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[ CAS No. 135-19-3 ] {[proInfo.proName]}

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Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
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Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 135-19-3
Chemical Structure| 135-19-3
Structure of 135-19-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 135-19-3 ]

CAS No. :135-19-3 MDL No. :MFCD00004067
Formula : C10H8O Boiling Point : -
Linear Structure Formula :- InChI Key :JWAZRIHNYRIHIV-UHFFFAOYSA-N
M.W : 144.17 Pubchem ID :8663
Synonyms :

Calculated chemistry of [ 135-19-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.97
TPSA : 20.23 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) : -5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 2.7
Log Po/w (WLOGP) : 2.55
Log Po/w (MLOGP) : 2.54
Log Po/w (SILICOS-IT) : 2.54
Consensus Log Po/w : 2.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.11
Solubility : 0.113 mg/ml ; 0.000781 mol/l
Class : Soluble
Log S (Ali) : -2.78
Solubility : 0.24 mg/ml ; 0.00167 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.47
Solubility : 0.0484 mg/ml ; 0.000336 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 135-19-3 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P271-P272-P273-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P333+P313-P391-P501 UN#:3077
Hazard Statements:H302+H332-H317-H318-H400 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 135-19-3 ]

* 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 [ 135-19-3 ]
  • Downstream synthetic route of [ 135-19-3 ]

[ 135-19-3 ] Synthesis Path-Upstream   1~47

  • 1
  • [ 135-19-3 ]
  • [ 100-97-0 ]
  • [ 1096-84-0 ]
  • [ 77204-14-9 ]
  • [ 77204-15-0 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 10, p. 859 - 862
  • 2
  • [ 133-89-1 ]
  • [ 135-19-3 ]
  • [ 6044-30-0 ]
YieldReaction ConditionsOperation in experiment
89% With Aloe*arborescens*glycosyltransferase*GT3 In dimethyl sulfoxide at 30℃; for 12 h; Enzymatic reaction General procedure: Generally 30-50 μmol of aglycon was solved in 0.5 mL DMSO and diluted with buffer solution (50 mM Tris HCl, pH 7.4, 25 mL total volume). UDP-Glc (60100 μmol) was added along with 50 mL of crude enzyme of AaGT3, extracted from 3 g in wet induced E. coli cells with pET28a-AaGT3. The reactions were performed at 30 °C for up to 12 h, followed by adding 5 × 100 mL of ethyl acetate to extract 5 times. The organic phase was evaporated to dryness under reduced pressure, and the residue was dissolved in 1.5 mL of methanol and purified by reverse-phase semi-preparative HPLC. The obtained products were analyzed by MS and NMR.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 22, p. 2118 - 2121
  • 3
  • [ 135-19-3 ]
  • [ 6044-30-0 ]
Reference: [1] Yakugaku Zasshi, 1952, vol. 72, p. 13[2] Chem.Abstr., 1952, p. 11114
[3] Journal of the Chemical Society, 1930, p. 2729,2732
  • 4
  • [ 135-19-3 ]
  • [ 589-21-9 ]
  • [ 1698-16-4 ]
Reference: [1] Patent: WO2012/15265, 2012, A1, . Location in patent: Page/Page column 14-15
  • 5
  • [ 622-88-8 ]
  • [ 135-19-3 ]
  • [ 1698-16-4 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1994, vol. 34, # 8, p. 697 - 706
  • 6
  • [ 135-19-3 ]
  • [ 581-43-1 ]
  • [ 575-38-2 ]
  • [ 575-44-0 ]
  • [ 582-17-2 ]
Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3099 - 3102
[2] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3099 - 3102
  • 7
  • [ 91-20-3 ]
  • [ 90-15-3 ]
  • [ 575-44-0 ]
  • [ 135-19-3 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 21, p. 6148 - 6151
  • 8
  • [ 141-75-3 ]
  • [ 135-19-3 ]
  • [ 5856-33-7 ]
Reference: [1] Organic Letters, 2008, vol. 10, # 21, p. 4951 - 4953
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 362
[3] Journal fuer Praktische Chemie (Leipzig), 1933, vol. <2> 137, p. 47,51
[4] Journal of the Chemical Society, 1965, p. 168 - 175
  • 9
  • [ 123-20-6 ]
  • [ 135-19-3 ]
  • [ 5856-33-7 ]
YieldReaction ConditionsOperation in experiment
106.9 mg With sodium carbonate In acetonitrile at 120℃; for 24 h; Schlenk technique General procedure: A mixture of phenol 1 (0.50 mmol), Na2CO3 (10.6 mg, 0.10mmol, 20 molpercent), and alkenyl carboxylate (2.0 mmol, 4.0 equiv)in MeCN (3 mL) was added to a Schlenk flask (25 mL) and stirredat r.t. The mixture was stirred at 120 °C until the reaction wasfinished. Then, the solvent was evaporated under reduced pressureand the residue was purified by column chromatography(petroleum ether/ethyl acetate 20:1 to 10:1) to afford theproduct 3.
Reference: [1] Synlett, 2018, vol. 29, # 17, p. 2321 - 2325
  • 10
  • [ 135-19-3 ]
  • [ 22955-77-7 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5371 - 5374
  • 11
  • [ 100-39-0 ]
  • [ 135-19-3 ]
  • [ 607-58-9 ]
  • [ 36441-31-3 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 2, p. 199 - 202
  • 12
  • [ 135-19-3 ]
  • [ 3401-47-6 ]
Reference: [1] Patent: KR2016/17530, 2016, A,
  • 13
  • [ 110-86-1 ]
  • [ 75-89-8 ]
  • [ 335-05-7 ]
  • [ 6226-25-1 ]
  • [ 135-19-3 ]
Reference: [1] Tetrahedron, 1965, vol. 21, p. 1 - 4
[2] , Gmelin Handbook: F: PerFHalOrg.2, 1.3.4, page 137 - 166,
  • 14
  • [ 135-19-3 ]
  • [ 16239-18-2 ]
Reference: [1] Green Chemistry, 2011, vol. 13, # 8, p. 2187 - 2196
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3307 - 3318
[3] Tetrahedron Letters, 2003, vol. 44, # 21, p. 4085 - 4088
[4] Journal of the American Chemical Society, 1921, vol. 43, p. 1952
[5] Journal fuer Praktische Chemie (Leipzig), 1921, vol. <2> 103, p. 367
[6] Journal of the American Chemical Society, 1927, vol. 49, p. 2851
[7] Chem. News J. Ind. Sci., 1889, vol. 59, p. 225[8] Chemische Berichte, 24 Ref. <1891>, 705,
[9] Chem. News J. Ind. Sci., 1891, vol. 63, p. 295[10] Chemische Berichte, 24 Ref. <1891>, 720,
[11] Organic Process Research and Development, 1999, vol. 3, # 2, p. 121 - 125
[12] Patent: CN106542971, 2017, A, . Location in patent: Paragraph 0035
[13] RSC Advances, 2018, vol. 8, # 32, p. 17806 - 17812
  • 15
  • [ 135-19-3 ]
  • [ 16239-18-2 ]
Reference: [1] Patent: US5792886, 1998, A,
  • 16
  • [ 7726-95-6 ]
  • [ 64-19-7 ]
  • [ 135-19-3 ]
  • [ 573-97-7 ]
  • [ 16239-18-2 ]
Reference: [1] Journal of the Indian Chemical Society, 1933, vol. 10, p. 595,597
  • 17
  • [ 7726-95-6 ]
  • [ 64-19-7 ]
  • [ 135-19-3 ]
  • [ 16239-18-2 ]
Reference: [1] Chemische Berichte, 24 Ref. <1891>, 705, 719,
[2] Chem. News J. Ind. Sci., 1889, vol. 59, p. 225[3] Chem. News J. Ind. Sci., 1891, vol. 63, p. 136
  • 18
  • [ 2524-64-3 ]
  • [ 135-19-3 ]
  • [ 18872-49-6 ]
YieldReaction ConditionsOperation in experiment
95% With pyridine N-oxide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In dichloromethane at 20℃; for 1 h; Inert atmosphere General procedure: To a solution of alcohol component (0.9 mmol), pyridine-N-oxide (0.045 mmol, 5 molpercent) andProton Sponge© (1.8 mmol) in CH2Cl2 (0.2 M) was added the specified phosphoryl chloride(1.0 mmol). The reaction mixture was stirred at room temperature for the time specifiedbefore the addition of MeOH (2 mL). The reaction mixture was then conc. in vacuo and crudematerial purified by flash chromatography to afford the desired product
Reference: [1] Synlett, 2015, vol. 26, # 7, p. 985 - 990
[2] Journal of the Chemical Society, 1951, p. 980,985
  • 19
  • [ 135-19-3 ]
  • [ 108-95-2 ]
  • [ 115-86-6 ]
  • [ 18872-49-6 ]
  • [ 7657-86-5 ]
  • [ 18872-50-9 ]
Reference: [1] Patent: EP1403272, 2004, A1, . Location in patent: Page 7-8
[2] Patent: EP1403272, 2004, A1, . Location in patent: Page 7
[3] Patent: EP1403272, 2004, A1, . Location in patent: Page 8
  • 20
  • [ 135-19-3 ]
  • [ 108-95-2 ]
  • [ 115-86-6 ]
  • [ 18872-49-6 ]
  • [ 18872-50-9 ]
Reference: [1] Patent: EP1403272, 2004, A1, . Location in patent: Page 7
  • 21
  • [ 135-19-3 ]
  • [ 18872-49-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 36, p. 8452 - 8456
  • 22
  • [ 135-19-3 ]
  • [ 947-65-9 ]
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 49, p. 17352 - 17353
  • 23
  • [ 135-19-3 ]
  • [ 5773-80-8 ]
Reference: [1] Patent: CN106542971, 2017, A,
  • 24
  • [ 135-19-3 ]
  • [ 1779-11-9 ]
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 49, p. 17352 - 17353
  • 25
  • [ 109-65-9 ]
  • [ 135-19-3 ]
  • [ 10484-56-7 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In acetonitrile at 125℃; for 1 h; Microwave irradiation General procedure: A mixture of 0.14 g (1.0 mmol) of 1- and 2-naphthol (1)and (6), in most cases 1.0 mmol of alkali carbonate (0.14 g of K2CO3 or 0.33 g of Cs2CO3), in certain cases 11.4 mg(0.05 mmol) of TEBAC and 1.2 mmol of alkyl halide (0.14ml of benzyl bromide, 0.10 ml of ethyl iodide, 0.12 mol ofbutyl bromide or 0.11 ml of i-propyl bromide) in a closedvial was irradiated (20–30 W) in a CEM Discover [300 W]MW reactor at 125 °C for the appropriate time. The reactionmixture was taken up in 25 ml of ethyl acetate and the suspensionwas filtered. Evaporation of the volatile componentsprovided the crude product that was passed through a thin(ca. 2–3 cm) layer of silica gel using ethyl acetate as theeluant to give an oil that was analysed by GC–MS or GC.Similar reactions were carried out in 3 ml of MeCN asthe solvent. The work-up was similar to that described forthe solventless alkylations above, but in this case, ethyl acetatedid not have to be added.The major components of the above reactions, such ascompounds 2, 7, 8, 10a-c and 13a,b were obtained in a pureform by repeated chromatography.Control experiments were performed with benzyl bromidein a similar way under conventional heating.
Reference: [1] Chemical Communications, 1998, # 20, p. 2245 - 2246
[2] Letters in Organic Chemistry, 2013, vol. 10, # 5, p. 330 - 336
  • 26
  • [ 135-19-3 ]
  • [ 71-36-3 ]
  • [ 10484-56-7 ]
Reference: [1] Green Chemistry, 2011, vol. 13, # 9, p. 2482 - 2488
[2] Zhurnal Obshchei Khimii, 1951, vol. 21, p. 584,588; engl. Ausg. S. 647, 650
  • 27
  • [ 109-69-3 ]
  • [ 135-19-3 ]
  • [ 10484-56-7 ]
Reference: [1] Chemistry Letters, 2004, vol. 33, # 7, p. 940 - 941
  • 28
  • [ 1112-67-0 ]
  • [ 135-19-3 ]
  • [ 10484-56-7 ]
Reference: [1] Acta Chimica Slovenica, 2010, vol. 57, # 1, p. 29 - 36
  • 29
  • [ 135-19-3 ]
  • [ 10484-56-7 ]
Reference: [1] Green Chemistry, 2015, vol. 17, # 3, p. 1408 - 1413
  • 30
  • [ 135-19-3 ]
  • [ 2033-42-3 ]
YieldReaction ConditionsOperation in experiment
74% With sulfuric acid; dihydrogen peroxide; potassium iodide In methanol at 0 - 20℃; To a stirred solution of 2-naphthol (1.0g, 6.9 mmol) and conc. H2SO4 (0.54 mL 10.4 mmol) in CH3OH (20 mL) at 0 °Cwas added KI (1.27 g, 7.62 mmol) and 30percent H2O2 (1.56 mL, 13.9 mmol). The mixture was stirred overnight at room temperature, and then poured into CH3Cl. The mixture was washed with saturated aq. NaHSO3,with water, and dried over MgSO4, concentrated in vacuo. The crude product was purified by flash column chromatography using hexane and EtOAc to give 1-iodo-2-naphthol as light yellow solid (1.40 g, 74percent), 1H NMR (300 MHz,CDCl3) d 7.91 (d, J = 8.6 Hz, 1H), 7.73–7.70 (m, 2H), 7.53 (dd, J = 7.1, 8.2 Hz, 1H), 7.36 (dd, J= 7.0, 8.1 Hz, 1H), 7.25-7.23 (m, peak merged with CDCl3, 1H), 5.79(s, 1H); 13C NMR (75 MHz, CDCl3) d 153.7, 134.7, 130.6, 130.2, 129.6, 128.3,128.1, 124.1, 116.4, 86.2; GC-MS m/z 270, 272 (M+).
Reference: [1] Chemistry Letters, 2011, vol. 40, # 12, p. 1343 - 1345
[2] Journal of Organic Chemistry, 1985, vol. 50, # 25, p. 5384 - 5387
[3] Synthesis, 2010, # 9, p. 1467 - 1472
[4] Synthesis, 2004, # 11, p. 1869 - 1873
[5] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2664 - 2667
[6] Journal of Chemical Research, 2006, # 9, p. 575 - 576
[7] Journal of Chemical Research, 2004, # 4, p. 294 - 295
[8] Chemistry - A European Journal, 2011, vol. 17, # 30, p. 8452 - 8461
[9] Organic Letters, 2015, vol. 17, # 12, p. 2886 - 2889
[10] Journal of the American Chemical Society, 2018, vol. 140, # 23, p. 7056 - 7060
[11] Canadian Journal of Chemistry, 1987, vol. 65, p. 2019 - 2023
[12] Synthetic Communications, 2006, vol. 36, # 13, p. 1915 - 1917
[13] Patent: JP2004/513951, 2004, A, . Location in patent: Page 21
[14] Angewandte Chemie - International Edition, 2013, vol. 52, # 13, p. 3668 - 3671[15] Angew. Chem., 2013, vol. 52, # 13, p. 3756 - 3759,4
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[23] Synthetic Communications, 2008, vol. 38, # 17, p. 2881 - 2888
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[26] Tetrahedron Letters, 2014, vol. 55, # 22, p. 3355 - 3357
[27] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2011, vol. 41, # 3, p. 258 - 261
[28] Heterocycles, 2015, vol. 90, # 2, p. 919 - 927
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[33] Gazzetta Chimica Italiana, 1890, vol. 20, p. 105
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  • 31
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  • [ 2033-42-3 ]
  • [ 135-19-3 ]
Reference: [1] Green Chemistry, 2016, vol. 18, # 24, p. 6462 - 6467
  • 32
  • [ 7553-56-2 ]
  • [ 127-09-3 ]
  • [ 546-67-8 ]
  • [ 64-19-7 ]
  • [ 135-19-3 ]
  • [ 2033-42-3 ]
Reference: [1] Journal of the Chemical Society, 1885, vol. 47, p. 523[2] Journal of the Chemical Society, 1895, vol. 67, p. 912
  • 33
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  • [ 712-79-8 ]
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  • 34
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  • [ 712-79-8 ]
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  • 35
  • [ 75-46-7 ]
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  • [ 712-79-8 ]
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  • 36
  • [ 384-67-8 ]
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  • [ 712-79-8 ]
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  • 37
  • [ 65094-22-6 ]
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  • [ 712-79-8 ]
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  • 38
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  • [ 712-79-8 ]
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  • 39
  • [ 1717-59-5 ]
  • [ 135-19-3 ]
  • [ 75-46-7 ]
  • [ 712-79-8 ]
Reference: [1] Journal of Fluorine Chemistry, 1989, vol. 44, p. 433 - 440
  • 40
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  • [ 118-03-6 ]
Reference: [1] Patent: CN106866467, 2017, A,
  • 41
  • [ 36592-58-2 ]
  • [ 135-19-3 ]
  • [ 2398-96-1 ]
YieldReaction ConditionsOperation in experiment
100 g With tetrabutylammomium bromide; sodium carbonate In toluene for 5 h; Reflux A solution of the compound N-methyl-N-(3-methylphenyl)thioformyl chloride represented by the formula D, dissolved in toluene 86.6ml, 56 g of 2-naphthol was added at room temperature, sodium carbonate 40 g, tetrabutylammonium bromide 0.8 g, toluene 200ml of toluene solution, after completion of the reaction, the reaction solution was heated to reflux for 5 h, cooled to room temperature after completion of the reaction, washed with water, dried, concentrated under reduced pressure and recrystallized from ethanol to give 100 g of the compound N-methyl-N-(3-methylphenyl) thiocarbamate as shown in formula E
Reference: [1] Patent: CN104341331, 2016, B, . Location in patent: Paragraph 0059; 0070-0071
  • 42
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  • [ 6836-22-2 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 29, p. 3885 - 3887
  • 43
  • [ 135-19-3 ]
  • [ 18741-85-0 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 3, p. 1112 - 1119
[2] Journal of Organic Chemistry, 1985, vol. 50, # 22, p. 4345 - 4349
  • 44
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  • [ 18741-85-0 ]
  • [ 18531-95-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 35, p. 9293 - 9295[2] Angew. Chem., 2013, vol. 125, # 35, p. 9463 - 9465,3
  • 45
  • [ 15231-91-1 ]
  • [ 616-38-6 ]
  • [ 17295-11-3 ]
  • [ 135-19-3 ]
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  • 46
  • [ 135-19-3 ]
  • [ 78119-82-1 ]
Reference: [1] Patent: CN105111054, 2017, B,
  • 47
  • [ 135-19-3 ]
  • [ 173831-50-0 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 10, p. 2382 - 2385
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