Home Cart 0 Sign in  
X

[ CAS No. 97-53-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 97-53-0
Chemical Structure| 97-53-0
Chemical Structure| 97-53-0
Structure of 97-53-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 97-53-0 ]

Related Doc. of [ 97-53-0 ]

Alternatived Products of [ 97-53-0 ]

Product Details of [ 97-53-0 ]

CAS No. :97-53-0 MDL No. :MFCD00008654
Formula : C10H12O2 Boiling Point : -
Linear Structure Formula :CH2CHCH2(CH3O)C6H3OH InChI Key :RRAFCDWBNXTKKO-UHFFFAOYSA-N
M.W : 164.20 Pubchem ID :3314
Synonyms :
4-Allyl-2-methoxyphenol;4-Allylguaiacol;NSC 209525;Allylguaiacol;Eugenic acid
Chemical Name :4-Allyl-2-methoxyphenol

Calculated chemistry of [ 97-53-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.06
TPSA : 29.46 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) : -5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 2.27
Log Po/w (WLOGP) : 2.13
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 2.48
Consensus Log Po/w : 2.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.569 mg/ml ; 0.00347 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.49 mg/ml ; 0.00298 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.79
Solubility : 0.265 mg/ml ; 0.00161 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 97-53-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P272-P273-P280-P302+P352-P305+P351+P338-P333+P313-P337+P313-P501 UN#:N/A
Hazard Statements:H317-H319-H401 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 97-53-0 ]

* 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 [ 97-53-0 ]
  • Downstream synthetic route of [ 97-53-0 ]

[ 97-53-0 ] Synthesis Path-Upstream   1~49

  • 1
  • [ 2216-99-1 ]
  • [ 97-53-0 ]
YieldReaction ConditionsOperation in experiment
90% With lithium chloride In <i>N</i>,<i>N</i>-dimethyl-aniline at 190℃; for 3 h; Inert atmosphere To a 500 ml 3 necked RBF equipped with an overhead stirrer, N2 inlet and a water condenser, were charged 5-allyl-3-methoxysalicylic acid (100 g, 0.48 mol., obtained above), N,N-dimethylaniline (20 ml, SRL 99.5percent pure) and anhydrous lithium chloride (0.750 g, 0.0176 mol., SRL 99percent pure). The above mixture was then heated gradually to 190 °C. The mixture begins to melt slowly as the bath temperature reaches 130 °C, becomes stirrable slurry at 150 °C and eventually a homogeneous liquid as the temperature approaches 190 °C. The reaction mixture was maintained at 190 °C for about 3h. Progress of the reaction was monitored by quenching aliquot sample with dilute hydrochloric acid followed by extraction with solvent (EDC or ether) and analyzing by HPLC (area percent) for the conversion of acid to eugenol. Having ensured the complete conversion of acid by HPLC, the reaction mixture was cooled to room temperature (25 °C) and diluted with 200 ml of 1,2- dichloroethane. To this dil. HC1 (28 ml of 35percent HC1 in 67 ml of water) was added such that the temperature of the reaction mixture does not shoot beyond 25 °C. The resultant mixture was then stirred for lh at room temperature followed by separation of the organic and aqueous layer. The resultant organic layer was passed through a bed of acidic sulphonated polystyrene resin cross linked with divinyl benzene (commonly known as Ion exchange resin, IER) to remove the residual N,N-dimethylaniline (Spec: <2 parts per million by weight (ppm). [0136] The solvent was distilled under vacuum (recovered) and the resultant dark brown liquid was purified by high vacuum distillation to give 71 g (Yield: 90percent) of pure para- eugenol (distilled at 112-116 °C at -10-12 mbar) with purity 99.7percent.
Reference: [1] Patent: WO2015/15445, 2015, A2, . Location in patent: Paragraph 0135-0136
[2] Justus Liebigs Annalen der Chemie, 1919, vol. 418, p. 102
[3] Justus Liebigs Annalen der Chemie, 1863, vol. 125, p. 19
  • 2
  • [ 143654-03-9 ]
  • [ 97-53-0 ]
YieldReaction ConditionsOperation in experiment
96% With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333 h; Green chemistry General procedure: MOM ether (5 mmol) and pTSA.H2O (7.7 mmol) weretriturated well in a mortar for 5 min (in the case of entry 10trituration time was about 15 min), reaction mixture was leftat room temperature for another 30 min. After completion ofthe reaction (monitored by TLC), cold water (4oC) wasadded. The products were separated by centrifugation. Theyields of the products ranged from 85-98percent. The purities andthe identities of the products were established by direct comparisonwith known compounds (TLC, Mp and IR). See supplementaryinformation for further details.
89% With bismuth(III) chloride In water; acetonitrile at 50℃; for 1 h; General procedure: BiCl3 (30 molpercent) was added to a stirred solution of MOM-protected phenol (1 mmol) in MeCN/H2O (5:0.1 mL; 5:0.1 v/v) and the mixture was stirred at 50 °C until reaction was complete (TLC control). The mixture was filtered over a pad of celite using CH2Cl2 (10 mL), and the resulting filtrate was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Flash column chromatography of the residue over silica gel (hexane/EtOAc mixture) afforded the desired pure phenol (76–95percent). All phenolic products were analyzed by IR and NMR spectroscopy and by comparison with authentic samples.
Reference: [1] Letters in Organic Chemistry, 2017, vol. 14, # 4, p. 231 - 235
[2] Synthetic Communications, 2016, vol. 46, # 7, p. 586 - 593
  • 3
  • [ 214330-24-2 ]
  • [ 97-53-0 ]
YieldReaction ConditionsOperation in experiment
87% With sodium tetrachloroaurate (III) dihydrate In methanol at 20℃; for 7 h; NaAuCl4·2 H2O (39.8 mg, 0.1 mmol, 0.05 equiv) was added to a solution of silyl ether 1030 (557 mg, 2 mmol) in MeOH (4 mL) at r.t., and the mixture was stirred at r.t. for 7 h. The mixture was then diluted with EtOAc (10 mL), filtered through activated alumina, and concentrated in vacuo. The residue was purified by flash column chromatography[silica gel, EtOAc–PE (1:5)] to give a pale-yellow oil; yield: 286mg (87percent). 1H NMR (300 MHz, CDCl3): δ = 6.86–6.83 (m, 1 H), 6.69–6.67 (m, 2 H),5.99–5.88 (m, 1 H), 5.49 (s, 1 H), 5.10–5.04 (m, 2 H), 3.87 (s, 3 H), 3.32(d, J = 6.6 Hz, 2 H).13C NMR (75 MHz, CDCl3): δ = 146.44, 143.92, 137.80, 131.89, 121.17,115.45, 114.26, 111.14, 55.83, 39.84.MS (ESI, MeOH): m/z = 187 [M + Na]+.HRMS-ESI: m/z [M + Na]+ calcd for C10H12NaO2: 187.0735; found:187.0735.
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 1, p. 55 - 64
  • 4
  • [ 90-05-1 ]
  • [ 107-05-1 ]
  • [ 97-53-0 ]
  • [ 579-60-2 ]
Reference: [1] Patent: WO2015/15445, 2015, A2, . Location in patent: Paragraph 0119-0121
[2] Patent: CN105294409, 2016, A, . Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046
  • 5
  • [ 4125-45-5 ]
  • [ 97-53-0 ]
Reference: [1] Synlett, 2008, # 13, p. 1957 - 1960
[2] Catalysis Science and Technology, 2013, vol. 3, # 10, p. 2541 - 2545
  • 6
  • [ 50-00-0 ]
  • [ 56521-01-8 ]
  • [ 97-53-0 ]
YieldReaction ConditionsOperation in experiment
59.51 %Chromat. With formic acid; zinc In ethanol at 65℃; for 4.5 h; A mixture of nitroeugenol (0.72mmol), formaldehyde (0.72 mmol) and Zn powder (7.32mmol) was dissolved in 25 mL of ethanol. Formic acid (4.5mmol) was then added to the mixture. Reaction was heated at 65 °C for approximately 4.5 h and filtered while hot. Filtrate was extracted with dichloromethane (3 × 25 mL) and the organic phases were combined, which then dried with Na2SO4. Mixture was filtered and evaporated. Afterwards, the obtained product was analyzed by using GC-MS.
Reference: [1] Asian Journal of Chemistry, 2017, vol. 29, # 4, p. 867 - 869
  • 7
  • [ 85614-43-3 ]
  • [ 97-53-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1919, vol. 418, p. 102
[2] Patent: WO2015/15445, 2015, A2, . Location in patent: Paragraph 0138
  • 8
  • [ 81391-19-7 ]
  • [ 97-53-0 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 10, p. 1983 - 1984
  • 9
  • [ 4125-43-3 ]
  • [ 97-53-0 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 41, p. 4945 - 4948
[2] Zhurnal Obshchei Khimii, 1941, vol. 11, p. 722,725[3] Chem.Abstr., 1942, p. 430
  • 10
  • [ 76513-64-9 ]
  • [ 50-00-0 ]
  • [ 97-53-0 ]
  • [ 74-85-1 ]
  • [ 420-56-4 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, # 35, p. 3343 - 3346
  • 11
  • [ 93-28-7 ]
  • [ 97-53-0 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 9, p. 1259 - 1264
  • 12
  • [ 90-05-1 ]
  • [ 107-05-1 ]
  • [ 97-53-0 ]
Reference: [1] Patent: US4048236, 1977, A,
  • 13
  • [ 4125-43-3 ]
  • [ 97-53-0 ]
  • [ 579-60-2 ]
YieldReaction ConditionsOperation in experiment
76 %Spectr. at 200℃; for 0.0333333 h; Microwave irradiation To a 5ml_ Biotage® microwave vial fitted with a magnetic stirrer, was charged with calcium bis-triflimide (16 mg, 26.7 μιτιοΙ) and O-allylguaiacol (438 mg, 2.67 mmol). The vial was then sealed and the resultant homogeneous mixture was stirred for 2 minutes at the temperature of 200°C, under an autogenous pressure and a microwave irradiation generated by the Biotage® microwave instrument. After cooling to room temperature, the resulting reaction mixture was analysed by 1H NMR to determine the conversion ratio (100percent) and isomeric composition (76percent of ortho- eugenol and 24percent of para- eugenol).
Reference: [1] Tetrahedron, 2007, vol. 63, # 45, p. 10949 - 10957
[2] Synthetic Communications, 2004, vol. 34, # 8, p. 1433 - 1440
[3] Journal of Chemical Research, Miniprint, 1991, # 7, p. 1758 - 1770
[4] Synlett, 2000, # 5, p. 615 - 618
[5] Advanced Synthesis and Catalysis, 2002, vol. 344, # 3-4, p. 434 - 440
[6] Patent: WO2016/4632, 2016, A1, . Location in patent: Paragraph 0041
  • 14
  • [ 103552-63-2 ]
  • [ 97-53-0 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 14, p. 1607 - 1610
  • 15
  • [ 144150-79-8 ]
  • [ 97-53-0 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 18, p. 2847 - 2850
  • 16
  • [ 6331-61-9 ]
  • [ 97-53-0 ]
Reference: [1] European Journal of Organic Chemistry, 2008, # 2, p. 337 - 342
  • 17
  • [ 1616917-77-1 ]
  • [ 97-53-0 ]
  • [ 4125-45-5 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 14, p. 6695 - 6702
  • 18
  • [ 16766-30-6 ]
  • [ 762-72-1 ]
  • [ 97-53-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 15, p. 2868 - 2871
  • 19
  • [ 79440-81-6 ]
  • [ 97-53-0 ]
Reference: [1] Archives of Biochemistry and Biophysics, 2014, vol. 541, # 1, p. 37 - 46
  • 20
  • [ 90-05-1 ]
  • [ 97-53-0 ]
  • [ 579-60-2 ]
Reference: [1] Patent: US4048236, 1977, A,
[2] Patent: US4048236, 1977, A,
[3] Patent: US4048236, 1977, A,
[4] Patent: US4048236, 1977, A,
[5] Patent: US4048236, 1977, A,
[6] Patent: US4048236, 1977, A,
[7] Patent: US4048236, 1977, A,
  • 21
  • [ 4873-09-0 ]
  • [ 90-05-1 ]
  • [ 97-53-0 ]
Reference: [1] Synlett, 2003, # 10, p. 1431 - 1434
  • 22
  • [ 121-33-5 ]
  • [ 97-53-0 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 10, p. 1983 - 1984
  • 23
  • [ 90-05-1 ]
  • [ 106-95-6 ]
  • [ 97-53-0 ]
Reference: [1] Chemical Communications, 2012, vol. 48, # 56, p. 7019 - 7021
  • 24
  • [ 129664-76-2 ]
  • [ 97-53-0 ]
  • [ 5932-68-3 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 7, p. 941 - 945
  • 25
  • [ 106-95-6 ]
  • [ 156682-54-1 ]
  • [ 97-53-0 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3328 - 3333
  • 26
  • [ 68800-55-5 ]
  • [ 97-53-0 ]
  • [ 87893-16-1 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1983, vol. 31, # 8, p. 2879 - 2883
  • 27
  • [ 97-54-1 ]
  • [ 97-53-0 ]
Reference: [1] ChemCatChem, 2013, vol. 5, # 10, p. 2848 - 2851
  • 28
  • [ 458-35-5 ]
  • [ 97-53-0 ]
Reference: [1] Archives of Biochemistry and Biophysics, 2014, vol. 541, # 1, p. 37 - 46
  • 29
  • [ 269410-22-2 ]
  • [ 97-53-0 ]
  • [ 4125-45-5 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 14, p. 6695 - 6702
  • 30
  • [ 917-64-6 ]
  • [ 93-15-2 ]
  • [ 97-53-0 ]
  • [ 501-19-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1940, vol. 544, p. 30,58
[2] Bulletin of the Chemical Society of Japan, 1936, vol. 11, p. 179,181
  • 31
  • [ 97-54-1 ]
  • [ 97-53-0 ]
  • [ 2503-46-0 ]
  • [ 24762-60-5 ]
  • [ 121-33-5 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 18, p. 4423 - 4434
  • 32
  • [ 90-05-1 ]
  • [ 97-53-0 ]
Reference: [1] Zhurnal Obshchei Khimii, 1941, vol. 11, p. 722,725[2] Chem.Abstr., 1942, p. 430
  • 33
  • [ 877-22-5 ]
  • [ 97-53-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1919, vol. 418, p. 102
  • 34
  • [ 6342-70-7 ]
  • [ 97-53-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1919, vol. 418, p. 102
  • 35
  • [ 96619-89-5 ]
  • [ 97-53-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1919, vol. 418, p. 102
  • 36
  • [ 5932-68-3 ]
  • [ 97-53-0 ]
  • [ 51020-86-1 ]
  • [ 458-35-5 ]
  • [ 121-33-5 ]
Reference: [1] Biocatalysis and Biotransformation, 2011, vol. 29, # 4, p. 147 - 150
  • 37
  • [ 129664-76-2 ]
  • [ 97-53-0 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 7, p. 941 - 945
  • 38
  • [ 1544578-98-4 ]
  • [ 97-53-0 ]
  • [ 51146-56-6 ]
Reference: [1] Medicinal Chemistry, 2013, vol. 9, # 7, p. 1006 - 1016
  • 39
  • [ 4125-43-3 ]
  • [ 3345-11-7 ]
  • [ 97-53-0 ]
  • [ 579-60-2 ]
Reference: [1] Chemische Berichte, 1990, vol. 123, # 7, p. 1591 - 1593
  • 40
  • [ 18604-54-1 ]
  • [ 87-72-9 ]
  • [ 97-53-0 ]
  • [ 498-05-5 ]
  • [ 18604-50-7 ]
Reference: [1] Bioscience, Biotechnology and Biochemistry, 2006, vol. 70, # 3, p. 691 - 698
  • 41
  • [ 123-75-1 ]
  • [ 93-28-7 ]
  • [ 4030-18-6 ]
  • [ 97-53-0 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 17, p. 1845 - 1846
  • 42
  • [ 106-95-6 ]
  • [ 97-53-0 ]
Reference: [1] Journal of Fluorine Chemistry, 2006, vol. 127, # 6, p. 720 - 729
  • 43
  • [ 2216-99-1 ]
  • [ 121-69-7 ]
  • [ 97-53-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1919, vol. 418, p. 102
  • 44
  • [ 85614-43-3 ]
  • [ 62-53-3 ]
  • [ 97-53-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1919, vol. 418, p. 102
  • 45
  • [ 2216-99-1 ]
  • [ 97-53-0 ]
  • [ 124-38-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1863, vol. 125, p. 17
  • 46
  • [ 97-53-0 ]
  • [ 487-11-6 ]
Reference: [1] Proceedings - Indian Academy of Sciences, Section A, 1949, vol. &lt;A&gt; 30, p. 114,118
[2] Patent: WO2013/133723, 2013, A1,
  • 47
  • [ 97-53-0 ]
  • [ 24743-14-4 ]
Reference: [1] Journal of Chemical Research, 2006, # 11, p. 691 - 695
[2] Synthesis, 2005, # 4, p. 551 - 554
  • 48
  • [ 97-53-0 ]
  • [ 57371-44-5 ]
Reference: [1] Organic Preparations and Procedures International, 2015, vol. 47, # 6, p. 443 - 448
  • 49
  • [ 97-53-0 ]
  • [ 2785-87-7 ]
  • [ 1678-92-8 ]
  • [ 4291-79-6 ]
  • [ 18979-60-7 ]
  • [ 5888-52-8 ]
  • [ 82166-21-0 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 19, p. 4492 - 4499
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 97-53-0 ]

Aryls

Chemical Structure| 2785-89-9

[ 2785-89-9 ]

4-Ethyl-2-methoxyphenol

Similarity: 0.97

Chemical Structure| 5888-51-7

[ 5888-51-7 ]

4-Ethyl-1,2-dimethoxybenzene

Similarity: 0.97

Chemical Structure| 10103-06-7

[ 10103-06-7 ]

2,3-Dimethoxynaphthalene

Similarity: 0.97

Chemical Structure| 7786-61-0

[ 7786-61-0 ]

2-Methoxy-4-vinylphenol

Similarity: 0.97

Chemical Structure| 93-51-6

[ 93-51-6 ]

2-Methoxy-4-methylphenol

Similarity: 0.94

Alkenes

Chemical Structure| 7786-61-0

[ 7786-61-0 ]

2-Methoxy-4-vinylphenol

Similarity: 0.97

Chemical Structure| 24743-14-4

[ 24743-14-4 ]

3-(3-Methoxyphenyl)-1-propene

Similarity: 0.94

Chemical Structure| 22255-22-7

[ 22255-22-7 ]

(E)-1,3-Dimethoxy-5-(4-methoxystyryl)benzene

Similarity: 0.89

Chemical Structure| 33626-08-3

[ 33626-08-3 ]

(E)-5-(4-Methoxystyryl)benzene-1,3-diol

Similarity: 0.89

Chemical Structure| 4180-23-8

[ 4180-23-8 ]

(E)-1-Methoxy-4-(prop-1-en-1-yl)benzene

Similarity: 0.88

Ethers

Chemical Structure| 2785-89-9

[ 2785-89-9 ]

4-Ethyl-2-methoxyphenol

Similarity: 0.97

Chemical Structure| 5888-51-7

[ 5888-51-7 ]

4-Ethyl-1,2-dimethoxybenzene

Similarity: 0.97

Chemical Structure| 10103-06-7

[ 10103-06-7 ]

2,3-Dimethoxynaphthalene

Similarity: 0.97

Chemical Structure| 7786-61-0

[ 7786-61-0 ]

2-Methoxy-4-vinylphenol

Similarity: 0.97

Chemical Structure| 93-51-6

[ 93-51-6 ]

2-Methoxy-4-methylphenol

Similarity: 0.94