Home Cart 0 Sign in  
X

[ CAS No. 175278-17-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 175278-17-8
Chemical Structure| 175278-17-8
Chemical Structure| 175278-17-8
Structure of 175278-17-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 175278-17-8 ]

Related Doc. of [ 175278-17-8 ]

Alternatived Products of [ 175278-17-8 ]

Product Details of [ 175278-17-8 ]

CAS No. :175278-17-8 MDL No. :MFCD00203478
Formula : C7H5BrF3NO Boiling Point : -
Linear Structure Formula :- InChI Key :ROSTYHNIIDIBEG-UHFFFAOYSA-N
M.W : 256.02 Pubchem ID :688296
Synonyms :

Calculated chemistry of [ 175278-17-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.23
TPSA : 35.25 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) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 3.11
Log Po/w (WLOGP) : 4.2
Log Po/w (MLOGP) : 2.37
Log Po/w (SILICOS-IT) : 2.38
Consensus Log Po/w : 2.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.6
Solubility : 0.0649 mg/ml ; 0.000253 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.0775 mg/ml ; 0.000303 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.52
Solubility : 0.077 mg/ml ; 0.000301 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.62

Safety of [ 175278-17-8 ]

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

Application In Synthesis of [ 175278-17-8 ]

* 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 [ 175278-17-8 ]
  • Downstream synthetic route of [ 175278-17-8 ]

[ 175278-17-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 461-82-5 ]
  • [ 175278-17-8 ]
YieldReaction ConditionsOperation in experiment
83% With N-bromosuccinamide In acetonitrile at 0 - 20℃; for 4 h; N-Bromosuccinamide (3.62 g, 20.34 mmol) was added to a solution of commercially available 4-(trifluoromethoxy)aniline (3.00 g, 1 6.95 mmol) in acetonitrile (30 mL) at 0°C. The resulting mixture was allowed to warm to roomtemperature and stirred for 4 hours. The solvent was removed under reduced pressure to give the crude product which was purified by column chromatography eluting in 10percent ethyl acetat/hexane to afford the title compound as brown oil (3.6 gm, 83percent): 1 H NMR (400 MHz, CDCI3) ö: 4.11 (bs, 2 H), 6.73 (d, 1 H), 6.99 (dd, 1 H), 7.31 (d, 1 H). LC-Ms (m/z): [M-H] = 253.1.
40%
Stage #1: With bromine In acetic acid at 20℃; for 2.16667 h;
Stage #2: With sodium hydroxide In water; acetic acid
4-Trifluoromethoxyaniline (1.0 g, 5.6 mmol) was dissolved in glacial acetic acid (10 mL). Bromine (585 μL, 11 mmol) dissolved in glacial acetic acid (2 mL) was added with stirring during 10 minutes at room temperature. The resulting mixture was stirred at room temperature for 2 hours and then poured into water (100 mL). The solid formed (2,5-dibromo-4-trifluoromethoxyaniline) was filtered off. The filtrate was made alkaline with solid sodium hydroxide and extracted with dichloromethane (100 mL), dried (MgSO4) and concentrated (30°C; 200 mBar) to afford 0.57 g (40percent) of 2-bromo-4-trifluoromethoxyaniline.1H NMR (DMSO-d6): δ 5.55 (2H, bs), 6.85 (1H, d), 7.10 (1H, dd), 7.37 (1H, d).
Reference: [1] Patent: WO2015/100232, 2015, A2, . Location in patent: Page/Page column 102
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 1, p. 113 - 128
[3] Patent: EP1183229, 2005, B1, . Location in patent: Page/Page column 143-144
[4] Organic Letters, 2011, vol. 13, # 20, p. 5636 - 5639
[5] Journal of the American Chemical Society, 2016, vol. 138, # 40, p. 13147 - 13150
[6] Chinese Journal of Chemistry, 2018, vol. 36, # 9, p. 815 - 818
  • 2
  • [ 88149-49-9 ]
  • [ 175278-17-8 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 20, p. 5636 - 5639
  • 3
  • [ 544-16-1 ]
  • [ 175278-17-8 ]
  • [ 468075-00-5 ]
Reference: [1] Patent: WO2004/31190, 2004, A1, . Location in patent: Page 39
  • 4
  • [ 175278-17-8 ]
  • [ 468075-00-5 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 3, p. 282 - 286
  • 5
  • [ 544-92-3 ]
  • [ 175278-17-8 ]
  • [ 549488-77-9 ]
YieldReaction ConditionsOperation in experiment
76% at 163℃; for 6.5 h; To a solution of 2-bromo-4-(trifluoromethoxy)aniline (15.1 g, 60.0 mmol) in N-methylpyrrolidone (100 mL) was added copper cyanide (10.6 g, 118 mmol) and the reaction mixture was stirred for 6.5 h at 163° C. After cooling to ambient temperature it was poured onto ice-water (300 mL) and aqueous ammonia (350 mL). The resulting brown precipitate was collected by filtration, washed with water (150 mL) and dissolved in dichloromethane (350 mL). The insoluble material was removed by filtration and the filtrate was washed with brine (100 mL) and dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 25:75:) afforded the title compound (9.09 g, 76percent) as a brown solid. MS: m/e=405.1 [2M+H]+.
Reference: [1] Patent: US2006/79507, 2006, A1, . Location in patent: Page/Page column 16
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 175278-17-8 ]

Fluorinated Building Blocks

Chemical Structure| 88149-49-9

[ 88149-49-9 ]

2,6-Dibromo-4-(trifluoromethoxy)aniline

Similarity: 0.93

Chemical Structure| 886762-08-9

[ 886762-08-9 ]

5-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.92

Chemical Structure| 175278-09-8

[ 175278-09-8 ]

4-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.90

Chemical Structure| 461-82-5

[ 461-82-5 ]

4-(Trifluoromethoxy)aniline

Similarity: 0.80

Chemical Structure| 1535-73-5

[ 1535-73-5 ]

3-Trifluoromethoxyaniline

Similarity: 0.79

Aryls

Chemical Structure| 88149-49-9

[ 88149-49-9 ]

2,6-Dibromo-4-(trifluoromethoxy)aniline

Similarity: 0.93

Chemical Structure| 886762-08-9

[ 886762-08-9 ]

5-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.92

Chemical Structure| 175278-09-8

[ 175278-09-8 ]

4-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.90

Chemical Structure| 59557-92-5

[ 59557-92-5 ]

2-Bromo-5-methoxyaniline

Similarity: 0.84

Chemical Structure| 461-82-5

[ 461-82-5 ]

4-(Trifluoromethoxy)aniline

Similarity: 0.80

Bromides

Chemical Structure| 88149-49-9

[ 88149-49-9 ]

2,6-Dibromo-4-(trifluoromethoxy)aniline

Similarity: 0.93

Chemical Structure| 886762-08-9

[ 886762-08-9 ]

5-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.92

Chemical Structure| 175278-09-8

[ 175278-09-8 ]

4-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.90

Chemical Structure| 59557-92-5

[ 59557-92-5 ]

2-Bromo-5-methoxyaniline

Similarity: 0.84

Chemical Structure| 95970-05-1

[ 95970-05-1 ]

2,6-Dibromo-4-methoxyaniline

Similarity: 0.80

Ethers

Chemical Structure| 88149-49-9

[ 88149-49-9 ]

2,6-Dibromo-4-(trifluoromethoxy)aniline

Similarity: 0.93

Chemical Structure| 886762-08-9

[ 886762-08-9 ]

5-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.92

Chemical Structure| 175278-09-8

[ 175278-09-8 ]

4-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.90

Chemical Structure| 59557-92-5

[ 59557-92-5 ]

2-Bromo-5-methoxyaniline

Similarity: 0.84

Chemical Structure| 461-82-5

[ 461-82-5 ]

4-(Trifluoromethoxy)aniline

Similarity: 0.80

Amines

Chemical Structure| 88149-49-9

[ 88149-49-9 ]

2,6-Dibromo-4-(trifluoromethoxy)aniline

Similarity: 0.93

Chemical Structure| 886762-08-9

[ 886762-08-9 ]

5-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.92

Chemical Structure| 175278-09-8

[ 175278-09-8 ]

4-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.90

Chemical Structure| 59557-92-5

[ 59557-92-5 ]

2-Bromo-5-methoxyaniline

Similarity: 0.84

Chemical Structure| 461-82-5

[ 461-82-5 ]

4-(Trifluoromethoxy)aniline

Similarity: 0.80

Trifluoromethyls

Chemical Structure| 88149-49-9

[ 88149-49-9 ]

2,6-Dibromo-4-(trifluoromethoxy)aniline

Similarity: 0.93

Chemical Structure| 886762-08-9

[ 886762-08-9 ]

5-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.92

Chemical Structure| 175278-09-8

[ 175278-09-8 ]

4-Bromo-2-(trifluoromethoxy)aniline

Similarity: 0.90

Chemical Structure| 461-82-5

[ 461-82-5 ]

4-(Trifluoromethoxy)aniline

Similarity: 0.80

Chemical Structure| 1535-73-5

[ 1535-73-5 ]

3-Trifluoromethoxyaniline

Similarity: 0.79