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[ CAS No. 589-17-3 ] {[proInfo.proName]}

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Chemical Structure| 589-17-3
Chemical Structure| 589-17-3
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Product Details of [ 589-17-3 ]

CAS No. :589-17-3 MDL No. :MFCD00040867
Formula : C7H6BrCl Boiling Point : -
Linear Structure Formula :- InChI Key :BSIIGUGKOPPTPZ-UHFFFAOYSA-N
M.W : 205.48 Pubchem ID :68528
Synonyms :

Calculated chemistry of [ 589-17-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.9
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -5.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.27
Log Po/w (XLOGP3) : 3.24
Log Po/w (WLOGP) : 3.04
Log Po/w (MLOGP) : 3.68
Log Po/w (SILICOS-IT) : 3.49
Consensus Log Po/w : 3.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.58
Solubility : 0.0537 mg/ml ; 0.000262 mol/l
Class : Soluble
Log S (Ali) : -2.91
Solubility : 0.251 mg/ml ; 0.00122 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.28
Solubility : 0.0109 mg/ml ; 0.000053 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 589-17-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 589-17-3 ]

* 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 [ 589-17-3 ]
  • Downstream synthetic route of [ 589-17-3 ]

[ 589-17-3 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 873-75-6 ]
  • [ 589-17-3 ]
YieldReaction ConditionsOperation in experiment
98% With oxalyl dichloride In dichloromethane at 20℃; Reflux General procedure: To 16 (0.6 g, 0.6 mmol) was added dichloromethane (5 mL) in a round-bottom flask. After 10 min, oxalyl chlorideor oxalyl bromide was added (0.6 mmol). The reaction mixture was magnetically stirred at room temperature. Uponcessation of gas evolution, 4 was added (0.5 mmol), and the reaction mixture was heated to reflux. After thereaction was complete according to TLC analysis, the mixture was cooled to room temperature and filtered. Thesolid on the funnel was washed with dichloromethane (3 × 10 mL), and the filtrate was concentrated under reducedpressure to afford the desired product 5 in an essentially pure state based on 1H and 13C NMR spectroscopicanalyses.
81.6% With dmap; thionyl chloride In dichloromethane at 20℃; for 0.166667 h; Cooling with ice [0193] To a solution of (4-bromo-phenyl)-methanol (19.0 g, 0.1015 mol) in dichloromethane (190 mL) was added thionyl chloride (18.89 mL 0.2539 mol) slowly at ice temperature and catalytic DMAP. Resulting reaction mass was stirred at room temperature for 10 minutes. Reaction mass was concentrated, diluted with ethyl acetate (500 mL) and washed with sodium bicarbonate solution (200 mL) , Organic layer was washed with water (2 x 200 mL) , dried over anhydrous sodium sulphate and filtered . Volatiles were concentrated under reduced pressure to obtain the product as pale yellow liquid (17.0 g, 81.6 percent).
80% With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane for 1.08333 h; Thionyl chloride (121 J..LL, 1.67 mmol) was added to benzotriazole (239 mg, 2.0 mmol).The resulting solution was dissolved in CHzClz (5 mL). After 5 min, this solution wasadded slowly to the solution of the alcohol 9a in CHzClz (10 mL). The benzotriazole saltstarted to precipitate. After 1h of reaction, the salt was filtered. The organic phase waswashed by water and NaOH solution (0.5 M). The organic phase was dried over MgS04and the solvent was removed under reduced pressure to give the desired chlorinatedcompound as a yellow oil (m = 220 mg, 80 percent). 1H NMR (300 MHz, CDCh): 8 (ppm) 4.91(dd, J = 12.0, 30.8 Hz, 2H), 7.18 (d, J = 8.0 Hz, 2H), 7.49 (d, J = 7.9 Hz, 2H).
Reference: [1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1397 - 1405
[2] Organic Letters, 2013, vol. 15, # 1, p. 108 - 111
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 24, p. 4016 - 4024
[4] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 11, p. 3434 - 3436
[5] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[6] Patent: WO2015/95821, 2015, A1, . Location in patent: Paragraph 0193
[7] Patent: WO2017/134188, 2017, A1, . Location in patent: Page/Page column 61
[8] Molecules, 2011, vol. 16, # 7, p. 5665 - 5673
[9] Journal of the Chemical Society, 1935, p. 1815,1818
[10] Journal of the American Chemical Society, 1951, vol. 73, p. 2813,2818
[11] Gazzetta Chimica Italiana, 1888, vol. 18, p. 239
[12] Canadian Journal of Chemistry, 1983, vol. 61, p. 1472 - 1480
[13] Tetrahedron Letters, 2014, vol. 55, # 19, p. 3045 - 3048
[14] Chemical Communications, 2017, vol. 53, # 54, p. 7545 - 7548
  • 2
  • [ 106-38-7 ]
  • [ 589-17-3 ]
YieldReaction ConditionsOperation in experiment
75% With N-chloro-succinimide; tetrachlorosilane In acetonitrile at 60 - 70℃; for 8 h; General procedure: To a mixture of NXS and substrate (1 or 6) in CH3CN at room temperature was added SiCl4 and the mixture left to stir until TLC showed the disappearance of the starting material. The reaction was then poured onto H2O and the mixture extracted with CH2Cl2. The extracts were combined, dried over MgSO4 and evaporated. The residue was purified by recrystallization (pet. ether-Et2O, 3:1) to give pure 2b-2g, 3b, or by silica gel column chromatography (hexane-EtOAc 10:1 or 30:1) to give pure 2a,h,i, 3a-5 or 7-9, respectively
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4026 - 4029
[2] Recueil des Travaux Chimiques des Pays-Bas, 1904, vol. 23, p. 101[3] Recueil des Travaux Chimiques des Pays-Bas, 1905, vol. 24, p. 2
[4] Bulletin de la Societe Chimique de France, 1927, vol. <4> 41, p. 331
[5] Journal of the Chemical Society, 1935, p. 1815,1818
[6] Monatshefte fuer Chemie, 1934, vol. 64, p. 153,157
[7] Bulletin de la Societe Chimique de France, 1951, p. 250,253
[8] Journal of the American Chemical Society, 1951, vol. 73, p. 2940
[9] Recueil des Travaux Chimiques des Pays-Bas, 1904, vol. 23, p. 101[10] Recueil des Travaux Chimiques des Pays-Bas, 1905, vol. 24, p. 2
  • 3
  • [ 24856-58-4 ]
  • [ 589-17-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 4, p. 1410 - 1412
  • 4
  • [ 1122-91-4 ]
  • [ 589-17-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 1, p. 108 - 111
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 24, p. 4016 - 4024
[3] Patent: WO2015/95821, 2015, A1,
[4] Chemical Communications, 2017, vol. 53, # 54, p. 7545 - 7548
[5] Patent: WO2017/134188, 2017, A1,
  • 5
  • [ 106-38-7 ]
  • [ 586-76-5 ]
  • [ 589-17-3 ]
Reference: [1] Synthetic Communications, 1999, vol. 29, # 13, p. 2211 - 2216
  • 6
  • [ 589-15-1 ]
  • [ 589-17-3 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 1, p. 55 - 56
[2] Gazzetta Chimica Italiana, 1888, vol. 18, p. 239
  • 7
  • [ 586-76-5 ]
  • [ 589-17-3 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2813,2818
  • 8
  • [ 100-44-7 ]
  • [ 589-17-3 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2813,2818
[2] Journal of the Chemical Society, 1934, p. 161,164
  • 9
  • [ 106-38-7 ]
  • [ 106-43-4 ]
  • [ 67627-98-9 ]
  • [ 589-17-3 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 15, p. 2881 - 2888
  • 10
  • [ 873-75-6 ]
  • [ 1609172-81-7 ]
  • [ 589-17-3 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 19, p. 3045 - 3048
  • 11
  • [ 106-38-7 ]
  • [ 106-43-4 ]
  • [ 104-83-6 ]
  • [ 622-95-7 ]
  • [ 589-17-3 ]
Reference: [1] Monatshefte fur Chemie, 1999, vol. 130, # 12, p. 1493 - 1497
  • 12
  • [ 106-38-7 ]
  • [ 106-43-4 ]
  • [ 104-83-6 ]
  • [ 589-15-1 ]
  • [ 589-17-3 ]
Reference: [1] Monatshefte fur Chemie, 1999, vol. 130, # 12, p. 1493 - 1497
  • 13
  • [ 108-86-1 ]
  • [ 542-88-1 ]
  • [ 1941-86-2 ]
  • [ 589-17-3 ]
Reference: [1] Journal of the Chemical Society, 1920, vol. 117, p. 525
[2] Journal of the Chemical Society, 1920, vol. 117, p. 525
  • 14
  • [ 50-00-0 ]
  • [ 108-86-1 ]
  • [ 578-51-8 ]
  • [ 589-17-3 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1927, vol. <4> 41, p. 331
  • 15
  • [ 7791-25-5 ]
  • [ 106-38-7 ]
  • [ 94-36-0 ]
  • [ 106-43-4 ]
  • [ 104-83-6 ]
  • [ 589-15-1 ]
  • [ 589-17-3 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2940
  • 16
  • [ 50-00-0 ]
  • [ 108-86-1 ]
  • [ 589-17-3 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 1485 - 1487[2] Zhurnal Organicheskoi Khimii, 1971, vol. 7, # 7, p. 1436 - 1438
  • 17
  • [ 10026-13-8 ]
  • [ 589-17-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1926, vol. 449, p. 264
  • 18
  • [ 106-38-7 ]
  • [ 7782-50-5 ]
  • [ 589-17-3 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1904, vol. 23, p. 101[2] Recueil des Travaux Chimiques des Pays-Bas, 1905, vol. 24, p. 2
[3] Bulletin de la Societe Chimique de France, 1927, vol. <4> 41, p. 331
  • 19
  • [ 108-86-1 ]
  • [ 542-88-1 ]
  • [ 589-17-3 ]
Reference: [1] Journal of the Chemical Society, 1920, vol. 117, p. 525
  • 20
  • [ 10026-13-8 ]
  • [ 589-17-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1926, vol. 449, p. 264
  • 21
  • [ 108-86-1 ]
  • [ 542-88-1 ]
  • [ 5435-44-9 ]
  • [ 1941-86-2 ]
  • [ 589-17-3 ]
Reference: [1] Journal of the Chemical Society, 1920, vol. 117, p. 525
  • 22
  • [ 7647-01-0 ]
  • [ 50-00-0 ]
  • [ 108-86-1 ]
  • [ 7646-78-8 ]
  • [ 578-51-8 ]
  • [ 589-17-3 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1927, vol. <4> 41, p. 331
  • 23
  • [ 589-17-3 ]
  • [ 105-53-3 ]
  • [ 70146-78-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3285 - 3306
[2] Journal of medicinal chemistry, 1970, vol. 13, # 5, p. 820 - 826
[3] Molecules, 2018, vol. 23, # 5,
  • 24
  • [ 50-00-0 ]
  • [ 589-17-3 ]
  • [ 4654-39-1 ]
YieldReaction ConditionsOperation in experiment
54%
Stage #1: With chloro-trimethyl-silane; ethylene dibromide; zinc In tetrahydrofuran at 70℃; for 2 h; Schlenk technique; Inert atmosphere
Stage #2: at 70℃; for 6 h; Schlenk technique; Inert atmosphere
General procedure: Phenethyl alcohol (3a) A two neck Schlenk flask equipped with a magnetic stirring bar and septum was heated with heat gun (~400 °C) for 10 min under high vacuum. After cooling to room temperature, the flask was flushed with argon (3 times). Zn-dust (654 mg, 2.0 equiv, 10.0 mmol) was added followed by THF (20 mL). 1,2-Dibromoethane (5 molpercent) was added and the reaction mixture was heated until ebullition occurs. After cooling to rt, chlorotrimethylsilane (1 molpercent) was added and the mixture was heated again till ebullition occurs. The flask was again cooled to rt and benzyl chloride (633 mg, 5.0 mmol, 1 equiv) was added as a solution in THF (10 mL) and it was heated at 70 °C for 2 h and cooled to rt. Paraformaldehyde (450 mg, 3.0 equiv. 15.0 mmol) was slowly added at rt and the flask was again heated at 70 °C for 6 h. The solution was cooled to rt and saturated NH4Cl solution was added. The phases were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with water (20 mL), brine (10 mL) and then dried over Na2SO4. The solvents were evaporated under reduced pressure and the residue was purified by silica gel column chromatography using cyclohexane or cyclohexane/ethyl acetate as an eluent to obtain phenethyl alcohol (3a) (510 mg, 83percent) as a colourless liquid.
Reference: [1] Synthetic Communications, 2017, vol. 47, # 10, p. 968 - 974
  • 25
  • [ 589-17-3 ]
  • [ 122-52-1 ]
  • [ 38186-51-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1974, p. 1506 - 1508
[2] Journal of Physical Organic Chemistry, 2017, vol. 30, # 12,
  • 26
  • [ 589-17-3 ]
  • [ 74-89-5 ]
  • [ 699-03-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4693 - 4707
  • 27
  • [ 589-17-3 ]
  • [ 53531-69-4 ]
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 12, p. 1675 - 1682
[2] Synlett, 2013, vol. 24, # 16, p. 2165 - 2169
  • 28
  • [ 589-17-3 ]
  • [ 26177-44-6 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1992, vol. 111, # 1, p. 22 - 28
  • 29
  • [ 75-07-0 ]
  • [ 589-17-3 ]
  • [ 80793-25-5 ]
YieldReaction ConditionsOperation in experiment
70% With choline In tetrahydrofuran; water; toluene at 75℃; for 5 h; Weighing 2.632g choline reagent, 15mLH 2 O, 2 ml tetrahydrofuran, 8.4 ml toluene in 100 ml in three-mouth bottle, heating to 75 °C. The 25.08g the bromine animal pen chlorine and 4.4g acetaldehyde dissolved in 12 ml of tetrahydrofuran, is dripped slowly into the reaction flask. To continue this temperature reaction 5h, TLC showed reaction is ended. Reaction liquid cooling to room temperature, add 50 ml water, ethyl acetate extraction three times, combining oil layer, dry anhydrous sodium sulfate, concentrated dry solvent, column chromatography to obtain 18.24g bombycinous A transparent oily liquid compound. MSm/z: 212 (M +), yield: 70percent
70% With choline chloride In tetrahydrofuran; water; toluene at 75℃; for 5 h; Weigh 2.632 g of choline reagent (choline reagent), 15 mL of H20, 2 mL of tetrahydrofuran, 8.4 mL of toluene in a 100 mL three-necked flask and heated to 75 ° C. 25.08 g of p-bromobenzyl chloride and 4.4 g of acetaldehyde were dissolved in 12 mL of tetrahydrofuran and slowly added dropwise to the reaction flask. At this temperature for 5 h, TLC showed the reaction to end.The reaction solution was cooled to room temperature, extracted with 50 mL of water and 100 mL of ethyl acetate. The combined wells were dried over anhydrous sodium sulfate and concentrated to dryness. Column chromatography gave 18.24 g of a pale yellow transparent oily liquid compound.yield: 70percent
Reference: [1] Patent: CN104513129, 2016, B, . Location in patent: Paragraph 0094; 0095; 0096; 0097
[2] Patent: CN104513140, 2016, B, . Location in patent: Paragraph 0036-0039
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