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[ CAS No. 108-36-1 ] {[proInfo.proName]}

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Chemical Structure| 108-36-1
Chemical Structure| 108-36-1
Structure of 108-36-1 * Storage: {[proInfo.prStorage]}

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Product Details of [ 108-36-1 ]

CAS No. :108-36-1 MDL No. :MFCD00000078
Formula : C6H4Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :JSRLURSZEMLAFO-UHFFFAOYSA-N
M.W : 235.90 Pubchem ID :7927
Synonyms :

Calculated chemistry of [ 108-36-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.84
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) : -5.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.35
Log Po/w (XLOGP3) : 3.75
Log Po/w (WLOGP) : 3.21
Log Po/w (MLOGP) : 3.79
Log Po/w (SILICOS-IT) : 3.25
Consensus Log Po/w : 3.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.22
Solubility : 0.0142 mg/ml ; 0.0000602 mol/l
Class : Moderately soluble
Log S (Ali) : -3.44
Solubility : 0.0851 mg/ml ; 0.000361 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.11
Solubility : 0.0184 mg/ml ; 0.000078 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.5

Safety of [ 108-36-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P280-P302+P352-P305+P351+P338+P310 UN#:3082
Hazard Statements:H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 108-36-1 ]

* 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 [ 108-36-1 ]
  • Downstream synthetic route of [ 108-36-1 ]

[ 108-36-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 108-36-1 ]
  • [ 75-36-5 ]
  • [ 33243-33-3 ]
YieldReaction ConditionsOperation in experiment
93% at 100℃; for 1.5 h; Inert atmosphere Argon under the protection,A solution of 1,3-dibromobenzene (4.1 g, 17.5 mmol)And AlCl3 (5.6 g, 42 mmol) were placed in a 50 ml two-necked flask,At room temperature,Acetyl chloride (2.0 ml, 28 mmol) was slowly added dropwise,Dripping finished system slowly heated to 100 , a large number of HCl gas release,High temperature reaction for 1.5 hours.System down to room temperature,Slowly pour into crushed ice and concentrated hydrochloric acid.The organic phase was washed with water, washed with Na2CO3 solution and brine, dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The compound 16a (4.5 g, 93percent yield) was isolated by column chromatography.
Reference: [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 6, p. 926 - 939
[2] Patent: CN106316958, 2017, A, . Location in patent: Paragraph 0145; 0146; 0152; 0153
[3] Journal of the Chemical Society, 1949, p. 1133,1136
[4] Roczniki Chemii, 1973, vol. 47, p. 2333 - 2337
  • 2
  • [ 75-15-0 ]
  • [ 7446-70-0 ]
  • [ 108-36-1 ]
  • [ 75-36-5 ]
  • [ 33243-33-3 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 1133,1136
  • 3
  • [ 123-75-1 ]
  • [ 108-36-1 ]
  • [ 219928-13-9 ]
YieldReaction ConditionsOperation in experiment
99% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 4.5 h; Sealed tube Commercial 1,3-dibromobenzene 1 (200.0mg, 0.85mmol), 12 pyrrolidine (60.5mg, 0.85mmol) and 157.0mg of a reagent constituted by 13 tris(dibenzylideneacetone)dipalladium(0), 14 BINAP and 15 t-BuONa (mol ratio: 0.05:0.15:2) were suspended in 16 toluene (2.5mL) and allowed to react in a sealed tube, at 80°C for 4.5h, under magnetic stirring. After cooling to room temperature, the mixture was filtered under reduced pressure and the resulting solution evaporated in vacuo. The residue was dissolved in CHCl3 and washed with a 10percent aqueous solution of 60 NaOH. The organic phase was dried over anhydrous Na2SO4, filtered, evaporated in vacuo, and purified by flash column chromatography on silica gel (petroleum ether), obtaining the intermediate 2 as a transparent oil (190.5mg, 0.84mmol). Yield: 99percent. 1H NMR (CDCl3, 400MHz) δ (ppm): 7.05 (t, 1H, J=8.0Hz), 6.76–6.74 (m, 1H), 6.68 (m, 1H), 6.46 (m, 1H), 3.27–3.24 (m, 4H), 2.05–1.99 (m, 4H).
54% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 4 h; Reflux 1,3-Dibromobenzene (1.0 g, 4.24 mmol), pyrrolidine (0.43 mL, 5.0 mmol), sodium tert-butoxide (1.14 g, 11.87mmol) and BINAP (0.2 g, 0.32 mmol) were dissolved in 17 mL of toluene. Pd2(dba)3 (0.097 g, 0.1 mmol) was addedthereto, and the mixture was stirred 4 hours under reflux. Solids were filtered through Celite and purified by columnchromatography to obtain the title compound (0.52 g, 54percent).1H-NMR (CDCl3) δ 7.05 (1H, t), 6.75 (1H, d), 6.67 (1H, m), 6.45 (1H, m), 3.26 (4H, m), 2.00 (4H, m)
45% With caesium carbonate In toluene at 120℃; Synthesis of 1-(3-bromophenyl)pyrrolidine
Into a 500 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1,3-dibromobenzene (20 g, 84.78 mmol, 1.00 equiv) in toluene (300 mL).
To this was added pyrrolidine (6.03 g, 84.80 mmol, 1.00 equiv).
Addition of Pd(OAc)2 (190 mg, 0.85 mmol, 0.01 equiv) was next.
This was followed by the addition of BINAP (760 mg, 2.53 mmol, 0.03 equiv).
To the mixture was added Cs2CO3 (69.1 g, 211.96 mmol, 2.50 equiv).
The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 120° C. in a bath of oil.
The reaction progress was monitored by TLC (EtOAc/PE=1:5).
A filtration was performed.
The filtrate was concentrated by evaporation under vacuum using a rotary evaporator.
The residue was purified by eluding through a column with a PE solvent system.
This resulted in 8.51 g (45percent) of 1-(3-bromophenyl)pyrrolidine as a light yellow liquid.
LC-MS (ES, m/z): [M+H]+ calcd for C10H13BrN 226, found 226
45% With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 120℃; Synthesis of 1-3-bromophenyl)pyrrolidine
Into a 500 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1,3-dibromobenzene (20 g, 84.78 mmol, 1.00 equiv) in toluene (300 mL).
To this was added pyrrolidine (6.03 g, 84.80 mmol, 1.00 equiv).
Addition of Pd(OAc)2 (190 mg, 0.85 mmol, 0.01 equiv) was next.
This was followed by the addition of BINAP (760 mg, 2.53 mmol, 0.03 equiv).
To the mixture was added Cs2CO3 (69.1 g, 211.96 mmol, 2.50 equiv).
The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 120° C. in a bath of oil.
The reaction progress was monitored by TLC (EtOAc/PE=1:5).
A filtration was performed.
The filtrate was concentrated by evaporation under vacuum using a rotary evaporator.
The residue was purified by eluding through a column with a PE solvent system.
This resulted in 8.51 g (45percent) of 1-(3-bromophenyl)pyrrolidine as a light yellow liquid.
LC-MS (ES, m/z): [M+H]+ calcd for C10H13BrN 226, found 226

Reference: [1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 24, p. 6427 - 6434
[2] Tetrahedron, 2008, vol. 64, # 13, p. 2938 - 2950
[3] Patent: EP3239143, 2017, A2, . Location in patent: Paragraph 0165
[4] Patent: US2008/318941, 2008, A1, . Location in patent: Page/Page column 44
[5] Patent: US2008/200471, 2008, A1, . Location in patent: Page/Page column 66
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