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Chemical Structure| 7499-06-1
Chemical Structure| 7499-06-1
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Product Details of [ 7499-06-1 ]

CAS No. :7499-06-1 MDL No. :MFCD00045842
Formula : C8H7ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CSAPESWNZDOAFU-UHFFFAOYSA-N
M.W : 170.59 Pubchem ID :82009
Synonyms :

Calculated chemistry of [ 7499-06-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.38
TPSA : 37.3 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) : -5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 2.35
Log Po/w (MLOGP) : 2.52
Log Po/w (SILICOS-IT) : 2.31
Consensus Log Po/w : 2.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.288 mg/ml ; 0.00169 mol/l
Class : Soluble
Log S (Ali) : -2.87
Solubility : 0.232 mg/ml ; 0.00136 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.77
Solubility : 0.29 mg/ml ; 0.0017 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 7499-06-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7499-06-1 ]

* 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 [ 7499-06-1 ]
  • Downstream synthetic route of [ 7499-06-1 ]

[ 7499-06-1 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 118-90-1 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
  • [ 133232-56-1 ]
  • [ 54811-38-0 ]
YieldReaction ConditionsOperation in experiment
38% With sulfuric acid; Iodine monochloride; periodic acid In water; acetic acid at 90℃; for 5.66667 h; Suspended in a 100 mL three-necked flask equipped with a reflux condenser were 25 mL of 30 weight percent sulfuric acid and 1.36 g (10 mmol) of 2-methylbenzoic acid, and 2.4 g (15 mmol) of iodine monochloride dissolved in 5 g of acetic acid was dropwise added thereto in 40 minutes. Reaction was carried out at 90°C for 5 hours, and the reaction mixture was poured into 90 mL of water. The precipitate was filtered and washed with a sodium sulfite aqueous solution to obtain a crystalline solid (yield: 1.6 g) as the product. This solid was analyzed to find that the product showed the following distribution: [] 2-methylbenzoic acid33 percent5-chloro-2-methylbenzoic acid13 percent3- chloro -2-methylbenzoic acid9 percent5-iodo-2-methylbenzoic acid38 percent3-iodo-2-methylbenzoic acid5 percentothers2 percent The above mixture was purified by recrystallization using acetic acid or isopropyl alcohol to try to isolate 5-iodo-2-methylbenzoic acid. However, a purity of the mixture was scarcely improved, and it was difficult to obtain 5-iodo-2-methylbenzoic acid.
Reference: [1] Patent: EP1595862, 2005, A1, . Location in patent: Page/Page column 11-12
  • 2
  • [ 118-90-1 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
[2] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 308
[3] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
[4] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
  • 3
  • [ 118-90-1 ]
  • [ 7782-50-5 ]
  • [ 64-19-7 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 308
  • 4
  • [ 7499-06-1 ]
  • [ 89-20-3 ]
Reference: [1] Chemische Berichte, 1885, vol. 18, p. 1759
[2] Journal of Organic Chemistry, 1960, vol. 25, p. 334 - 343
  • 5
  • [ 124-38-9 ]
  • [ 95-73-8 ]
  • [ 118-90-1 ]
  • [ 5162-82-3 ]
  • [ 7499-06-1 ]
  • [ 99-94-5 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 6, p. 1631 - 1636
[2] Tetrahedron, 1988, vol. 44, # 6, p. 1631 - 1636
  • 6
  • [ 124-38-9 ]
  • [ 95-73-8 ]
  • [ 118-90-1 ]
  • [ 95-49-8 ]
  • [ 5162-82-3 ]
  • [ 7499-06-1 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 6, p. 1631 - 1636
  • 7
  • [ 103039-12-9 ]
  • [ 7499-06-1 ]
Reference: [1] Patent: WO2006/19768, 2006, A1, . Location in patent: Page/Page column 156-157
  • 8
  • [ 118-90-1 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
  • [ 133232-56-1 ]
  • [ 54811-38-0 ]
YieldReaction ConditionsOperation in experiment
38% With sulfuric acid; Iodine monochloride; periodic acid In water; acetic acid at 90℃; for 5.66667 h; Suspended in a 100 mL three-necked flask equipped with a reflux condenser were 25 mL of 30 weight percent sulfuric acid and 1.36 g (10 mmol) of 2-methylbenzoic acid, and 2.4 g (15 mmol) of iodine monochloride dissolved in 5 g of acetic acid was dropwise added thereto in 40 minutes. Reaction was carried out at 90°C for 5 hours, and the reaction mixture was poured into 90 mL of water. The precipitate was filtered and washed with a sodium sulfite aqueous solution to obtain a crystalline solid (yield: 1.6 g) as the product. This solid was analyzed to find that the product showed the following distribution: [] 2-methylbenzoic acid33 percent5-chloro-2-methylbenzoic acid13 percent3- chloro -2-methylbenzoic acid9 percent5-iodo-2-methylbenzoic acid38 percent3-iodo-2-methylbenzoic acid5 percentothers2 percent The above mixture was purified by recrystallization using acetic acid or isopropyl alcohol to try to isolate 5-iodo-2-methylbenzoic acid. However, a purity of the mixture was scarcely improved, and it was difficult to obtain 5-iodo-2-methylbenzoic acid.
Reference: [1] Patent: EP1595862, 2005, A1, . Location in patent: Page/Page column 11-12
  • 9
  • [ 124-38-9 ]
  • [ 95-73-8 ]
  • [ 118-90-1 ]
  • [ 5162-82-3 ]
  • [ 7499-06-1 ]
  • [ 99-94-5 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 6, p. 1631 - 1636
[2] Tetrahedron, 1988, vol. 44, # 6, p. 1631 - 1636
  • 10
  • [ 104-83-6 ]
  • [ 7499-06-1 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, p. 334 - 343
  • 11
  • [ 124-38-9 ]
  • [ 95-73-8 ]
  • [ 118-90-1 ]
  • [ 95-49-8 ]
  • [ 5162-82-3 ]
  • [ 7499-06-1 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 6, p. 1631 - 1636
  • 12
  • [ 98588-89-7 ]
  • [ 7499-06-1 ]
Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1236[2] Journal of the American Chemical Society, 1959, vol. 81, p. 6450,6453
  • 13
  • [ 69773-58-6 ]
  • [ 7499-06-1 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, p. 334 - 343
  • 14
  • [ 6320-45-2 ]
  • [ 7499-06-1 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, p. 334 - 343
  • 15
  • [ 118-90-1 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
[2] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 308
[3] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
[4] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
  • 16
  • [ 118-90-1 ]
  • [ 7499-06-1 ]
Reference: [1] Israel Journal of Chemistry, 1971, vol. 9, p. 111 - 118
  • 17
  • [ 18964-63-1 ]
  • [ 7499-06-1 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 824 - 827[2] Zhurnal Organicheskoi Khimii, 1968, vol. 4, # 5, p. 848 - 851
  • 18
  • [ 50712-70-4 ]
  • [ 7499-06-1 ]
Reference: [1] Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1929, vol. <A> 143, p. 18
  • 19
  • [ 95-79-4 ]
  • [ 7499-06-1 ]
Reference: [1] Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1929, vol. <A> 143, p. 18
  • 20
  • [ 615-60-1 ]
  • [ 7697-37-2 ]
  • [ 7499-06-1 ]
  • [ 7499-07-2 ]
Reference: [1] Chemische Berichte, 1885, vol. 18, p. 1759
[2] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 308
  • 21
  • [ 118-90-1 ]
  • [ 7782-50-5 ]
  • [ 64-19-7 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 308
  • 22
  • [ 7499-06-1 ]
  • [ 668262-52-0 ]
Reference: [1] Israel Journal of Chemistry, 1971, vol. 9, p. 111 - 118
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365
  • 23
  • [ 118-90-1 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
  • [ 133232-56-1 ]
  • [ 54811-38-0 ]
YieldReaction ConditionsOperation in experiment
38% With sulfuric acid; Iodine monochloride; periodic acid In water; acetic acid at 90℃; for 5.66667 h; Suspended in a 100 mL three-necked flask equipped with a reflux condenser were 25 mL of 30 weight percent sulfuric acid and 1.36 g (10 mmol) of 2-methylbenzoic acid, and 2.4 g (15 mmol) of iodine monochloride dissolved in 5 g of acetic acid was dropwise added thereto in 40 minutes. Reaction was carried out at 90°C for 5 hours, and the reaction mixture was poured into 90 mL of water. The precipitate was filtered and washed with a sodium sulfite aqueous solution to obtain a crystalline solid (yield: 1.6 g) as the product. This solid was analyzed to find that the product showed the following distribution: [] 2-methylbenzoic acid33 percent5-chloro-2-methylbenzoic acid13 percent3- chloro -2-methylbenzoic acid9 percent5-iodo-2-methylbenzoic acid38 percent3-iodo-2-methylbenzoic acid5 percentothers2 percent The above mixture was purified by recrystallization using acetic acid or isopropyl alcohol to try to isolate 5-iodo-2-methylbenzoic acid. However, a purity of the mixture was scarcely improved, and it was difficult to obtain 5-iodo-2-methylbenzoic acid.
Reference: [1] Patent: EP1595862, 2005, A1, . Location in patent: Page/Page column 11-12
  • 24
  • [ 64-17-5 ]
  • [ 7499-06-1 ]
  • [ 56427-54-4 ]
YieldReaction ConditionsOperation in experiment
87% for 48 h; Heating / reflux 5-chloro-2-methylbenzoic acid (5.04 g, 29.5 mmol) was dissolved in 100 mL ethanol in a 250 mL round bottom flask fitted with a water condenser. 0.5 mL concentrated sulfuric acid was added and the solution heated to reflux. The solution was heated for 48 h and cooled to ambient temperature. The ethanol was removed under reduced pressure. The resultant oil was taken up in 300 mL diethyl ether and washed with saturated aqueous sodium bicarbonate (2 x 300 mL). The organic layer was dried over NA2SO4, filtered and concentrated under reduced pressure to yield 5.12 (87percent) of ethyl 5-chloro-2-methylbenzoate as a clear oil. 'H NMR (400 MHz, CDC13) 8 7.88 (d, 1H), 7.35 (dd, 1H), 7.18 (d, 1H), 4.36 (q, 2H), 2.56 (s, 3H), 1.40 (t, 3H). Ethyl 5-chloro-2-methylbenzoate (16.60 g, 83.56 mmol) and diethyl- (3- pyridyl) borane (13.52 g, 91.92 mmol) were dissolved in 100 mL tetrahydrofuran in a 500 mL round bottom flask equipped with a magnetic stirrer. Sodium carbonate (26.57 g, 250.69 mmol) and 50 mL water were added followed by palladium acetate (0.38g, 1.67 mmol) and (2'-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (AmPhos, 0.92g, 2.51 mmol) and 25 mL ethanol. The mixture was heated at reflux for 6 h then cooled to ambient temperature. The mixture was diluted with 600 mL water and extracted with diethyl ether (2 x 300 mL). The organic phases were combined and extracted with 1 N HCI (3 x 200 mL). The acidic extractions were combined and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with diethyl ether (3 x 500 mL) and the extracts were combined and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 19.57g (97percent) of ethyl 5- (3-PYRIDYL)-2-METHYLBENZOATE as a brown oil. MS (LC-MS) 242.2 (M + H) +. 'H NMR (400 MHz, CDCI3) 8 8.87 (d, 1H), 8.61 (dd, 1H), 8.13 (d, 1H), 7.95 (dd, 1 H), 7.62 (dd, 1 H), 7.44 (dd, 1 H), 7.37 (d, 1 H), 4.40 (t, 2H), 2.65 (s, 3H), 1.42 (q, 3H). A 500 mL hydrogenation vessel was charged with 2. 0g PLATINUM (II) oxide and purged with nitrogen. Ethyl 5- (3-PYRIDYL)-2-METHYLBENZOATE (19.57g, 81.10 mmol) was added as a solution in 200 mL acetic acid. The suspension was hydrogenated at 45 psi for 18 h. The catalyst was filtered through celite and the filter plug was washed with 200 mL acetic acid. The filtrate was concentrated under reduced pressure. The resultant oil was taken up in 500 mL water and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with ethyl acetate (2 x 500 mL) and the extracts were combined and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was taken up in 200 mL hot ethanol. L- (+)-tartaric acid (12.17g, 81.1 mmol) was added into the ethanol solution and was allowed to stir at ambient temperature for 48 h, forming a white precipitate that was collected by filtration. The white solid was recrystallized from hot 5percent H2O/ETHANOL (300 mL) and then from 350 mL hot 20percent H20/ETHANOL to yield 11.25g (35percent, 95.8percent ee) of (S)-ethyl 5- (3-PIPERIDINYL)-2-METHYLBENZOATE-L-TARTARIC acid salt as a white solid. The mother liquors were combined and concentrated under reduced pressure. The resultant oil was taken up in 300 mL water and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with ethyl acetate (2 x 300 mL) and the extracts were combined and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was taken up in 200 mL hot ethanol. D- (-)-tartaric acid (6.82g, 45.4 mmol) was added into the ethanol solution and was allowed to stir at ambient temperature for 48 h, forming a white precipitate that was collected by filtration. The white solid was recrystallized from hot 5percent H20/ETHANOL (300 mL) and then from 350 mL hot 20percent H20/ETHANOL to yield 13. 51g (42percent, 100percent ee) of (R)-ethyl 5- (3-PIPERIDINYL)-2-METHYLBENZOATE-D-TARTARIC acid salt as a white solid. MS (LC-MS) 248.2 (M + H) +. 1H NMR (400 MHZ, CDCI3) 6 7. 73 (d, 1H), 7.24 (dd, 1H), 7.18 (d, 1H), 4.35 (q, 2H), 3.18 (t, 2H), 2.78 (t, 1H), 2.68 (m, 2H), 2.54 (s, 3H), 2.38 (br, 1H), 2.01 (d, 1H), 1.82 (m, 1 H), 1.64 (6,2H), 1.40 (t, 3H). HPLC analysis: Chiralcel AD, 1 mL/min, 10percent ethanol/heptane 0.025percent diethylamine, rt = 8.36 min, 9.00 min (R)-Ethyl 5- (3-PIPERIDINYL)-2-METHYLBENZOATE-D-TARTARIC acid (2.02 g, 5.08 mmol) was dissolved in 100 mL ethyl acetate and washed with 100 mL saturated aqueous NAHCO3. The organic phase was dried over NA2SO4 and concentrated under reduced pressure. The resultant oil was taken up in 10 mL toluene and imidazole-1-carboxylic acid 4-trifluoromethyl-benzyl ester (1.37 g, 5.08 mmol) was added. The reaction was stirred for 72 h at room temperature under nitrogen. The reaction was diluted with water (200 mL), acidified with 1 N aqueous hydrochloric acid and extracted with diethyl ether (2 x 150 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was flash chromatographed with 10percent ethyl acetate/hexanes to yield 2.12 G (93percent) of the desired (R)-3- (3-ETHOXYCARBONYL-4- METHYL-PHENYL)-PIPERIDINE-1-CARBOXYLIC acid 4-trifluoromethyl-benzyl ester as a clear oil. MS (LC-MS) 450.1 (M + H) +. 'H NMR (400 MHz, CDC13) 8 7.75 (brs, 1 H), 7.60 (brs, 2H), 7.46 (brs, 2H) 7.23 (s, 1H), 7.18 (d, 1H), 5.20 (s, 2H), 4.36 (q, 2H), 4.23 (brm, 2H), 2.92 (br, 2H), 2.77 (m, 1H), 2.55 (s, 3H), 2.02 (d, 1H), 1.82 (d, 1H), 1.61 (m, 4H), 1.39 (t, 3H). A mixture of (R)-3- (3-ETHOXYCARBONYL-4-METHYL-PHENYL)-PIPERIDINE-L-CARBOXYLIC acid 4-trifluoromethyl-benzyl ester (2.12 g, 4.72 mmol), potassium carbonate (1.30 g, 9.43 mmol), methanol (25 mL) and water (6 mL) was heated at reflux for 3 h, cooled to room temperature and concentrated under reduced pressure. The resulting residue was taken up in water (150 mL), acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to yield 1.98 G (99percent) (R)-3- (3- CARBOXY-4-METHYL-PHENYL)-PIPERIDINE-1-CARBOXYLIC acid 4-trifluoromethyl-benzyl ester as a white solid. MS (LC-MS) 420.0 (M + H) +. 'H NMR (400 MHz, CD30D) 8 7. 80 (d, 1 H), 7.67 (d, 2H), 7.55 (brs, 2H), 7.32 (d, 1H), 7.22 (d, 1H), 5.22 (s, 2H), 4.17 (d, 2H), 2.90 (brm, 2H), 2.72 (t, 1H), 2.53 (s, 3H), 2.02 (d, 1H), 1.82 (m, 2H), 1.61 (m, 1H).
Reference: [1] Patent: WO2004/48334, 2004, A1, . Location in patent: Page 147-149
[2] Patent: US2009/312323, 2009, A1, . Location in patent: Page/Page column 12
[3] RSC Advances, 2018, vol. 8, # 12, p. 6306 - 6314
  • 25
  • [ 7499-06-1 ]
  • [ 75-03-6 ]
  • [ 56427-54-4 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 42, p. 14937 - 14942
[2] Pharmacological Research, 2016, vol. 113, p. 610 - 625
  • 26
  • [ 7499-06-1 ]
  • [ 1028252-13-2 ]
Reference: [1] Patent: US2008/119461, 2008, A1,
  • 27
  • [ 7499-06-1 ]
  • [ 294190-18-4 ]
Reference: [1] Patent: WO2012/142513, 2012, A1,
[2] Patent: WO2013/173441, 2013, A2,
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1556 - 1564
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