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[ CAS No. 2039-86-3 ] {[proInfo.proName]}

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Chemical Structure| 2039-86-3
Chemical Structure| 2039-86-3
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Product Details of [ 2039-86-3 ]

CAS No. :2039-86-3 MDL No. :MFCD00000088
Formula : C8H7Br Boiling Point : -
Linear Structure Formula :- InChI Key :KQJQPCJDKBKSLV-UHFFFAOYSA-N
M.W : 183.05 Pubchem ID :74870
Synonyms :

Calculated chemistry of [ 2039-86-3 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.23
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) : -4.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.38
Log Po/w (XLOGP3) : 3.69
Log Po/w (WLOGP) : 2.98
Log Po/w (MLOGP) : 3.59
Log Po/w (SILICOS-IT) : 3.31
Consensus Log Po/w : 3.19

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.73
Solubility : 0.0343 mg/ml ; 0.000188 mol/l
Class : Soluble
Log S (Ali) : -3.38
Solubility : 0.0763 mg/ml ; 0.000417 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.69
Solubility : 0.0369 mg/ml ; 0.000202 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.54

Safety of [ 2039-86-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2039-86-3 ]

* 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 [ 2039-86-3 ]
  • Downstream synthetic route of [ 2039-86-3 ]

[ 2039-86-3 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 2039-86-3 ]
  • [ 22726-00-7 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: at 80℃; for 2 h; Sealed tube; Green chemistry
Stage #2: at 80℃; for 1 h; Sealed tube; Green chemistry
General procedure: A sealed tube equipped with a magnetic stirring bar was charged with styrene 1 (1.0mmol), NBS (2.0 mmol) and water (2.0mL) at room temperature. The resulting mixture was heated to 80 °C for 2h. After disappearance of the reactant (monitored by TLC), reaction mixture was cooled to room temperature. To this reaction mixture molecular iodine (2.2 mmol) and 30percent aq. ammonia solution or n-butylamine (10 mmol) were added and it was heated to 80 °C for 1h. After completion of the reaction (monitored by TLC), saturated Na2S2O3 solution (10 mL) was added to the reaction mixture, and it was extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine solution (10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue obtained was purified by column chromatography on 60–120 mesh silica gel using ethyl acetate: n-hexane (1:2) as the eluent to obtain the corresponding aromatic amide 2.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 29, p. 2820 - 2823
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9889 - 9894
  • 2
  • [ 2039-86-3 ]
  • [ 1878-67-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 12, p. 2132 - 2141
[2] RSC Advances, 2016, vol. 6, # 8, p. 6719 - 6723
  • 3
  • [ 2039-86-3 ]
  • [ 2725-82-8 ]
YieldReaction ConditionsOperation in experiment
90 %Spectr. With dimethylamine borane; ReBr2(NO)(CH3CN)(PTA)2 In ethanol at 70℃; for 40 h; Inert atmosphere General procedure: A solution of the proper olefin substrates (0.5 mmol), dimethylamine-borane (0.25 mmol) and 1 molpercent of the rhenium complex (with 10-15 molpercent of tBuOK according to Table 3) in the given solvent (0.8e1.0 ml) was stirred for given time at 70 °C under nitrogen atmosphere. Upon completion, the reaction mixture was filtered over Celite. The resulting solution was analyzed by 1H NMR spectroscopy. The obtained 1H NMR data of the alkanes were identical to those of the literature [35,49-55]. The yields are listed in Tables 2 and 3.
Reference: [1] ACS Catalysis, 2016, vol. 6, # 9, p. 6318 - 6323
[2] Journal of the American Chemical Society, 1937, vol. 59, p. 1176
[3] Journal of Organometallic Chemistry, 2011, vol. 696, # 9, p. 1803 - 1808
[4] Journal of Materials Chemistry A, 2015, vol. 3, # 48, p. 24525 - 24531
  • 4
  • [ 2039-86-3 ]
  • [ 100-41-4 ]
  • [ 2725-82-8 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 19, p. 6107 - 6110
  • 5
  • [ 2039-86-3 ]
  • [ 40422-70-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5622 - 5626
  • 6
  • [ 75-11-6 ]
  • [ 2039-86-3 ]
  • [ 1798-85-2 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With diethylzinc; 2,4,6-Trichlorophenol In hexanes; dichloromethane at -40℃; for 0.5 h;
Stage #2: at 20℃;
Stage #3: With potassium permanganate; water In tetrahydrofuran at 0 - 20℃; for 1 h;
1.0 M Diethyl zinc in hexanes (27.3 ml, 27.3 mmol) was added to a solution of 2,4, 6- [TRICHLOROPHENOL] (5.4g, 27.3 mmol) in dichloromethane (100 ml) at-40°C. After stirring for 15 minutes, diiodo-methane (2.2 mL, 27.3 mmol) was added at-40°C and stirred for an additional 15 minutes. 1-Bromo-3-vinyl-benzene (2.5 g, 13.7 mmol) was then added to the reaction mixture, allowed to warm to room temperature, and left stirring overnight. The reaction mixture was diluted with dichloromethane, washed with 1N [HC1] (2X), saturated sodium bicarbonate (2X), saturated sodium sulfite, 1N sodium hydroxide, and saturated brine, dried over magnesium sulfate, filtered and concentrated. GC-MS revealed that the reaction mixture contained [L-BROMO-3-CYCLOPROPYL-BENZENE] and 1-bromo-3-vinyl-benzene. To remove the bromo-3-vinyl-benzene, the crude mixture was reacted with potassium permanganate. A solution of potassium permanganate/water (1.5 g/20 mL) was added drop-wise to a solution of the crude mixture [(-3.] 5 g) in THF (40 mL) at [0°C] and then allowed to warm to room temperature. After 1 hour, the reaction was diluted with diethyl ether, washed with water and saturated brine, dried over anhydrous sodium sulfate filtered and concentrated. Purication by flash column chromatography eluted with 100 hexanes afforded [1-BROMO-3-CYCLOPROPYL-BENZENE] (2.20g, [81percent).] 1.6 M n-Butyllithium in hexanes (3.2 mL, 5.1 mmol) was added drop-wise to a solution of [L-BROMO-3-CYCLOPROPYL-BENZENE] [AT-78°C] and stirred for 1 hour. This reaction mixture was then transferred via canula to a 250 mL round bottom flask equipped with a stirrer bar approximately [1/4 FULL] of solid carbon dioxide and stirred and for 1 hour. The reaction mixture was concentrated and then the residue was diluted with water. The aqueous layer was washed with dichloromethane [(3X),] acidified with 1 N [HC1] to [PH-2,] and extracted with ethyl acetate. The organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 3-cyclopropyl-benzoic (356 mg, 43percent, white [SOLID). IH NMR (DMSO), 6] (ppm): 12.90 (bs, 1H), 7.71 (d, 1H), 7.64 (s, 1H), 7.34 (m, 2H), 2.01 (m, 1H), 0.99 (m, 2H), 0.70 (m, 2H).
Reference: [1] Patent: WO2004/14881, 2004, A2, . Location in patent: Page 136-137
[2] Patent: WO2005/121106, 2005, A1, . Location in patent: Page/Page column 54
  • 7
  • [ 2039-86-3 ]
  • [ 1372474-95-7 ]
  • [ 1798-85-2 ]
Reference: [1] Science, 2012, vol. 335, # 6075, p. 1471 - 1474
  • 8
  • [ 2039-86-3 ]
  • [ 4109-94-8 ]
  • [ 1798-85-2 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1966, p. 218 - 222[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1966, # 2, p. 240 - 245
  • 9
  • [ 2039-86-3 ]
  • [ 34598-49-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 43, p. 12683 - 12686[2] Angew. Chem., 2015, vol. 127, # 43, p. 12874 - 12877,4
  • 10
  • [ 2039-86-3 ]
  • [ 28229-69-8 ]
Reference: [1] Patent: US6063789, 2000, A,
[2] ACS Catalysis, 2017, vol. 7, # 8, p. 5225 - 5233
  • 11
  • [ 2039-86-3 ]
  • [ 58971-11-2 ]
Reference: [1] ACS Catalysis, 2017, vol. 7, # 8, p. 5225 - 5233
[2] ACS Catalysis, 2017, vol. 7, # 8, p. 5225 - 5233
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