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Chemical Structure| 135-02-4
Chemical Structure| 135-02-4
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Product Details of [ 135-02-4 ]

CAS No. :135-02-4 MDL No. :MFCD00003308
Formula : C8H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PKZJLOCLABXVMC-UHFFFAOYSA-N
M.W : 136.15 Pubchem ID :8658
Synonyms :
o-Anisaldehyde

Calculated chemistry of [ 135-02-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.32
TPSA : 26.3 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) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.73
Log Po/w (XLOGP3) : 1.72
Log Po/w (WLOGP) : 1.51
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.98
Consensus Log Po/w : 1.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.08
Solubility : 1.13 mg/ml ; 0.00832 mol/l
Class : Soluble
Log S (Ali) : -1.89
Solubility : 1.76 mg/ml ; 0.0129 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.44
Solubility : 0.492 mg/ml ; 0.00361 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 135-02-4 ]

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

Application In Synthesis of [ 135-02-4 ]

* 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 [ 135-02-4 ]
  • Downstream synthetic route of [ 135-02-4 ]

[ 135-02-4 ] Synthesis Path-Upstream   1~41

  • 1
  • [ 135-02-4 ]
  • [ 80-73-9 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
  • 2
  • [ 135-02-4 ]
  • [ 3482-14-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 11, p. 2647 - 2666
  • 3
  • [ 135-02-4 ]
  • [ 19090-04-1 ]
Reference: [1] Tetrahedron, 1989, vol. 45, # 5, p. 1441 - 1446
  • 4
  • [ 135-02-4 ]
  • [ 111258-23-2 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 24, p. 7500 - 7501
[2] Organic Letters, 2011, vol. 13, # 8, p. 2012 - 2014
[3] Tetrahedron, 2014, vol. 70, # 3, p. 702 - 707
[4] European Journal of Medicinal Chemistry, 2014, vol. 83, p. 409 - 418
  • 5
  • [ 135-02-4 ]
  • [ 6850-57-3 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1998, vol. 32, # 12, p. 641 - 643[2] Khimiko-Farmatsevticheskii Zhurnal, 1998, vol. 32, # 12, p. 18 - 20
[3] Bulletin de la Societe Chimique de France, 1954, p. 615,617
[4] Organic and Biomolecular Chemistry, 2016, vol. 14, # 39, p. 9306 - 9311
[5] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 24 - 33
  • 6
  • [ 135-02-4 ]
  • [ 6850-57-3 ]
  • [ 612-16-8 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 12, p. 2055 - 2058
[2] Tetrahedron, 2008, vol. 64, # 7, p. 1213 - 1217
  • 7
  • [ 860567-26-6 ]
  • [ 6850-57-3 ]
  • [ 135-02-4 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1904, vol. 337, p. 233
  • 8
  • [ 540-69-2 ]
  • [ 135-02-4 ]
  • [ 6850-57-3 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 2249
  • 9
  • [ 135-02-4 ]
  • [ 58333-75-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1998 - 2008
  • 10
  • [ 135-02-4 ]
  • [ 32940-15-1 ]
Reference: [1] Tetrahedron, 1989, vol. 45, # 5, p. 1441 - 1446
[2] Tetrahedron, 1989, vol. 45, # 5, p. 1441 - 1446
  • 11
  • [ 135-02-4 ]
  • [ 29866-54-4 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 888 - 896
[2] Journal of the American Chemical Society, 2006, vol. 128, # 34, p. 11044 - 11053
  • 12
  • [ 135-02-4 ]
  • [ 7035-09-8 ]
YieldReaction ConditionsOperation in experiment
80% With N-chloro-succinimide In N,N-dimethyl-formamide EXAMPLE 20
5-Chloro-2-methoxy-alpha-phenylbenzeneacetonitrile
To a solution of o-anisaldehyde (136 g, 1.0 mole) in DMF (1000 ml) was added N-chlorosuccinimide (147 g, 1.10 mole).
The reaction mixture was stirred 20 hours at 60°, cooled, poured into ice-water, and extracted with Et2 O.
The solvent was removed in vacuo to yield 172 g of crystals.
Recrystallization from cyclohexane (800 ml) gave 137 g (80percent) of 5-chloro-2-methoxybenzaldehyde, m.p. 77°-79°.
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 31, p. 3131 - 3134
[2] Synthetic Communications, 1989, vol. 19, # 5and6, p. 799 - 804
[3] Organic Letters, 2015, vol. 17, # 19, p. 4782 - 4785
[4] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7529 - 7537
[5] Chemische Berichte, 1952, vol. 85, p. 72,77
[6] Journal of Organic Chemistry, 1960, vol. 25, p. 546 - 551
[7] Patent: US4602035, 1986, A,
  • 13
  • [ 507-40-4 ]
  • [ 135-02-4 ]
  • [ 7035-09-8 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 702
  • 14
  • [ 135-02-4 ]
  • [ 6342-77-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2891 - 2898
[2] Tetrahedron, 1989, vol. 45, # 5, p. 1441 - 1446
[3] Tetrahedron, 1989, vol. 45, # 5, p. 1441 - 1446
[4] Collection of Czechoslovak Chemical Communications, 1958, vol. 23, p. 1902,1907
[5] Chemistry Letters, 2013, vol. 42, # 9, p. 1051 - 1052
[6] Patent: WO2014/182950, 2014, A1,
[7] Patent: WO2016/77240, 2016, A2,
  • 15
  • [ 141-82-2 ]
  • [ 135-02-4 ]
  • [ 6099-03-2 ]
YieldReaction ConditionsOperation in experiment
98% With piperidine In pyridine at 85℃; [00323j Synthesis of compound 9.2. A 500-mL 3-necked round-bottom flask was charged with solution of compound 9.1 (20 g, 146.90 mmol, 1.00 equiv) in pyridine (250 mL), propanedioic acid (18.3 g, 175.86 mmol, 1.20 equiv), and piperidine (2.5 g, 29.36 mmol, 0.20 equiv). Reaction was stirred overnight at 85 °C. Upon completion, solvents were reduced under vacuum and pH value of the solution was adjusted to 3.0 using HC1. Resulting solids were collected by filtration, which provided 25.6 g (98percent) of compound 9.2 as a white solid.
Reference: [1] Patent: WO2014/182950, 2014, A1, . Location in patent: Paragraph 00322; 00323
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 336 - 343
[3] Journal of the Indian Chemical Society, 1988, vol. 65, # 3, p. 187 - 191
[4] Molecules, 2009, vol. 14, # 10, p. 4166 - 4179
[5] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 15, p. 4513 - 4519
[6] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 53 - 56
[7] Molecules, 2014, vol. 19, # 10, p. 16058 - 16081
[8] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 554 - 557
  • 16
  • [ 64-19-7 ]
  • [ 135-02-4 ]
  • [ 6099-03-2 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: at 10 - 100℃; for 1.5 h;
Stage #2: at 185 - 190℃; for 10 h; Reflux
General procedure: Acrylic acids 3a-f were prepared according to Chiriac et al.10 A 500 mL three necked round bottom flask equipped with a reflux condenser carrying calcium chloride guard tube, kept in ice-bath, was charged with acetic acid (0.7 mol). Under stirring, sodium borohydride (0.133 mol) was added slowly in small portions into the flask. During this the temperature was maintained below 10°C. The mixture was stirred for half hour at RT and then for one hour at 90-100°C in an oil bath. To this solution, aldehyde (0.1 mol) was added and then N-methyl pyrrolidone (9.91 g) was added as solvent. This solution was refluxed at 185-90°C for 10 hr in an oil bath. After cooling to RT, the above reaction mixture was treated with 50 mL of water and then with saturated sodium bicarbonate solution with vigorous shaking. There was an alkaline reaction and after completion of the reaction it was filtered. To remove the unreactive aldehyde, the filtrate was distilled under vacuum, until the distillate was no longer cloudy. The solution was treated with hydrochloric acid solution (2.7 N) till there was no further reaction. The precipitates of acid were obtained. Absence of spot of aldehyde on thin layer chromatographic plates revealed the homogeneity of acid.
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 12, p. 1513 - 1520
  • 17
  • [ 2033-24-1 ]
  • [ 135-02-4 ]
  • [ 6099-03-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 88, p. 71942 - 71954
  • 18
  • [ 108-24-7 ]
  • [ 135-02-4 ]
  • [ 6099-03-2 ]
Reference: [1] Green Chemistry, 2011, vol. 13, # 8, p. 2130 - 2134
  • 19
  • [ 4887-24-5 ]
  • [ 135-02-4 ]
  • [ 6099-03-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 18, p. 6183 - 6196
  • 20
  • [ 135-02-4 ]
  • [ 6099-03-2 ]
Reference: [1] Chemistry Letters, 2013, vol. 42, # 9, p. 1051 - 1052
  • 21
  • [ 141-82-2 ]
  • [ 135-02-4 ]
  • [ 6099-03-2 ]
  • [ 103095-63-2 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1928, p. 119
  • 22
  • [ 22738-82-5 ]
  • [ 7732-18-5 ]
  • [ 141-82-2 ]
  • [ 124-38-9 ]
  • [ 6099-03-2 ]
  • [ 135-02-4 ]
Reference: [1] Journal of the Chemical Society, 1888, vol. 53, p. 143
  • 23
  • [ 135-02-4 ]
  • [ 35431-26-6 ]
Reference: [1] Monatshefte fuer Chemie, 1971, vol. 102, p. 425 - 430
  • 24
  • [ 135-02-4 ]
  • [ 33538-83-9 ]
Reference: [1] Chemistry Letters, 2013, vol. 42, # 9, p. 1051 - 1052
  • 25
  • [ 135-02-4 ]
  • [ 25016-02-8 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 6, p. 1385 - 1392
[2] Chemische Berichte, 1882, vol. 15, p. 2025
[3] Chemische Berichte, 1884, vol. 17, p. 1387
[4] Chemische Berichte, 1882, vol. 15, p. 2025
[5] Chemische Berichte, 1884, vol. 17, p. 1387
[6] Journal of the Chemical Society [Section] C: Organic, 1971, p. 3693 - 3701
  • 26
  • [ 135-02-4 ]
  • [ 25016-02-8 ]
  • [ 22065-49-2 ]
Reference: [1] Current Science, 1935, vol. 4, p. 26
[2] Current Science, 1935, vol. 4, p. 26
  • 27
  • [ 135-02-4 ]
  • [ 22532-61-2 ]
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 34, p. 11044 - 11053
  • 28
  • [ 75-07-0 ]
  • [ 135-02-4 ]
  • [ 1504-74-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 1, p. 4 - 7
[2] Bulletin de la Societe Chimique de France, 1963, p. 1171 - 1175
[3] Bulletin de la Societe Chimique de France, 1967, p. 865 - 870
  • 29
  • [ 75-07-0 ]
  • [ 135-02-4 ]
  • [ 1504-74-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 1, p. 4 - 7
  • 30
  • [ 2136-75-6 ]
  • [ 135-02-4 ]
  • [ 1504-74-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 4, p. 752 - 755
  • 31
  • [ 109-92-2 ]
  • [ 135-02-4 ]
  • [ 1504-74-1 ]
Reference: [1] Journal of pharmaceutical sciences, 1971, vol. 60, # 8, p. 1188 - 1192
  • 32
  • [ 135-02-4 ]
  • [ 74-88-4 ]
  • [ 67639-61-6 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 6, p. 1078 - 1083
  • 33
  • [ 135-02-4 ]
  • [ 74-89-5 ]
  • [ 6851-80-5 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With acetic acid In methanol; water at 20℃; for 16 h;
Stage #2: With sodium tetrahydroborate In methanol; water at 0 - 20℃; for 3 h;
Step A: To a solution of 2-anisaldehyde (5.56 g, 40 mmol) in methanol (40 mL) was added methylamine (40 wt percent solution in water, 6.9 mL, 80 mol) and acetic acid (240 mg, 4 mmol). The reaction mixture was stirred at room temperature for 16 hours and then cooled in an ice bath. To this ice-cooled mixture was added sodium borohydride (1.51 g, 40 mmol) in portions. The reaction mixture was stirred at room temperature for 3 hours. Most of the solvent was removed under the reduced pressure. The residue was diluted with water (100 mL) and ethyl acetate (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate twice. The combined extracts were washed with brine, dried over sodium sulfate and concentrated to provide the desired 2-methoxybenzyl methylamine (4.7 g, 79percent): 1H NMR (CDCl3, 500 MHz) δ 7.23 (d, J=7.4 Hz, 2H), 6.91 (t, J=7.4 Hz, 1H), 6.86 (d, J=7.9 Hz, 1H), 3.83 (s, 3H), 3.75 (s, 2H), 2.42 (s, 3H); ESI MS m/Z=152 [M+H]+. This crude product was used in the next step without further purification.
78.6%
Stage #1: at 20℃;
Stage #2: With sodium tetrahydroborate In methanol for 6 h;
General procedure: To a mixture of benzaldehydes (10 mmol) in methanol (20 mL), the methylamine or ethylamine(10 mmol) was added. The reaction mixturewas stirred at room temperature for 3-4 h, and then sodium borohydride (5.0mmol) was added in batches and the mixture was further stirred for anotherperiod of 6 h. The reaction was then quenched by the addition of water (10 mL),and washed with diethyl ether (20 mL× 3). The combined organic phases werewashed with saturated aqueous NaCl (30 mL), dried over Na2SO4,and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography usingmixtures of CH2Cl2/CH3OH as eluent to obtainthe light yellow oil 7a-d.
Reference: [1] Patent: US2006/52378, 2006, A1, . Location in patent: Page/Page column 144
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2539 - 2543
[3] Journal of the American Chemical Society, 1944, vol. 66, p. 1875,1879
[4] European Journal of Medicinal Chemistry, 2014, vol. 76, p. 314 - 331
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 911 - 923
[6] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 22, p. 5053 - 5059
  • 34
  • [ 135-02-4 ]
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Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1942, vol. 280, p. 213,224
[2] Organic Letters, 2011, vol. 13, # 4, p. 600 - 603
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7219 - 7222
  • 35
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  • [ 135-02-4 ]
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Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1987, vol. 320, # 7, p. 647 - 654
  • 36
  • [ 135-02-4 ]
  • [ 126712-07-0 ]
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 34, p. 11044 - 11053
[2] Patent: WO2011/103442, 2011, A2,
  • 37
  • [ 135-02-4 ]
  • [ 22976-68-7 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 7, p. 4203 - 4208
  • 38
  • [ 612-16-8 ]
  • [ 80866-82-6 ]
  • [ 135-02-4 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 9, p. 1571 - 1577
  • 39
  • [ 135-02-4 ]
  • [ 88275-87-0 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 25, p. 4415 - 4416
  • 40
  • [ 135-02-4 ]
  • [ 193546-31-5 ]
Reference: [1] Catalysis Communications, 2019, p. 28 - 32
  • 41
  • [ 59-48-3 ]
  • [ 135-02-4 ]
  • [ 186611-04-1 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 17, p. 3874 - 3877
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