70733-25-4|3-Bromo-5-methylbenzene-1,2-diamine| Ambeed

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

Quality Control of [ 70733-25-4 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 70733-25-4 ]

CAS No. :	70733-25-4
Formula :	C₇H₉BrN₂
M.W :	201.06
SMILES Code :	NC1=CC(C)=CC(Br)=C1N
MDL No. :	MFCD18088524
InChI Key :	WHVCTNJQZXBGDH-UHFFFAOYSA-N
Pubchem ID :	12490137

Safety of [ 70733-25-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 70733-25-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	2.0
Molar Refractivity	47.92
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.04 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.51
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.62
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.94
Log P_o/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.	1.91
Log P_o/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	1.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.7

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.55
Solubility	0.565 mg/ml ; 0.00281 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.	-2.33
Solubility	0.951 mg/ml ; 0.00473 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	-2.92
Solubility	0.24 mg/ml ; 0.00119 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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.38 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	0.0
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)	1.48

Application In Synthesis of [ 70733-25-4 ]

* 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 [ 70733-25-4 ]

[ 70733-25-4 ] Synthesis Path-Downstream 1~35

1
[ 827-24-7 ]
[ 70733-25-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With ammonia hydrochloride; zinc powder; In tetrahydrofuran; methanol; at 40℃; for 1.0h;	2-bromo-4-methyl-6-nitroaniline (5.00 g, 21.64 mmol) was dissolved in MeOH(148 mL) and THF (18.50 mL). Ammonium chloride (23.15 g, 433 mmol) then zinc (14.15 g, 216 mmol) were added and the reaction mixture was heated to 40 C for lh. The reaction mixture was cooled to ambient temperature, concentrated in vacuo, re-dissolved in EtOAc and saturated Na2CO3, and stirred vigorously for 10 minutes. The mixture was filtered through a sintered glass funnel and washed with more EtOAc. Theorganic layer was further washed twice with water, washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to yield Intermediate I-iSA (4.35 g, 21.63 mmol, 100 % yield). ‘H NMR (400MHz, CHLOROFORM-d) 6.81 (s, 1H), 6.48 (s, 1H), 3.66 (br. s., 2H), 3.46 (br. s., 2H), 2.19 (s, 3H). LC-MS: method H, RT = 0.93 mm, MS (ESI) m/z: 201.0 (M+H)
100%	With ammonia hydrochloride; zinc powder; In tetrahydrofuran; methanol; at 40℃; for 1.0h;	2-bromo-4-methyl-6-nitroaniline (5.00 g, 21.64 mmol) was dissolved in MeOH (148 mL) and THF (18.50 mL). Ammonium chloride (23.15 g, 433 mmol) then zinc (14.15 g, 216 mmol) were added and the reaction mixture was heated to 40 C for lh. The reaction mixture was cooled to ambient temperature, concentrated in vacuo, re-dissolved in EtOAc and saturated Na2CO3, and stirred vigorously for 10 minutes. Themixture was filtered through a sintered glass funnel and washed with more EtOAc. The organic layer was further washed twice with water, washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to yield Intermediate I-iSA (4.35 g, 21.63 mmol, 100 % yield). ‘H NMR (400MHz, CHLOROFORM-d) 6.81 (s, 1H), 6.48 (s, 1H), 3.66 (br. s., 2H), 3.46 (br. s., 2H), 2.19 (s, 3H). LC-MS: method H, RT = 0.93 mm,MS (ESI) m/z: 201.0 (M+H)
97%	With hydrogenchloride; stannous chloride; In ethanol; water monomer; at 60℃; for 3.0h;Inert atmosphere;	To a solution of Example 35a (20.0 g, 86.6 mmol, 1.0 eq) in EtOH (120 mL) and conc. HCl (40 mL) was added SnCl2 (97.4 g, 433 mmol, 5.0 eq). The reaction mixture was stirred at 60C for 3 h under N2. After cooled to room temperature, the mixture was poured into 2M NaOH aqueous solution (750 mL) at 0C. DCM (800 mL) was added to the mixture, and the white solid was removed by filtration. The organic layer was separated, and the aqueous phase was extracted with DCM (500 mL*2). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated. The crude was purified by silica gel flash column chromatography to afford the product Example 35b (16.8 g, 97% yield) as a yellow solid. LCMS [M+1]+ = 201.2.

67%	With hydrogenchloride; stannous chloride; In ethanol; water monomer; at 60℃; for 3.0h;Inert atmosphere;	To a solution of Intermediate la (84 g, 363.6 mmol) in EtOH (464 m ) and cone. HC1 (116 m ) was added SnCL (408g, 2.16 mol). The reaction mixture was stirred at 60C for 3 h under N2. After cooled to room temperature, the mixture was poured into 2M NaOH aqueous solution (750 mb) to pH = 12 at 0C. DCM (800 mb) was added to the mixture, and the white solid was removed by filtration. The organic layer was separated, and the aqueous phase was extracted with DCM (500 mb*2). The combined organic extracts were washed with brine, dried over Na2SC>4, and concentrated. The crude was purified by silica gel flash column chromatography (Petroleum Ether/EtOAc = 2/1) to afford the product Intermediate lb (49 g, 67% yield) as a yellow solid. ECMS [M+l] + = 201.2.
67%	With hydrogenchloride; stannous chloride; In ethanol; water monomer; at 60℃; for 3.0h;Inert atmosphere;	To a solution of Intermediate la (84 g, 363.6 mmol) in EtOH (464 m ) and cone. HC1 (116 m ) was added SnCL (408g, 2.16 mol). The reaction mixture was stirred at 60C for 3 h under N2. After cooled to room temperature, the mixture was poured into 2M NaOH aqueous solution (750 mb) to pH = 12 at 0C. DCM (800 mb) was added to the mixture, and the white solid was removed by filtration. The organic layer was separated, and the aqueous phase was extracted with DCM (500 mb*2). The combined organic extracts were washed with brine, dried over Na2SC>4, and concentrated. The crude was purified by silica gel flash column chromatography (Petroleum Ether/EtOAc = 2/1) to afford the product Intermediate lb (49 g, 67% yield) as a yellow solid. ECMS [M+l] + = 201.2.
35%	With hydrogenchloride; tin(II) chloride dihydrochloride; In ethanol; at 60℃; for 4.0h;Inert atmosphere;	In argon atmosphere, to an EtOH solution (100 mL) of commercially available 2-bromo-4-methyl-6-nitroaniline (5 g, 21.6 mmol) was added Tin(II) chloride dehydrate (16 g, 84.4 mmol) in small portions, followed by c.HCl (12 mL) dropwise over 10 min. The mixture was stirred at 60C for 4 h. On completion, the mixture was quenched with saturated NaHCO3 aqueous (50 mL) carefully, extracted with EA (3 × 50 mL). The combined organic layer was washed with brine, dried with anhydrous Na2SO4, evaporated at reduced pressure to give title compound as a red solid in 35% yield. 1H NMR (300 MHz, Chloroform-d) δ 6.51 (s, 1H), 6.38 (s, 1H), 4.26 (broad s, 4H), 2.07 (s, 3H).

References: [1]Patent: WO2018/13776,2018,A1 .Location in patent: Page/Page column 98.
[2]Patent: WO2018/13774,2018,A1 .Location in patent: Page/Page column 139.
[3]Patent: WO2020/185755,2020,A1 .Location in patent: Paragraph 00483.
[4]Organic Letters,2006,vol. 8,p. 4989 - 4992.
[5]Patent: WO2022/60973,2022,A1 .Location in patent: Paragraph 00144-00145.
[6]Patent: WO2022/60973,2022,A1 .Location in patent: Paragraph 00144-00145.
[7]European Journal of Medicinal Chemistry,2021,vol. 225.
[8]Chemische Berichte,1890,vol. 23,p. 1044.

2
[ 70733-25-4 ]
[ 2450-45-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1978,vol. 16,p. 892 - 894.

3
[ 7521-41-7 ]
[ 70733-25-4 ]
3-(4-Bromo-6-methyl-1H-benzoimidazol-2-yl)-pyridin-2-ylamine [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 866 - 867.

4
[ 70733-25-4 ]
[ 94059-15-1 ]
[ 116222-29-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 1095 - 1096.

5
[ 70733-25-4 ]
[ 2255-74-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 180 - 182.

6
[ 70733-25-4 ]
[ 2533-69-9 ]
[ 916060-44-1 ]