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[ CAS No. 5779-93-1 ] {[proInfo.proName]}

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Chemical Structure| 5779-93-1
Chemical Structure| 5779-93-1
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Product Details of [ 5779-93-1 ]

CAS No. :5779-93-1 MDL No. :MFCD00798004
Formula : C9H10O Boiling Point : -
Linear Structure Formula :- InChI Key :UIFVCPMLQXKEEU-UHFFFAOYSA-N
M.W : 134.18 Pubchem ID :34224
Synonyms :

Calculated chemistry of [ 5779-93-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.76
TPSA : 17.07 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 : No
Log Kp (skin permeation) : -5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 2.3
Log Po/w (WLOGP) : 2.12
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 2.92
Consensus Log Po/w : 2.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.425 mg/ml ; 0.00317 mol/l
Class : Soluble
Log S (Ali) : -2.3
Solubility : 0.678 mg/ml ; 0.00505 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.09
Solubility : 0.11 mg/ml ; 0.000818 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 5779-93-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5779-93-1 ]

* 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 [ 5779-93-1 ]
  • Downstream synthetic route of [ 5779-93-1 ]

[ 5779-93-1 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 526-73-8 ]
  • [ 5779-93-1 ]
  • [ 603-79-2 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 5, p. 791 - 793
  • 2
  • [ 5779-93-1 ]
  • [ 37678-61-8 ]
Reference: [1] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 185 - 200
[2] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 3, p. 677 - 682
[3] Bulletin de la Societe Chimique de France, 1971, p. 2256 - 2259
  • 3
  • [ 5724-56-1 ]
  • [ 5779-93-1 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With diisobutylaluminium hydride In toluene at 5 - 21℃;
Stage #2: With hydrogenchloride; water In toluene at 25℃;
Preparation of 2.3-dimethylbenzaldehydeDIBAL-H Toluene 2,3-Dimethylbenzonitrile (50.0 g, 381 mmol) was dissolved in 100 mL toluene. The solution was cooled in an ice bath to 5 0C. The solution was stirred as DibalH solution (476 mL of IM in toluene, 476 mmol) was added slowly keeping temperature below 21 0C. This solution was reverse quenched slowly into vigorously stirred 2N HCl (800 mL), keeping the temperature below 25 0C. The water layer was removed and organic layer was washed twice with 6N HCl. The organic layer was concentrated to pale yellow oil, 46.3g (91percent yield).
Reference: [1] Patent: WO2008/88690, 2008, A2, . Location in patent: Page/Page column 11; 15
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 3087 - 3091
[3] Tetrahedron Letters, 1981, vol. 22, p. 161 - 162
[4] Monatshefte fuer Chemie, 1933, vol. 63, p. 79,95
  • 4
  • [ 576-23-8 ]
  • [ 68-12-2 ]
  • [ 5779-93-1 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With magnesium In tetrahydrofuran for 1 h; Inert atmosphere; Reflux
Stage #2: at 20℃; for 2 h;
Was added under nitrogen atmosphere in a reaction flask26.4Magnesium turnings (1.1 mol)And 160 ml of tetrahydrofuran, 18.5 g of 2,3-dimethylbromobenzene (0.1 mol) was added dropwise with stirring at room temperature,and100 ml of tetrahydrofuran,Triggering reaction,Then, 166.5 g of the solution was added dropwise2,3-dimethylbromobenzene (0.9 mol) and 1000 ml of tetrahydrofuran,Upon completion of the addition,The reaction was refluxed for 1 hour.The resulting Grignard reagent was cooled in an ice bath,73 g of N, N-dimethylformamide (1.0 mol) and 300 ml of tetrahydrofuran were added dropwiseFuran mixture,Control reaction temperature is not higher than 20 degrees,After completion of the addition, the reaction was continued at room temperature for 2 hours.After completion of the reactionPlus 1000 ml of saturated ammonium chloride solution for hydrolysis 1 hour,The organic phase was then separated by standing, and the aqueous phase was extracted with ethyl acetateThe organic phase was washed with 500 mL of saturated brine and allowed to stand for separation. The organic phase was stirred and dried with 50 g of anhydrous sodium sulfateThe filtrate was concentrated to dryness under reduced pressure to give 2,3-dimethylbenzaldehyde in a yield of 96percent and a purity of 96.2percent.
Reference: [1] Patent: CN105503551, 2016, A, . Location in patent: Paragraph 0012; 00013
  • 5
  • [ 31599-60-7 ]
  • [ 68-12-2 ]
  • [ 5779-93-1 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With magnesium In tetrahydrofuran for 1 h; Inert atmosphere; Reflux
Stage #2: at 20 - 30℃; for 5 h;
Under nitrogen protection, 24 g of magnesium turnings (1 mol) and 160 ml of tetrahydrofuran were added to a reaction flask and stirred at room temperature18.5 g was added dropwise2,3-dimethyliodobenzene (0.1 mol) and100 ml of tetrahydrofuran,Triggering reaction,Then, 166.5 g of 2,3-dimethyliodobenzene (0.9 mol) was added dropwise1000 ml of tetrahydrofuran mixture, drop finished, reflux reaction 1hour. The resulting Grignard reagent was cooled in an ice bath, and 73 g of N, N-dimethylformamide (1.0 mol) and 300 ml of tetrahydrofuranFuran mixture to control the reaction temperature is not higher than 30 degrees, dropping is completed at room temperature for 5 hours. After completion of the reaction1000 ml of saturated ammonium chloride solution for 1 hour hydrolysis, and then separated from the organic phase, the aqueous phase extracted with ethyl acetate aThe organic phase was washed with 500 mL of saturated brine and allowed to stand for separation. The organic phase was stirred and dried with 50 g of anhydrous sodium sulfate1 hour, filtered and the filtrate was concentrated to dryness under reduced pressure to give 2,3-dimethylbenzaldehyde in a yield of 93percent and a purity of 95percent
Reference: [1] Patent: CN105503551, 2016, A, . Location in patent: Paragraph 0020; 00021
  • 6
  • [ 608-23-1 ]
  • [ 68-12-2 ]
  • [ 5779-93-1 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With magnesium In tetrahydrofuran for 5 h; Inert atmosphere; Reflux
Stage #2: at 20 - 30℃; for 5 h;
Under the protection of nitrogen, added in a reaction bottle 24 g mgnesium filings (1mol) and 160 ml of tetrahydrofuran, under stirring at room temperature is dropped to 18.5 g 2,3-dimethyl-chlorobenzene (0.1mol) and 100 ml of a mixed solution of tetrahydrofuran, initiate the reaction, and then to continue dropping 166.5 g 2,3-dimethyl-chlorobenzene (0.9mol) and 1000 ml of a mixed solution of tetrahydrofuran, completion of the dropping, reflux reaction 5 hours. With ice-bath cooling the resulting Grignard reagent, dropping 73 g N, N-dimethyl formamide (1.0mol) and 300 ml of a mixed solution of tetrahydrofuran, controlling the reaction temperature is not higher than 30 degrees, the dropping to the reaction at room temperature 5 hours. Reaction of adding the end of 1000 ml of saturated ammonium chloride solution to hydrolyze 1 hour, the organic phase is separated, the aqueous phase is extracted with ethyl acetate once, combined with the phase, using 500 ml saturated salt water washing, layering, organic phase with 50g mixing and drying by anhydrous sodium sulfate 1 hour, filtered, filtrate concentrated to dry, is 2,3-dimethoxy benzaldehyde, the yield is 82percent, the purity of 85percent.
Reference: [1] Patent: CN105503551, 2016, A, . Location in patent: Paragraph 0018; 00019
  • 7
  • [ 95-47-6 ]
  • [ 4885-02-3 ]
  • [ 5973-71-7 ]
  • [ 5779-93-1 ]
Reference: [1] Molecules, 2015, vol. 20, # 4, p. 5409 - 5422
  • 8
  • [ 81093-21-2 ]
  • [ 5779-93-1 ]
Reference: [1] Patent: WO2009/53709, 2009, A1, . Location in patent: Page/Page column 15
  • 9
  • [ 95-47-6 ]
  • [ 68-12-2 ]
  • [ 5973-71-7 ]
  • [ 5779-93-1 ]
Reference: [1] Patent: WO2016/71921, 2016, A2, . Location in patent: Page/Page column 6; 7
  • 10
  • [ 13651-14-4 ]
  • [ 5779-93-1 ]
Reference: [1] Tetrahedron Letters, 1981, vol. 22, p. 161 - 162
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 3087 - 3091
[3] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 185 - 200
  • 11
  • [ 68717-07-7 ]
  • [ 5779-93-1 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 843 - 846
  • 12
  • [ 95-47-6 ]
  • [ 201230-82-2 ]
  • [ 5973-71-7 ]
  • [ 5779-93-1 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 9, p. 2677 - 2680
  • 13
  • [ 526-73-8 ]
  • [ 64-19-7 ]
  • [ 5779-93-1 ]
  • [ 13651-57-5 ]
  • [ 62346-87-6 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 20, p. 6356 - 6362
  • 14
  • [ 526-73-8 ]
  • [ 5779-93-1 ]
  • [ 603-79-2 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 5, p. 791 - 793
  • 15
  • [ 87-59-2 ]
  • [ 5779-93-1 ]
Reference: [1] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 185 - 200
[2] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 185 - 200
[3] Monatshefte fuer Chemie, 1933, vol. 63, p. 79,95
  • 16
  • [ 603-79-2 ]
  • [ 5779-93-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 3087 - 3091
[2] Tetrahedron Letters, 1981, vol. 22, p. 161 - 162
[3] Monatshefte fuer Chemie, 1933, vol. 63, p. 79,95
  • 17
  • [ 50-00-0 ]
  • [ 100-97-0 ]
  • [ 13651-55-3 ]
  • [ 5779-93-1 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 2654,2656
  • 18
  • [ 576-23-8 ]
  • [ 5779-93-1 ]
Reference: [1] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 185 - 200
[2] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 185 - 200
  • 19
  • [ 15012-36-9 ]
  • [ 5779-93-1 ]
Reference: [1] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 185 - 200
  • 20
  • [ 28162-13-2 ]
  • [ 5779-93-1 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 843 - 846
  • 21
  • [ 21900-46-9 ]
  • [ 5779-93-1 ]
Reference: [1] Monatshefte fuer Chemie, 1933, vol. 63, p. 79,95
  • 22
  • [ 526-73-8 ]
  • [ 5779-93-1 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1967, p. 556 - 560
  • 23
  • [ 75-17-2 ]
  • [ 87-59-2 ]
  • [ 5779-93-1 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1971, p. 2256 - 2259
  • 24
  • [ 5779-93-1 ]
  • [ 13651-14-4 ]
Reference: [1] Journal of Natural Products, 2014, vol. 77, # 9, p. 2134 - 2137
  • 25
  • [ 5779-93-1 ]
  • [ 81093-21-2 ]
Reference: [1] Journal of Natural Products, 2014, vol. 77, # 9, p. 2134 - 2137
  • 26
  • [ 5779-93-1 ]
  • [ 96797-15-8 ]
  • [ 176721-01-0 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With isopropylmagnesium bromide In tetrahydrofuran; dichloromethane at 10 - 20℃; for 1 h;
Stage #2: at 10 - 25℃; for 1 h;
Example 1 (step a); Preparation of (2,3-Dimethylphenyl)-(3-trityl-3H-imidazol-4-yl)methanol A solution of isopropylmagnesium bromide in tetrahydrofuran (48 mL, 0.046 mol) was added to a stirred solution of 4-iodo-1-trityl-1 H-imidazole (19.0 g, 0.046 mol) in dichloromethane (180 mL) at 10 to 15°C. The reaction mixture was allowed to warm to the ambient temperature and was stirred at ambient temperature for 1 hour. The reaction mixture was then cooled to 10-15°C, at which point a solution of 2,3-dimethylbenzaldehyde (6.2 mL, 0.046 mol) in dichloromethane (10 mL) was added, while not exceeding 20 to 25°C. After additional stirring for 1 hour at ambient temperature a 10percent aqueous ammonium chloride solution (200 mL) was added to the reaction mixture. The organic layer was separated and washed with an aqueous sodium chloride solution (150 mL), thereafter the organic layer was concentrated to a volume of 40 mL. A precipitate of (2,3-dimethylphenyl)-(3-trityl-3H-imidazol-4-yl)methanol was obtained upon cooling the distillation residue to 4°C and it was separated by filtration, then washed with dichloromethane (50 mL). The intermediate (2,3-dimethylphenyl)-(3-trityl-3H-imidazol-4-yl)methanol was dried at ambient temperature. The yield was 17.4 g (84 percent) of a white or off-white powder, having a melting temperature of 203.0 to 207.0°C.
Reference: [1] Patent: EP1918282, 2008, A1, . Location in patent: Page/Page column 5
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