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Chemical Structure| 634-36-6
Chemical Structure| 634-36-6
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Product Details of [ 634-36-6 ]

CAS No. :634-36-6 MDL No. :MFCD00008358
Formula : C9H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :CRUILBNAQILVHZ-UHFFFAOYSA-N
M.W : 168.19 Pubchem ID :12462
Synonyms :

Calculated chemistry of [ 634-36-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.92
TPSA : 27.69 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) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.29
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.71
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 1.71

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.02
Solubility : 1.61 mg/ml ; 0.00958 mol/l
Class : Soluble
Log S (Ali) : -1.72
Solubility : 3.2 mg/ml ; 0.019 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.77
Solubility : 0.284 mg/ml ; 0.00169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 634-36-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 634-36-6 ]

* 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 [ 634-36-6 ]
  • Downstream synthetic route of [ 634-36-6 ]

[ 634-36-6 ] Synthesis Path-Upstream   1~36

  • 1
  • [ 634-36-6 ]
  • [ 24313-88-0 ]
Reference: [1] Chemische Berichte, 1888, vol. 21, p. 615
[2] Journal of the American Chemical Society, 2015, vol. 137, # 21, p. 6920 - 6931
  • 2
  • [ 634-36-6 ]
  • [ 1535-67-7 ]
  • [ 2103-57-3 ]
YieldReaction ConditionsOperation in experiment
72%
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.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 10, p. 2033 - 2040
  • 3
  • [ 634-36-6 ]
  • [ 10025-87-3 ]
  • [ 2103-57-3 ]
YieldReaction ConditionsOperation in experiment
74% at 70 - 80℃; for 10 h; With a thermometer,Stirring and heating sets of three bottles,123 g of the above intermediate 1,2,3-trimethoxybenzene was added,DMF 123 g,Dropping 246 g of phosphorus oxychloride,Dropping the end of heating to 70-80 ° C insulation 10 hours,Cooling The reaction solution was poured into 500 g of ice water for hydrolysis,300 ml of ethyl acetate was extracted three times,Ethyl acetate was recovered under reduced pressure,The distillate was collected by distillation under reduced pressure,Cooling to obtain 115 g of white crystals,The product purity was 99.5percent and the total yield was 74percent by high performance gas chromatography.
Reference: [1] Patent: CN102875344, 2016, B, . Location in patent: Paragraph 0010; 0021; 0023
  • 4
  • [ 634-36-6 ]
  • [ 2103-57-3 ]
YieldReaction ConditionsOperation in experiment
24% With acetic acid In tetrahydrofuran; <i>N</i>-methyl-acetamide; hexane (1)
A mixed solution of 20 g of 1,2,3-trimethoxybenzene and 100 ml of tetrahydrofuran (THF) was cooled to -78° C., and 140 ml of a hexane solution containing 1M sec-butyl lithium (sec-BuLi) was added dropwise thereto.
After stirring the mixture at the same temperature for 45 minutes, 11 ml of dimethylformamide (DMF) was added to the reaction mixture.
The mixture was stirred at -50° C. or lower for 45 minutes.
Then, a 10percent acetic acid aqueous solution was added to the mixture, and the resulting mixture was extracted with diethyl ether.
The extract was washed and dried, and the solvent was removed under reduced pressure.
The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=9:1) to give 5.7 g of 2,3,4-trimethoxybenzaldehyde (yield: 24percent, oily product).
Reference: [1] Patent: US5849732, 1998, A,
  • 5
  • [ 50-00-0 ]
  • [ 634-36-6 ]
  • [ 2103-57-3 ]
YieldReaction ConditionsOperation in experiment
82.9% for 5 h; Reflux The organic layer containing the intermediate (III) obtained above was placed in a 500 ml reaction flask, anhydrous magnesium chloride (13.5 g, 0.23 mol) was added, 35.4 g of paraformaldehyde was added in batches, and the dropwise addition was started. (38.6g, 0.28mol) potassium carbonate, after completion of the addition, heated to reflux, the reaction for 5 hours, the reaction solution was cooled to room temperature after the reaction was completed, then the reaction solution was slowly added dropwise to the amount of water, stirring was maintained for 30 minutes, static The layers are separated, the organic layer is collected, the organic layer is depressurized and the solvent is removed, and the fraction is collected by distillation under reduced pressure. The fraction is cooled and becomes white crystal (I) 24.4 g. The total yield is 82.9percent. Purity (HPLC area normalization method) 99.6percent.
Reference: [1] Patent: CN107382690, 2017, A, . Location in patent: Paragraph 0021; 0022; 0024; 0026; 0028
  • 6
  • [ 4885-02-3 ]
  • [ 634-36-6 ]
  • [ 2103-57-3 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 10, p. 2868 - 2870
  • 7
  • [ 634-36-6 ]
  • [ 93-61-8 ]
  • [ 2103-57-3 ]
Reference: [1] Journal of Organic Chemistry, 1954, vol. 19, p. 1548,1549
[2] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2900,2902; engl. Ausg. S. 2860, 2862
[3] Journal of the American Chemical Society, 1956, vol. 78, p. 1184,1186
  • 8
  • [ 141-82-2 ]
  • [ 634-36-6 ]
  • [ 573-11-5 ]
  • [ 2103-57-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 545 - 550
  • 9
  • [ 74-90-8 ]
  • [ 634-36-6 ]
  • [ 2103-57-3 ]
Reference: [1] Chemische Berichte, 1930, vol. 63, p. 3029,3043
[2] Helvetica Chimica Acta, 1924, vol. 7, p. 362
  • 10
  • [ 634-36-6 ]
  • [ 25245-29-8 ]
YieldReaction ConditionsOperation in experiment
54% at 20℃; Ionic liquid; Darkness General procedure: To a solution of 54 mg (0.5 mmol) of anisole in 1 mL of BMIM BF4 was added 158 mg (0.51 mmol) of N-iodosaccharin. The reaction was stirred at room temperature protected from light for 8-12 h. The product was then isolated by extraction with ether (3 .x. 3 mL), followed by evaporation of the solvent to afford the desired iodinated product. In some cases, the product was contaminated with small amounts of BMIM BF4. This could be removed via filtration with ether through a short plug of silica. Alternatively, it could be avoided entirely by extraction of the product from the reaction using 1:1 ether/hexanes in place of pure ether. The identity of all products were confirmed by comparison (spectral and mp) with either commercially available samples or data reported in the literature as indicated in Table 1.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 18, p. 2413 - 2414
  • 11
  • [ 634-36-6 ]
  • [ 487-11-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 3, p. 933 - 937[2] Angew. Chem., 2012, vol. 125, # 3, p. 967 - 971,5
  • 12
  • [ 634-36-6 ]
  • [ 16932-44-8 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 19, p. 5386 - 5390
  • 13
  • [ 634-36-6 ]
  • [ 10385-36-1 ]
YieldReaction ConditionsOperation in experiment
80% at 80℃; for 24 h; Sealed tube General procedure: 1 mL [Bmim]NO3, 0.5 mmolsubstrate and 0.25 mmol Br2 were added to a dried 45 mL tube equipped witha magnetic stirring (note: the air in the tube was not removed). Then thereaction tube was sealed to perform the reaction at 80 C for 24 h. Once thereaction time was reached, the mixture was cooled to room temperature and3 mL water was added. Then the desired product was extracted with CH2Cl2(3 10 mL). GC analysis of the mixture provided the GC yield of the product.The product in another parallel experiment was purified by columnchromatography, and identified by 1H NMR and 13C NMR.
78% With N-Bromosuccinimide In tetrachloromethane 1-Bromo-2,3,4-trimethoxy-benzene (9)
Pyrogallol trimethyl ether (5.1 g) was suspended in CCl4 (60 mL) and N-bromosuccinimide (6.5 g, 1.2 eq.) was added.
The reaction mixture was heated at reflux for 20 hours.
The succinimide was collected and the filtrate concentrated in vacuo to a brown oil.
The oil was separated by gravity column chromatography (hexane-ethyl acetate, 19: 1) and yielded the title compound as a yellow oil (5.9 g, 78percent): EIMS m/z 234 ((M+ -CH3, 81Br), 232 (M+ -CH3, 79Br), 107, 95, 69, 58, 44; 1H NMR (CDCl3, 300 MHZ) δ 7.21 (1H, d, J=9.0 Hz, H6), 6.58 (1H, d, J=9.0 Hz, H5), 3.91 (3H, s, OCH3), 3.89 (3H, s, OCH3), 3.85 (3H, s, OCH3).
73% With carbon tetrabromide; anthraquinone-2-carboxylic acid In ethanol at 20℃; for 20 h; Irradiation General procedure: A pyrex test tube containing solid of 1,3,5-trimethoxybenzene (1a, 0.3 mmol), carbon tetrabromide (0.075 mmol), AQN-2-CO2H (0.03 mmol) and dry EtOH (5 mL) was irradiated for 20 h at roomtemperature with stirring by a 21W fluorescent lamp under air. The reactionmixture was concentrated in vacuo, quenched with aq Na2S2O3 and extractedwith EtOAc. The organic layer was dried over MgSO4 and concentrated invacuo. Purification of the residue by flash chromatography on silica gel(hexane/ethyl acetate = 6:1) provided 2-bromo-1,3,5-trimethoxybenzene (2a)(66.8 mg, 90percent,) as a white solid.
Reference: [1] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328
[2] Australian Journal of Chemistry, 1992, vol. 45, # 12, p. 1967 - 1982
[3] Journal of Chemical Research - Part S, 1998, # 10, p. 662 - 663
[4] Russian Journal of Organic Chemistry, 2007, vol. 43, # 9, p. 1282 - 1284
[5] Synthetic Communications, 2005, vol. 35, # 14, p. 1947 - 1952
[6] Australian Journal of Chemistry, 1991, vol. 44, # 5, p. 705 - 728
[7] Synthetic Communications, 1998, vol. 28, # 4, p. 669 - 676
[8] Synthetic Communications, 1998, vol. 28, # 8, p. 1463 - 1470
[9] Tetrahedron, 2005, vol. 61, # 8, p. 2117 - 2121
[10] Advanced Synthesis and Catalysis, 2004, vol. 346, # 1, p. 77 - 82
[11] Journal of the Serbian Chemical Society, 2011, vol. 76, # 5, p. 685 - 692
[12] Canadian Journal of Chemistry, 1994, vol. 72, # 1, p. 227 - 236
[13] Monatshefte fur Chemie, 2013, vol. 144, # 2, p. 179 - 181
[14] Organic Preparations and Procedures International, 1998, vol. 30, # 2, p. 218 - 222
[15] Phosphorus, Sulfur and Silicon and the Related Elements, 2005, vol. 180, # 5-6, p. 1235 - 1240
[16] Tetrahedron Letters, 2004, vol. 45, # 25, p. 4887 - 4890
[17] Organic Letters, 2004, vol. 6, # 23, p. 4379 - 4381
[18] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6452 - 6455
[19] Journal of Medicinal Chemistry, 2000, vol. 43, # 14, p. 2731 - 2737
[20] Patent: US2003/220304, 2003, A1,
[21] Synthetic Communications, 2007, vol. 37, # 8, p. 1381 - 1388
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[23] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3417 - 3420
[24] ACS Catalysis, 2016, vol. 6, # 2, p. 1113 - 1121
[25] Journal of Organic Chemistry, 1958, vol. 23, p. 16
[26] Monatshefte fuer Chemie, 1925, vol. 46, p. 89
[27] Monatshefte fuer Chemie, 1928, vol. 49, p. 184
[28] Journal of the Chemical Society, 1955, p. 4435,4439
[29] Tetrahedron, 1973, vol. 29, p. 3833 - 3843
[30] Synthetic Communications, 2006, vol. 36, # 16, p. 2401 - 2405
[31] Tetrahedron Letters, 2009, vol. 50, # 7, p. 831 - 833
  • 14
  • [ 634-36-6 ]
  • [ 95279-92-8 ]
  • [ 10385-36-1 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 15, p. 2783 - 2786
  • 15
  • [ 634-36-6 ]
  • [ 3901-07-3 ]
  • [ 10385-36-1 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 15, p. 2783 - 2786
  • 16
  • [ 634-36-6 ]
  • [ 5396-64-5 ]
  • [ 10385-36-1 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 15, p. 2783 - 2786
  • 17
  • [ 634-36-6 ]
  • [ 53744-27-7 ]
  • [ 10385-36-1 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 15, p. 2783 - 2786
  • 18
  • [ 447-53-0 ]
  • [ 634-36-6 ]
  • [ 10385-36-1 ]
  • [ 2018-87-3 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 15, p. 2783 - 2786
  • 19
  • [ 634-36-6 ]
  • [ 10385-36-1 ]
  • [ 92670-09-2 ]
Reference: [1] Tetrahedron, 2000, vol. 56, # 45, p. 8901 - 8913
[2] Tetrahedron Letters, 2004, vol. 45, # 25, p. 4887 - 4890
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2005, vol. 180, # 5-6, p. 1235 - 1240
  • 20
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  • 21
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  • 22
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Reference: [1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 10, p. 3930 - 3935
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[3] Organic Letters, 2001, vol. 3, # 3, p. 417 - 420
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[5] Journal of the American Chemical Society, 1954, vol. 76, p. 4550
  • 23
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[2] Journal of the American Chemical Society, 1957, vol. 79, p. 3582,3585
  • 24
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  • [ 64-19-7 ]
  • [ 13909-73-4 ]
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  • 25
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[3] Recueil des Travaux Chimiques des Pays-Bas, 1945, vol. 64, p. 214,216
[4] Chemische Berichte, 1911, vol. 44, p. 1550
[5] Journal of the Chemical Society, 1914, vol. 105, p. 2794
  • 26
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  • [ 634-36-6 ]
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  • 27
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  • [ 166093-42-1 ]
  • [ 13909-73-4 ]
Reference: [1] Journal of the Chinese Chemical Society (Taipei, Taiwan), 1994, vol. 41, # 5, p. 573 - 578
  • 28
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  • [ 13909-73-4 ]
  • [ 38975-83-6 ]
Reference: [1] Journal of the Chinese Chemical Society (Taipei, Taiwan), 1994, vol. 41, # 5, p. 573 - 578
  • 29
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  • [ 13909-73-4 ]
Reference: [1] Journal of the Chinese Chemical Society (Taipei, Taiwan), 1994, vol. 41, # 5, p. 573 - 578
  • 30
  • [ 2680-03-7 ]
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  • [ 16718-42-6 ]
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  • 31
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  • [ 16932-45-9 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 19, p. 5386 - 5390
  • 32
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  • [ 610-02-6 ]
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  • 33
  • [ 2675-79-8 ]
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  • [ 43212-67-5 ]
  • [ 134029-62-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 50, p. 15544 - 15548[2] Angew. Chem., 2016, vol. 128, # 50, p. 15773 - 15777,5
  • 34
  • [ 634-36-6 ]
  • [ 573-11-5 ]
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[2] Helvetica Chimica Acta, 1924, vol. 7, p. 362
[3] Helvetica Chimica Acta, 1920, vol. 3, p. 266
[4] Roczniki Chemii, 1961, vol. 35, p. 813 - 820
  • 35
  • [ 141-82-2 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 545 - 550
  • 36
  • [ 634-36-6 ]
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