Home Cart 0 Sign in  
X

[ CAS No. 112970-44-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 112970-44-2
Chemical Structure| 112970-44-2
Chemical Structure| 112970-44-2
Structure of 112970-44-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 112970-44-2 ]

Related Doc. of [ 112970-44-2 ]

Alternatived Products of [ 112970-44-2 ]

Product Details of [ 112970-44-2 ]

CAS No. :112970-44-2 MDL No. :MFCD07787450
Formula : C7H8BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :TUNIZJPEKHLBPR-UHFFFAOYSA-N
M.W : 202.05 Pubchem ID :10910575
Synonyms :

Calculated chemistry of [ 112970-44-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.04
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) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 2.05
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 1.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.67
Solubility : 0.434 mg/ml ; 0.00215 mol/l
Class : Soluble
Log S (Ali) : -2.26
Solubility : 1.1 mg/ml ; 0.00546 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.192 mg/ml ; 0.000948 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 112970-44-2 ]

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 [ 112970-44-2 ]

* 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 [ 112970-44-2 ]
  • Downstream synthetic route of [ 112970-44-2 ]

[ 112970-44-2 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 67853-37-6 ]
  • [ 112970-44-2 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride; iron In ethanol for 1.5 h; Reflux Step 1.
Synthesis of 2-bromo-3-methoxyaniline (C23)
Iron (1.94 g, 34 mmol) was added to a solution of 2-bromo-1-methoxy-3-nitrobenzene (2.50 g, 10.77 mmol) in ethanol (18 mL) and concentrated hydrochloric acid (1 mL), and the reaction was heated at reflux for 1.5 hours.
The mixture was cooled to room temperature, filtered through Celite and concentrated in vacuo to afford the title compound as a solid. Yield: 2.57 g, 10.77 mmol, 100percent. LCMS m/z 202.1 (M+1).
1H NMR (400 MHz, CD3OD) δ 3.77 (s, 3H), 6.30 (d, J=8.0 Hz, 1H), 6.43 (d, J=8.0 Hz, 1H), 6.98 (dd, J=8.0, 8.0 Hz, 1H).
96% With iron; ammonium chloride In ethanol; water for 1 h; Heating / reflux Iron powder (1.08 mol) and ammonium chloride (862 mmol) were added to a solution of the bromide (216 mmol) in ethanol (200 mL) and water (140 mL) and the reaction mixture was heated at reflux for 1 h.
The suspension was filtered and concentrated and the residue was extracted with ethyl acetate (3*200 mL).
The combined organic layers were dried (sodium sulfate) and concentrated to give the bromoaniline in 96percent yield as a yellow liquid.
96% With hydrogenchloride; iron In ethanol; water at 85℃; for 2 h; To a suspension of 2-bromo-1-methoxy-3-nitrobenzene (3.90 g, 16.81 mmol) and iron powder (2.82 g, 50.4 mmol) in EtOH (50 mL) was added concentrated HC1 (3.08 mL, 37.0 mmol). The mixture was heated at 85 °C for 2.0 h. HPLC indicated a completion of the reaction. After cooled to room temperature, the solvent was removed under vacuum. The residue was suspended in EtOAc and saturated sodium bicarbonate.The insoluble material was removed by filtration through a pad of wet celite. The organic layer of the filtrate was collected, washed with brine, dried over sodium sulfate. After evaporation of solvent, Intermediate iSA (3.25 g, 16.09 mmol, 96 percentyield) was obtained as brown oil. It was used for the next step without further purification. ‘H NMR (500MHz, chloroform-d) 7.08 (t, J=8.1 Hz, 1H), 6.45 (dd, J8.0, 1.4 Hz, 1H), 6.34 (dd,J=8.3, 1.1 Hz, 1H), 3.89 (s, 2H); LC-MS: method A, RT = 1.21 mm, MS (ESI) m/z: 202.0 and 204.0 (M+H)
95% With iron; ammonium chloride In tetrahydrofuran; methanol; water for 1 h; Reflux 2-bromo-1-methoxy-3-nitrobenzene (1 g, 4.31 mmol), Fe (1.68 g, 30.17 mmol) and NH4Cl (1.61 g, 30.17 mmol)were dissolved in THF (4 mL)/MeOH (4 mL)/H2O (2 mL) solution and stirred for 1 hour under reflux. After terminationof the reaction, the reaction solution was cooled to room temperature, diluted with saturated NaHCO3 solution andextracted with EtOAc. The extract solution was concentrated under reduced pressure and purified by column chromatography(eluent, EtOAc/Hex = 1/5) to obtain the title compound (0.83 g, 95 percent yield).1H NMR (500 MHz, CDCl3) δ 7.05(dd, 1H), 6.42(d, 1H), 6.31(d, 1H), 3.86(s, 3H)
91% With acetic acid In ethanol for 3.5 h; Heating / reflux 2-Bromo-3-nitroanisole B3 (1.00 g; 4.31 MMOL) was dissolved in glacial acetic acid (11.0 mL) and ethanol (11.0 mL). To this solution was added iron powder (0.98 g; 17.5 MMOL). The mixture was stirred at reflux for 3.5 h and worked up. The reaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 and the product extracted with CH2CI2 (3X 50 mL). The extracts were dried (NA2SO4), filtered and CONCENTRATED IN VACUO to afford the crude product, 2-bromo-3 methoxyaniline B4 (91 percent; 0. 79 g) as a pale yellow oil. MS 201.8 (MH) + ; Homogeneity by HPLC (TFA) 220 nm: 95percent.
91% With iron; acetic acid In ethanol for 3.5 h; Heating / reflux Step C:; 2-Bromo-3-nitroanisole 1b3 (1.00 g; 4.31 mmol) was dissolved in glacialacetic acid (11.0 mL)/ethanol (11.0 mL) and to the solution was added iron powder(0.98 g; 17.5 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. Thereaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 and theproduct extracted with CH2CI2 (3X 50 mL). The extracts were dried (Na2SO4), filteredand concentrated in vacua to afford the crude product, 2-bromo-3 methoxyaniline 1b4(91percent; 0.79 g) as a pale yellow oil. MS 201.8 (MH)+; Homogeneity by HPLC (TFA) (at)220nm: 95percent
91% With iron; acetic acid In ethanol for 3.5 h; Heating / reflux 2-Bromo-3-nitroanisole 1b3 (1.00 g; 4.31 mmol) was dissolved in glacial acetic acid (11.0 mL)/ethanol (11.0 mL) and to the solution was added iron powder (0.98 g; 17.5 mmol).
The mixture was stirred at reflux for 3.5 hr and worked up.
The reaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 and the product extracted with CH2Cl2(3*50 mL).
The extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the crude product, 2-bromo-3 methoxyaniline 1b4 (91percent; 0.79 g) as a pale yellow oil. MS 201.8 (MH)+; Homogeneity by HPLC (TFA)at;220 nm: 95percent
91% With iron; acetic acid In ethanol for 3.5 h; Heating / reflux 2-Bromo-3-nitroanisole 2b3 (1.00 g; 4.31 mmol) was dissolved in glacialacetic acid (11.0 mL )/ethanol (11.0 mL) and to the solution was added iron powder(0.98 g; 17.5 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. Thereaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 andthe product extracted with CH2CI2( 3X 50 mL). The extracts were dried (Na2SO4),filtered and concentrated in vacuo to afford the crude product, 2-bromo-3methoxyaniline 2b4 (91percent; 0.79 g) as a pale yellow oil. MS 201.8 (MH)+;Homogeneity by HPLC (TFA) (at) 220nm: 95percent
91%
Stage #1: With iron; acetic acid In ethanol for 3.5 h; Heating / reflux
Stage #2: With sodium carbonate In ethanol; water
Step C; 2-Bromo-3-nitroanisole 2B3 (1.00 g; 4.31 mmol) was dissolved in glacial acetic acid (11.0 mL)/ethanol (11.0 mL) and to the solution was added iron powder (0.98 g; 17.5 mmol). The mixture was stirred at reflux for 3.5 h and worked up. The reaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 and the product extracted with CH2CI2 (3X 50 mL). The extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the crude product, 2-bromo-3 methoxyaniline 2B4 (91percent; 0.79 g) as a pale yellow oil. MS 201.8 (MH)+; Homogeneity by HPLC (TFA) (at) 220nm: 95percent
89% With water; iron; ammonium chloride In tetrahydrofuran at 70℃; for 2.5 h; A solution of 2-bromo-l-methoxy-3 -nitrobenzene (500 mg, 2.16 mmol) in CH3OH (5 mL) and THF (5 mL) was added to a solution OfNH4Cl (572 mg, 10.7 mmol) in water (5 mL). Then, iron (325 mesh, 601 mg, 10.7 mmol) was added and the resulting mixture was heated to 70 °C under nitrogen. After 2.5 h, the reaction mixture was cooled to room temperature, filtered over kieselguhr, diluted with AcOEt, and successively washed with a saturated solution OfNaHCO3 in water and brine. The organic layer was dried (Na2SO4) and evaporated. The residue was triturated in CH2Cl2, the filtered to give 390 mg (89 percent) of the target product 37 as a beige solid.

Reference: [1] Patent: US2012/252758, 2012, A1, . Location in patent: Page/Page column 27
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9287 - 9295
[3] Patent: US2007/78147, 2007, A1, . Location in patent: Page/Page column 67
[4] Patent: WO2018/13774, 2018, A1, . Location in patent: Page/Page column 318
[5] Patent: EP3239143, 2017, A2, . Location in patent: Paragraph 0441
[6] Patent: WO2004/103996, 2004, A1, . Location in patent: Page 40-41
[7] Patent: WO2006/7700, 2006, A1, . Location in patent: Page/Page column 62
[8] Patent: US2006/19905, 2006, A1, . Location in patent: Page/Page column 24-25
[9] Patent: WO2006/85, 2006, A1, . Location in patent: Page/Page column 75-76
[10] Patent: WO2007/9227, 2007, A1, . Location in patent: Page/Page column 35
[11] Patent: WO2007/14919, 2007, A1, . Location in patent: Page/Page column 91
[12] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 - 1176
[13] Synthetic Communications, 2007, vol. 37, # 16, p. 2777 - 2786
[14] Bulletin of the Chemical Society of Japan, 1978, vol. 51, p. 2437 - 2438
[15] Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5352 - 5362
  • 2
  • [ 603-85-0 ]
  • [ 112970-44-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5352 - 5362
[2] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 - 1176
  • 3
  • [ 16554-45-3 ]
  • [ 112970-44-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5352 - 5362
[2] Bulletin of the Chemical Society of Japan, 1978, vol. 51, p. 2437 - 2438
  • 4
  • [ 168335-61-3 ]
  • [ 112970-44-2 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 4, p. 1150 - 1160
[2] Angewandte Chemie - International Edition, 2008, vol. 47, # 5, p. 888 - 890
  • 5
  • [ 56619-93-3 ]
  • [ 112970-44-2 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 4, p. 1150 - 1160
  • 6
  • [ 809231-02-5 ]
  • [ 112970-44-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5095 - 5100
  • 7
  • [ 101935-40-4 ]
  • [ 112970-44-2 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 - 1176
  • 8
  • [ 112970-44-2 ]
  • [ 75-05-8 ]
  • [ 923289-30-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5095 - 5100
  • 9
  • [ 112970-44-2 ]
  • [ 1175277-80-1 ]
Reference: [1] Patent: WO2018/13774, 2018, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 112970-44-2 ]

Aryls

Chemical Structure| 35736-52-8

[ 35736-52-8 ]

2,4-Dibromo-5-methoxyaniline

Similarity: 0.98

Chemical Structure| 59557-92-5

[ 59557-92-5 ]

2-Bromo-5-methoxyaniline

Similarity: 0.92

Chemical Structure| 19056-40-7

[ 19056-40-7 ]

4-Bromo-3-methoxyaniline

Similarity: 0.92

Chemical Structure| 116557-46-1

[ 116557-46-1 ]

3-Bromo-2-methoxyaniline

Similarity: 0.89

Chemical Structure| 16618-68-1

[ 16618-68-1 ]

3-Bromo-5-methoxyaniline

Similarity: 0.88

Bromides

Chemical Structure| 35736-52-8

[ 35736-52-8 ]

2,4-Dibromo-5-methoxyaniline

Similarity: 0.98

Chemical Structure| 59557-92-5

[ 59557-92-5 ]

2-Bromo-5-methoxyaniline

Similarity: 0.92

Chemical Structure| 19056-40-7

[ 19056-40-7 ]

4-Bromo-3-methoxyaniline

Similarity: 0.92

Chemical Structure| 116557-46-1

[ 116557-46-1 ]

3-Bromo-2-methoxyaniline

Similarity: 0.89

Chemical Structure| 16618-68-1

[ 16618-68-1 ]

3-Bromo-5-methoxyaniline

Similarity: 0.88

Ethers

Chemical Structure| 35736-52-8

[ 35736-52-8 ]

2,4-Dibromo-5-methoxyaniline

Similarity: 0.98

Chemical Structure| 59557-92-5

[ 59557-92-5 ]

2-Bromo-5-methoxyaniline

Similarity: 0.92

Chemical Structure| 19056-40-7

[ 19056-40-7 ]

4-Bromo-3-methoxyaniline

Similarity: 0.92

Chemical Structure| 116557-46-1

[ 116557-46-1 ]

3-Bromo-2-methoxyaniline

Similarity: 0.89

Chemical Structure| 16618-68-1

[ 16618-68-1 ]

3-Bromo-5-methoxyaniline

Similarity: 0.88

Amines

Chemical Structure| 35736-52-8

[ 35736-52-8 ]

2,4-Dibromo-5-methoxyaniline

Similarity: 0.98

Chemical Structure| 59557-92-5

[ 59557-92-5 ]

2-Bromo-5-methoxyaniline

Similarity: 0.92

Chemical Structure| 19056-40-7

[ 19056-40-7 ]

4-Bromo-3-methoxyaniline

Similarity: 0.92

Chemical Structure| 116557-46-1

[ 116557-46-1 ]

3-Bromo-2-methoxyaniline

Similarity: 0.89

Chemical Structure| 16618-68-1

[ 16618-68-1 ]

3-Bromo-5-methoxyaniline

Similarity: 0.88