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[ CAS No. 7703-74-4 ] {[proInfo.proName]}

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Chemical Structure| 7703-74-4
Chemical Structure| 7703-74-4
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Product Details of [ 7703-74-4 ]

CAS No. :7703-74-4 MDL No. :MFCD00191795
Formula : C7H7Br2N Boiling Point : -
Linear Structure Formula :- InChI Key :QUTSYCOAZVHGGT-UHFFFAOYSA-N
M.W :264.95 Pubchem ID :603610
Synonyms :

Calculated chemistry of [ 7703-74-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.91
TPSA : 12.89 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) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 2.04
Log Po/w (WLOGP) : 2.57
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 3.33
Consensus Log Po/w : 2.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.08
Solubility : 0.22 mg/ml ; 0.000832 mol/l
Class : Soluble
Log S (Ali) : -1.94
Solubility : 3.05 mg/ml ; 0.0115 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -4.54
Solubility : 0.00764 mg/ml ; 0.0000288 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.81

Safety of [ 7703-74-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P310-P321-P330-P332+P313-P362-P403+P233-P405-P501 UN#:1759
Hazard Statements:H302-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7703-74-4 ]

* 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 [ 7703-74-4 ]
  • Downstream synthetic route of [ 7703-74-4 ]

[ 7703-74-4 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 7703-74-4 ]
  • [ 5431-44-7 ]
Reference: [1] Synthesis, 1984, vol. NO. 9, p. 747 - 752
  • 2
  • [ 108-48-5 ]
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  • [ 7703-74-4 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 3830
  • 3
  • [ 108-48-5 ]
  • [ 591-51-5 ]
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  • [ 7703-74-4 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 3830
  • 4
  • [ 1195-59-1 ]
  • [ 7703-74-4 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With hydrogen bromide In water at 125℃;
Stage #2: With sodium hydrogencarbonate In water
Example 15 2,6-Bis(bromomethyl)pyridine. To pyridine-2,6-diyldimethanol (2 g, 14 mmol) was added 60percent HBr (15 mL) slowly. The reaction was heated at 125° C. for 6 h then cooled to room temperature. The resulting residue was dissolved in H2O (50 mL) to give a yellow solution. To this solution was added saturated NaHCO3 to pH 8. The resulting aqueous solution was extracted with CH2Cl2 (4.x.50 mL), and the combined organic layers were dried over Na2SO4. The solvent was removed by rotary evaporation, and the resulting material was purified by flash column chromatography (EtOAc/hexanes, 1:9-1:4) to yield 2,6-bis(bromomethyl)pyridine (3.5 g, 96percent) as a white solid: 1H NMR (500 MHz, CDCl3) δ 4.53 (s, 4H), 7.36-7.38 (d, J=8.0 Hz, 2H), 7.68-7.71 (dd, J=7.5, 8.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 33.8, 123.1, 138.4, 157.0; LC-TOF (M+H+) calcd for C7H8Br2N 263.90235, found 263.90193.
82%
Stage #1: With hydrogen bromide In water for 10 h; Reflux
Stage #2: With sodium hydroxide In water
To a solution of saturated HBr (15 mL) was added pyridine-2,6-diyldimethanol (140 mg, 1 mmol) (5). The reaction mixture was stirred at reflux temperature for 10 h. Then the PH value of solvent is buffered close to 9 by addition of 10percent NaOH. The solvent was taken up in methylene chloride, dried by MgSO4 and evaporated. The product was obtained following purification by silica gel column chromatography as a colorless solid powder 6 (184 mg, yield 82percent).
50% for 15 h; Reflux Compound 7 (2 g, 14.4 mmol) was heated for 15 h in 48percent HBr5solution (20 mL). The solution was cooled with an ice bath and 10 MNaOH was added until pH = 12 was reached. After extraction withCH2Cl2, the organic phase was dried with MgSO4, filtered and the CH2Cl2evaporated to give a white solid. The products were separated by column chromatography to give 1.9 g compound 5 (50 percent). 1H NMR (400 MHz,CDCl3) δ 7.71 (t, J = 7.7 Hz, 1H), 7.37 (d, J = 7.7 Hz, 2H), 4.54 (s, 4H).
12.3 g at 60℃; for 19 h; The 2,6-dimethylolpyridine (10.0g, 71. 9mmol) by adding 250 ml three flasks, constant voltage used in the dropping funnel slowly dropping 48percent of HBr (95 ml) solution dissolved, after maintaining the 60 °C magnetic stirring for 19 hours. After the end of the reaction cooled to the room temperature, and then to continue to use the ice ice salt bath cooling and saturation of the sodium accent carbonate to alkaline. The generated white solid after filtering, washing several times with distilled water, then the n-hexane recrystallization under the room temperature condition, to obtain the colorless transparent acicular crystal (12.3g, 65percent). Mass spectrum: ES - MS (CH3CN), m/z (percent): 266.00 (100) [M + H]+. 2. 6 - dibromo methyl pyridine (B) in acetonitrile electrospray mass spectrum chart of Figure 1.

Reference: [1] Patent: US2010/203613, 2010, A1, . Location in patent: Page/Page column 10
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2039 - 2048
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 47, p. 9601 - 9620
[4] European Journal of Organic Chemistry, 1999, # 9, p. 2373 - 2381
[5] European Journal of Organic Chemistry, 2017, vol. 2017, # 35, p. 5252 - 5261
[6] Tetrahedron Letters, 2008, vol. 49, # 12, p. 1993 - 1996
[7] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000, vol. 55, # 8, p. 723 - 729
[8] Dalton Transactions, 2010, vol. 39, # 38, p. 9055 - 9062
[9] Inorganic Chemistry, 2018, vol. 57, # 10, p. 5939 - 5947
[10] Tetrahedron Letters, 2017, vol. 58, # 10, p. 991 - 994
[11] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 6988 - 6993
[12] Organic and Biomolecular Chemistry, 2012, vol. 10, # 36, p. 7372 - 7381
[13] Tetrahedron, 2009, vol. 65, # 36, p. 7573 - 7579
[14] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9923 - 9931
[15] Molecular Crystals and Liquid Crystals, 2007, vol. 470, # 1, p. 369 - 381
[16] Synthesis, 2008, # 18, p. 2996 - 3008
[17] Journal of Organic Chemistry, 1999, vol. 64, # 11, p. 4191 - 4195
[18] Chemical Communications, 2017, vol. 53, # 22, p. 3189 - 3192
[19] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 9, p. 2237 - 2247
[20] Synthetic Communications, 2011, vol. 41, # 22, p. 3403 - 3408
[21] Asian Journal of Chemistry, 2011, vol. 23, # 6, p. 2411 - 2416
[22] Tetrahedron Letters, 2013, vol. 54, # 43, p. 5771 - 5774
[23] Inorganic Chemistry Communications, 2012, vol. 21, p. 16 - 20
[24] New Journal of Chemistry, 2005, vol. 29, # 1, p. 99 - 108
[25] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009, vol. 72, # 1, p. 198 - 203
[26] Tetrahedron, 2018, vol. 74, # 21, p. 2641 - 2649
[27] Journal of the Chemical Society, 1958, p. 3594,3601
[28] Journal of the American Chemical Society, 1953, vol. 75, p. 3830
[29] Tetrahedron, 1989, vol. 45, # 6, p. 1611 - 1622
[30] Synlett, 1999, # 11, p. 1749 - 1750
[31] Helvetica Chimica Acta, 2008, vol. 91, # 11, p. 2089 - 2096
[32] Dalton Transactions, 2011, vol. 40, # 29, p. 7541 - 7550
[33] Journal of the Chinese Chemical Society, 2013, vol. 60, # 3, p. 245 - 250
[34] Patent: CN106518896, 2017, A, . Location in patent: Paragraph 0047; 0048
  • 5
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YieldReaction ConditionsOperation in experiment
37% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 6 h; Inert atmosphere; Reflux; Irradiation In a separate flask, a mixture of 2,6-bis(methyl)pyridine(3.5 mL, 30 mmol) and N-bromosuccinimide (NBS) (10.70 g, 60.12 mmol) in CCl4 (400mL) was refluxed in the presence of azodiisobutyronitrile (AIBN) (0.15 g, 0.9 mmol) for 6 h under theirritation of 200 W lamp. After being cooled to room temperature, the mixture was filtered and the filtrate was concentrated in vacuo. Purification was achieved by flashed column chromatography using ethyl acetate / petroleum ether = 1 / 10 as eluent. The second band solution was collected, combined and evaporated in vacuo to afford the product as a white crystal (4.5 g, 37percent). 1H NMR (δ, ppm,400 M, CDCl3): 4.55(s, CH2), 7.38 (d, Py, J= 7.76 Hz), 7.72 (q, Py).
Reference: [1] Synthesis, 2001, # 14, p. 2078 - 2080
[2] Journal of Organic Chemistry, 1986, vol. 51, # 6, p. 929 - 931
[3] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 173 - 178
[4] Synthesis, 2009, # 11, p. 1807 - 1810
[5] Inorganica Chimica Acta, 2014, vol. 423, # PA, p. 332 - 339
[6] Russian Journal of Organic Chemistry, 2002, vol. 38, # 4, p. 606 - 608
[7] RSC Advances, 2014, vol. 4, # 106, p. 61790 - 61798
[8] Physical Chemistry Chemical Physics, 2012, vol. 14, # 11, p. 3909 - 3914
  • 6
  • [ 108-48-5 ]
  • [ 96-21-9 ]
  • [ 7703-74-4 ]
YieldReaction ConditionsOperation in experiment
95% With 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 24 h; The 2,6-dimethyl pyridine (0.11g, 10mmol) dissolved in 30mLCCl4in, subsequently to the above-mentioned reaction solution slowly adds by drops two bromine sea UK (5.72g, 20mmol) and AIBN of (164 mg, 1mol percent) CCl4solution. 80 °C reflux reaction under 24h. After the reaction, cooling to room temperature, filtered, the filtrate saturation NaHCO3solution (45 ml × 2), saturated NaCl solution (50 ml) washing, anhydrous MgSO4drying, column chromatography separation (petroleum ether/ethyl acetate = 60:1, V/V), yield 95percent
Reference: [1] Patent: CN105399661, 2016, A, . Location in patent: Paragraph 0037; 0038
  • 7
  • [ 499-83-2 ]
  • [ 7703-74-4 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 3830
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 6988 - 6993
[3] Tetrahedron Letters, 2017, vol. 58, # 10, p. 991 - 994
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9923 - 9931
  • 8
  • [ 1195-59-1 ]
  • [ 7703-74-4 ]
Reference: [1] Patent: US5767276, 1998, A,
  • 9
  • [ 1195-59-1 ]
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  • [ 40054-01-1 ]
Reference: [1] European Journal of Inorganic Chemistry, 2002, # 12, p. 3284 - 3291
[2] Journal of Organic Chemistry, 1990, vol. 55, # 6, p. 1890 - 1901
[3] Tetrahedron Letters, 2008, vol. 49, # 12, p. 1993 - 1996
[4] Synthesis, 2003, # 14, p. 2145 - 2154
  • 10
  • [ 1195-59-1 ]
  • [ 7789-60-8 ]
  • [ 7703-74-4 ]
Reference: [1] Dalton Transactions, 2014, vol. 43, # 35, p. 13399 - 13409
  • 11
  • [ 5453-67-8 ]
  • [ 7703-74-4 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 43, p. 5771 - 5774
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 6988 - 6993
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9923 - 9931
[4] Tetrahedron, 2018, vol. 74, # 21, p. 2641 - 2649
  • 12
  • [ 15658-60-3 ]
  • [ 7703-74-4 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 3830
[2] Tetrahedron Letters, 2017, vol. 58, # 10, p. 991 - 994
  • 13
  • [ 108-48-5 ]
  • [ 68470-59-7 ]
  • [ 7703-74-4 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 3830
  • 14
  • [ 108-48-5 ]
  • [ 591-51-5 ]
  • [ 68470-59-7 ]
  • [ 7703-74-4 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 3830
  • 15
  • [ 122637-39-2 ]
  • [ 7703-74-4 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 43, p. 5771 - 5774
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