Home Cart 0 Sign in  
X

[ CAS No. 93-03-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 93-03-8
Chemical Structure| 93-03-8
Chemical Structure| 93-03-8
Structure of 93-03-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 93-03-8 ]

Related Doc. of [ 93-03-8 ]

Alternatived Products of [ 93-03-8 ]

Product Details of [ 93-03-8 ]

CAS No. :93-03-8 MDL No. :MFCD00004638
Formula : C9H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :OEGPRYNGFWGMMV-UHFFFAOYSA-N
M.W : 168.19 Pubchem ID :7118
Synonyms :
3,4-Dimethoxybenzyl alcohol
Chemical Name :(3,4-Dimethoxyphenyl)methanol

Calculated chemistry of [ 93-03-8 ]      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 : 1.0
Molar Refractivity : 45.55
TPSA : 38.69 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) : -6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.13
Log Po/w (XLOGP3) : 0.61
Log Po/w (WLOGP) : 1.04
Log Po/w (MLOGP) : 0.92
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.44
Solubility : 6.12 mg/ml ; 0.0364 mol/l
Class : Very soluble
Log S (Ali) : -1.0
Solubility : 16.9 mg/ml ; 0.101 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.48
Solubility : 0.562 mg/ml ; 0.00334 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 93-03-8 ]

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

Application In Synthesis of [ 93-03-8 ]

* 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 [ 93-03-8 ]
  • Downstream synthetic route of [ 93-03-8 ]

[ 93-03-8 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 93-03-8 ]
  • [ 5653-40-7 ]
Reference: [1] Patent: CN106632271, 2017, A,
  • 2
  • [ 93-03-8 ]
  • [ 13794-72-4 ]
Reference: [1] Patent: CN106632271, 2017, A,
  • 3
  • [ 93-03-8 ]
  • [ 1016-58-6 ]
YieldReaction ConditionsOperation in experiment
20 g at 0 - 20℃; for 6 h; In the 500mL multi-bottle,Add 3,4-dimethoxybenzyl alcohol16.8 g (0.1 mol), followed by addition of 150 g of acetic anhydride,Cooling to 0 slowly dropping nitric acid 6g, slowly stirring the reaction solution, after the drop to warm up to room temperature, after 6h reaction steamIn addition to acetic anhydride, then add distilled water 300mL, and then slowly add saturated sodium carbonate solution, adjust the pH of the reaction solution is neutral, with twoThe reaction solution was extracted three times with 200 mL of methyl chloride to separate the organic phase and the solvent was evaporated to give 2-nitro-4,5-dimethoxybenzyl alcohol20g.
Reference: [1] Patent: CN106632271, 2017, A, . Location in patent: Paragraph 0029; 0030; 0031
  • 4
  • [ 93-03-8 ]
  • [ 21852-32-4 ]
YieldReaction ConditionsOperation in experiment
100% With phosphorus tribromide In benzene at 20℃; General procedure: benzyl alcohols (1 mmol) in dry benzene (15 mL) and phosphorus tribromides (0.5 mL) and stirred at room temperature to get respective benzyl bromides in quantitative yields, usual work-up.
92% With phosphorus pentoxide; potassium bromide In acetonitrile at 20℃; for 0.416667 h; General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.
88% With phosphorus tribromide In water; toluene 4-Bromomethyl-1.2-dimethoxybenzene
A solution of phosphorus tribromide (0.35 cm3, 3.66 mmol) in dried toluene (5 cm3) was added dropwise to a solution of 3,4-dimethoxybenzyl alcohol (1.23 g, 7.34 mmol), in dried toluene (10 cm3) at 0° C. under nitrogen.
After 15 minutes, the solution was stirred at room temperature for a further 2 hours, poured onto crushed ice/water (10 cm3) and extracted with toluene (3*20 cm3).
The toluene extracts were combined and washed with water (40 cm3), sodium bicarbonate (40 cm3), water (40 cm3), dried (MgSO4), and evaporated under reduced pressure to give the bromide (1.49 g, 88percent) as white needles, mp 34-37° C.
νmax(NaCl)/cm-1 3002, 2958, 2936, 2835, 1605 (ArH), 1593 (ArH), 1519 (ArH), 1265, 1245, 1212, 1160, 1143;
δH (400 MHz, CDCl3): 3.88 (6H, d, J=7.6 Hz, 2*OMe), 4.50 (2H, s, CH2Br), 6.80-6.96 (3H, m, ArH); bromide unstable at room temperature, therefore, no CHN or MS recorded;
85% With phosphorus tribromide In dichloromethane at 20℃; for 3 h; Inert atmosphere To 3,4-dimethoxybenzyl alcohol (1680 mg, 10.0 mmol) in 20ml CH2Cl2 was added PBr3 (4065mg, 15.0mmol) dropwise under N2. The mixture was stirred for 3 h atroom temperature. 40 ml distilled water was added to the reaction mixture to quench excess PBr3, then extracted with chloroform. The organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed in vacuo to afford (10) as a pale yellow oil that solidifies into a white solid on standing, 85percent. 1H NMR (400 MHz, CDCl3): δ6.955 (dd, J = 2.10, 8.16 Hz, 1H), 6.915 (d, J = 207 Hz, 1H), 6.811 (d, J = 8.17 Hz, 1H), 4.505 (s, 2H), 3.899 (s, 3H), 3.881 (s, 3H).
65% With phosphorus tribromide In dichloromethane at 20℃; Inert atmosphere; Molecular sieve To a flame dried flask cooled under argon was added (3,4-dimethoxyphenyl)methanol (0.169 grams, 1.0 mmol, 1.0M in dichloromethane, stored over 4 angstrom molecular sieves, purchased from Fisher Scientific).
While stirring at room temperature a solution of phosphorous tribromide (1.4 mL, 1.0M in dichloromethane, purchased from Fisher Scientific) was added slowly.
Once complete, the reaction was diluted with water and the organic layer removed.
The aqueous layer was washed twice more with dichloromethane, and the organic material combined.
The organic material was next washed with aqueous sodium bicarbonate (saturated), dried with sodium sulfate, filtered and concentrated.
Purification was done using a Teledyne ISCO on a silica support using a hexanes ethyl acetate gradient.
Yield 65percent. 1H NMR δ 6.96 (dd, 1H), 6.92 (d, 1H), 6.82 (d, 1H), 4.52 (s, 2H), 3.91 (s, 3H), 3.89 (s, 3H).
59% With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 60℃; for 1 h; To a solution of 3,4-dimethoxybenzyl alcohol (10 g,59.5 inmol) , carbon tetrabromide (22 g, 65.4 iranol) , and THF(250 mL) was added triphenylphosphine (17 g, 65.4 mmol) inTHF (75 mL) . The reaction was heated at 60 °C for 1 h andconcentrated to an oil. To the residue was added 1:1 .CH2Cl2:Et20 and the resulting solid was filtered. Thefiltrate was concentrated and chromatographed on florisilwith CH2Cl2 to give the title compound (8.05 g, 59percent).ijSIMR (300 MHz, DMSO-dg): 8 3.79 (m, 3H), 3.80 (m, 3H) , 5,35(s, 2H), 7.04 (m, 3H).
53.4% With phosphorus tribromide In diethyl ether at 20℃; for 1 h; In a 100 mL round-bottomed flask, 4D (2 g, 12.0 mmol) was added and dissolved in methanol (30 mL). Sodium borohydride (454 mg, 12.0 mmol) was added in portions at room temperature. The reaction was continued for 1 h at room temperature and the reaction solution was concentrated to a small volume. ,Water and ethyl acetate were added to separate the layers. The organic phase was collected, dried over anhydrous sodium sulfate, and spin-dried to give 4E as a colorless oil.The 4E was dissolved in diethyl ether (25 mL) and phosphorous tribromide (712 μL, 7.50 mmol) was added dropwise at room temperature. The addition was complete and the reaction was carried out at room temperature for 1 h.The reaction solution was placed in an ice bath, saturated sodium bicarbonate was added to quench the reaction, and the mixture was further extracted with ethyl acetate, dried over anhydrous sodium sulfate, and spin-dried to obtain white solid 4F (1.48 g, yield 53.4percent).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 8, p. 941 - 944
[2] Journal of Steroid Biochemistry and Molecular Biology, 2013, vol. 137, p. 332 - 344
[3] Synthesis, 1998, # 9, p. 1357 - 1361
[4] Organic Process Research and Development, 2002, vol. 6, # 2, p. 190 - 191
[5] Organic Letters, 2017, vol. 19, # 8, p. 2054 - 2057
[6] Journal of Organic Chemistry, 2007, vol. 72, # 6, p. 2251 - 2254
[7] Canadian Journal of Chemistry, 1991, vol. 69, # 7, p. 1156 - 1160
[8] Tetrahedron Letters, 2016, vol. 57, # 2, p. 168 - 171
[9] Journal of Organic Chemistry, 2008, vol. 73, # 15, p. 6045 - 6047
[10] Monatshefte fur Chemie, 2008, vol. 139, # 6, p. 673 - 684
[11] Patent: US6225352, 2001, B1,
[12] Biological and Pharmaceutical Bulletin, 2001, vol. 24, # 11, p. 1277 - 1281
[13] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 22, p. 6127 - 6133
[14] Journal of the American Chemical Society, 2007, vol. 129, # 36, p. 11265 - 11278
[15] Journal of Organic Chemistry, 1986, vol. 51, # 18, p. 3490 - 3493
[16] European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 781 - 787
[17] Journal of the American Chemical Society, 2017, vol. 139, # 34, p. 11998 - 112002
[18] Journal of the Indian Chemical Society, 1989, vol. 66, # 8-10, p. 656 - 659
[19] Journal of Organic Chemistry, 2010, vol. 75, # 16, p. 5721 - 5724
[20] Journal of Organic Chemistry, 1996, vol. 61, # 25, p. 8940 - 8948
[21] Patent: US2014/275075, 2014, A1, . Location in patent: Paragraph 0202; 0203
[22] Chemical Communications, 2016, vol. 52, # 71, p. 10747 - 10750
[23] Tetrahedron Letters, 1997, vol. 38, # 6, p. 1079 - 1080
[24] Patent: WO2004/108677, 2004, A1, . Location in patent: Page 157
[25] Patent: CN107540636, 2018, A, . Location in patent: Paragraph 0171; 0172
[26] Justus Liebigs Annalen der Chemie, 1926, vol. 446, p. 94
[27] Gazzetta Chimica Italiana, 1926, vol. 56, p. 144
[28] Journal of the Chemical Society, 1925, vol. 127, p. 1447
[29] Chemical and Pharmaceutical Bulletin, 1977, vol. 25, # 9, p. 2287 - 2291
[30] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 75, # 1-4, p. 35 - 38
[31] Journal of Organic Chemistry, 1994, vol. 59, # 20, p. 5999 - 6007
[32] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 8, p. 821 - 826
[33] Pest Management Science, 2000, vol. 56, # 10, p. 875 - 881
[34] Journal of Organic Chemistry, 2002, vol. 67, # 19, p. 6711 - 6717
[35] Patent: WO2008/70529, 2008, A2, . Location in patent: Page/Page column 50
[36] European Journal of Organic Chemistry, 2009, # 34, p. 6034 - 6042
[37] Chemical Biology and Drug Design, 2011, vol. 78, # 1, p. 101 - 111
[38] Patent: US2012/214837, 2012, A1, . Location in patent: Page/Page column 24-25
[39] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 125 - 136
[40] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 18, p. 5971 - 5975
[41] Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1252 - 1275
[42] Organic Letters, 2014, vol. 16, # 2, p. 484 - 487
[43] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 2092 - 2098
[44] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 740 - 751
[45] Organic and Biomolecular Chemistry, 2015, vol. 13, # 17, p. 4879 - 4895
[46] Organic and Biomolecular Chemistry, 2015, vol. 13, # 40, p. 10136 - 10149
[47] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 8, p. 902 - 907
[48] ChemMedChem, 2016, vol. 11, # 20, p. 2347 - 2360
[49] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 36 - 51
[50] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 13, p. 3285 - 3297
[51] Heterocycles, 2014, vol. 88, # 1, p. 755 - 763
[52] Tetrahedron Letters, 2017, vol. 58, # 33, p. 3311 - 3315
[53] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 12, p. 2131 - 2135
[54] MedChemComm, 2018, vol. 9, # 11, p. 1862 - 1870
  • 5
  • [ 93-03-8 ]
  • [ 21852-32-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 821 - 824
  • 6
  • [ 93-03-8 ]
  • [ 37895-73-1 ]
YieldReaction ConditionsOperation in experiment
91% With lithium bromide monohydrate; [bis(acetoxy)iodo]benzene In 2,2,2-trifluoroethanol at 20℃; for 0.166667 h; General procedure: To a solution of alkoxybenzylalcohol 1 (0.2 mmol) in CF3CH2OH (1 mL) were added LiBr·H2O (0.6 mmol) and PhI(OAc)2 (0.6 mmol) atroom temperature. After completion of the reaction as indicated by TLC monitoring, saturated aq. Na2SO3 wasadded and the mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, driedover anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by silica gel columnchromatography to afford pure dibrominated compounds 3.
Reference: [1] Synlett, 2018, vol. 29, # 17, p. 2275 - 2278
  • 7
  • [ 93-03-8 ]
  • [ 4998-07-6 ]
Reference: [1] Patent: CN106632271, 2017, A,
  • 8
  • [ 93-03-8 ]
  • [ 35202-54-1 ]
Reference: [1] Patent: US2014/163220, 2014, A1,
  • 9
  • [ 93-03-8 ]
  • [ 35202-55-2 ]
Reference: [1] Patent: US2014/163220, 2014, A1,
  • 10
  • [ 93-03-8 ]
  • [ 94687-10-2 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 17, p. 6415 - 6418
[2] Angewandte Chemie, International Edition, 2015, vol. 54, # 1, p. 258 - 262[3] Angewandte Chemie,
[4] Patent: WO2015/138563, 2015, A1,