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[ CAS No. 624-31-7 ] {[proInfo.proName]}

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Chemical Structure| 624-31-7
Chemical Structure| 624-31-7
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Product Details of [ 624-31-7 ]

CAS No. :624-31-7 MDL No. :MFCD00001059
Formula : C7H7I Boiling Point : -
Linear Structure Formula :- InChI Key :UDHAWRUAECEBHC-UHFFFAOYSA-N
M.W : 218.04 Pubchem ID :12207
Synonyms :

Calculated chemistry of [ 624-31-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.12
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.23
Log Po/w (XLOGP3) : 3.82
Log Po/w (WLOGP) : 2.6
Log Po/w (MLOGP) : 3.53
Log Po/w (SILICOS-IT) : 3.32
Consensus Log Po/w : 3.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.15
Solubility : 0.0153 mg/ml ; 0.0000702 mol/l
Class : Moderately soluble
Log S (Ali) : -3.52
Solubility : 0.0666 mg/ml ; 0.000305 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.74
Solubility : 0.0396 mg/ml ; 0.000182 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.58

Safety of [ 624-31-7 ]

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 [ 624-31-7 ]

* 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 [ 624-31-7 ]
  • Downstream synthetic route of [ 624-31-7 ]

[ 624-31-7 ] Synthesis Path-Upstream   1~34

  • 1
  • [ 108-01-0 ]
  • [ 624-31-7 ]
  • [ 106-44-5 ]
  • [ 51344-14-0 ]
YieldReaction ConditionsOperation in experiment
64% With potassium hydroxide; silver(l) oxide In dimethyl sulfoxide at 100℃; for 24 h; General procedure: To a test tube containing a magnetic rod was added 4-iodotoluene, 1.0 mmol, Cu2O (14.3 mg, 0.1 mmol), KOH (169 mg, 3.0 mmol), 2-dimethylaminoethanol , 0.3 mL, 3.0 mmol) and DMSO / H2O (1.5 mL / 0.5 mL). After flushing with argon, the mixture was stirred at 100 & lt; 0 & gt; C for 24 hours in a preheated oil bath. After cooling to ambient temperature, the reaction mixture was distributed in aqueous HCl (5percent) and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc / n-Hexane) to give phenol.
Reference: [1] Patent: KR2017/91976, 2017, A, . Location in patent: Paragraph 0046; 0047
[2] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 12, p. 2833 - 2840
[3] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 12, p. 2833 - 2840
  • 2
  • [ 624-31-7 ]
  • [ 51628-12-7 ]
YieldReaction ConditionsOperation in experiment
68.9% With N-Bromosuccinimide In tetrachloromethane; water; dimethyl sulfoxide Referential Example 3
Synthesis of 4-iodophenylacetonitrile
A mixture of 4.36 g (20.0 mmol) of p-iodotoluene (purchased from Tokyo Kasei), 3.92 g (22.0 mmol) of N-bromosuccinimide (purchased from Tokyo Kasei) and 60 ml of carbon tetrachloride (purchased from Wako Junyaku Kogyo) was refluxed under irradiation by an incandescent lamp for 4 hours to give 2.67 g (yield: 45.0percent) of 4-iodobenzyl bromide (as a white crystalline).
Subsequently, to a solution of 0.49 g (10.0 mmol) of sodium cyanide (purchased from Kokusan Kagaku) in 10 ml of dimethyl sulfoxide (purchased from Aldrich) heated at 50° C. was added 1.48 g (5.0 mmol) of the above 4-iodobenzyl bromide, the mixture was stirred at ambient temperature for 3 hours, the resultant reaction mass was dissolved in water and extracted with hexane, and hexane was removed to give 0.84 g (yield: 68.9percent) of 4-iodophenylacetonitrile as a white crystalline.
68.9% With N-Bromosuccinimide In tetrachloromethane; water; dimethyl sulfoxide Referential Example 9
Synthesis of 4-iodophenylacetonitrile
A mixture of 4.36 g (20.0 mmol) of p-iodotoluene (purchased from Tokyo Kasei), 3.9 g (22 mmol) of N-bromosuccinimide (purchased from Tokyo Kasei) and 60 ml of carbon tetrachloride (purchased from Wako Junyaku Kogyo) was refluxed under the irradiation by means of an incandescent lamp for 4 hours to give 2.67 g (yield: 45.0percent) of 4-iodobenzyl bromide (as a white crystalline).
Subsequently, to 0.49 g (10 mmol) of sodium cyanide (purchased from Kokusan Kagaku) in 10 ml of dimethyl sulfoxide (purchased from Aldrich) solution heated at 50° C. was added 1.48 g (5.00 mmol) of the above 4-iodobenzyl bromide, the mixture was stirred at ambient temperature for 3 hours, the resultant reaction mass was dissolved in water and extracted with hexane, and hexane was removed to give 0.84 g (yield: 68.9percent) of 4-iodophenylacetonitrile as a white crystalline.
Reference: [1] Patent: US5574062, 1996, A,
[2] Patent: US5574062, 1996, A,
[3] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1114 - 1126
  • 3
  • [ 624-31-7 ]
  • [ 16004-15-2 ]
  • [ 51628-12-7 ]
YieldReaction ConditionsOperation in experiment
45% With N-Bromosuccinimide In tetrachloromethane; water; dimethyl sulfoxide Referential Example 4
[Preparation of 4-Iodophenylacetonitrile]
A mixture of p-iodotoluene (4.36 g, 20 mmol, purchased from Tokyo Kasei) and N-bromosuccinimide (3.92 g, 22 mmol, purchased from Tokyo Kasei) in 60 ml of carbontetrachloride (purchased from Wako Junyaku Kogyo) was refluxed for 4 hours under irradiation by means of an incandescent lamp to give 2.67 g (yield: 45.0percent) of 4-iodobenzyl bromide as a white crystalline.
To a hot solution (50° C.) of sodium cyanide 0.49 g, 10.0 mmom, purchased from Kokusan Kagaku) in 10 ml of dimethyl sulfoxide (purchased from Aldrich) was added the above 4-iodobenzyl bromide (1.48 g, 5.0 mmol) and the mixture was stirred for three hours at ambient temperature.
To the resultant reaction mass was added water and extracted with hexane.
The solvent was removed to give 0.84 g (yield: 69percent) of 4-iodophenylacetonitrile as a white crystalline.
Reference: [1] Patent: US5589506, 1996, A,
[2] Patent: US5589506, 1996, A,
  • 4
  • [ 624-31-7 ]
  • [ 107-21-1 ]
  • [ 106-44-5 ]
  • [ 15149-10-7 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 12, p. 2833 - 2840
[2] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 12, p. 2833 - 2840
  • 5
  • [ 109-72-8 ]
  • [ 201230-82-2 ]
  • [ 624-31-7 ]
  • [ 1671-77-8 ]
  • [ 19277-56-6 ]
Reference: [1] Organic Letters, 2003, vol. 5, # 7, p. 1103 - 1106
  • 6
  • [ 109-72-8 ]
  • [ 201230-82-2 ]
  • [ 624-31-7 ]
  • [ 1595-05-7 ]
  • [ 1671-77-8 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 14, p. 4852 - 4855
  • 7
  • [ 110-62-3 ]
  • [ 624-31-7 ]
  • [ 1671-77-8 ]
Reference: [1] Applied Organometallic Chemistry, 2018, vol. 32, # 2,
  • 8
  • [ 624-31-7 ]
  • [ 40400-13-3 ]
Reference: [1] Patent: EP2351563, 2011, A1,
  • 9
  • [ 624-31-7 ]
  • [ 16004-15-2 ]
YieldReaction ConditionsOperation in experiment
60.3% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 7 h; Heating / reflux; Photolysis Synthesis of Compound 1D [0026] p-Iodotoluene (Compound 1C, 25 g), N-bromosuccinimide (23.5 g) and benzoyl peroxide (375 mg) were added to carbon tetrachloride (375 ml) and refluxed with heating for 7 hours under photoirradiation. Further, the reaction mixture was stirred overnight at room temperature, then insoluble matters were removed by filtration, and the filtrate was concentrated under reduced pressure. The concentrated residue was recrystallized from ethyl acetate and hexane to obtain Compound 1D (yield: 60.3percent). [0027] NMR chemical shift, CDCl3, TMS as standard [0028] d 7.72 (d, 2H), 7.14 (d, 2H), 4.39 (s, 2H)
Reference: [1] Macromolecules, 2013, vol. 46, # 12, p. 4754 - 4763
[2] Acta Crystallographica Section C: Crystal Structure Communications, 2003, vol. 59, # 4, p. o216-o218
[3] Journal of Materials Chemistry C, 2015, vol. 3, # 4, p. 734 - 741
[4] Chemistry - An Asian Journal, 2017, vol. 12, # 6, p. 690 - 697
[5] Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 223 - 229
[6] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1114 - 1126
[7] Tetrahedron, 2003, vol. 59, # 7, p. 1021 - 1032
[8] Angewandte Chemie - International Edition, 2018, vol. 57, # 3, p. 800 - 804[9] Angew. Chem., 2018, vol. 57, # 3, p. 800 - 804,5
[10] Patent: US2004/228793, 2004, A1, . Location in patent: Page/Page column 4
[11] Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 1057 - 1062
[12] Chemistry - A European Journal, 2012, vol. 18, # 23, p. 7229 - 7242
[13] Journal of the Chemical Society, 1949, p. 1089,1096
[14] Chem. Penicillin, <Princeton 1949>, S. 94,
[15] Journal of the American Chemical Society, 1948, vol. 70, p. 2310,2313
[16] American Chemical Journal, 1880, vol. 2, p. 250
[17] American Chemical Journal, 1879, vol. 1, p. 103
[18] Chemische Berichte, 1878, vol. 11, p. 55
[19] American Chemical Journal, 1908, vol. 40, p. 466
[20] Recueil des Travaux Chimiques des Pays-Bas, 1923, vol. 42, p. 522
[21] Journal of the American Chemical Society, 1949, vol. 71, p. 3360
[22] Journal of Organic Chemistry, 1949, vol. 14, p. 228,232
[23] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 43 - 67
[24] Tetrahedron Letters, 1994, vol. 35, # 3, p. 481 - 484
[25] Journal of the American Chemical Society, 2001, vol. 123, # 5, p. 946 - 953
[26] Advanced Synthesis and Catalysis, 2004, vol. 346, # 7, p. 767 - 776
[27] Patent: EP1647546, 2006, A1, . Location in patent: Page/Page column 54
[28] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197
[29] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410
  • 10
  • [ 624-31-7 ]
  • [ 34241-39-9 ]
  • [ 16004-15-2 ]
YieldReaction ConditionsOperation in experiment
45% With N-Bromosuccinimide In tetrachloromethane Step 1
4-Iodobenzyl bromide
A mixture of 4-iodotoluene (21.8 g, 100 mmol), N-bromosuccinimide (18.69 g, 105 mmol) and αα-azobisisobutyronitrile (100 mg) in carbon tetrachloride (100 ml) was refluxed for 20 hours.
The reaction was cooled, the precipitate filtered, washed with carbon tetrachloride (50 ml), and the filtrate evaporated.
The residue was chromatographed on silica, eluding with petrol (60°-80° C.) to give the product as a white solid (13 g, 45percent); δH (CDCl3) 4.42 (2H, ArCH2 Br), 7.11 (2H, d, J 15.3 Hz, 2-H, 6-H), 7.67 (2H, d, J 15.3 Hz, 3'-H, 5'-H).
Reference: [1] Patent: US5861407, 1999, A,
  • 11
  • [ 624-31-7 ]
  • [ 34241-39-9 ]
  • [ 16004-15-2 ]
Reference: [1] Patent: US5965738, 1999, A,
  • 12
  • [ 624-31-7 ]
  • [ 99-99-0 ]
  • [ 5326-39-6 ]
  • [ 41252-97-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1281 - 1286
  • 13
  • [ 624-31-7 ]
  • [ 99-99-0 ]
  • [ 1608-47-5 ]
  • [ 32704-08-8 ]
  • [ 32704-10-2 ]
  • [ 5326-39-6 ]
  • [ 41252-97-5 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 11, p. 2029 - 2035[2] Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 11, p. 2251 - 2258
  • 14
  • [ 869373-61-5 ]
  • [ 624-31-7 ]
  • [ 5458-84-4 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 9, p. 1654 - 1658
  • 15
  • [ 624-31-7 ]
  • [ 26670-89-3 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 1410
  • 16
  • [ 624-31-7 ]
  • [ 99-99-0 ]
  • [ 5326-39-6 ]
  • [ 41252-97-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1281 - 1286
  • 17
  • [ 624-31-7 ]
  • [ 41252-97-5 ]
Reference: [1] Chemische Berichte, 1897, vol. 30, p. 3001
  • 18
  • [ 624-31-7 ]
  • [ 99-99-0 ]
  • [ 1608-47-5 ]
  • [ 32704-08-8 ]
  • [ 32704-10-2 ]
  • [ 5326-39-6 ]
  • [ 41252-97-5 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 11, p. 2029 - 2035[2] Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 11, p. 2251 - 2258
  • 19
  • [ 624-31-7 ]
  • [ 42906-19-4 ]
Reference: [1] Dyes and Pigments, 2011, vol. 88, # 3, p. 333 - 343
[2] Dyes and Pigments, 2017, vol. 140, p. 431 - 440
  • 20
  • [ 624-31-7 ]
  • [ 62-53-3 ]
  • [ 20440-95-3 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 52, p. 9275 - 9278
[2] Journal of Organic Chemistry, 1999, vol. 64, # 2, p. 670 - 674
[3] Inorganic Chemistry Communications, 2011, vol. 14, # 9, p. 1352 - 1357
[4] Dyes and Pigments, 2011, vol. 88, # 3, p. 333 - 343
[5] Dyes and Pigments, 2017, vol. 140, p. 431 - 440
  • 21
  • [ 66-71-7 ]
  • [ 624-31-7 ]
  • [ 20440-95-3 ]
Reference: [1] Patent: US5648542, 1997, A,
  • 22
  • [ 624-31-7 ]
  • [ 620-84-8 ]
  • [ 20440-95-3 ]
Reference: [1] Russian Journal of Organic Chemistry, 1997, vol. 33, # 8, p. 1100 - 1102
  • 23
  • [ 624-31-7 ]
  • [ 620-84-8 ]
  • [ 4316-53-4 ]
  • [ 20440-95-3 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 9, p. 2716 - 2723
  • 24
  • [ 624-31-7 ]
  • [ 620-84-8 ]
  • [ 122-39-4 ]
  • [ 4316-53-4 ]
  • [ 20440-95-3 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 9, p. 2716 - 2723
  • 25
  • [ 624-31-7 ]
  • [ 106-40-1 ]
  • [ 58047-42-0 ]
Reference: [1] New Journal of Chemistry, 2015, vol. 39, # 3, p. 1840 - 1851
[2] RSC Advances, 2015, vol. 5, # 37, p. 28879 - 28884
[3] Journal of Organic Chemistry, 1999, vol. 64, # 2, p. 670 - 674
[4] RSC Advances, 2014, vol. 4, # 32, p. 16385 - 16390
[5] Journal of Materials Chemistry A, 2013, vol. 1, # 23, p. 6949 - 6960
[6] Patent: CN103601757, 2016, B, . Location in patent: Page/Page column 13
  • 26
  • [ 624-31-7 ]
  • [ 3366-72-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1973, p. 25 - 33
  • 27
  • [ 624-31-7 ]
  • [ 637-60-5 ]
Reference: [1] Chinese Journal of Chemistry, 2018, vol. 36, # 11, p. 1003 - 1006
[2] RSC Advances, 2014, vol. 4, # 7, p. 3364 - 3367
  • 28
  • [ 201230-82-2 ]
  • [ 624-31-7 ]
  • [ 6638-79-5 ]
  • [ 122334-36-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 57, p. 30019 - 30027
[2] Chemistry - A European Journal, 2014, vol. 20, # 20, p. 5885 - 5889
  • 29
  • [ 624-31-7 ]
  • [ 124750-53-4 ]
Reference: [1] Farmaco, 1997, vol. 52, # 3, p. 147 - 155
  • 30
  • [ 624-31-7 ]
  • [ 1991-87-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1506 - 1509[2] Angew. Chem., 2017, vol. 129, # 6, p. 1528 - 1531,4
  • 31
  • [ 52670-38-9 ]
  • [ 624-31-7 ]
  • [ 124643-45-4 ]
Reference: [1] Dalton Transactions, 2012, vol. 41, # 39, p. 12259 - 12269
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 16, p. 4652 - 4656
  • 32
  • [ 624-31-7 ]
  • [ 23432-40-8 ]
Reference: [1] Australian Journal of Chemistry, 2011, vol. 64, # 4, p. 454 - 470
  • 33
  • [ 624-31-7 ]
  • [ 38846-64-9 ]
  • [ 189008-33-1 ]
YieldReaction ConditionsOperation in experiment
71% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 80℃; for 1 h; Inert atmosphere General procedure: A mixture of 2-ethynylbenzaldehyde (12a) (1.00 g, 7.68 mmol), 1-bromo-2-iodo-benzene (13a) (1.18 mL, 9.22 mmol), CuI (146 mg, 0.77 mmol), PdCl2(PPh3)2 (107 mg, 0.15 mmol), and Et3N (15 mL) in THF (15 mL) was stirred at 80 °C for 2 h under argon, and filtrated through a pad of Celite. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography over silica gel with hexane-EtOAc (15:1).
Reference: [1] Chemistry - A European Journal, 1997, vol. 3, # 5, p. 807 - 816
[2] Chemical Communications, 2012, vol. 48, # 61, p. 7634 - 7636
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 36, p. 10928 - 10932[4] Angew. Chem., 2017, vol. 129, # 36, p. 11068 - 11072,5
[5] Tetrahedron, 2011, vol. 67, # 29, p. 5168 - 5175
  • 34
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  • [ 138500-85-3 ]
Reference: [1] Dalton Transactions, 2016, vol. 45, # 35, p. 13726 - 13741
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