149-150 °C, Yield-75 percent.
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 11, p. 3241 - 3247
[2] Synthetic Communications, 2000, vol. 30, # 20, p. 3801 - 3807
[3] Tetrahedron, 2013, vol. 69, # 3, p. 1050 - 1056
[4] Chinese Chemical Letters, 2011, vol. 22, # 10, p. 1159 - 1162
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5811 - 5819
[6] Synthetic Communications, 2003, vol. 33, # 9, p. 1499 - 1507
[7] Journal of the Indian Chemical Society, 2005, vol. 82, # 6, p. 573 - 574
[8] European Journal of Medicinal Chemistry, 1998, vol. 33, # 2, p. 123 - 131
[9] Journal of the Indian Chemical Society, 2011, vol. 88, # 6, p. 827 - 833
[10] Asian Journal of Chemistry, 2015, vol. 27, # 12, p. 4379 - 4382
[11] Chemische Berichte, 1898, vol. 31, p. 3234
[12] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 5, p. 926
[13] Chemische Berichte, 1898, vol. 31, p. 3234
[14] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 5, p. 926
[15] Journal of the American Chemical Society, 1922, vol. 44, p. 823
[16] Tetrahedron Letters, 2006, vol. 47, # 50, p. 8981 - 8982
[17] Chemische Berichte, 1898, vol. 31, p. 3234
[18] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 5, p. 926
[19] Journal of Organic Chemistry, 1993, vol. 58, # 18, p. 4913 - 4918
[20] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 1, p. 158 - 162
[21] Patent: US2002/62763, 2002, A1,
[22] Journal of the Indian Chemical Society, 2007, vol. 84, # 10, p. 1011 - 1015
[23] Russian Journal of Organic Chemistry, 2009, vol. 45, # 11, p. 1644 - 1650
[24] Journal of Organic Chemistry, 2010, vol. 75, # 19, p. 6468 - 6476
[25] Revue Roumaine de Chimie, 2010, vol. 55, # 9, p. 559 - 564
[26] Medicinal Chemistry Research, 2012, vol. 21, # 1, p. 75 - 84
[27] European Journal of Organic Chemistry, 2016, vol. 2016, # 21, p. 3592 - 3602
[28] MedChemComm, 2017, vol. 8, # 7, p. 1477 - 1484
  • 4
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YieldReaction ConditionsOperation in experiment
84% at 110℃; for 8 h; General procedure: To a solution of 3,4-dihydropyrimidinone (1) (1 mmol) and paraformaldehyde (2 mmol) in tetrachloroethylene (2 mL), diethyl phosphite was added (2 mmol). After completion monitored by TLC, the reaction mixture was concentrated under reduced pressure. The products were separated by silica gel column chromatography eluted with petroleum ethyl acetate/petroleum ether.
Reference: [1] Tetrahedron, 2011, vol. 67, # 13, p. 2462 - 2467
  • 5
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Reference: [1] Journal of Organometallic Chemistry, 2009, vol. 694, # 21, p. 3452 - 3455
[2] Chemische Berichte, 1898, vol. 31, p. 1229
  • 6
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Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 11, p. 3241 - 3247
  • 7
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  • [ 550-44-7 ]
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Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 11, p. 3241 - 3247
  • 8
  • [ 85-44-9 ]
  • [ 118-29-6 ]
Reference: [1] Chemische Berichte, 1898, vol. 31, p. 1229
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5811 - 5819
  • 9
  • [ 124536-28-3 ]
  • [ 550-44-7 ]
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  • [ 23244-58-8 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 25, p. 2949 - 2950
  • 10
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Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 11, p. 3241 - 3247
  • 11
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  • [ 107-31-3 ]
  • [ 23244-58-8 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 25, p. 2949 - 2950
[2] Tetrahedron Letters, 1991, vol. 32, # 25, p. 2949 - 2950
  • 12
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Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 11, p. 3241 - 3247
  • 13
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Reference: [1] Chemical Communications, 2014, vol. 50, # 79, p. 11738 - 11741
  • 14
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Reference: [1] Tetrahedron, 1998, vol. 54, # 26, p. 7517 - 7524
  • 15
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Reference: [1] Tetrahedron, 1998, vol. 54, # 26, p. 7517 - 7524
  • 16
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Reference: [1] Chemische Berichte, 1898, vol. 31, p. 1229
  • 17
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 93 - 96
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  • [ 1954-06-9 ]
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Reference: [1] Journal of Agricultural and Food Chemistry, 2003, vol. 51, # 20, p. 5990 - 5995
  • 19
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Reference: [1] Journal of Agricultural and Food Chemistry, 2003, vol. 51, # 20, p. 5990 - 5995
  • 20
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Reference: [1] Chemische Berichte, 1898, vol. 31, p. 1229
  • 21
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Reference: [1] Chemische Berichte, 1898, vol. 31, p. 3234
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 21, p. 3592 - 3602
  • 22
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  • [ 20877-81-0 ]
  • [ 60-29-7 ]
  • [ 88-96-0 ]
Reference: [1] Patent: US5985872, 1999, A,
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