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Product Details of [ 830-79-5 ]

CAS No. :830-79-5 MDL No. :MFCD00003313
Formula : C10H12O4 Boiling Point : -
Linear Structure Formula :- InChI Key :CRBZVDLXAIFERF-UHFFFAOYSA-N
M.W :196.20 Pubchem ID :70019
Synonyms :

Calculated chemistry of [ 830-79-5 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.31
TPSA : 44.76 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) : -6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.13
Log Po/w (XLOGP3) : 1.3
Log Po/w (WLOGP) : 1.52
Log Po/w (MLOGP) : 0.55
Log Po/w (SILICOS-IT) : 2.03
Consensus Log Po/w : 1.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.93
Solubility : 2.31 mg/ml ; 0.0118 mol/l
Class : Very soluble
Log S (Ali) : -1.84
Solubility : 2.83 mg/ml ; 0.0144 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.73
Solubility : 0.363 mg/ml ; 0.00185 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 830-79-5 ]

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 [ 830-79-5 ]

* 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 [ 830-79-5 ]
  • Downstream synthetic route of [ 830-79-5 ]

[ 830-79-5 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 621-23-8 ]
  • [ 68-12-2 ]
  • [ 830-79-5 ]
YieldReaction ConditionsOperation in experiment
98% at -5 - 0℃; Inert atmosphere Example 82,4,6-Trimethoxy-benzaldehyde2,4,6-Trimethoxy-benzene (40gm, 0.22x103 mmol) was added to dimethylformamide and stirred at a temperature in the range of -5 to 0°C under N2 atmosphere, followed by addition of phosphorus oxychloride (48 gm, 0.5x103 mmol) drop wise over a period of 30-45 minutes. The reaction mixture was stirred for one hour at 0°C, poured over crushed ice followed by saturated sodium carbonate solution. Precipitate obtained was filtered and washed with water to obtain the title compound.Yield: 46 gm (98percent); 1 HNMR (CDCI3): δ 10.35 (s, 1 H), 6.67 (s, 2H), 3.88 (s, 6H), 3.87 (s, 3H); MS: m/e 197 (M+1 ).
98% at 20 - 30℃; for 1 h; In a round bottom flask, POCl3 (7.3 ml, 80 mmol) was added to a mixture of 1,3,5-trimethoxybenzene (8.41 g, 50 mmol) in DMF (15 ml). The temperature of reaction mixture was kept below 30° C. by slowly adding POCl3. After addition of POCl3, the mixture was still stirred at room temperature for an addition 1 hour. The reaction mixture was added into a cold saturated NaHCO3 solution. The pH of the solution was adjusted to remain above 7. Precipitation of desired product occurred. The off-white product was filtered and rinsed with NaHCO3 aq., then with HCl aq. 0.5M and then with water. Off-white solid was collected and vacuum dried at room temperature to yield 14a (9.60 g, 48 mmol, 98percent).
91.6% at 0 - 20℃; for 1 h; Dimethylformamide (9.0 mL, 8.4 g, 0.116 mol) was addedto trimethoxy-phloroglucinol (15.0 g, 0.089 mol) andcooled at 0 °C. Phosphorousoxychloride (9.1 mL, 15.0 g)was added dropwise to this cooling mixture slowly underanhydrous conditions. The mixture was then allowed to stand for 1 h at room temperature. The reaction was monitoredby TLC using 40percent ethyl acetate in Hexane as mobilephase. After completion the reaction mixture was pouredinto crushed-ice and basified with 8M KOH. The solidprecipitate obtained was filtered and dried at 80 °C (VasuBabu et al. 2013). Pale pink color powder with 91.6percent ofyield obtained with melting point 119–121 °C (Scheme 1).
74.68%
Stage #1: for 0.5 h;
Stage #2: at 30℃; for 3 h;
Using 1,3,5-trimethoxybenzene (I) as raw material, the reaction intermediate 2,4,6-trimethoxybenzaldehyde (IV) was prepared by Vilsmeier-Haauc acylation reaction.[0036]In a 250 ml three-neck flask equipped with a stirrer and placed in an ice bath,Add 8.76 g (0.12 mol) DMF,Then add 9.8g (0.064mol) P0C13 slowly to the three-necked flask.The Vi 1 smeier complex is formed after 0.5 h of reaction.Then 10.10g (0.06mol)1 , 3 , 5-trimethoxybenzene was gradually added to this complexation solution.Then, the ice bath was removed, the condenser was placed, the reaction flask was transferred to a 30°C water bath and the reaction was stirred for 3 h to form an intermediate. The intermediate reaction solution was poured into a beaker of 60 ml of ice water and stirred with a glass rod. After mixing, seal the membrane at the mouth of the beaker and place it in a refrigerator at 4 °C for cooling and crystallization. The following day's extraction gave 8.8 g of a beige-white powdery product with a yield of 74.68percent.
101 g at 0℃; for 1 h; 100 g of the compound SM (phloroglucinol trimethylether) and 500 ml of DMF were mixed,Ice salt bath cooling to below 0 ,Dropping 201 g (2.2 eq) of phosphorus oxychloride, controlling the temperature below 0 ° C,Canada completed, the following 0 insulation reaction 1h,TLC followed the completion of the reaction; the reaction solution poured into ice water, potassium carbonate solution adjusted to weakly alkaline (pH 8-10), crystallization overnight, filtered to obtain a white solid, dried to 101g product (Compound I) Hydrogen nuclear magnetic resonance (HNMR) spectrum shown in Figure 1.

Reference: [1] Journal of Chemical Research, Miniprint, 1991, # 9, p. 2401 - 2413
[2] Patent: WO2011/121505, 2011, A1, . Location in patent: Page/Page column 42
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 28, p. 6359 - 6369
[4] Patent: US2017/182051, 2017, A1, . Location in patent: Paragraph 0122
[5] Journal of Chemical Research, 2015, vol. 39, # 8, p. 458 - 461
[6] Tetrahedron, 2015, vol. 71, # 26-27, p. 4557 - 4564
[7] Medicinal Chemistry Research, 2018, vol. 27, # 6, p. 1690 - 1704
[8] Organic and Biomolecular Chemistry, 2015, vol. 13, # 2, p. 520 - 526
[9] Patent: CN107382730, 2017, A, . Location in patent: Paragraph 0034-0036
[10] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 403 - 411
[11] Patent: CN105601604, 2016, A, . Location in patent: Paragraph 0144; 0145; 0146; 0147; 0148
[12] Patent: CN107837247, 2018, A, . Location in patent: Paragraph 0058; 0066; 0067
  • 2
  • [ 621-23-8 ]
  • [ 1535-67-7 ]
  • [ 830-79-5 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With tin(IV) chloride In dichloromethane at 20℃; for 2 h; Inert atmosphere
Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; dimethyl sulfoxide at 20℃; for 2 h;
General procedure: In a round-bottomed flask equipped with a stirring bar and rubber septum was placed a 1 M solution of SnCl4 in anhydrous CH2Cl2 (1 mL, 1 mmol). To this solution was added PhSCF2H (1; 240.2 mg, 1.5 mmol) in anhydrous CH2Cl2 (1.5 mL), followed by a solution of an aromatic compound (0.5 mmol) in anhydrous CH2Cl2 (1 mL). The reaction was allowed to proceed for 2 h before it was quenched with a solution of IBX (140 mg, 0.5 mmol) in DMSO/H2O (4 mL; 3:1 v:v). After 2 h of stirring at rt, the reaction mixture was quenched by addition of a saturated aqueous solution of sodium thiosulfate (10 mL), then basified with a saturated aqueous solution of sodium hydrogen carbonate (10 mL), followed by stirring and extraction with CH2Cl2 (3 × 10 mL). The combined organic layers were washed with water (3 × 10 mL) and brine (10 mL), dried (anhydrous MgSO4), filtered and concentrated (aspirator). The residue was purified by PTLC, radial chromatography or column chromatography to furnish analytically pure product. 2,4,6-Trimethoxybenzaldehyde (4b) White solid (97.12 mg, 99 percent) from EtOAc/hexanes; mp 118–120 °C; Rf = 0.23 (hexanes/EtOAc, 5:1). IR (KBr): 2976, 2949, 2880, 1664 (C=O), 1600, 1475, 1333, 1161, 1127, 1025 cm–1. 1H NMR (300 MHz, CDCl3): δ = 10.36 (s, 1 H), 6.09 (s, 2 H), 3.89 (s, 9H). 13C NMR (75 MHz, CDCl3): δ = 187.6 (CO), 166.2 (C), 164.1 (2 × C), 108.9 (C), 90.3 (2 × CH), 56.0 (2 × CH3), 55.5 (CH3). HRMS (ESI-TOF): m/z [M + Na]+ calcd for C10H12O4Na: 219.0633; found: 219.0627.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 10, p. 2033 - 2040
  • 3
  • [ 621-23-8 ]
  • [ 4885-02-3 ]
  • [ 830-79-5 ]
YieldReaction ConditionsOperation in experiment
44%
Stage #1: With titanium tetrachloride In dichloromethane at 0℃; for 1 h; Inert atmosphere
Stage #2: at 0℃; for 0.75 h; Inert atmosphere
General procedure: The appropriate benzene derivative (3.2–10.6 mmol) was dissolved in dry DCM (10–20 mL), purged with Ar, and cooled with an ice bath to 0 °C. Next, TiCl4 (2.2 eq.) was added dropwise. The reaction mixture was stirred for 1 h. Afterwards, dichloromethyl methyl ether (1.1 eq.) was added, and the mixture was left to react for a further 45 min. As a reaction quencher, a saturated solution of NH4Cl (25 mL) was added. The mixture was then left for 2 h. The organic layer was separated and washed with 0.1 N HCl solution (3 × 50 mL) and brine (3 × 50 mL). The organic layer was dried over MgSO4 and filtered, and the solvent was evaporated under vacuum to furnish the desired aldehydes (Figure 1). The purified products were homogeneous by HPLC and were characterized and purified by using various physical techniques.
Reference: [1] Molecules, 2015, vol. 20, # 4, p. 5409 - 5422
  • 4
  • [ 61040-78-6 ]
  • [ 830-79-5 ]
YieldReaction ConditionsOperation in experiment
99% With potassium osmate; chloroamine-T In water; <i>tert</i>-butyl alcohol for 0.416667 h; General procedure: Chloramine-T (0.5 equiv) was added to a solution of K2[OsO2 (OH)4] (3 molpercent) in t-BuOH/H2O (1:1) followed by the addition of alcohol (1.0 mmol) and kept on stirring till completion (confirmed by TLC). The reaction was quenched by adding sodium sulphite(Na2SO3) and stirred for 30 min. The mixture after extraction with ethyl acetate (twice), usualworkup and purification over silica gel column using Hexane:EtOAc (95:5) afforded pure products.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 48, p. 6407 - 6410
  • 5
  • [ 67-56-1 ]
  • [ 621-23-8 ]
  • [ 68-12-2 ]
  • [ 830-79-5 ]
  • [ 2510-49-8 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78 - 20℃; for 2 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 6
  • [ 621-23-8 ]
  • [ 119072-54-7 ]
  • [ 830-79-5 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 17, p. 3351 - 3353
  • 7
  • [ 621-23-8 ]
  • [ 93-61-8 ]
  • [ 830-79-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2407 - 2419
  • 8
  • [ 621-23-8 ]
  • [ 4885-02-3 ]
  • [ 830-79-5 ]
  • [ 591228-81-8 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 7, p. 3438 - 3444
  • 9
  • [ 621-23-8 ]
  • [ 877680-53-0 ]
  • [ 830-79-5 ]
  • [ 103281-94-3 ]
Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2008, vol. 63, # 4, p. 395 - 406
  • 10
  • [ 324527-63-1 ]
  • [ 830-79-5 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 7, p. 628 - 631
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 7, p. 628 - 631
  • 11
  • [ 366001-22-1 ]
  • [ 830-79-5 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 7, p. 628 - 631
  • 12
  • [ 832-58-6 ]
  • [ 830-79-5 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 7, p. 628 - 631
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 7, p. 628 - 631
  • 13
  • [ 621-23-8 ]
  • [ 74-90-8 ]
  • [ 830-79-5 ]
Reference: [1] Monatshefte fuer Chemie, 1903, vol. 24, p. 866
  • 14
  • [ 708-76-9 ]
  • [ 74-88-4 ]
  • [ 830-79-5 ]
Reference: [1] Monatshefte fuer Chemie, 1903, vol. 24, p. 861,863
  • 15
  • [ 621-23-8 ]
  • [ 1478-41-7 ]
  • [ 830-79-5 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1563 - 1568
  • 16
  • [ 621-23-8 ]
  • [ 103-70-8 ]
  • [ 830-79-5 ]
Reference: [1] Journal of the Chemical Society, 1952, p. 4964,4966
  • 17
  • [ 621-23-8 ]
  • [ 830-79-5 ]
Reference: [1] Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3006 - 3014
  • 18
  • [ 127-08-2 ]
  • [ 197142-05-5 ]
  • [ 830-79-5 ]
  • [ 61040-78-6 ]
  • [ 882-33-7 ]
  • [ 149286-58-8 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 36, p. 12287 - 12298
  • 19
  • [ 110-05-4 ]
  • [ 830-79-5 ]
  • [ 2571-54-2 ]
  • [ 75-65-0 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 12, p. 2399 - 2409
  • 20
  • [ 830-79-5 ]
  • [ 570-02-5 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 32, p. 24936 - 24943
[2] Tetrahedron Letters, 2008, vol. 49, # 6, p. 1083 - 1086
[3] Applied Organometallic Chemistry, 2011, vol. 25, # 6, p. 437 - 442
[4] Monatshefte fuer Chemie, 1903, vol. 24, p. 866
  • 21
  • [ 830-79-5 ]
  • [ 212555-23-2 ]
Reference: [1] Patent: JP2017/81888, 2017, A,
[2] Journal of the American Chemical Society, 2018, vol. 140, # 42, p. 13594 - 13598
  • 22
  • [ 59-48-3 ]
  • [ 830-79-5 ]
  • [ 186611-52-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2958 - 2963
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