Home Cart 0 Sign in  
X

[ CAS No. 28165-50-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 28165-50-6
Chemical Structure| 28165-50-6
Chemical Structure| 28165-50-6
Structure of 28165-50-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 28165-50-6 ]

Related Doc. of [ 28165-50-6 ]

Alternatived Products of [ 28165-50-6 ]

Product Details of [ 28165-50-6 ]

CAS No. :28165-50-6 MDL No. :MFCD08277300
Formula : C6H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :LOBRHADLNRMHOO-UHFFFAOYSA-N
M.W : 188.02 Pubchem ID :15531506
Synonyms :

Calculated chemistry of [ 28165-50-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.57
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 1.99
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 1.34
Consensus Log Po/w : 1.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.75
Solubility : 0.332 mg/ml ; 0.00177 mol/l
Class : Soluble
Log S (Ali) : -2.59
Solubility : 0.486 mg/ml ; 0.00259 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.32
Solubility : 0.906 mg/ml ; 0.00482 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 28165-50-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 28165-50-6 ]

* 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 [ 28165-50-6 ]
  • Downstream synthetic route of [ 28165-50-6 ]

[ 28165-50-6 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 91631-57-1 ]
  • [ 38373-20-5 ]
  • [ 16750-67-7 ]
  • [ 823-54-1 ]
  • [ 40925-68-6 ]
  • [ 107986-47-0 ]
  • [ 28165-50-6 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 10, p. 2002 - 2010
  • 2
  • [ 107986-35-6 ]
  • [ 16750-67-7 ]
  • [ 823-54-1 ]
  • [ 40925-68-6 ]
  • [ 116278-71-8 ]
  • [ 116278-72-9 ]
  • [ 28165-50-6 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 20, p. 4762 - 4769
  • 3
  • [ 91631-57-1 ]
  • [ 38373-20-5 ]
  • [ 16750-67-7 ]
  • [ 823-54-1 ]
  • [ 40925-68-6 ]
  • [ 107986-47-0 ]
  • [ 28165-50-6 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 10, p. 2002 - 2010
  • 4
  • [ 107986-35-6 ]
  • [ 16750-67-7 ]
  • [ 823-54-1 ]
  • [ 40925-68-6 ]
  • [ 116278-71-8 ]
  • [ 116278-72-9 ]
  • [ 28165-50-6 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 20, p. 4762 - 4769
  • 5
  • [ 67-56-1 ]
  • [ 28165-50-6 ]
  • [ 116557-46-1 ]
YieldReaction ConditionsOperation in experiment
55% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20 - 25℃; for 1.08333 h; Preparation 22Stepl[00236j To a slurry of 2-amino-6-bromophenol (4.00 g, 21.27 mmol) in methanol (2.152 mL, 53.2 mmol) and THF (10 mL) at room temperature was added triphenylphosphine (11.16 g, 42.5 mmol). After stirring for a few minutes, diisopropylazodicarboxylate (DIAD, 12.41 mL, 63.8 mmol) was then added dropwise via syringe over 5 minutes. After the addition was complete, the reaction was allowed to stir at room temperature for 1 h. The resulting mixture was then concentrated to remove the volatiles and the resulting residue was purified by silica gel flash chromatography using hexanes/ethyl acetate as the eluent. Fractions containing the major UV-active productwere combined and concentrated under vacuum to afford 2.35 g (55percent) of a dark brown oil as the desired product. HPLC (Method N) RT = 1.33 minutes. LCMS MH+ 202/204 (observed bromide isotope pattern).
55% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1 h; Step 4 To a slurry of 2-amino-6-bromophenol (4.00 g, 21.27 mmol) in methanol (2.152 mL, 53.2 mmol) and THF (10 mL) at rt was added triphenylphosphine (11.16 g, 42.5 mmol). After stirring for a few minutes, DIAD (12.41 mL, 63.8 mmol) was then added dropwise via syringe over ~5 min. (exothermic). After the addition was complete, the reaction which had warmed due to the exothermic reaction was allowed to stir at rt for ~1 h. The resulting mixture was then concentrated to remove the volatiles and the resulting residue was purified by silica gel flash chromatography using hexanes/ethyl acetate as the eluant. Fractions containing the major uv active product were combined and concentrated under vacuum to afford 2.35 g (55percent) of a dark brown oil as the desired product. HPLC (method N) RT = 1.33 min. LCMS MH+ 202/204 (observed bromide isotope pattern).
55%
Stage #1: With triphenylphosphine In tetrahydrofuran at 20℃;
Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 1 h;
To a slurry of 2-amine-6-bromophenol (4.00 g, 21.27 mmol) in methanol (2.152 mL, 53.2 mmol) and THF (10 mL) at rt was added triphenylphosphine (11.16 g, 42.5 Mmol).After stirring for several minutes, DIAD (12.41 mL, 63.8 mmol) (exotherm) was added dropwise via the syringe over about 5 minutes. After the addition was complete, the reaction, which had been heated by the exothermic reaction, was stirred for about 1 h at rt. The resulting mixture was then concentrated to remove the volatiles and the resulting residue was purified by flash chromatography on silica gel using hexane / ethyl acetate as the eluent. The fractions containing the major product of uv activity were combined and concentrated in vacuo to afford 2.35 g (55percent) of the desired product as a dark brown oil.
Reference: [1] Patent: WO2014/74660, 2014, A1, . Location in patent: Paragraph 00236
[2] Patent: WO2015/69310, 2015, A1, . Location in patent: Paragraph 00176
[3] Patent: TWI582077, 2017, B, . Location in patent: Page/Page column 82; 83
  • 6
  • [ 28165-50-6 ]
  • [ 376592-93-7 ]
Reference: [1] Patent: CN105801444, 2016, A,
  • 7
  • [ 1445-45-0 ]
  • [ 28165-50-6 ]
  • [ 1239489-82-7 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4287 - 4299
[2] Patent: EP2394987, 2011, A1, . Location in patent: Page/Page column 12
  • 8
  • [ 506-68-3 ]
  • [ 28165-50-6 ]
  • [ 1211527-07-9 ]
Reference: [1] Patent: WO2016/206101, 2016, A1, . Location in patent: Page/Page column 63
  • 9
  • [ 28165-50-6 ]
  • [ 1211527-07-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 6, p. 1592 - 1596
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 28165-50-6 ]

Aryls

Chemical Structure| 40925-68-6

[ 40925-68-6 ]

2-Amino-4-bromophenol

Similarity: 0.93

Chemical Structure| 38191-34-3

[ 38191-34-3 ]

2-Amino-5-bromophenol

Similarity: 0.91

Chemical Structure| 116557-46-1

[ 116557-46-1 ]

3-Bromo-2-methoxyaniline

Similarity: 0.90

Chemical Structure| 115929-62-9

[ 115929-62-9 ]

3-Bromo-2,5-dimethoxyaniline

Similarity: 0.88

Chemical Structure| 1037298-16-0

[ 1037298-16-0 ]

2-Amino-4,5-dibromophenol

Similarity: 0.88

Bromides

Chemical Structure| 40925-68-6

[ 40925-68-6 ]

2-Amino-4-bromophenol

Similarity: 0.93

Chemical Structure| 38191-34-3

[ 38191-34-3 ]

2-Amino-5-bromophenol

Similarity: 0.91

Chemical Structure| 116557-46-1

[ 116557-46-1 ]

3-Bromo-2-methoxyaniline

Similarity: 0.90

Chemical Structure| 115929-62-9

[ 115929-62-9 ]

3-Bromo-2,5-dimethoxyaniline

Similarity: 0.88

Chemical Structure| 1037298-16-0

[ 1037298-16-0 ]

2-Amino-4,5-dibromophenol

Similarity: 0.88

Amines

Chemical Structure| 40925-68-6

[ 40925-68-6 ]

2-Amino-4-bromophenol

Similarity: 0.93

Chemical Structure| 38191-34-3

[ 38191-34-3 ]

2-Amino-5-bromophenol

Similarity: 0.91

Chemical Structure| 116557-46-1

[ 116557-46-1 ]

3-Bromo-2-methoxyaniline

Similarity: 0.90

Chemical Structure| 115929-62-9

[ 115929-62-9 ]

3-Bromo-2,5-dimethoxyaniline

Similarity: 0.88

Chemical Structure| 1037298-16-0

[ 1037298-16-0 ]

2-Amino-4,5-dibromophenol

Similarity: 0.88