Home Cart Sign in  
Chemical Structure| 583-75-5 Chemical Structure| 583-75-5

Structure of 4-Bromo-2-methylaniline
CAS No.: 583-75-5

Chemical Structure| 583-75-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 583-75-5 ]

CAS No. :583-75-5
Formula : C7H8BrN
M.W : 186.05
SMILES Code : C1=C(Br)C=CC(=C1C)N
MDL No. :MFCD00007825
InChI Key :PCHYYOCUCGCSBU-UHFFFAOYSA-N
Pubchem ID :11423

Safety of [ 583-75-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 583-75-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 1.0
Molar Refractivity 43.51
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

26.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.89
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.95
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.35
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.57
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.26
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.2

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.72
Solubility 0.358 mg/ml ; 0.00193 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.12
Solubility 1.41 mg/ml ; 0.00757 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.28
Solubility 0.0981 mg/ml ; 0.000527 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.05 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.07

Application In Synthesis of [ 583-75-5 ]

* 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.

  • Downstream synthetic route of [ 583-75-5 ]

[ 583-75-5 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 52414-98-9 ]
  • [ 583-75-5 ]
YieldReaction ConditionsOperation in experiment
With 2 wt% Pd/C; hydrogen; at 120℃; under 7500.75 Torr; Examples 27 to 34 investigated the effect of carbon-supported large-particle palladium catalysts on the synthesis of halogenated aromatic amines by solvent-free hydrogenation of different halogenated aromatic nitro compounds. In a 500 ml reactor, 200 g of different halogenated aromatic nitro compounds were added, 2 g of a 2 wt% palladium catalyst containing a large particle size in Example 5, shutting down the reactor; first with nitrogen replacement reactor inside the air three times, and then replaced with hydrogen three times, And then heated to 120 C, and the hydrogen pressure rose to 1MPa, open stirring to 1000r/min; to maintain the reaction temperature and pressure until the end of the reaction; cooling cooling, remove the reactor liquid, filter separation The catalyst was used and the water in the filtrate was separated by phase separation to give the desired product Halogenated aromatic amine. The reaction product was analyzed by gas chromatography. The results are shown in Table 4.
  • 2
  • [ 583-75-5 ]
  • [ 52414-98-9 ]
YieldReaction ConditionsOperation in experiment
74% With dihydrogen peroxide; trifluoroacetic anhydride; In dichloromethane; at 0℃; for 1.58333h;Heating / reflux; Example 37; 2-methoxy-N-(2-methyl-4-(1-(2-(methylamino)ethyl)piperidin-4-yl)phenyl)benzamide (199); Step 1 4-bromo-2-methyl-1 -nitrobenzene (193); [0383] To a mixture of H2O2 (3 95 ml, 64 5 mmol) in DCM (32 0 ml) cooled at O 0C was added TFAA (10 93 ml, 77 mmol) and the mixture was stirred for 5 minutes at that temperature then the ice bath was removed and a reflux condenser was installed and a solution of 4-bromo-2-methylaniline (3 g, 16 12 mmol) in DCM (6 4 ml) was added drop-wise over approx 30 minutes The reaction was heated at reflux for an additional hour then it it was cooled, washed with 30 mL of water then 30 mL of sat NaHCO3 and the organic layer was dried over MgSO4 and concentrated under vacuum The crude material was purified by flash to afford 193 (2 57 g, 1 1 9 mmol, 74%) 1H NMR (CDCI3) delta (ppm) 7 88 (d, J = 8 6 Hz, 1 H),7 53 (d, J = 2 2 Hz, 1 H), 7 49 (dd, J = 8 6, 2 2 Hz, 1 H), 2 60 (s, 3H)
With sulfuric acid; dihydrogen peroxide; In hexane; water; acetic acid; Step A: Preparation of 5-bromo-2-nitrotoluene A solution of 4-bromotoluidine (27.9 g, 150 mmoles) in glacial acetic acid (600 ml) is stirred while 30% hydrogen peroxide (180 ml) and concentrated sulfuric acid (12 ml) are added. The mixture is heated in an oil bath at 100. When the pot temperature reaches 65 the mixture darkens and there is a mild exotherm. The bath is removed and the temperature rises to 105. When the reaction subsides, the bath is replaced and reflux is maintained for two hours. The mixture is cooled and poured onto ice (1500 g). The product crystallizes slowly with scratching. Another liter of cold water is added and the product is filtered and washed. The damp solid is dissolved in hexane, filtered, dried and evaporated to a residue which crystallizes to give 14.3 g of 5-bromo-2-nitrotoluene, containing minor contaminants by tlc [silica gel-dichloromethane/hexane (3:7)] which were removed by column chromatography using the same solvent system. Final weight; 12.8 g.
  • 3
  • [ 320-72-9 ]
  • [ 583-75-5 ]
  • [ 79402-03-2 ]
  • 4
  • [ 75-17-2 ]
  • [ 583-75-5 ]
  • [ 24078-12-4 ]
  • 5
  • [ 52414-98-9 ]
  • [ 7732-18-5 ]
  • Na2S2 [ No CAS ]
  • [ 88070-23-9 ]
  • [ 583-75-5 ]
  • 6
  • [ 7647-01-0 ]
  • [ 958990-53-9 ]
  • [ 30273-41-7 ]
  • [ 53848-17-2 ]
  • [ 583-75-5 ]
  • 7
  • [ 958990-53-9 ]
  • [ 7732-18-5 ]
  • [ 30273-41-7 ]
  • [ 53848-17-2 ]
  • [ 583-75-5 ]
  • 8
  • [ 95-53-4 ]
  • [ 53848-17-2 ]
  • [ 583-75-5 ]
YieldReaction ConditionsOperation in experiment
General procedure: Catalytic reaction was carried out in a 50 mL two necked round bottom flask, which charged with 0.05 g of catalyst, substrate (2 mmol) in acetic acid (5 mL) and KBr (2.2 mmol). 30% H2O2 (2.2 mmol) was then added drop wise to the reaction mixture. The content in the flask was stirred continuously at room temperature. After specified time of the reaction, the catalyst was filtered and the solid was washed with ether. The combined filtrates were washed with saturated sodium bicarbonate solution and then shaken with ether in a separating funnel. The organic extract was dried over anhydrous sodium sulfate. The products were analysed by Varian 3400 gas chromatograph equipped with a 30 m CP-SIL8CB capillary column and a Flame Ionization Detector. Identity of the products was also confirmed by using an Agilent GC-MS.
  • 9
  • [ 583-75-5 ]
  • [ 63558-65-6 ]
  • (4-bromo-2-methyl-phenyl)-(5-iodo-pyrimidin-4-yl)-amine [ No CAS ]
  • 10
  • [ 95-53-4 ]
  • [ 30273-41-7 ]
  • [ 53848-17-2 ]
  • [ 583-75-5 ]
  • 11
  • [ 52414-98-9 ]
  • [ 4637-24-5 ]
  • [ 583-75-5 ]
  • [ 105205-48-9 ]
YieldReaction ConditionsOperation in experiment
With pyrrolidine; In N,N-dimethyl-formamide; at 110℃; for 1.5h; 4-Bromo-2-(2,2-dimethoxyethyl)-1-nitrobenzene (66): Compound 64 (500 mg, 2.315 mmol) (Olsen et al., U.S. Pat. No. 4,287,201) was dissolved in anhydrous dimethylformamide (10 mL) in a dry argon purged flask fitted with a magnetic stir bar and condenser. Dimethylformamide dimethylacetal (828 mg, 6.945 mmol) and pyrrolidine (165 mg, 2.315 mmol) are added to the flask and mixture heated 110 C. for 90 minutes. After cooling to room temperature, the reaction mixture was diluted with diethyl ether and H2O, transferred to a separatory funnel and the organic layer collected. The organic layer washed with H2O (twice) and the combined aqueous layers back extracted with diethyl ether (twice). The combined organic layers were dried over anhydrous sodium sulphate, filtered, concentrated to yield a dark red oil, 65, which is utilized without purification. The crude enamine is dissolved in anhydrous methanol, treated with chlorotrimethylsilane (3 equivalents) and refluxed for 20 hours. The reaction was concentrated under reduced pressure and the residue was partitioned between a saturated sodium bicarbonate solution and ethyl acetate. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulphate, filtered, concentrated and the residue purified via chromatography on silica gel (EtOAc:Hexanes, 1:9) to yield a pale brown solid, 66 (330 mg, 49.2%). 1H NMR (CDCl3) delta 3.20 (d, 2H, J=5.2 Hz), 3.35 (s, 6H), 4.55 (t, 1H, J=5.2 Hz), 7.51 (dd, 1H, J=8.5, 2.1 Hz), 7.58 (d, 1H, J=1.9 Hz), 7.78 (d, 1H, J=8.6 Hz); ESI-MS (m/z, %): 312/314 (M+Na+, 90%), 198/200 (100%); ESI-HRMS calculated for C10H12NO4NaBr (M+Na+), calculated: 311.9841; observed: 311.9826.
  • 13
  • [ 116247-92-8 ]
  • [ 583-75-5 ]
  • [ 1025392-58-8 ]
YieldReaction ConditionsOperation in experiment
B. (4-Bromo-2-methyl-phenyl)-( 1 -pyrimidin-2-yl-piperidin-4-yl)-amine : To the mixture of 4-bromo-2-methylaniline (285 mg, 1.5 mmol) and l-pyrimidin-2-yl-piperidin- 4-one (266 mg, 1.5 mmol) in MeOH/AcOH (10:1, 5 ml) was added BH3-Py in THF (8M, 188 mul). The mixture was stirred at rt for 2h. The reaction mixture was concentrated and to the residue was added HCl (10%, 10 ml). The resulting mixture was stirred at room temperature for 30 min., then with cooling, the mixture was adjusted to alkaline with solid Na2CO3 and water. The aqueous layer was extracted with EtOAc (5 x 30 ml). The EPO <DP n="19"/>EtOAc was dried (Na2SO4) and concentrated. The residue was subjected to ISCO to give the titled compound as a white solid (140 mg). HPLC: column, Luna Phenyl-Hexyl 5 mum 4.6x50 mm, 10-90% solvent B (acetonitrile) in solvent A (IO mM ammonium acetate aq) over 3 min., flow rate 3 ml/min, retention time, 2.71 min.; MS (MH+: 347 and 349). 1H NMR (400 MHz, chloroform- d), delta ppm 1.46 (ddd, J=24.30, 10.86, 4.04 Hz, 2H), 2.10 (s, 3 H), 2.17 (dd, J=13.14, 2.78 Hz, 2 H), 3.20 (ddd, J=14.00, 11.87, 2.78 Hz, 1 H), 3.40 (br. s., 1 H), 3.60 (br. s., 1 H), 4.68 (ddd, J=13.52, 3.41, 3.28 Hz, 2 H), 6.50 (t, J=4.67 Hz, 1 H), 6.57 (d, J=8.59 Hz, 1 H), 7.19 (s, 1 H), 7.23 (dd, J=8.59, 2.27 Hz, 1 H), 8.33 (d, J=4.80 Hz, 2 H).; B. (4-Bromo-2-methyl-phenyl)-( 1 -pyrimidin^-yl-piperidin^-yl)- amine : To the mixture of bromoaniline (285 mg, 1.5 mmol) and ketone (266 mg, 1.5 mmol) in MeOH/AcOH (10:1, 5 ml) was added BH3-Py in THF (8M, 188 mul). The mixture was stirred at rt for 2h. The reaction mixture was concentrated and to the residue was added HCl (10%, 10 ml). The resulting mixture was stirred at rt for 30 min., then with cooling, EPO <DP n="25"/>the mixture was adjusted to alkaline with solid Na2CO3 and water. The aq. layer was extracted with EtOAc (5x 30 ml). The EtOAc was dried (Na2SO4) and concentrated. The residue was subjected to ISCO to give the titled compound as a white solid (140 mg).
  • 14
  • [ 583-75-5 ]
  • [ 915095-89-5 ]
  • 16
  • [ 216019-28-2 ]
  • [ 583-75-5 ]
  • C16H19N [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux; Toluene (9 mL), ethanol (6 mL) and water (3 mL) were added into the mixture of MO(0.95 g, 5 mniol) 4-hromo2chloroaniline, (3..isopropyiphenyi) horonic acid (0.82 g, 5mmoi) and potassium carbonate (1.73 g, 12.5 mmol), stirred with nitrogen replacementfor three times. Additional replacement with nitrogen was performed for three times after0.3 g of tetraphenyiphenyiphosphine palladium was added. Then the reaction was warmed up for refiux reaction overnight. The product was filtered and concentrated, then 2() mL of dichioromethane and 10 mL of water were added and stirred for 1() mm. The liquid was separated and washed with 10 mL of water twice, dried with anhydroussodium sulfate, filtered, concentrated and purified by column chromatography. 0.83 g of M15 was achieved, with yield of 73%.
  • 17
  • [ 216019-28-2 ]
  • [ 583-75-5 ]
  • 2-((3'-isopropyl-3-methyl-[1,1-biphenyl]-4-yl)carbamoyl)cyclopent-1-ene-1-carboxylic acid [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 583-75-5 ]

Aryls

Chemical Structure| 39478-78-9

A109306 [39478-78-9]

5-Bromo-2-methylaniline

Similarity: 0.97

Chemical Structure| 76153-06-5

A123533 [76153-06-5]

5-Bromo-3-methylbenzene-1,2-diamine

Similarity: 0.95

Chemical Structure| 24596-19-8

A561600 [24596-19-8]

4-Bromo-2,6-dimethylaniline

Similarity: 0.93

Chemical Structure| 22364-25-6

A400170 [22364-25-6]

4-Bromo-2,3-dimethylaniline

Similarity: 0.93

Chemical Structure| 74586-53-1

A259368 [74586-53-1]

3-Bromo-5-methylaniline

Similarity: 0.92

Bromides

Chemical Structure| 39478-78-9

A109306 [39478-78-9]

5-Bromo-2-methylaniline

Similarity: 0.97

Chemical Structure| 76153-06-5

A123533 [76153-06-5]

5-Bromo-3-methylbenzene-1,2-diamine

Similarity: 0.95

Chemical Structure| 24596-19-8

A561600 [24596-19-8]

4-Bromo-2,6-dimethylaniline

Similarity: 0.93

Chemical Structure| 22364-25-6

A400170 [22364-25-6]

4-Bromo-2,3-dimethylaniline

Similarity: 0.93

Chemical Structure| 74586-53-1

A259368 [74586-53-1]

3-Bromo-5-methylaniline

Similarity: 0.92

Amines

Chemical Structure| 39478-78-9

A109306 [39478-78-9]

5-Bromo-2-methylaniline

Similarity: 0.97

Chemical Structure| 76153-06-5

A123533 [76153-06-5]

5-Bromo-3-methylbenzene-1,2-diamine

Similarity: 0.95

Chemical Structure| 24596-19-8

A561600 [24596-19-8]

4-Bromo-2,6-dimethylaniline

Similarity: 0.93

Chemical Structure| 22364-25-6

A400170 [22364-25-6]

4-Bromo-2,3-dimethylaniline

Similarity: 0.93

Chemical Structure| 74586-53-1

A259368 [74586-53-1]

3-Bromo-5-methylaniline

Similarity: 0.92