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[ CAS No. 90-14-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 90-14-2
Chemical Structure| 90-14-2
Structure of 90-14-2 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 90-14-2 ]

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Product Details of [ 90-14-2 ]

CAS No. :90-14-2 MDL No. :MFCD00003876
Formula : C10H7I Boiling Point : -
Linear Structure Formula :- InChI Key :NHPPIJMARIVBGU-UHFFFAOYSA-N
M.W : 254.07 Pubchem ID :7004
Synonyms :

Calculated chemistry of [ 90-14-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.67
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 4.16
Log Po/w (WLOGP) : 3.44
Log Po/w (MLOGP) : 4.18
Log Po/w (SILICOS-IT) : 3.99
Consensus Log Po/w : 3.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.71
Solubility : 0.00497 mg/ml ; 0.0000196 mol/l
Class : Moderately soluble
Log S (Ali) : -3.87
Solubility : 0.0344 mg/ml ; 0.000136 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.03
Solubility : 0.00239 mg/ml ; 0.0000094 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.34

Safety of [ 90-14-2 ]

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 [ 90-14-2 ]

* 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 [ 90-14-2 ]
  • Downstream synthetic route of [ 90-14-2 ]

[ 90-14-2 ] Synthesis Path-Upstream   1~39

  • 1
  • [ 201230-82-2 ]
  • [ 90-14-2 ]
  • [ 879-18-5 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 45, p. 16841 - 16844
  • 2
  • [ 90-14-2 ]
  • [ 122-04-3 ]
  • [ 636-98-6 ]
  • [ 879-18-5 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 32, p. 10140 - 10144
  • 3
  • [ 90-14-2 ]
  • [ 100-20-9 ]
  • [ 1711-02-0 ]
  • [ 879-18-5 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 32, p. 10140 - 10144
  • 4
  • [ 90-14-2 ]
  • [ 86-74-8 ]
  • [ 22034-43-1 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 2, p. 559 - 568
[2] Organic Letters, 2015, vol. 17, # 14, p. 3640 - 3642
  • 5
  • [ 13922-41-3 ]
  • [ 90-14-2 ]
YieldReaction ConditionsOperation in experiment
89% With 1,10-Phenanthroline; oxygen; potassium iodide; copper(ll) bromide In N,N-dimethyl-formamide at 80℃; for 20 h; General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol percent), 1,10-phen (7.2 mg, 20 mol percent) and DMF (2 mL). The mixture was stirred at 80 or 130 °C. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.
87% With iodine; potassium carbonate In acetonitrile at 80℃; for 9 h; Inert atmosphere; Schlenk technique; Sealed tube General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8–12 h. The resulting solution was cooled to r.t. and H2O(10 mL) was added. The aq layer was extracted with EtOAc (3 × 5 mL). For products 2s and 2t, HCl (1 M) was added tothe aq solution until pH 2 before extraction. The combinedorganic phase was dried over anhydrous Na2SO4, filteredand concentrated by rotary evaporation. Purification of theresidue by column chromatography on silica gel providedthe desired product 2a–v
86% With perfluoroisopropyl iodide; copper; hydroquinone In N,N-dimethyl-formamide at 20℃; for 24 h; General procedure: (4-Nitrophenyl)boronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol,), (CF3)2CFI (0.178 g, 0.6 mmol), and DMF (2 mL) were placed in a closed tube with a rubber stopper. The mixture was reacted at room temperature equipped with an air balloon for 24 h. The resulting suspension was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness. The crude product was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate = 20: 1 (v/v) as eluent to give 0.086 g of 2j as a light yellow solid (0.35 mmol, 87percent).
85% With copper(II) nitrate trihydrate; iodine In acetonitrile at 20℃; for 6 h; Sealed tube General procedure: 0.05 mmol Cu(NO3)2·3H2O, 1 mmol I2, 1 mmol arylboronic acids and 0.8 mL acetonitrile were added into an about 15 mL tube. Subsequently, the reaction tube was sealed to perform the reaction for 6 h without inert gas protection. Once the reaction time was reached, 10 mL water was added. The mixture was then extracted with dichloromethane (3 x 15 mL). The combined organic layers were washed with aqueous sodium hyposulfite, distilled water, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography and identified by 1H NMR, 13C NMR or GC-MS data.

Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1993 - 1995
[2] Synlett, 2014, vol. 25, # 7, p. 995 - 1000
[3] Journal of Fluorine Chemistry, 2016, vol. 189, p. 59 - 67
[4] Chemistry - A European Journal, 2011, vol. 17, # 20, p. 5652 - 5660
[5] Catalysis Communications, 2013, vol. 32, p. 15 - 17
  • 6
  • [ 90-11-9 ]
  • [ 90-14-2 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere
Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃; for 0.25 h; Inert atmosphere
General procedure: Aryl bromide (10 mmol) was dissolved in dry THF (30 mL) and cooled to -78 °C under anargon atmosphere. n-Butyllithium (1.6 M in n-hexane; 7.5 mL; 12 mmol) was addeddropwise. After 15 minutes a solution of I2 (3.81 g; 15 mmol) in dry THF (10 mL) was addedand the reaction mixture was allowed to warm to room temperature overnight.For workup the reaction mixture was concentrated in vacuo. H2O was added to the residueand it was extracted with DCM (3x). The combined organic phases were washed withsaturated Na2S2O5 solution and H2O. After drying over MgSO4 and concentration underreduced pressure, the crude product was purified by column chromatography.
92 %Chromat. With copper(I) oxide; <i>L</i>-proline; potassium iodide In ethanol at 110℃; for 30 h; Schlenk technique; Inert atmosphere; Sealed tube General procedure: A Schlenk tube was charged with Cu2O (7.2 mg, 10 molpercent), l-proline (11.5 mg, 20 molpercent), aryl (or heteroaryl) bromide (1 or 3,0.50 mmol), potassium iodide (KI) (249 mg, 0.75 mmol), and EtOH(1.5 mL) under nitrogen atmosphere. The Schlenk tube was sealedwith a teflon valve, and then the reaction mixture was stirred at110C for a period (the reaction progress was monitored by GCanalysis). After the reaction was completed, GC yield of high volatileproduct was determined using an appropriate internal standard(chlorobenzene or 1-chloro-4-methylbenzene) or the solvent wasremoved under reduced pressure. The residue obtained was puri-fied via silica gel chromatography (eluent: petroleum ether/ethylacetate = 10/1) to afford aryl iodides 2a–2o or heteroaryl iodides4a–4g.
Reference: [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1499 - 1503
[2] Synlett, 2013, vol. 24, # 20, p. 2730 - 2734
[3] Synthetic Communications, 2012, vol. 42, # 2, p. 170 - 175
[4] Journal of the American Chemical Society, 2015, vol. 137, # 26, p. 8328 - 8331
[5] Catalysis Today, 2016, vol. 274, p. 129 - 132
[6] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 2110 - 2117
  • 7
  • [ 166328-07-0 ]
  • [ 90-14-2 ]
YieldReaction ConditionsOperation in experiment
66% With caesium tribromide In water; N,N-dimethyl-formamide at 80℃; for 3 h; General procedure: To a solution of trifluoroborate (1 mmol) in 3 mL of aqueous DMF (2:1 v/v), cesium triiodide (1 mmol) was added. The mixture was stirred at 80 °C for the appropriate time (Table 3) and then diluted with 10 mL of ether. The aqueous layer was extracted twice with ether (5 mL) and the combined organic phase was dried over anhydrous Na2SO4. After evaporation of the solvent the residue was purified by silica gel column chromatography [elute: hexane (or pentane)-ethyl acetate (or Et2O)].
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 2, p. 343 - 345
[2] Tetrahedron, 2012, vol. 68, # 19, p. 3738 - 3743
  • 8
  • [ 91-20-3 ]
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Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3548 - 3553
[2] Journal of Chemical Research, 2006, # 9, p. 575 - 576
[3] Synlett, 1998, # 3, p. 286 - 288
[4] Advanced Synthesis and Catalysis, 2005, vol. 347, # 15, p. 1925 - 1928
[5] Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2058 - 2060
[6] Synthetic Communications, 2004, vol. 34, # 15, p. 2829 - 2833
[7] Synlett, 1998, # 5, p. 534 - 536
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[9] Russian Chemical Bulletin, 2001, vol. 50, # 12, p. 2411 - 2415
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[11] Tetrahedron Letters, 1986, vol. 27, # 20, p. 2207 - 2210
[12] Journal of the Chemical Society, 1952, p. 150,152
[13] Journal of the Indian Chemical Society, 1933, vol. 10, p. 595,597
[14] Chemische Berichte, 1932, vol. 65, p. 395,399[15] Chemische Berichte, 1933, vol. 66, p. 1280,1284
[16] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 9, p. 2847 - 2848
[17] Acta Chemica Scandinavica, 1989, vol. 43, # 5, p. 481 - 484
[18] Journal of Organic Chemistry, 2003, vol. 68, # 24, p. 9510 - 9512
  • 9
  • [ 134-32-7 ]
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Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 22, p. 3167 - 3168
[2] Canadian Journal of Chemistry, 2005, vol. 83, # 3, p. 213 - 219
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 6, p. 1846 - 1850[4] Angew. Chem., 2015, vol. 127, # 6, p. 1866 - 1870,5
  • 10
  • [ 879-18-5 ]
  • [ 90-14-2 ]
Reference: [1] Nature Chemistry, 2018, vol. 10, # 10, p. 1016 - 1022
[2] Tetrahedron, 1987, vol. 43, # 19, p. 4321 - 4328
  • 11
  • [ 21792-52-9 ]
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Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 25, p. 10482 - 10487
[2] Journal of Organic Chemistry, 2005, vol. 70, # 25, p. 10482 - 10487
  • 12
  • [ 86-55-5 ]
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Reference: [1] Synthetic Communications, 1988, vol. 18, # 12, p. 1327 - 1330
[2] Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11527 - 11536
[3] Tetrahedron, 1987, vol. 43, # 19, p. 4321 - 4328
  • 13
  • [ 85-47-2 ]
  • [ 90-14-2 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 45, p. 5950 - 5953
  • 14
  • [ 99747-74-7 ]
  • [ 90-14-2 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 25, p. 8621 - 8627
  • 15
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  • [ 86-57-7 ]
  • [ 90-14-2 ]
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  • 16
  • [ 86-55-5 ]
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  • [ 90-14-2 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11527 - 11536
  • 17
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Reference: [1] Bulletin of the Chemical Society of Japan, 1993, vol. 66, # 7, p. 2121 - 2123
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  • 18
  • [ 1730-04-7 ]
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  • [ 569-41-5 ]
  • [ 90-12-0 ]
  • [ 199111-38-1 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8681 - 8686
  • 19
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  • [ 612-55-5 ]
  • [ 90-14-2 ]
Reference: [1] Russian Journal of Organic Chemistry, 2005, vol. 41, # 6, p. 855 - 859
[2] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938
  • 20
  • [ 16176-22-0 ]
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 37, p. 12073 - 12076
  • 21
  • [ 98978-44-0 ]
  • [ 90-14-2 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 37, p. 12073 - 12076
  • 22
  • [ 110055-84-0 ]
  • [ 64-19-7 ]
  • [ 90-14-2 ]
  • [ 7782-50-5 ]
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[2] Journal of the American Chemical Society, 1959, vol. 81, p. 2374,2376
[3] Journal of the American Chemical Society, 1959, vol. 81, p. 2374,2376
[4] Journal of the American Chemical Society, 1959, vol. 81, p. 2374,2376
  • 23
  • [ 1576-35-8 ]
  • [ 149512-01-6 ]
  • [ 119-64-2 ]
  • [ 90-14-2 ]
  • [ 103-19-5 ]
  • [ 52258-16-9 ]
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  • 24
  • [ 607-51-2 ]
  • [ 90-14-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1868, vol. 147, p. 173
  • 25
  • [ 91-20-3 ]
  • [ 612-55-5 ]
  • [ 90-14-2 ]
  • [ 36316-88-8 ]
Reference: [1] Journal of Catalysis, 1994, vol. 147, # 1, p. 186 - 198
[2] Journal of Catalysis, 1994, vol. 147, # 1, p. 186 - 198
  • 26
  • [ 91-20-3 ]
  • [ 108-67-8 ]
  • [ 2100-25-6 ]
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  • [ 22187-05-9 ]
  • [ 90-14-2 ]
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  • 27
  • [ 624-74-8 ]
  • [ 703-55-9 ]
  • [ 90-14-2 ]
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  • 28
  • [ 1730-04-7 ]
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  • [ 90-14-2 ]
  • [ 162132-31-2 ]
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  • 29
  • [ 91-20-3 ]
  • [ 90-14-2 ]
  • [ 90-13-1 ]
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  • 30
  • [ 7790-99-0 ]
  • [ 66172-96-1 ]
  • [ 90-14-2 ]
  • [ 5153-28-6 ]
Reference: [1] Journal of the Chemical Society, 1921, vol. 119, p. 913 - 926
[2] , Gmelin Handbook: Bi: Org.Verb., 1.3.3.2.5, page 80 - 82,
  • 31
  • [ 1950-78-3 ]
  • [ 91-20-3 ]
  • [ 90-14-2 ]
  • [ 2943-42-2 ]
  • [ 104-15-4 ]
  • [ 108-88-3 ]
  • [ 71-43-2 ]
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  • 32
  • [ 30365-83-4 ]
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  • [ 88-89-1 ]
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  • 33
  • [ 506-78-5 ]
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  • [ 90-14-2 ]
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  • 34
  • [ 60-29-7 ]
  • [ 67-66-3 ]
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  • [ 90-14-2 ]
  • [ 5153-28-6 ]
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  • 35
  • [ 90-14-2 ]
  • [ 100-51-6 ]
  • [ 607-58-9 ]
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  • 36
  • [ 90-14-2 ]
  • [ 607-58-9 ]
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  • 37
  • [ 90-14-2 ]
  • [ 112239-00-6 ]
  • [ 20246-81-5 ]
  • [ 200880-14-4 ]
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  • 38
  • [ 90-14-2 ]
  • [ 87808-49-9 ]
  • [ 93012-36-3 ]
  • [ 116495-70-6 ]
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  • 39
  • [ 589-87-7 ]
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  • [ 604-53-5 ]
  • [ 92-86-4 ]
  • [ 204530-94-9 ]
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