Home Cart 0 Sign in  

[ CAS No. 887581-09-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 887581-09-1
Chemical Structure| 887581-09-1
Structure of 887581-09-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 887581-09-1 ]

Related Doc. of [ 887581-09-1 ]

Alternatived Products of [ 887581-09-1 ]

Product Details of [ 887581-09-1 ]

CAS No. :887581-09-1 MDL No. :MFCD07786684
Formula : C8H10BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :PWFPLVSPVFJSSZ-UHFFFAOYSA-N
M.W : 216.08 Pubchem ID :24691009
Synonyms :

Calculated chemistry of [ 887581-09-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.31
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) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 1.44
Log Po/w (WLOGP) : 1.76
Log Po/w (MLOGP) : 1.95
Log Po/w (SILICOS-IT) : 2.1
Consensus Log Po/w : 1.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.946 mg/ml ; 0.00438 mol/l
Class : Soluble
Log S (Ali) : -1.79
Solubility : 3.54 mg/ml ; 0.0164 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.43
Solubility : 0.0803 mg/ml ; 0.000372 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 887581-09-1 ]

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 [ 887581-09-1 ]

* 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 [ 887581-09-1 ]
  • Downstream synthetic route of [ 887581-09-1 ]

[ 887581-09-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 7507-86-0 ]
  • [ 887581-09-1 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With tert-butyldimethylsilane; methyl carbamate; trifluoroacetic acid In acetonitrile at 80℃; for 6 h;
Stage #2: With water; lithium hydroxide In tetrahydrofuran; methanol at 80℃; for 16 h;
To a stirred solution of bromobenzaldehyde 1b (1.0 g, 4.6 mmol) and methyl carbamate (524 mg, 7.0 mmol) in acetonitrile (12 mL), were added sequentially TFA (0.71 mL, 9.3 mmol) and tert-butyldiemthylsilane (TBDMSH) (1.53 mL, 9.3 mmol) and the resulting solution was stirred at 80 °C for 6 h. The reaction mixture was concentrated in vacuo and the residue dissolved in a mixture of THF, MeOH and aq. LiOH [1.95 g, 46.5 mmol in H2O (5 mL)] (1:1:1, total 15 mL) and heated at 80 °C for 16 h. The reaction mixture was cooled to RT and then treated with aqueous NaOH [700 mg in H2O (10 mL)] and the mixture was extracted with ethyl acetate (3 .x. 20 mL). The combined organic layers were washed with saturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent and purification of the crude material by flash chromatography (short column, ethyl acetate/hexane, 1:1 to 100percent ethyl acetate, then 5:95 methanol/ethyl acetate to 10:90 methanol/ethyl acetate) furnished the benzylamine 3b (960 mg, 95percent) as pale yellowish viscous liquid. 1H NMR (400 MHz, CDCl3): = 7.40 (d, J = 8.6 Hz, 1H, Ar-H), 6.93 (d, J = 3.0 Hz, 1H, Ar-H), 6.67 (dd, J = 8.6, 3.0 Hz, 1H, Ar-H), 3.86 (s, 2H, CH2NH2), 3.78 (s, 3H, OCH3), 2.12 (br. s, 2H, CH2NH2); 13C NMR (100 MHz, CDCl3): = 159.3 (C), 142.5 (C), 133.4 (CH), 114.8 (CH), 114.1 (CH), 113.7 (C), 55.4 (OCH3), 46.8 (CH2NH2); HRMS (ESI) calcd for C8H11BrNO [M+H]+ 216.0018, found 216.0017.
Reference: [1] Tetrahedron, 2012, vol. 68, # 6, p. 1745 - 1749
  • 2
  • [ 138642-47-4 ]
  • [ 887581-09-1 ]
YieldReaction ConditionsOperation in experiment
36%
Stage #1: With borane-THF In tetrahydrofuran at 20℃; Cooling with ice
Stage #2: With water; sodium carbonate In tetrahydrofuran
Step A:
1-(2-Bromo-5-methoxyphenyl)methanamine
2-Bromo-5-methoxybenzonitrile (10.0 g, 47.2 mmol) was dissolved in dry tetrahydrofuran (100 mL) in a flame-dried flask and cooled in an ice bath.
A solution of borane in tetrahydrofuran (75 mL, 75 mmol, 1.0 M) was added dropwise over a period of 30 minutes.
The reaction mixture was stirred overnight at rt, then quenched slowly with ice water and Na2CO3 (saturated aqueous solution).
After removal of THF, the residue was extracted with large amounts of EtOAc three times.
The combined organic layers were washed with water, dried, and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product as a white powder (3.65 g, 36percent). LCMS for C8H10BrNO (M+H)+: m/z=216.9, 219.0.
Reference: [1] Patent: US2010/190804, 2010, A1, . Location in patent: Page/Page column 75-76
[2] Patent: WO2004/14384, 2004, A2, . Location in patent: Page/Page column 235-236; 239
  • 3
  • [ 99848-43-8 ]
  • [ 887581-09-1 ]
YieldReaction ConditionsOperation in experiment
47%
Stage #1: With dimethylsulfide borane complex In tetrahydrofuran at 0 - 70℃;
Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0℃; for 0.583333 h; Heating / reflux
Stage #3: With sodium hydrogencarbonate In tetrahydrofuran; water
Step 2:
1-(2-bromo-5-methoxyphenyl)methanamine
Immediately prior to reaction, 2-bromo-5-methoxybenzamide (6.4 mmol) was azeotropically dried with toluene and then further dried under vacuum.
This dry material was suspended in THF (15 mL) and the suspension was cooled to 0° C.
To the reaction mixture was added 2M borane-dimethylsulfide complex in THF (8 mL) via syringe.
The reaction mixture was heated at 70° C. and allowed to stir overnight.
The mixture was cooled to 0° C. and treated with conc. HCl (0.5 mL).
Vigorous gas evolution is observed, and the reaction mixture was allowed to stir at 0° C. for 15 min and then concentrated.
The residue was diluted with water (10 mL) and heated at reflux for 20 min.
The mixture was allowed to cool to rt and was basified with sat NaHCO3.
The mixture was extracted with EtOAc.
The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated.
The residue was purified by column chromatography to give 1-(2-bromo-5-methoxyphenyl)methanamine (3.1 mmol, 47percent). LCMS: (FA) ES+216.
Reference: [1] Patent: US2008/171754, 2008, A1, . Location in patent: Page/Page column 105
  • 4
  • [ 19614-12-1 ]
  • [ 887581-09-1 ]
Reference: [1] Synlett, 2008, # 18, p. 2851 - 2855
[2] Synthesis, 2009, # 18, p. 3127 - 3135
[3] ACS Combinatorial Science, 2012, vol. 14, # 3, p. 211 - 217
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 887581-09-1 ]

Aryls

Chemical Structure| 166530-78-5

[ 166530-78-5 ]

(5-Bromo-2-methoxyphenyl)methanamine

Similarity: 0.90

Chemical Structure| 1261448-82-1

[ 1261448-82-1 ]

(4-Bromo-3-methoxyphenyl)methanamine

Similarity: 0.87

Chemical Structure| 27060-75-9

[ 27060-75-9 ]

1-Bromo-4-methoxy-2-methylbenzene

Similarity: 0.84

Chemical Structure| 1097778-99-8

[ 1097778-99-8 ]

2-(Aminomethyl)-5-bromophenol

Similarity: 0.83

Chemical Structure| 150192-39-5

[ 150192-39-5 ]

(2-Bromo-5-methoxyphenyl)methanol

Similarity: 0.81

Bromides

Chemical Structure| 166530-78-5

[ 166530-78-5 ]

(5-Bromo-2-methoxyphenyl)methanamine

Similarity: 0.90

Chemical Structure| 1261448-82-1

[ 1261448-82-1 ]

(4-Bromo-3-methoxyphenyl)methanamine

Similarity: 0.87

Chemical Structure| 27060-75-9

[ 27060-75-9 ]

1-Bromo-4-methoxy-2-methylbenzene

Similarity: 0.84

Chemical Structure| 1097778-99-8

[ 1097778-99-8 ]

2-(Aminomethyl)-5-bromophenol

Similarity: 0.83

Chemical Structure| 150192-39-5

[ 150192-39-5 ]

(2-Bromo-5-methoxyphenyl)methanol

Similarity: 0.81

Ethers

Chemical Structure| 166530-78-5

[ 166530-78-5 ]

(5-Bromo-2-methoxyphenyl)methanamine

Similarity: 0.90

Chemical Structure| 1261448-82-1

[ 1261448-82-1 ]

(4-Bromo-3-methoxyphenyl)methanamine

Similarity: 0.87

Chemical Structure| 27060-75-9

[ 27060-75-9 ]

1-Bromo-4-methoxy-2-methylbenzene

Similarity: 0.84

Chemical Structure| 150192-39-5

[ 150192-39-5 ]

(2-Bromo-5-methoxyphenyl)methanol

Similarity: 0.81

Chemical Structure| 68155-69-1

[ 68155-69-1 ]

1-Bromo-4-ethoxy-2-methylbenzene

Similarity: 0.81

Amines

Chemical Structure| 166530-78-5

[ 166530-78-5 ]

(5-Bromo-2-methoxyphenyl)methanamine

Similarity: 0.90

Chemical Structure| 1261448-82-1

[ 1261448-82-1 ]

(4-Bromo-3-methoxyphenyl)methanamine

Similarity: 0.87

Chemical Structure| 1097778-99-8

[ 1097778-99-8 ]

2-(Aminomethyl)-5-bromophenol

Similarity: 0.83

Chemical Structure| 1261581-85-4

[ 1261581-85-4 ]

2-Bromo-6-methoxybenzamide

Similarity: 0.78

Chemical Structure| 152626-77-2

[ 152626-77-2 ]

4-Bromo-5-methoxy-2-methylaniline

Similarity: 0.78