Home Cart 0 Sign in  
X

[ CAS No. 82998-57-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 82998-57-0
Chemical Structure| 82998-57-0
Chemical Structure| 82998-57-0
Structure of 82998-57-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 82998-57-0 ]

Related Doc. of [ 82998-57-0 ]

Alternatived Products of [ 82998-57-0 ]

Product Details of [ 82998-57-0 ]

CAS No. :82998-57-0 MDL No. :MFCD00010392
Formula : C8H7IO2 Boiling Point : -
Linear Structure Formula :- InChI Key :LDDHMKANNXWUAK-UHFFFAOYSA-N
M.W : 262.04 Pubchem ID :621640
Synonyms :

Calculated chemistry of [ 82998-57-0 ]

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 : 51.08
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) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.73
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 2.63
Consensus Log Po/w : 2.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.35
Solubility : 0.116 mg/ml ; 0.000445 mol/l
Class : Soluble
Log S (Ali) : -2.89
Solubility : 0.34 mg/ml ; 0.0013 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.11
Solubility : 0.203 mg/ml ; 0.000774 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.64

Safety of [ 82998-57-0 ]

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 [ 82998-57-0 ]

* 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 [ 82998-57-0 ]
  • Downstream synthetic route of [ 82998-57-0 ]

[ 82998-57-0 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 2458-12-0 ]
  • [ 5162-82-3 ]
  • [ 82998-57-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 5, p. 1333 - 1337
  • 2
  • [ 82998-57-0 ]
  • [ 35944-64-0 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 8, p. 899 - 902
  • 3
  • [ 90347-66-3 ]
  • [ 82998-57-0 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With water; sodium hydroxide In methanol at 20℃; for 14 h;
Stage #2: With hydrogenchloride In water
3-iodo-4-methylbenzoic acid. Methyl-3-Iodo-4-methylbenzoate (3 g, 109 mmol, 1 eq) dissolved in MeOH (30 ml) was added sodium hydroxide (1.3 g, 327 mmol, 3 eq) followed by the addition of water (15 ml). The above solution was stirred at room temperature for 14 h. The solution was concentrated under vacuum, and then added water. The pH of the reaction was bought to 3 using Cone. HCl. The solid obtained was filtered and dried under vacuum, Yield: 2.7 g (96 percent). 1HNMR (400MHz, DMSO-d6): δ 2.44 (s, 3H), 7.45 (d, 7- 8.00 Hz ,1H), 7.85 (d, J= 3.18 Hz, IH), 8.31 (s, IH).
96% With water; sodium hydroxide In methanol at 20℃; for 14 h; Methyl-3-Iodo-4-methylbenzoate (3 g, 109 mmol, 1 eq) dissolved in MeOH (30 ml) was added sodium hydroxide (1.3 g, 327 mmol, 3 eq) followed by the addition of water (15 ml). The above solution was stirred at room temperature for 14 h. The solution was concentrated under vacuum, and then added water. The pH of the reaction was bought to 3 using Conc.HCl. The solid obtained was filtered and dried under vacuum. Yield: 2.7 g (96 percent). 1HNMR (400MHz, DMSO-d6): δ 2.44 (s, 3H), 7.45 (d, J= 8.00 Hz , 1H), 7.85 (d, J= 3.18 Hz, 1H), 8.31 (s, 1H).
Reference: [1] Patent: WO2010/30538, 2010, A2, . Location in patent: Page/Page column 197
[2] Patent: WO2011/112186, 2011, A1, . Location in patent: Page/Page column 196
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 17, p. 5004 - 5008
  • 4
  • [ 99-94-5 ]
  • [ 82998-57-0 ]
Reference: [1] Journal of the Iranian Chemical Society, 2012, vol. 9, # 3, p. 321 - 326
[2] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 4, p. 951 - 956
[3] Journal of applied chemistry of the USSR, 1984, vol. 57, # 1 pt 2, p. 121 - 123
[4] Journal of Organic Chemistry, 2009, vol. 74, # 16, p. 6287 - 6290
[5] Synthesis, 2004, # 3, p. 441 - 445
[6] Molecules, 2005, vol. 10, # 3, p. 671 - 675
[7] Molecules, 2004, vol. 9, # 7, p. 595 - 601
[8] Molecules, 2005, vol. 10, # 10, p. 1307 - 1317
[9] Synthesis, 2006, # 7, p. 1195 - 1199
[10] Molecules, 2005, vol. 10, # 2, p. 394 - 400
[11] Tetrahedron, 2004, vol. 60, # 41, p. 9113 - 9119
[12] Tetrahedron Letters, 1989, vol. 30, # 8, p. 899 - 902
[13] Chemische Berichte, 1893, vol. 26, p. 1733
  • 5
  • [ 42872-79-7 ]
  • [ 82998-57-0 ]
Reference: [1] Journal of the Chemical Society, 1913, vol. 103, p. 236
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2940 - 2948
  • 6
  • [ 2458-12-0 ]
  • [ 82998-57-0 ]
Reference: [1] Chemische Berichte, 1893, vol. 26, p. 1733
  • 7
  • [ 2458-12-0 ]
  • [ 5162-82-3 ]
  • [ 82998-57-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 5, p. 1333 - 1337
  • 8
  • [ 96-98-0 ]
  • [ 82998-57-0 ]
Reference: [1] Chemische Berichte, 1893, vol. 26, p. 1733
  • 9
  • [ 60710-80-7 ]
  • [ 82998-57-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2940 - 2948
  • 10
  • [ 67-56-1 ]
  • [ 82998-57-0 ]
  • [ 90347-66-3 ]
YieldReaction ConditionsOperation in experiment
98% at 0 - 60℃; Compound 5.3. Methyl 3-iodo-4-methylbenzoate. To a solution of 3-iodo-4- methylbenzoic acid (28.0 g, 0.107 mol) in MeOH (300 mL) at 0 °C was carefully added concentrated H2SO4 (30 mL). The mixture was heated at 60 °C overnight, then cooled and the solvent removed under reduced pressure. The residue was carefully poured onto ice- water (200 mL) and the mixture was extracted with EtOAc (500 mL). The organics was washed with water (100 mL), saturated NaHC03 (100 mL), brine (100 mL), dried (MgS04), filtered, and concentrated to yield the title compound as a brown oi 1 (29.0 g, 98percent). 'H NMR (400 MHz, CDCI3) δ 8.47 (d, J = 1 .7 Hz, 1 H), 7.90 (dd, J = 7.9 Hz, 1.7 Hz, 1 H), 7.29 (d, J= 7.9 Hz , 1 H), 3.90 (s, 2H), 2.48 (s, 3H).
98% at 60℃; Compound 5.3. Methyl 3-iodo-4-methylbenzoate.
To a solution of 3-iodo-4- methylbenzoic acid (28.0 g, 0.107 mol) in MeOH (300 mL) at 0 °C was carefully added concentrated H2SO4 (30 mL). The mixture was heated at 60 °C overnight, then cooled and the solvent removed under reduced pressure. The residue was carefully poured onto ice-water (200 mL) and the mixture was extracted with EtOAc (500 mL). The organics was washed with water (100 mL), saturated NaHC03 (100 mL), brine (100 mL), dried (MgS04), filtered, and concentrated to yield the title compound as a brown oil (29.0 g, 98percent). XH NMR (400 MHz, CDCI3) δ 8.47 (d, J= 1.7 Hz, 1H), 7.90 (dd, J= 7.9 Hz, 1.7 Hz, 1H), 7.29 (d, J= 7.9 Hz , 1H), 3.90 (s, 2H), 2.48 (s, 3H)
95%
Stage #1: With hydrogenchloride In 1,4-dioxane at 80℃; for 72 h;
Stage #2: With potassium carbonate In 1,4-dioxane; water; ethyl acetate
a) Methyl 3-iodo-4-methylbenzoate A suspension of 3-iodo-4-methylbenzoic acid (15.00 g, 60.00 mmol) and a 4M solution of hydrochloric acid in dioxane (20.00 mL, 80.0 mmol) in methanol (20 mL) was heated in a sealed tube at 80 °C with stirring. After stirring for 3 days, the mixture was cooled and ethyl acetate and saturated aqueous potassium carbonate solution were added. The organic layer was washed with brine, dried (MgSO4) and evaporated in vacuo to give the title compound (15.00 g, 95percent). LRMS (m/z): 277 (M+1)+.
95% With hydrogenchloride In 1,4-dioxane at 80℃; for 72 h; sealed tube INTERMEDIATE 8; [2-methyl-5-(5-methyl-1 ,3,4-oxadiaz -2-yl)phenyl]boronic acid; a) Methyl 3-iodo-4-methylbenzoate; A suspension of 3-iodo-4-methylbenzoic acid (15.00 g, 60.00 mmol) and a 4M solution of hydrochloric acid in dioxane (20.00 mL, 80.0 mmol) in methanol (20 mL) was heated in a sealed tube at 80 °C with stirring. After stirring for 3 days, the mixture was cooled and ethyl acetate and saturated aqueous potassium carbonate solution were added. The organic layer was washed with brine, dried (MgS04) and evaporated in vacuo to give the title compound (15.00 g, 95percent).LR S (m/z): 277 (M+1)+.

Reference: [1] Collection of Czechoslovak Chemical Communications, 1999, vol. 64, # 4, p. 649 - 672
[2] Patent: WO2014/8197, 2014, A1, . Location in patent: Page/Page column 71
[3] Patent: WO2015/95767, 2015, A1, . Location in patent: Page/Page column 86
[4] Patent: EP2322176, 2011, A1, . Location in patent: Page/Page column 21
[5] Patent: WO2011/57757, 2011, A1, . Location in patent: Page/Page column 36-37
[6] Journal of Organic Chemistry, 2001, vol. 66, # 24, p. 8127 - 8134
[7] Organic and Biomolecular Chemistry, 2009, vol. 7, # 24, p. 5129 - 5136
[8] Patent: US2009/203666, 2009, A1, . Location in patent: Page/Page column 8-9
[9] European Journal of Organic Chemistry, 2013, # 16, p. 3223 - 3231
[10] Patent: US2017/305920, 2017, A1, . Location in patent: Paragraph 0199; 200
[11] Patent: EP2162190, 2016, B1, . Location in patent: Paragraph 0080; 0081
  • 11
  • [ 82998-57-0 ]
  • [ 144-55-8 ]
  • [ 90347-66-3 ]
Reference: [1] Patent: US2010/197659, 2010, A1,
  • 12
  • [ 186581-53-3 ]
  • [ 82998-57-0 ]
  • [ 90347-66-3 ]
Reference: [1] Journal of Chemical Ecology, 2001, vol. 27, # 2, p. 257 - 271
  • 13
  • [ 82998-57-0 ]
  • [ 73183-34-3 ]
  • [ 515131-35-8 ]
YieldReaction ConditionsOperation in experiment
71% With potassium acetate In N,N-dimethyl-formamide at 100℃; for 6 h; Inert atmosphere Reference Example 8
4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) benzoic acid (Compound A8)
3-Iodo-4-methyl benzoic acid (26.2 g, 100 mmol) was dissolved in DMF (300 mL), and then bis(pinacolate)diboron (38.1 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium (8.17 g, 10.0 mmol) and potassium acetate (49.0 g, 500 mmol) were added thereto, followed by stirring under argon atmosphere at 100°C for 6 hours.
To the reaction mixture was added 1 mol/L of hydrochloric acid, followed by extraction with ethyl acetate, an organic layer was washed with brine, followed by drying over anhydrous magnesium sulfate, and activated carbon (1 g) was added thereto, followed by stirring at room temperature for 1 hour.
The reaction mixture was filtered through celite, followed by washing with ethyl acetate:
The solvent was evaporated, and the resulting crystals were recrystallized from isopropyl ether, followed by filtration to obtain Compound A8 (18.5 g, 71percent).
1H NMR (300 MHz, CDCl3) δ (ppm) 1.36 (s, 12H), 2.61 (s, 3H), 7.26 (d, J = 8.1 Hz, 1H), 8.02 (dd, J = 8.1, 1.8 Hz, 1H), 8.49 (d, J = 1.8 Hz, 1H).
65% With potassium acetate In N,N-dimethyl-formamide at 80℃; REFERENCE EXAMPLE 19; 4-Methyl-3-(4,4,5,5-tetramethyl[1 ,3,2]dioxaborolan-2-yl)benzoic acid; To a solution of 3-iodo-4-methylbenzoic acid (3.71 g, 14.2 mmol) in DMF (130 mL), bis(pinacolato)diboron (7.20 g, 28.4 mmol), [1 ,1'-bis(diphenylphosphino) EPO <DP n="47"/>ferrocene]dichloro-palladium (II) (1.04 g, 1.28 mmol) and potassium acetate (6.95 g, 70.9 mmol) were added under argon. The mixture was heated at 80 0C overnight and then allowed to cool to room temperature. The solvent was evaporated and the residue was diluted with water and EtOAc. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed twice with 3N HCI and dried over Na2SO4. The solvent was evaporated and the crude product thus obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford the title compound impurified with starting bis(pinacolato)diboron. The product was slurried in hexane, filtered and dried under vacuum to afford 2.41 g of pure material (yield: 65percent). 1H NMR (300 MHz1 CDCI3) δ (TMS): 1.36 (s, 12 H), 2.61 (s, 3 H)1 7.25 (d, J = 8.1 Hz1 1 H), 8.02 (dd, J = 8.1 Hz1 J1 = 2.1 Hz, 1 H)1 8.48 (d, J = 2.1 Hz, 1 H). LC-MS (method 1): tR = 7.57 min; m/z = 261.0 [M-H]".
Reference: [1] Patent: EP2269993, 2011, A1, . Location in patent: Page/Page column 53
[2] Patent: WO2007/339, 2007, A1, . Location in patent: Page/Page column 44-45
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 19, p. 5671 - 5686
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 15, p. 4428 - 4432
[5] Patent: WO2006/104917, 2006, A2, . Location in patent: Page/Page column 78-79
[6] Patent: WO2003/93248, 2003, A1, . Location in patent: Page/Page column 27-28
[7] Patent: US2007/54916, 2007, A1, . Location in patent: Page/Page column 29
[8] Patent: WO2004/10995, 2004, A1, . Location in patent: Page/Page column 27
[9] Patent: WO2006/104915, 2006, A2, . Location in patent: Page/Page column 123
[10] Patent: WO2006/104889, 2006, A2, . Location in patent: Page/Page column 115-116
[11] Patent: WO2007/147104, 2007, A2, . Location in patent: Page/Page column 76
[12] Patent: WO2007/147103, 2007, A2, . Location in patent: Page/Page column 108-109
[13] Patent: WO2007/147109, 2007, A2, . Location in patent: Page/Page column 103-104
  • 14
  • [ 82998-57-0 ]
  • [ 170230-88-3 ]
  • [ 99-94-5 ]
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 2, p. 795 - 809
  • 15
  • [ 82998-57-0 ]
  • [ 882679-40-5 ]
Reference: [1] Patent: WO2014/8197, 2014, A1,
[2] Patent: WO2015/95767, 2015, A1,
Same Skeleton Products
Historical Records

Pharmaceutical Intermediates of
[ 82998-57-0 ]

Ponatinib Related Intermediates

Chemical Structure| 694499-26-8

[ 694499-26-8 ]

4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline

Chemical Structure| 943320-61-4

[ 943320-61-4 ]

3-Ethynylimidazo[1,2-b]pyridazine

Chemical Structure| 42137-88-2

[ 42137-88-2 ]

N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide

Chemical Structure| 1074-82-4

[ 1074-82-4 ]

Potassium 1,3-dioxoisoindolin-2-ide

Chemical Structure| 89976-12-5

[ 89976-12-5 ]

1-Methyl-4-nitro-2-(trifluoromethyl)benzene

Related Functional Groups of
[ 82998-57-0 ]

Aryls

Chemical Structure| 1829-21-6

[ 1829-21-6 ]

2-Iodo-4-methylbenzoic acid

Similarity: 0.96

Chemical Structure| 88-67-5

[ 88-67-5 ]

2-Iodobenzoic acid

Similarity: 0.94

Chemical Structure| 52548-14-8

[ 52548-14-8 ]

2-Iodo-5-methylbenzoic acid

Similarity: 0.94

Chemical Structure| 54811-38-0

[ 54811-38-0 ]

5-Iodo-2-methylbenzoic acid

Similarity: 0.94

Chemical Structure| 91131-72-5

[ 91131-72-5 ]

4-(tert-Butyl)-3-iodobenzoic acid

Similarity: 0.92

Carboxylic Acids

Chemical Structure| 1829-21-6

[ 1829-21-6 ]

2-Iodo-4-methylbenzoic acid

Similarity: 0.96

Chemical Structure| 88-67-5

[ 88-67-5 ]

2-Iodobenzoic acid

Similarity: 0.94

Chemical Structure| 52548-14-8

[ 52548-14-8 ]

2-Iodo-5-methylbenzoic acid

Similarity: 0.94

Chemical Structure| 54811-38-0

[ 54811-38-0 ]

5-Iodo-2-methylbenzoic acid

Similarity: 0.94

Chemical Structure| 91131-72-5

[ 91131-72-5 ]

4-(tert-Butyl)-3-iodobenzoic acid

Similarity: 0.92