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[ CAS No. 82072-23-9 ] {[proInfo.proName]}

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Product Details of [ 82072-23-9 ]

CAS No. :82072-23-9 MDL No. :MFCD06797497
Formula : C8H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :OEPGAYXSRGROSQ-UHFFFAOYSA-N
M.W : 199.05 Pubchem ID :7127825
Synonyms :

Calculated chemistry of [ 82072-23-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.67
TPSA : 17.07 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) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 2.25
Log Po/w (SILICOS-IT) : 2.99
Consensus Log Po/w : 2.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.73
Solubility : 0.367 mg/ml ; 0.00184 mol/l
Class : Soluble
Log S (Ali) : -2.13
Solubility : 1.47 mg/ml ; 0.00741 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.61
Solubility : 0.0492 mg/ml ; 0.000247 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 82072-23-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P362+P364-P405-P501 UN#:3261
Hazard Statements:H302+H312-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 82072-23-9 ]

* 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 [ 82072-23-9 ]
  • Downstream synthetic route of [ 82072-23-9 ]

[ 82072-23-9 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 28188-41-2 ]
  • [ 82072-23-9 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With diisobutylaluminium hydride In tetrahydrofuran; toluene at 0℃; for 2.5 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; dichloromethane; toluene for 1 h;
Synthesis of Compounds 60 and 61
Compounds 60 and 61 were synthesized from α-bromomethyl-tolunitril.
To a solution of α-bromomethyl-tolunitril (15.3 mmol) in toluene (30 mL) was added DIBAL-H in THF (1.0 M, 1.4 eq.) at 0° C. within 30 minutes.
After stirring at 0° C. for 2 h, the reaction mixture was poured into a mixture of 40 mL of methylene chloride and 100 mL of 10percent HCl.
The resulting mixture was stirred for 1 h and the organic layer was washed with water and then brine, and the aqueous was extracted with methylene chloride twice.
After dried over Na2SO4, filtered, and concentrated, the obtained semi-oily product was stored in a refrigerator to give 3-(bromomethyl)benzaldehyde as a white crystalline solid in quantitative yield.
Reaction of the resulting compound with acetone in ethanol following the procedure descripted in Scheme 4 yielded Compound 61 as a light yellow crystalline solid. ESI MS m/z: 420.9 [M+H]+; 1H NMR (400 MHz, CDCl3) δ: 7.71 (d, 2H, J=16.0 Hz, H-1, 5), 7.63-7.60 (m, 2H, aromatic ring H), 7.54-7.50 (m, 2H, aromatic ring H), 7.44-7.37 (m, 4H, aromatic ring H), 7.08 (d, 2H, J=16.0 Hz, H-2, 4), 4.50 (s, 4H, -CH2Br).
93% With diisobutylaluminium hydride In tetrahydrofuran; toluene at 0℃; for 2 h; To a solution of 3-(bromomethyl)benzonitrile (212mg, 1.081 mmol) in 2.5mL Toluene was added dropwise 1M DIBAL-H in THF (1.5 ml, 1.5 mmol) at 0° C. After stirring at 0°C for 2 h the reaction was diluted with DCM and IN aq. HCl and stirred for 1 hour. The organic layer was washed with brine, dried over sodium sulfate, and concentrated yielding the titled compound as an orange oil. (200mg, 0.970 mmol, 93percent yield)
88% With diisobutylaluminium hydride In toluene at -78 - 0℃; for 1.5 h; 3- (Bromomethyl) benzonitrile (1.0 g, 5.10 mmol) was dissolved in toluene (17 L), cooled to 0 C and 1.5 M DIBAL (4.08 L, 6.12 mmol) dissolved in toluene was slowly added dropwise. The reaction solution was stirred at 0 ° C for 1.5 hours, and 1N HCl solution was slowly added thereto.The reaction solution was diluted with CH2Cl2 and washed with water. The organic solvent was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (n-Hex / EtOAc = 9/1) to obtain the target compound 3- (bromomethyl) benzaldehyde (880 mg, 88percent).
71%
Stage #1: With diisobutylaluminium hydride In chloroform; chlorobenzene at 5℃; for 1 h; Cooling with ice
Stage #2: With hydrogenchloride; water In hexane; chloroform; chlorobenzene
Step 1:
3-Bromomethyl-benzaldehyde
A solution of 3-cyanobenzyl bromide (available from Aldrich; 10.1 g, 51.5 mmol) in chlorobenzene (100 mL) was cooled in an ice-water bath.
A solution of diisobutylaluminum hydride in hexanes (available from Aldrich; 1 M; 65 mL, 65 mmol) was added over 25 minutes, and the reaction mixture was stirred below 5° C. for 1 h.
Chloroform (100 mL) was added, followed by 10percent aqueous hydrochloric acid (dropwise).
The layers were separated and the organic layer was washed with water.
Each aqueous layer was back extracted with chloroform, and the organic phases were combined, dried over sodium sulfate, filtered, evaporated and purified by chromatography, eluting with 0-40percent ethyl acetate/hexanes to give pure fractions and a number of impure fractions.
The impure fractions were chromatographed a second time, eluting with 0-27percent ethyl acetate/hexanes.
Fractions homogeneous for the product from the two chromatographic separations were combined and concentrated.
The residue was dissolved in ether and layered with hexane.
The mixture was chilled overnight and the solid was filtered off, washed with hexane and dried under high vacuum at room temperature to give 3-bromomethyl-benzaldehyde (7.32 g, 71percent).

Reference: [1] Patent: US2012/46247, 2012, A1, . Location in patent: Page/Page column 29
[2] Chemical Communications, 2014, vol. 50, # 56, p. 7424 - 7426
[3] Patent: WO2017/223086, 2017, A1, . Location in patent: Page/Page column 84
[4] Tetrahedron, 1997, vol. 53, # 20, p. 6755 - 6790
[5] Patent: KR2018/56603, 2018, A, . Location in patent: Paragraph 0363; 0365-0367
[6] Journal of the American Chemical Society, 1992, vol. 114, # 12, p. 4889 - 4898
[7] Journal of the American Chemical Society, 1991, vol. 113, # 11, p. 4208 - 4218
[8] Organic and Biomolecular Chemistry, 2010, vol. 8, # 5, p. 1181 - 1187
[9] Journal of the American Chemical Society, 1997, vol. 119, # 33, p. 7726 - 7733
[10] Patent: US2011/124686, 2011, A1, . Location in patent: Page/Page column 25
[11] Archiv der Pharmazie, 1997, vol. 330, # 8, p. 247 - 252
[12] Dalton Transactions, 2012, vol. 41, # 23, p. 7092 - 7097
  • 2
  • [ 52010-98-7 ]
  • [ 82072-23-9 ]
YieldReaction ConditionsOperation in experiment
46.8% With N-Bromosuccinimide; triphenylphosphine In dichloromethane for 4.5 h; N-Bromosuccinimide (NBS, 19.6 g) was added to a solution of 2a or 2b (10.0 g) in dichloromethane(120 mL). Triphenylphosphine (2.0 equiv, 38.5 g, 0.146 mol) was divided into four equal aliquots andan aliquot was added to the reaction every 30 min. After the reaction was completed, the solution wasmixed with cold water (120 mL). The aqueous phase was extracted two times with dichloromethaneand the organic phase was washed with a saturated NaCl solution and dried over Na2SO4 for 8 h.The mixture was purified by silica gel chromatography with petroleum ether–ethyl acetate = 25:1 aseluent to give compound 3a 8.5 g (58.0percent yield) and 3b 6.8 g (46.8percent yield), respectively.
46.8% With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 3 h; Cooling with ice Take a 500mL eggplant flask, peeled and weighed 10.0g intermediate II-2 (0.073mol; 1.0equiv),1b was dissolved by adding 150 mL of methylene chloride and 19.6 g of N-bromosuccinimide solid was added with stirring.Then ice-bath conditions to the eggplant-shaped flask was added in four batches of triphenylphosphine solids, a total of 38.5g (0.146mol; 2.0equiv), each batch interval of half an hour until triphenylphosphine plus Bi, remove the ice bath ,The reaction was continued at room temperature for more than 3h, TLC TLC plate, UV analyzer (254nm) to monitor the progress of the reaction.After the raw material point II-2 disappears, the reaction is stopped and the reaction solution is poured into a beaker containing 150 ml of cold water.The aqueous phase was then poured into a separatory funnel mixture, the aqueous phase was extracted with 150 ml of methylene chloride,The combined dichloromethane layers were washed with saturated aqueous sodium chloride solution. Then,The organic phase is dried over anhydrous sodium sulphate or anhydrous magnesium sulphate overnight. Filter out the desiccant,Weigh about 60-100 mesh silica gel powder about 15g added to the filtrate, steaming to dry sand,Silica gel column chromatography, the elution system of choice for the petroleum ether: ethyl acetate = 99: 1,The resulting benzylic alcohol hydroxy-brominated reaction product was collected to give 6.8 g of III-2 as a white solid in a yield of 46.8percent.
46.8% With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 3 h; Cooling with ice Take a 500mL eggplant-shaped bottle,Peel 10.0 g of intermediate II-2 (0.073 mol; 1.0 equiv).Dissolve 1b by adding 150 mL of dichloromethane.19.6 g of N-bromosuccinimide solid was added with stirring.Then, triphenylphosphine was added to the eggplant flask in four batches under ice-cooling conditions.A total of 38.5g (0.146mol; 2.0equiv),Each batch is separated by half an hour.After triphenylphosphine is added,Remove the ice bath,Continue to react at room temperature for more than 3 hours,Thin layer TLC board,An ultraviolet analyzer (254 nm) monitors the progress of the reaction. After the material point of II-2 disappears,Stop the reaction,Pour the reaction solution into a beaker containing 150 ml of cold water.Then, the aqueous organic phase mixture is poured into a separatory funnel for extraction.The aqueous phase is extracted with 150 ml of dichloromethane.Combine the dichloromethane layer,Add saturated aqueous sodium chloride solution.Then,The organic phase was dried over anhydrous sodium sulfate or anhydrous magnesium sulfate overnight.Filter out the desiccant,Weigh about 15g of 60-100 mesh silica gel powder into the filtrate.Rotary to dry sand,Silica gel column chromatography separation,The elution system selected was petroleum ether:ethyl acetate = 99:1.The resulting benzylic hydroxyl alcohol bromo reaction product is collected,A total of 6.8 g of III-2 white solid was obtained.Yield: 46.8percent.
Reference: [1] Journal of Organometallic Chemistry, 2010, vol. 695, # 1, p. 82 - 89
[2] Molecules, 2016, vol. 21, # 7,
[3] Patent: CN107522647, 2017, A, . Location in patent: Paragraph 0084; 0085
[4] Patent: CN107522654, 2017, A, . Location in patent: Paragraph 0069; 0070
[5] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983, vol. 37, # 8, p. 693 - 698
[6] Organic and Biomolecular Chemistry, 2010, vol. 8, # 5, p. 1181 - 1187
[7] Journal of Organometallic Chemistry, 2011, vol. 696, # 15-16, p. 2857 - 2862
  • 3
  • [ 7647-01-0 ]
  • [ 28188-41-2 ]
  • [ 82072-23-9 ]
YieldReaction ConditionsOperation in experiment
77% With dibal-H In toluene Compound 8
A 2 L round-bottom was charged with 3-(bromomethyl)-benzonitrile 7 (48.0 g) and dry toluene (480 mL).
After cooling to 0° C., DIBAL-H (1.0 M in PhMe, 306 mL) was added over a 90 min period via pressure-equalizing addition funnel under N2.
Once addition was complete, the reaction was allowed to stir an additional 90 min.
Then 1.0 M aq HCl (1.2 L) was added carefully, and the reaction was allowed to stir for 15 min.
The organic phase was collected, and the aq phase was extracted (2*250 mL Et2O).
All organic extracts were combined, dried (MgSO4), filtered, and concentrated.
The oily residue was purified on a 330 g normal phase silica gel column (combiflash, EtOAc/Hex 10:90 to 50:50, gradient), giving the 3-(bromomethyl)-benzaldehyde (37.14 g, 77percent yield).
1H-NMR (300 MHz, CDCl3) d: 9.98 (s, 1H), 7.86 (app. s, 1H), 7.77 (app.d, J=7.6 Hz, 1H), 7.63 (app. d, J=7.7 Hz, 1H), 7.48 (app. dd, J=7.7, 7.6 Hz, 1H), 4.51 (s, 2H). LCMS-ESI failed to provide reliable data.
Reference: [1] Patent: US2011/150836, 2011, A1,
  • 4
  • [ 626-19-7 ]
  • [ 82072-23-9 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1543 - 1554
[2] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983, vol. 37, # 8, p. 693 - 698
[3] Journal of Organometallic Chemistry, 2011, vol. 696, # 15-16, p. 2857 - 2862
[4] Molecules, 2016, vol. 21, # 7,
[5] Patent: CN107522647, 2017, A,
  • 5
  • [ 82072-22-8 ]
  • [ 82072-23-9 ]
Reference: [1] Patent: US4389410, 1983, A,
  • 6
  • [ 1191-15-7 ]
  • [ 28188-41-2 ]
  • [ 82072-23-9 ]
Reference: [1] Patent: US6489487, 2002, B1,
  • 7
  • [ 620-23-5 ]
  • [ 82072-23-9 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 16, p. 1861 - 1865
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