[ CAS No. 152626-77-2 ] {[proInfo.proName]}

Name: 152626-77-2|4-Bromo-5-methoxy-2-methylaniline|97%
Brand: Ambeed
SKU: A175336
Rating: 97 (26 reviews)

,{[proInfo.pro_purity]}

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

DV 2D 3D

3d Animation Molecule Structure of 152626-77-2

Structure of 152626-77-2 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 152626-77-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 152626-77-2 ]

SDS Specification

Alternatived Products of [ 152626-77-2 ]

Product Details of [ 152626-77-2 ]

CAS No. :	152626-77-2	MDL No. :	MFCD11007879
Formula :	C₈H₁₀BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HCWSMYJWPZRXOD-UHFFFAOYSA-N
M.W :	216.08	Pubchem ID :	15278592
Synonyms :

Calculated chemistry of [ 152626-77-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.0
TPSA :	35.25 Å²

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) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	2.27
Log Po/w (WLOGP) :	2.36
Log Po/w (MLOGP) :	2.22
Log Po/w (SILICOS-IT) :	2.23
Consensus Log Po/w :	2.23

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.95
Solubility :	0.244 mg/ml ; 0.00113 mol/l
Class :	Soluble
Log S (Ali) :	-2.65
Solubility :	0.487 mg/ml ; 0.00225 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.41
Solubility :	0.0835 mg/ml ; 0.000386 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

Safety of [ 152626-77-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 152626-77-2 ]

* 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 [ 152626-77-2 ]
Downstream synthetic route of [ 152626-77-2 ]

[ 152626-77-2 ] Synthesis Path-Upstream 1~5

1
[ 50868-72-9 ]
[ 1321600-81-0 ]
[ 152626-77-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With N-Bromosuccinimide In chloroform at 5 - 20℃;	N-Bromosuccinimide (0.80 g, 4.50 mmol) was added portionwise over a 1 h period to an ice-chilled solution of 5-methoxy-2-methylaniline (0.62 g, 4.50 mmol) in chloroform (10 mL). The reaction mixture was then stirred at 5-10 °C for 4 h, before it was allowed to warm at room temperature. The mixture was then washed with sodium hydroxide (2 M, 10 mL) and water (2.x.20 mL), dried over anhydrous sodium sulfate and filtered. The solvent was evaporated and the residue was chromatographed (silica gel, dichloromethane) to afford 4,6-dibromo-5-methoxy-2-methylaniline (0.12 g, 9percent) as an orange liquid. ¹H NMR (400 MHz, CDCl₃) δ 2.20 (s, 3H, CH₃), 3.84 (s, 3H, OCH₃), 3.85 (br s, 2H, NH₂), 7.17 (s, 1H, ArH); ¹³C NMR (100 MHz, CDCl₃) δ 17.7, 60.4, 104.0, 105.2, 120.2, 132.5, 143.0, 152.5. Another fraction was also eluted, to afford 4-bromo-5-methoxy-2-methylaniline (0.75 g, 77percent) as a light grey solid: mp 103-105 °C; R_f (80percent EtOAc/CH₂Cl₂) 0.75; IR (neat) ν_max 3462, 3402, 3332, 3223, 2965, 2932, 2854, 1633, 1602, 1574, 1500, 1454, 1398, 1296, 1211, 1051, cm^-1; ¹H NMR (400 MHz, CDCl₃) δ 2.08 (s, 3H, CH₃), 3.80 (s, 3H, OCH₃), 3.81 (br s, 2H, NH₂), 6.29 (s, 1H, ArH), 7.16 (s, 1H, ArH); ¹³C NMR (100 MHz, CDCl₃) δ 16.3, 56.2, 99.6, 100.0, 116.2, 134.2, 144.1, 154.7; Anal. Calcd for C₈H₁₀BrNO: C 44.47; H 4.66; N 6.48. Found: C 44.54; H 4.39; N 6.33percent.

Reference： [1] Tetrahedron, 2011, vol. 67, # 32, p. 5798 - 5805

2
[ 50868-72-9 ]
[ 152626-77-2 ]

Reference： [1] Patent: WO2017/102635, 2017, A1, . Location in patent: Page/Page column 48; 49
[2] Patent: WO2018/91430, 2018, A1, . Location in patent: Page/Page column 44

3
[ 134-19-0 ]
[ 152626-77-2 ]

Reference： [1] Patent: US5444038, 1995, A,

4
[ 871878-59-0 ]
[ 152626-77-2 ]

Reference： [1] Journal of the Chemical Society, 1925, vol. 127, p. 995

5
[ 50868-75-2 ]
[ 152626-77-2 ]

Reference： [1] Journal of the Chemical Society, 1925, vol. 127, p. 995

[ 152626-77-2 ] Synthesis Path-Downstream 1~26

1
[ 152626-77-2 ]
(4-bromo-5-methoxy-2-methyl-phenyl)-hydrazine [ No CAS ]

Reference： [1]Journal of the Chemical Society,1925,vol. 127,p. 995

2
[ 871878-59-0 ]
[ 152626-77-2 ]

Reference： [1]Journal of the Chemical Society,1925,vol. 127,p. 995

3
[ 152626-77-2 ]
[ 98-88-4 ]
benzoic acid-(4-bromo-5-methoxy-2-methyl-anilide) [ No CAS ]

Reference： [1]Journal of the Chemical Society,1925,vol. 127,p. 995

4
[ 50868-75-2 ]
[ 152626-77-2 ]

Reference： [1]Journal of the Chemical Society,1925,vol. 127,p. 995

5
aqueous sodium nitrite [ No CAS ]
[ 134-19-0 ]
[ 152626-77-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; hydrogen bromide; sodium hydrogensulfite; copper(I) bromide; In dichloromethane; water;	a mixture of 2-methoxy-5-methyl-4-nitroaniline (20 g, 110 mmol) in 140 mL of water was heated under reflux and 48% hydrobromic acid (56 mL) was added dropwise and the mixture was heated for 20 minutes. The resulting suspension was cooled to 0 C. and treated with 40 mL of aqueous sodium nitrite (7.6 g, 110 mmol) dropwise keeping the temperature at 0 C. The suspension was added carefully dropwise to a 0 C. solution of cuprous bromide (18.1 g, 126 mmol) in 96 mL of water and 38 mL of 48% HBr. The mixture was stirred at 0 C. for 30 minutes and at room temperature for 1 hour and finally on a steam bath for 20 minutes to complete the reaction. The solid precipitate was suction filtered and dissolved in methylene chloride, washed with 400 mL of 10% sodium hydroxide, 5% sodium bisulfite, and water. The organic layer was dried, filtered, and evaporated in vacuo to give 24.9 g of dark brown solid. This was recrystallized from hexane to give 13.4 g of bromo compound. Preparation of 4-bromo-5-methoxy-2-methylaniline:

Reference： [1]Patent: US5444038,1995,A

6
[ 50-00-0 ]
[ 152626-77-2 ]
2,8-dibromo-1,7-dimethoxy-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		4-Bromo-5-methoxy-2-methylaniline (720 mg, 3.33 mmol) and paraformaldehyde (160 mg, 5.33 mmol) were dissolved in trifluoroacetic acid (40 mL) and stirred under argon atmosphere in dark for 48 h. The reaction mixture was then basified with a solution of concentrated ammonia (40 mL) in water (80 mL). A saturated sodium hydrogen carbonate solution (100 mL) was added and the aqueous mixture was extracted into dichloromethane (3×50 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude material was chromatographed (silica gel, dichloromethane) to afford (+/-)-19 (720 mg, 94%) as a white powder: mp 209-211 C; Rf (CH2Cl2) 0.38; IR (neat) numax 2970, 2944, 2907, 1462, 1439, 1419, 1330, 1202, 1008 cm-1; 1H NMR (400 MHz, CDCl3) delta 2.36 (s, 6H, CH3), 3.73 (s, 6H, OCH3), 4.12 (d, J 17.4 Hz, 2H, CH2), 4.22 (s, 2H, CH2), 4.45 (d, J 17.4 Hz, 2H, CH2), 7.24 (s, 2H, ArH); 13C NMR (100 MHz, CDCl3) delta 16.4, 51.4, 60.1, 66.5, 110.5, 123.2, 130.4, 132.7, 146.1, 151.9; Anal. Calcd for C19H20Br2N2O2: C 48.74; H 4.31; N 5.98. Found: C 48.34; H 4.11; N 5.90%.

Reference： [1]Tetrahedron,2011,vol. 67,p. 5798 - 5805

7
[ 152626-77-2 ]
2,8-dibromo-1,7-dihydroxy-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 5798 - 5805

8
[ 50868-72-9 ]
[ 1321600-81-0 ]
[ 152626-77-2 ]

Yield	Reaction Conditions	Operation in experiment
9%; 77%	With N-Bromosuccinimide; In chloroform; at 5 - 20℃;	N-Bromosuccinimide (0.80 g, 4.50 mmol) was added portionwise over a 1 h period to an ice-chilled solution of 5-methoxy-2-methylaniline (0.62 g, 4.50 mmol) in chloroform (10 mL). The reaction mixture was then stirred at 5-10 C for 4 h, before it was allowed to warm at room temperature. The mixture was then washed with sodium hydroxide (2 M, 10 mL) and water (2×20 mL), dried over anhydrous sodium sulfate and filtered. The solvent was evaporated and the residue was chromatographed (silica gel, dichloromethane) to afford 4,6-dibromo-5-methoxy-2-methylaniline (0.12 g, 9%) as an orange liquid. 1H NMR (400 MHz, CDCl3) delta 2.20 (s, 3H, CH3), 3.84 (s, 3H, OCH3), 3.85 (br s, 2H, NH2), 7.17 (s, 1H, ArH); 13C NMR (100 MHz, CDCl3) delta 17.7, 60.4, 104.0, 105.2, 120.2, 132.5, 143.0, 152.5. Another fraction was also eluted, to afford 4-bromo-5-methoxy-2-methylaniline (0.75 g, 77%) as a light grey solid: mp 103-105 C; Rf (80% EtOAc/CH2Cl2) 0.75; IR (neat) numax 3462, 3402, 3332, 3223, 2965, 2932, 2854, 1633, 1602, 1574, 1500, 1454, 1398, 1296, 1211, 1051, cm-1; 1H NMR (400 MHz, CDCl3) delta 2.08 (s, 3H, CH3), 3.80 (s, 3H, OCH3), 3.81 (br s, 2H, NH2), 6.29 (s, 1H, ArH), 7.16 (s, 1H, ArH); 13C NMR (100 MHz, CDCl3) delta 16.3, 56.2, 99.6, 100.0, 116.2, 134.2, 144.1, 154.7; Anal. Calcd for C8H10BrNO: C 44.47; H 4.66; N 6.48. Found: C 44.54; H 4.39; N 6.33%.

Reference： [1]Tetrahedron,2011,vol. 67,p. 5798 - 5805

9
[ 152626-77-2 ]
[ 1613504-83-8 ]