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[ CAS No. 134-11-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 134-11-2
Chemical Structure| 134-11-2
Chemical Structure| 134-11-2
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Product Details of [ 134-11-2 ]

CAS No. :134-11-2 MDL No. :MFCD00002438
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :XDZMPRGFOOFSBL-UHFFFAOYSA-N
M.W : 166.17 Pubchem ID :67252
Synonyms :

Calculated chemistry of [ 134-11-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.7
TPSA : 46.53 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) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 1.96
Log Po/w (WLOGP) : 1.78
Log Po/w (MLOGP) : 1.64
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 1.71

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.28
Solubility : 0.878 mg/ml ; 0.00528 mol/l
Class : Soluble
Log S (Ali) : -2.56
Solubility : 0.455 mg/ml ; 0.00274 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.842 mg/ml ; 0.00507 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 134-11-2 ]

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

Application In Synthesis of [ 134-11-2 ]

* 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 [ 134-11-2 ]
  • Downstream synthetic route of [ 134-11-2 ]

[ 134-11-2 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 321-21-1 ]
  • [ 134-11-2 ]
  • [ 700-85-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 14, p. 2644 - 2649
  • 2
  • [ 134-11-2 ]
  • [ 42926-52-3 ]
Reference: [1] Journal of the American Chemical Society, 1939, vol. 61, p. 1418
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 8, p. 1539 - 1544
[3] Journal of the American Chemical Society, 1942, vol. 64, p. 1691,1692
[4] The Journal of pharmacy and pharmacology, 1962, vol. 14, p. 587 - 596
[5] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 202 - 211
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 11, p. 1373 - 1380
[7] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 1, p. 21 - 31
[8] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 12, p. 3933 - 3939
[9] Chemical and Pharmaceutical Bulletin, 2003, vol. 51, # 9, p. 1075 - 1080
[10] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 7, p. 2623 - 2628
[11] European Journal of Medicinal Chemistry, 2006, vol. 41, # 12, p. 1421 - 1429
[12] European Journal of Organic Chemistry, 2000, # 11, p. 2119 - 2133
[13] Patent: EP1634883, 2006, A1, . Location in patent: Page/Page column 12-13
[14] Patent: US2006/167107, 2006, A1, . Location in patent: Page/Page column 4
[15] Patent: US2008/58335, 2008, A1, . Location in patent: Page/Page column 16
[16] Patent: WO2009/67613, 2009, A1, . Location in patent: Page/Page column 52
[17] Medicinal Chemistry Research, 2011, vol. 20, # 4, p. 408 - 420
[18] Patent: WO2014/34958, 2014, A1, . Location in patent: Page/Page column 73-74
[19] Synthesis (Germany), 2016, vol. 48, # 10, p. 1550 - 1560
[20] Patent: CN103755709, 2016, B, . Location in patent: Paragraph 0061
  • 3
  • [ 134-11-2 ]
  • [ 938-73-8 ]
Reference: [1] Synthesis (Germany), 2016, vol. 48, # 10, p. 1550 - 1560
  • 4
  • [ 6609-57-0 ]
  • [ 938-73-8 ]
  • [ 134-11-2 ]
Reference: [1] Monatshefte fuer Chemie, 1891, vol. 12, p. 396
  • 5
  • [ 134-11-2 ]
  • [ 21018-13-3 ]
Reference: [1] Journal of Chemical Research, 2011, vol. 35, # 4, p. 234 - 237
[2] Journal of Chemical Research, 2011, vol. 35, # 6, p. 364 - 367
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3615 - 3621
[4] Journal of Chemical Research, 2012, vol. 36, # 7, p. 383 - 386
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297
[6] European Journal of Medicinal Chemistry, 2014, vol. 87, p. 175 - 185
[7] Letters in Organic Chemistry, 2015, vol. 12, # 9, p. 637 - 644
[8] Comptes Rendus Chimie, 2015, vol. 18, # 12, p. 1320 - 1327
  • 6
  • [ 6290-24-0 ]
  • [ 134-11-2 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 70℃; for 2 h;
Stage #2: With hydrogenchloride; water In dimethyl sulfoxide at 0 - 10℃;
To a stirred solution of Ethyl 2-Ethoxy-benzoate (10 g, 240 mmol) in dimethyl sulfoxide (40 mL) was added potassium tert-butoxide (10 g, 890 mmol) in portions. The solution was heated to 70° C. on a water bath for 2 h, and the progress of the reaction was monitored by TLC using a hexane-ethyl acetate (8:2) solvent system. The reaction mass was cooled to 10° C., poured into ice water, and then acidified with 5percent dilute hydrochloric acid. The precipitated solid was filtered and washed thoroughly with distilled water, and the crude mass was recrystallized in hexane (50 mL) to yield an off-white solid of 2-Ethoxy-benzoic Acid (7.6 g, 80percent)
Reference: [1] Patent: US2006/167107, 2006, A1, . Location in patent: Page/Page column 4
[2] Justus Liebigs Annalen der Chemie, 1922, vol. 429, p. 169
[3] Journal of the Chemical Society, Chemical Communications, 1992, # 11, p. 823 - 824
  • 7
  • [ 14178-42-8 ]
  • [ 134-11-2 ]
Reference: [1] Angewandte Chemie, International Edition, 2015, vol. 54, # 1, p. 272 - 275[2] Angewandte Chemie, 2014, vol. 127, # 1, p. 274 - 277,4
  • 8
  • [ 65-85-0 ]
  • [ 134-11-2 ]
Reference: [1] Angewandte Chemie, International Edition, 2015, vol. 54, # 1, p. 272 - 275[2] Angewandte Chemie, 2014, vol. 127, # 1, p. 274 - 277,4
  • 9
  • [ 64-67-5 ]
  • [ 69-72-7 ]
  • [ 134-11-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 4, p. 1111 - 1117
[2] Journal of Fluorescence, 2012, vol. 22, # 5, p. 1237 - 1248
  • 10
  • [ 938-73-8 ]
  • [ 134-11-2 ]
Reference: [1] Journal of Chemical Research, 2005, # 2, p. 119 - 120
  • 11
  • [ 3686-55-3 ]
  • [ 134-11-2 ]
Reference: [1] Journal of Mass Spectrometry, 2008, vol. 43, # 9, p. 1224 - 1234
  • 12
  • [ 6609-57-0 ]
  • [ 938-73-8 ]
  • [ 134-11-2 ]
Reference: [1] Monatshefte fuer Chemie, 1891, vol. 12, p. 396
  • 13
  • [ 6609-57-0 ]
  • [ 134-11-2 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2016, vol. 37, # 9, p. 1509 - 1514
  • 14
  • [ 611-20-1 ]
  • [ 134-11-2 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2016, vol. 37, # 9, p. 1509 - 1514
  • 15
  • [ 7631-93-8 ]
  • [ 75-03-6 ]
  • [ 134-11-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1869, vol. 150, p. 10
  • 16
  • [ 124-38-9 ]
  • [ 103-73-1 ]
  • [ 134-11-2 ]
Reference: [1] Journal of Organometallic Chemistry, 1967, vol. 9, p. 193 - 204
  • 17
  • [ 3686-55-3 ]
  • [ 74-89-5 ]
  • [ 134-11-2 ]
Reference: [1] Chem. Zentralbl., 1907, vol. 78, # II, p. 49
  • 18
  • [ 7664-93-9 ]
  • [ 50357-86-3 ]
  • [ 134-11-2 ]
  • [ 7803-49-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1901, vol. 31 II, p. 31
  • 19
  • [ 141-52-6 ]
  • [ 37470-42-1 ]
  • [ 10435-55-9 ]
  • [ 134-11-2 ]
Reference: [1] Chemische Berichte, 1900, vol. 33, p. 2510
  • 20
  • [ 141-52-6 ]
  • [ 134-11-2 ]
  • [ 14160-71-5 ]
  • [ 56414-14-3 ]
Reference: [1] Chemische Berichte, 1900, vol. 33, p. 2510
  • 21
  • [ 134-11-2 ]
  • [ 200575-16-2 ]
YieldReaction ConditionsOperation in experiment
81% at 0 - 25℃; for 18 h; Example 1 Preparation of 5-chlorosulphonyl-2-ethoxy benzoic acid (II)
In a 250ml three-neck flack, 2-ethoxy benzoic acid (50g, 0.30mol) was added dropwise to an ice-cooled mixtures of sulfoxide dichloride (22 ml, 0.30mol)and chlorosulfonic acid (82.6ml, 1.24mol) under stirring..
At the same time, the temperature of the reacting mixture was kept below 25°C.
The resulting mixture was stirred at room temperature for 18 hours and then poured into ice water with stirring, and white deposit appeared..
The reaction mixture was stirred for another 1 hour and filtered, washed with water and dried in vacuum, gave 64.4g of crude product as white solid (II) (yield 81percent)..
m.p. 108-110°C.
30 g at 20 - 25℃; for 16 h; 2-ethoxybenzoic acid (25 g) at 25°C was added to a mixture of thionyl chloride (11 mL), and chlorosulfonic acid (41.3 mL) and the resultant reaction mixture was stirred at RT for 16 h. An off white solid was separated out which is stirred for 1 h. And the reaction mixture was quenched - - with ice (270 g) and water (60 mL). The obtained solid was separated by filtration and solid was washed with water (2xl00mL) and dried under vacuum to afford the title compound as a solid (30 g). 1H NMR (400MHz, CDC13) δ = 8.83 (s, 1H), 8.20 (br d, J=8.8 Hz, 1H), 7.23 (d, J=8.8 Hz, 1H), 4.45 (q, J=6.6 Hz, 2H), 1.64 (t, J=6.6 Hz, 3H), LCMS (M-H) =263.1, purity=95percent.
Reference: [1] Organic Process Research and Development, 2000, vol. 4, # 1, p. 17 - 22
[2] Patent: EP1400522, 2004, A1, . Location in patent: Page 5
[3] Patent: US5955611, 1999, A,
[4] Patent: US6723719, 2004, B1, . Location in patent: Page column 63
[5] Patent: WO2017/85056, 2017, A1, . Location in patent: Page/Page column 54; 55
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