Home Cart 0 Sign in  

[ CAS No. 13073-25-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 13073-25-1
Chemical Structure| 13073-25-1
Structure of 13073-25-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 13073-25-1 ]

Related Doc. of [ 13073-25-1 ]

Alternatived Products of [ 13073-25-1 ]

Product Details of [ 13073-25-1 ]

CAS No. :13073-25-1 MDL No. :MFCD02683216
Formula : C6H4BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VEJSIOPQKQXJAT-UHFFFAOYSA-N
M.W : 218.00 Pubchem ID :13545453
Synonyms :

Calculated chemistry of [ 13073-25-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.99
TPSA : 66.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : -0.1
Consensus Log Po/w : 1.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.93
Solubility : 0.254 mg/ml ; 0.00116 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.122 mg/ml ; 0.000559 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.06
Solubility : 1.89 mg/ml ; 0.00867 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 13073-25-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P280-P337+P313-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13073-25-1 ]

* 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 [ 13073-25-1 ]
  • Downstream synthetic route of [ 13073-25-1 ]

[ 13073-25-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 577-19-5 ]
  • [ 13073-25-1 ]
  • [ 5847-59-6 ]
  • [ 5470-65-5 ]
  • [ 76361-99-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 6.2, p. 1149 - 1152[2] Zhurnal Organicheskoi Khimii, 1991, vol. 27, # 6, p. 1317 - 1320
  • 2
  • [ 13073-25-1 ]
  • [ 74-88-4 ]
  • [ 116557-46-1 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16 h;
Stage #2: With ammonium chloride; zinc In ethanol at 20℃; for 6 h;
[00162] Intermediate 9A. 3-Bromo-2-methoxyaniline: Potassium carbonate (6.47 g, 46.8 mmol) and methyl iodide (2.86 mL, 46.8 mmol) were added to a solution of 2- bromo-6-nitrophenol (5.10 g, 23.4 mmol) in DMF (100 mL) at room temperature and the resulting reaction mixture was stirred for 16 h. The reaction was quenched with water (100 mL) and diluted with EtOAc (500 mL). The aqueous layer was extracted with EtOAc. The combined organics were washed with saturated aHC03 solution and brine, dried over MgS04, filtered, and evaporated. The crude was dissolved in EtOH (100 mL) and zinc (15.30 g, 233.9 mmol) and ammonium chloride (12.52 g, 233.9 mmol) were added. The reaction mixture was stirred at room temperature for 6 h. The reaction was diluted with EtOAc, filtered through CELITE®, and evaporated. The crude was purified by flash chromatography (10-20percent EtOAc/hexanes) to give Intermediate 9A (4.6 g, 97percent) as a yellow oil. LCMS (ESI) m/z 202, 204 (M+H, M+2+H)+, RT = 1.38 min (Method A).
Reference: [1] Patent: WO2014/22343, 2014, A1, . Location in patent: Paragraph 00162
  • 3
  • [ 13073-25-1 ]
  • [ 116557-46-1 ]
Reference: [1] Journal of the American Chemical Society, 1934, vol. 56, p. 1787,1790
[2] Patent: WO2014/74661, 2014, A1,
[3] Patent: WO2014/154760, 2014, A1,
[4] Patent: WO2015/69310, 2015, A1,
[5] Patent: EP2987787, 2016, A1,
[6] Patent: TWI582077, 2017, B,
[7] Patent: WO2008/120003, 2008, A1,
  • 4
  • [ 13073-25-1 ]
  • [ 101935-40-4 ]
Reference: [1] Tetrahedron, 2018, vol. 74, # 21, p. 2547 - 2560
  • 5
  • [ 13073-25-1 ]
  • [ 101935-40-4 ]
Reference: [1] Tetrahedron, 2018, vol. 74, # 21, p. 2547 - 2560
  • 6
  • [ 577-19-5 ]
  • [ 13073-25-1 ]
  • [ 5847-59-6 ]
  • [ 5470-65-5 ]
  • [ 76361-99-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 6.2, p. 1149 - 1152[2] Zhurnal Organicheskoi Khimii, 1991, vol. 27, # 6, p. 1317 - 1320
  • 7
  • [ 13073-25-1 ]
  • [ 74-88-4 ]
  • [ 98775-19-0 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate In acetoneReflux To a mixture of the compound represented by the structural formula (O-1) (19.6 g, 90.0 mmol) and potassium carbonate (24.9 g, 180 mmol) in acetone (400 mL), iodomethane (25.6 g, 180 mmol) was added.
The mixture was refluxed overnight.
After cooling, the mixture was filtered, and washed with ethyl acetate (100 mL).
The filtrate was concentrated in vacuo.
The residue was dissolved in ethyl acetate, the solution was washed with brine, dried over Na2SO4, and concentrated to give 1-bromo-2-methoxy-3-nitrobenzene represented by the structural formula (O-2) as yellow solid (20.2 g, yield 97percent).
1H-NMR Spectrum (300MHz, DMSO-d6):δ (ppm): 3.92 (s, 3H), 7.32 (d, 1H, J=8.1Hz), 7.94-8.03 (m, 2H)
96%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide for 0.5 h;
Stepi[00172j 2-Bromo-6-nitrophenol (5.0 g, 22.9 mmol) was dissolved in DMF (3 mL), potassium carbonate (4.75 g, 34.4 mmol) was added and the reaction was stirred for 30 minutes. Next iodomethane (2.15 mL, 34.4 mmol) was added and the reaction was stirred overnight. The crude reaction was filtered, diluted with ethyl acetate and washed with brine (twice) and water (twice). The organic layer was dried over sodium sulfate, filtered and concentrated to provide Int9 (5.12 g, 96percent). LC retention time 0.92 [J].
95%
Stage #1: With potassium carbonate In acetone at 70℃; for 1 h;
Stage #2: for 8 h; Reflux
A mixture of 2-Bromo-6-nitro-phenol (43.6 g, 0.2 mol), K2CO3 (82.9 g, 0.6 mol), acetone (600 mL) is stirred at 70° C. for 1 h. Then MeI (85.14 g, 0.6 mol) is slowly added to the reaction mixture and refluxed for 8 h. After reaction, filtered and the filtrate is extracted with ethyl acetate (3×1000 mL). The combined SnCl2 organic phase is washed with water and brine, dried over Na2SO4, concentrated in vacuo to obtain the desired product. Yield: 44 g (95percent) HPLC-MS: M+H=232/234; tRet=2.04 min; AM12
95%
Stage #1: With potassium carbonate In acetone at 70℃; for 1 h;
Stage #2: for 8 h; Reflux
l-Bromo-2-methoxy-3-nitro-benzene A mixture of 2-Bromo-6-nitro-phenol (43.6 g, 0.2mol), K2CO3 (82.9 g, 0.6 mol), acetone (600mL) is stirred at 70 °C for lh. Then Mel (85.14g, 0.6 mol) is slowly added to the reaction mixture and refluxed for 8h. After reaction, filtered and the filtrate is extracted with ethyl acetate (3 x lOOOmL). The combined SnC12organic phase is washed with water and brine, dried over Na2S04, concentrated in vacuo to obtain the desired product. Yield: 44g (95percent) HPLC-MS: M+H=232/234; tRet =2.04 min; AM12
90% With potassium carbonate In acetone at 70℃; for 40 h; Step 2 1-Bromo-2-methoxy-3-nitro-benzene; 2-Bromo-6-nitro-phenol 1b (46.55 g, 0.214 mol) was dissolved in 500 mL of acetone followed by addition of potassium carbonate (35.36 g, 0.256 mol) and iodomethane (20.1 mL, 0.32 mol). The reaction mixture was heated to reflux at 70 °C for 40 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure and diluted with 1300 mL of ethyl acetate and 500 mL of water. The aqueous layer was extracted with ethyl acetate (300 mL.x.2). The combined organic extracts were washed with 4 N hydrochloric acid and saturated aqueous sodium bicarbonate and then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 1-bromo-2-methoxy-3-nitro-benzene 1c (44.59 g, yield 90.0percent) as a brown solid. MS m/z (ESI): 234 [M+1]
90% With potassium carbonate In acetone at 70℃; for 40 h; Step 2 1-Bromo-2-methoxy-3-nitro-benzene; 2-Bromo-6-nitro-phenol 1b (46.55 g, 0.214 mol) was dissolved in 500 mL of acetone followed by addition of potassium carbonate (35.36 g, 0.26 mol) and iodo- methane (20.1 mL, 0.32 mol). The reaction mixture was heated to reflux at 70°C for 40 hours. The reaction mixture was concentrated under reduced pressure and diluted with 1300 mL of ethyl acetate and 500 mL of water. The aqueous layer was extracted with ethyl acetate (300 mLx2). The combined organic extracts were washed with 4 M hydrochloric acid and saturated sodium bicarbonate solution and then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 1-bromo-2-methoxy-3-nitro-benzene 1c (44.59 g, yield 90.0percent) as a brown solid. MS m/z (ESI): 234 [M+1]
90% With potassium carbonate In acetone at 70℃; for 40 h; 2-bromo-6-nitrophenol 1b (46.55g, 0.214mol) was dissolved in 500mL acetone. To this was added potassium carbonate (35.36g, 0.26mol) and iodomethane (20.1mL, 0.32mol) then the solution was heated at reflux 70°C for 40 hours. The reaction solution was concentrated under reduced pressure. Added 1300mL ethyl acetate and 500mL water. The aqueous phase was extracted with ethyl acetate (300mL × 2). The combined organic phases were washed with 4M hydrochloric acid and saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The result was purified by column chromatography on silica gel to give 1-bromo-2-methoxy-3-nitrobenzene 1c (44.59g, brown solid). Yield: 90.0percent.
89% With potassium carbonate In N,N-dimethyl-formamide at 20℃; Preparation 12 To a solution of 2-bromo-6-nitrophenol (5 g, 22.94 mmol) in DMF (18 ml) was added potassium carbonate (9.51 g, 68.8 mmol) and the resulting mixture was stirred for 15 min, then iodomethane (2.87 ml, 45.9 mmol) was added. The resulting mixture was stirred at rt overnight. HPLC and LCMS indicated complete conversion to product. Cold water added (75 mL), stir/sonicate, solid was collected by filtration. This material was then dissolved in EtOAc (150 mL). This solution was washed lx 10percent LiCl, lx brine. dried over sodium sulfate, then filtered and concentrated. Loaded onto a 120g silica gel cartridge, then purified by flash chromatography eluting with 0-50percent EtOAc in hexanes. Fractions containing the product were concentrated to afford a pale yellow solid as the product l-bromo-2-methoxy-3 -nitrobenzene (4.997 g, 20.46 mmol, 89percent yield). LCMS ave very weak MH+.
89%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide for 0.25 h;
Stage #2: at 20℃;
To a solution of 2-bromo-6-nitrophenol (5 g, 22.94 mmol) in DMF (18 ml) was added potassium carbonate (9.51 g, 68.8 mmol) and the resulting mixture was stirred for 15 min and then iodomethane (2.87 ml, 45.9 mmol). The resulting mixture was stirred overnight at rt. HPLC and LCMS instructions were fully converted to product. Add cold water (75 mL), perform agitation / sonic processing, and collect solids by filtration. The material was then dissolved in EtOAc (150 mL). The solution was washed with 10percent LiCl, washed 1x with brine, dried over sodium sulfate, filtered and concentrated. Was loaded onto a 120 g silica gel cartridge and then purified by flash chromatography eluting with 0-50percent EtOAc in hexanes. Concentrate the fractions containing the product to afford the product as a pale yellow solid 1-bromo-2-methoxy-3-nitrobenzene (4.997 g, 20.46 mmol, 89percent yield).
83.6% With potassium carbonate In acetoneHeating / reflux To a mixture of 2-bromo-6-nitrophenol (5.0 g, 22.9 mmol) and potassium carbonate (6.3 g,45.8 mmol) in acetone (100 mL) was added iodomethane (2.85 mL, 45.8 mmol) under stirring and the mixture was then heated to reflux overnight. The mixture was cooled to room temperature, filtered through Celite, the filter cake washed with ethyl acetate, and the filtrate concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed 3x with IN NaOH, once with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized twice from 2-propanol / water to give 4.45 g (83.6percent) of the title compound as beige, very fine needles.MS (ESI: 232 / 234 (M+H+) for C7H6BrNO1H-NMR (DMSO-d^ δ: ppm 3.98 (s, 3H); 7.39 (t, IH); 8.02 (dd, IH); 8.08 (dd, IH).
2.1 g With potassium carbonate In acetone at 80℃; for 6 h; To a mixture of K2CO3 (2.54 g) and 2-bromo-6-nitrophenol (2 g) in acetone (15 mL) at room temperature was added Mel (3.442 mL). The reaction mixture was heated to 80° C. for 6 h, after cooling the reaction, the mixture was filtered and the filtrate was concentrated to afford 2-bromo-6-nitrophenyl methyl ether (D31) (2.1 g). δH (CDCl3, 400 MHz): 3.96 (3H, s), 4.91 (1H, m), 7.06 (1H, t), 7.19 (1H, s), 7.72 (1H, m).

Reference: [1] Patent: EP2987787, 2016, A1, . Location in patent: Paragraph 0129-0130
[2] Patent: WO2014/74661, 2014, A1, . Location in patent: Paragraph 00172
[3] Patent: US2014/296229, 2014, A1, . Location in patent: Paragraph 0254; 0255; 0256
[4] Patent: WO2014/154760, 2014, A1, . Location in patent: Page/Page column 55
[5] Patent: EP2236500, 2010, A1, . Location in patent: Page/Page column 15
[6] Patent: EP2441457, 2012, A1, . Location in patent: Page/Page column 12-13
[7] Patent: TWI530497, 2016, B, . Location in patent: Page/Page column 25; 26
[8] Patent: WO2015/69310, 2015, A1, . Location in patent: Paragraph 00184
[9] Patent: TWI582077, 2017, B, . Location in patent: Page/Page column 87
[10] Patent: WO2008/120003, 2008, A1, . Location in patent: Page/Page column 50
[11] Patent: WO2011/113309, 2011, A1, . Location in patent: Page/Page column 35
[12] Patent: US2013/12491, 2013, A1, . Location in patent: Paragraph 0202; 0203
  • 8
  • [ 13073-25-1 ]
  • [ 77-78-1 ]
  • [ 98775-19-0 ]
Reference: [1] Journal of the American Chemical Society, 1934, vol. 56, p. 1787,1790
  • 9
  • [ 13073-25-1 ]
  • [ 376592-93-7 ]
Reference: [1] Patent: EP2865662, 2015, A1,
[2] Patent: CN105801444, 2016, A,
[3] Patent: CN107915678, 2018, A,
  • 10
  • [ 13073-25-1 ]
  • [ 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
[ 13073-25-1 ]

Aryls

Chemical Structure| 7693-52-9

[ 7693-52-9 ]

4-Bromo-2-nitrophenol

Similarity: 0.95

Chemical Structure| 5847-59-6

[ 5847-59-6 ]

2-Bromo-4-nitrophenol

Similarity: 0.92

Chemical Structure| 139138-08-2

[ 139138-08-2 ]

2-Amino-4-bromo-6-nitrophenol

Similarity: 0.90

Chemical Structure| 52427-05-1

[ 52427-05-1 ]

2-Bromo-5-nitrophenol

Similarity: 0.90

Chemical Structure| 76361-99-4

[ 76361-99-4 ]

3-Bromo-2-nitrophenol

Similarity: 0.89

Bromides

Chemical Structure| 7693-52-9

[ 7693-52-9 ]

4-Bromo-2-nitrophenol

Similarity: 0.95

Chemical Structure| 5847-59-6

[ 5847-59-6 ]

2-Bromo-4-nitrophenol

Similarity: 0.92

Chemical Structure| 139138-08-2

[ 139138-08-2 ]

2-Amino-4-bromo-6-nitrophenol

Similarity: 0.90

Chemical Structure| 52427-05-1

[ 52427-05-1 ]

2-Bromo-5-nitrophenol

Similarity: 0.90

Chemical Structure| 76361-99-4

[ 76361-99-4 ]

3-Bromo-2-nitrophenol

Similarity: 0.89

Nitroes

Chemical Structure| 7693-52-9

[ 7693-52-9 ]

4-Bromo-2-nitrophenol

Similarity: 0.95

Chemical Structure| 5847-59-6

[ 5847-59-6 ]

2-Bromo-4-nitrophenol

Similarity: 0.92

Chemical Structure| 139138-08-2

[ 139138-08-2 ]

2-Amino-4-bromo-6-nitrophenol

Similarity: 0.90

Chemical Structure| 52427-05-1

[ 52427-05-1 ]

2-Bromo-5-nitrophenol

Similarity: 0.90

Chemical Structure| 76361-99-4

[ 76361-99-4 ]

3-Bromo-2-nitrophenol

Similarity: 0.89