[ CAS No. 184970-28-3 ] {[proInfo.proName]}

Name: 184970-28-3|4-Bromo-2-(bromomethyl)-1-methoxybenzene|95%
Brand: Ambeed
SKU: A219877
Price: 28.0 USD
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Quality Control of [ 184970-28-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 184970-28-3 ]

CAS No. :	184970-28-3	MDL No. :	MFCD07324845
Formula :	C₈H₈Br₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MZJDFNYHPWAVQP-UHFFFAOYSA-N
M.W :	279.96	Pubchem ID :	4962739
Synonyms :

Calculated chemistry of [ 184970-28-3 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.47
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.68
Log Po/w (XLOGP3) :	3.14
Log Po/w (WLOGP) :	3.2
Log Po/w (MLOGP) :	3.32
Log Po/w (SILICOS-IT) :	3.5
Consensus Log Po/w :	3.17

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.83
Solubility :	0.0418 mg/ml ; 0.000149 mol/l
Class :	Soluble
Log S (Ali) :	-3.0
Solubility :	0.278 mg/ml ; 0.000992 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.63
Solubility :	0.00655 mg/ml ; 0.0000234 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.76

Safety of [ 184970-28-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501	UN#:	3261
Hazard Statements:	H302-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 184970-28-3 ]

* 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 [ 184970-28-3 ]
Downstream synthetic route of [ 184970-28-3 ]

[ 184970-28-3 ] Synthesis Path-Upstream 1~4

1
[ 184970-28-3 ]
[ 40530-18-5 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197

2
[ 184970-28-3 ]
[ 144649-99-0 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197

3
[ 80866-82-6 ]
[ 184970-28-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With phosphorus tribromide In dichloromethane at 0℃; for 0.25 h;	4-Bromo-2-(bromomethyl)-1-methoxybenzene. To a solution of (5-bromo-2-methoxyphenyl)methanol (1.0 g, 4.6 mmol) in dichloromethane (10 mL) at 0° C. was added tribromophosphine (1 M in dichloromethane, 9.2 mL, 9.2 mmol). The ice bath was removed and the reaction stirred for 15 min. The reaction was concentrated, poured onto cold saturated sodium bicarbonate, extracted with pentane, dried over magnesium sulfate, and concentrated to give 1.15 g (89percent) as a white crystalline solid. ¹H NMR (500 MHz, CDCl₃) δ ppm 7.44 (d, J=2.5 Hz, 1H), 7.38 (dd, J=8.9, 6.1 Hz, 1H), 4.47 (s, 2H), 3.87 (s, 3H); ¹³C NMR (126 MHz, CDCl₃) δ ppm 156.7, 133.6, 132.8, 128.4, 112.8, 112.7, 56.0, 27.5.
63%	With Oxalyl bromide; Triphenylphosphine oxide In chloroform for 7 h;	To a solution of Ph₃PO (48.1 mg, 0.173 mmol) in CHCl₃ (1.50 mL) was added oxalyl bromide (16.2 mL, 0.173 mmol) and the solution was stirred for 5 min. To the stirring solution was added 17 (250 mg, 1.15 mmol) in CHCl₃ (1.00 mL) and oxalyl bromide (83.8 mL, 0.978 mmol) in CHCl₃ (1.00 mL) over 7 hours via syringe pump. The solution was concentrated under reduced pressure and purification by flash chromatography (petroleum ether/EtOAc, 10:1) gave 18 (201 mg, 63percent) as a colourless solid, mp 114-116 °C, R_f 0.89 (petroleum ether/EtOAc, 10:1). IR: ν_max (CHCl₃) 3011, 2966, 2942, 2841, 1677, 1596, 1490, 1463, 1442, 1300, 1277, 1257, 1182, 1030 cm^-1. ¹H MNR: (400 MHz, CDCl₃) δ 7.46 (1H, d, J=8.8, ArH_meta), 7.39 (1H, dd, J=8.8, 2.4, ArH_meta), 6.77 (1H, J=8.8, ArH_ortho), 4.49 (2H, s, ArCH₂Br), 3.89 (3H, s, ArOCH₃). ¹³C NMR: (100 MHz, CDCl₃) δ 156.5 (Cq), 133.4 (CH), 132.7 (CH), 128.2 (Cq), 112.6 (Cq), 112.5 (CH), 55.8 (CH₃), 27.5 (CH₂). HRMS: (EI) m/z calculated for C₈H₈OBr₂ 277.8936, m/z found 277.8930.

Reference： [1] Patent: US2007/249607, 2007, A1, . Location in patent: Page/Page column 73
[2] Tetrahedron Letters, 2011, vol. 52, # 20, p. 2554 - 2556

4
[ 14804-31-0 ]
[ 184970-28-3 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197
[2] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410
[3] Patent: US2018/155298, 2018, A1, . Location in patent: Paragraph 1052; 1053

[ 184970-28-3 ] Synthesis Path-Downstream 1~68

1
[ 529-19-1 ]
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-benzonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1602 - 1604

2
[ 53440-32-7 ]
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-benzylsulfanyl)-phenyl]-1,4,5,6,-tetrahydropyrimidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1602 - 1604

3
[ 185147-06-2 ]
[ 184970-28-3 ]
[ 742105-39-1 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1602 - 1604

4
[ 118-90-1 ]
[ 184970-28-3 ]
[ 88857-57-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

5
[ 80866-82-6 ]
[ 184970-28-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With phosphorus tribromide; In dichloromethane; at 0℃; for 0.25h;	4-Bromo-2-(bromomethyl)-1-methoxybenzene. To a solution of (5-bromo-2-methoxyphenyl)methanol (1.0 g, 4.6 mmol) in dichloromethane (10 mL) at 0 C. was added tribromophosphine (1 M in dichloromethane, 9.2 mL, 9.2 mmol). The ice bath was removed and the reaction stirred for 15 min. The reaction was concentrated, poured onto cold saturated sodium bicarbonate, extracted with pentane, dried over magnesium sulfate, and concentrated to give 1.15 g (89%) as a white crystalline solid. 1H NMR (500 MHz, CDCl3) delta ppm 7.44 (d, J=2.5 Hz, 1H), 7.38 (dd, J=8.9, 6.1 Hz, 1H), 4.47 (s, 2H), 3.87 (s, 3H); 13C NMR (126 MHz, CDCl3) delta ppm 156.7, 133.6, 132.8, 128.4, 112.8, 112.7, 56.0, 27.5.
63%	With Oxalyl bromide; Triphenylphosphine oxide; In chloroform; for 7h;	To a solution of Ph3PO (48.1 mg, 0.173 mmol) in CHCl3 (1.50 mL) was added oxalyl bromide (16.2 mL, 0.173 mmol) and the solution was stirred for 5 min. To the stirring solution was added 17 (250 mg, 1.15 mmol) in CHCl3 (1.00 mL) and oxalyl bromide (83.8 mL, 0.978 mmol) in CHCl3 (1.00 mL) over 7 hours via syringe pump. The solution was concentrated under reduced pressure and purification by flash chromatography (petroleum ether/EtOAc, 10:1) gave 18 (201 mg, 63%) as a colourless solid, mp 114-116 C, Rf 0.89 (petroleum ether/EtOAc, 10:1). IR: numax (CHCl3) 3011, 2966, 2942, 2841, 1677, 1596, 1490, 1463, 1442, 1300, 1277, 1257, 1182, 1030 cm-1. 1H MNR: (400 MHz, CDCl3) delta 7.46 (1H, d, J=8.8, ArHmeta), 7.39 (1H, dd, J=8.8, 2.4, ArHmeta), 6.77 (1H, J=8.8, ArHortho), 4.49 (2H, s, ArCH2Br), 3.89 (3H, s, ArOCH3). 13C NMR: (100 MHz, CDCl3) delta 156.5 (Cq), 133.4 (CH), 132.7 (CH), 128.2 (Cq), 112.6 (Cq), 112.5 (CH), 55.8 (CH3), 27.5 (CH2). HRMS: (EI) m/z calculated for C8H8OBr2 277.8936, m/z found 277.8930.

Reference： [1]Patent: US2007/249607,2007,A1 .Location in patent: Page/Page column 73
[2]Tetrahedron Letters,2011,vol. 52,p. 2554 - 2556

6
[ 158144-85-5 ]
[ 184970-28-3 ]
[ 954123-89-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydride; In N,N-dimethyl-formamide; at 0℃; for 0.583333h;	tert-Butyl 4-((5-bromo-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate. To a solution of tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate (0.40 g, 1.37 mmol) and <strong>[184970-28-3]4-bromo-2-(bromomethyl)-1-methoxybenzene</strong> (0.46 g, 1.65 mmol) in dimethylformamide (4 mL) at 0 C. was added sodium hydride (66 mg, 2.75 mmol). After 20 min at 0 C., the ice bath was removed and the reaction stirred for 15 min. The reaction was poured into a separatory funnel containing ether and water. The ethereal was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (10% ethyl acetate/hexanes?25% ethyl acetate/hexanes) gave 640 mg (95%) as a colorless viscous oil. 1H NMR (500 MHz, CDCl3) delta ppm 7.20-7.45 (m, 7H), 6.65 (d, J=8.9 Hz, 1H), 4.36 (s, 2H), 3.76 (m, 2H), 3.72 (s, 3H), 3.44 (s, 2H), 3.08 (m, 2H), 2.19 (m, 2H), 1.91 (m, 2H), 1.44 (s, 9H); 13C NMR (126 MHz, CDCl3) delta ppm 155.8, 155.1, 143.0, 130.8, 129.5, 128.6, 127.3, 126.5, 113.0, 111.8, 104.3, 79.8, 79.4, 67.6, 55.6, 41.8, 40.3, 32.0, 28.6.

Reference： [1]Patent: US2007/249607,2007,A1 .Location in patent: Page/Page column 73-74

7
[ 184970-28-3 ]
2-{2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-phenyl}-1,5-dimethyl-1H-imidazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

8
[ 184970-28-3 ]
[ 685126-55-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

9
[ 184970-28-3 ]
2-{2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-phenyl}-1,4-dimethyl-1H-imidazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

10
[ 184970-28-3 ]
[ 685126-56-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

11
[ 184970-28-3 ]
[ 685126-60-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

12
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-chloro-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

13
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-hydroxy-1-methyl-ethyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

14
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-chloro-1-methyl-ethyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

15
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-hydroxy-1-methyl-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

16
[ 184970-28-3 ]
[ 685126-61-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

17
[ 184970-28-3 ]
2-{2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-phenyl}-4-ethyl-1-methyl-1H-imidazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

18
[ 184970-28-3 ]
2-{2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-phenyl}-5-ethyl-1-methyl-1H-imidazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

19
[ 184970-28-3 ]
[ 685126-59-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

20
[ 184970-28-3 ]
2-{2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-phenyl}-4-isopropyl-1-methyl-1H-imidazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

21
[ 184970-28-3 ]
[ 685126-64-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

22
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-chloro-1-methyl-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

23
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(1-chloromethyl-2-methyl-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

24
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-methylamino-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

25
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(1-chloromethyl-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

26
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-hydroxy-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

27
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(1-methyl-2-methylamino-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

28
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(1-methyl-2-methylamino-ethyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

29
[ 184970-28-3 ]
2-{2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-phenyl}-1,4,5-trimethyl-1H-imidazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

30
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(1-hydroxymethyl-2-methyl-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

31
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-chloro-butyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

32
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-hydroxy-butyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

33
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(1-hydroxymethyl-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

34
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-methyl-1-methylaminomethyl-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

35
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(1-methylaminomethyl-propyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

36
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-N-(2-methylamino-butyl)-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3721 - 3725

37
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-thiobenzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1602 - 1604

38
[ 184970-28-3 ]
2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-3-fluoro-thiobenzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1602 - 1604

39
[ 184970-28-3 ]
2-{2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-phenyl}-4,5-dihydro-1H-imidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1602 - 1604

40
[ 184970-28-3 ]
2-{2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-phenyl}-1,4,5,6-tetrahydro-pyrimidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1602 - 1604

41
[ 184970-28-3 ]
M⁽²⁵³⁾L₀₀₇₆₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1602 - 1604

42
[ 184970-28-3 ]
[ 685127-05-3 ]

Yield	Reaction Conditions	Operation in experiment
66%		A solution of 3-fluoro-2-methylbenzoic acid (5.0 g, 1.0 equiv) in THF (175 mL) was cooled to -78 C. under an atmosphere of argon. TMEDA (9.86 mL, 2.0 equiv) was added via syringe. s-BuLi (1.4 M in cyclohexane, 49 mL, 2.1 equiv) was added dropwise via addition funnel over 30 min. After stirring for 2.5 hr, the bromide (13.7 g, 1.5 equiv) in THF (25 mL) was added dropwise. Upon completion of the addition, the solution was allowed to stir and warm to room temperature overnight. The reaction was quenched by the addition of water and then diluted with hexanes. The aqueous and organic phases were separated and the organic phase was washed with water. The aqueous phase was acidified to pH=1 with 1N HCl and then extracted with EtOAc. The resulting organic solution was dried over Na2SO4, filtered and concentrated. The residue was rinsed with dichloromethane, filtered, and dried to give the desired product (7.6 g, 66%).

Reference： [1]Patent: US2004/82779,2004,A1 .Location in patent: Page 95

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3h;Reflux;	General procedure: To the previously synthesized ether (4.97 g, 23.1 mmol) in carbon tetrachloride (80 mL) was added N-bromosuccinimide (4.93 g, 27.6 mmol) and benzoyl peroxide (100 mg). The resulting solution was heated to reflux for 3 hrs, allowed to cool, partially evaporated and then filtered. The filtrate was evaporated in vacuo to afford 4-bromo-2-(bromomethyl)-l-ethoxybenzene which could be used without further purification.

44
[ 105191-13-7 ]
[ 184970-28-3 ]
C₂₀H₁₇BrN₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2034 - 2039

45
[ 184970-28-3 ]
[ 1289648-04-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2034 - 2039

46
[ 184970-28-3 ]
C₁₈H₁₃BrN₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2034 - 2039

47
[ 3536-96-7 ]
[ 184970-28-3 ]
[ 114303-65-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	With [2,2]bipyridinyl; copper(l) iodide; In benzene; at 5 - 20℃;	To a solution of 18 (100 mg, 0.375 mmol) in benzene (2.50 mL) at 5 C was added and CuI (8.08 mg, 35.7 mumol), 2,2'-bipyridine (6.62 mg ,37.5 mumol) and CH2CHMgBr (0.571 mL, 0.357 mmol of a 1.6 M solution in THF). The solution was warmed to rt and stirred for 24 h. The reaction mixture was quenched with NH4Cl (2.50 mL of a 1.00 M aqueous solution) and the solution was stirred for 30 min before being diluted with EtOAc (10.0 mL), washed with NH4Cl (3 x 10.0 mL of a 1.00 M aqueous solution) and brine (3 x 10.0 mL), dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (petroleum ether/EtOAc, 4:1) gave 19 (51.9 mg, 64%) as a colourless oil, Rf 0.53 (petroleum ether/EtOAc, 4:1). IR: numax (CHCl3) 3081, 3011, 2960, 2940, 2910, 2837, 1638, 1593, 1490, 1464, 1441, 1303, 1247, 1135, 1033, 997 cm-1. 1H MNR: (400 MHz, CDCl3) delta 7.30 (1H, dd, J=8.7, 2.5, ArHmeta), 7.25 (1H, d, J=2.5, ArHmeta), 6.73 (1H, d, J=6.73, ArHortho), 5.95 (1H, ddt, J=17.4, 9.4, 6.5, ArCH2CHCH2), 5.08 (1H, dd, J=9.4, 1.6, ArCH2CHCH2cis), 5.07 (1H, dd, J=17.4, 1.6, ArCH2CHCH2trans), 3.81 (3H, s, ArOCH3), 3.35 (2H, d, J=6.5, ArCH2CHCH2). 13C NMR: (100 MHz, CDCl3) delta 156.4 (Cq), 136.0 (CH), 132.4 (CH), 131.0 (Cq), 129.9 (CH), 116.1 (CH2), 112.7 (Cq), 112.0 (CH), 55.6 (CH3), 33.9 (CH2). HRMS: (EI+) m/z calculated for C10H11OBr 225.9988, m/z found 225.9980.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2554 - 2556

48
[ 184970-28-3 ]
[ 68592-15-4 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2554 - 2556

49
[ 1331750-40-3 ]
[ 184970-28-3 ]
[ 1331750-46-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With resin-supported 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine; In acetonitrile; at 90℃; for 3h;Microwave irradiation;	tert-butyl 2-(N-(5-bromo-2-methoxybenzyl)-2,2-dimethylchroman-6-sulfonamido)acetate To the solution of tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate (500 mg, 1.407 mmol) in MeCN (15 mL) was added resin-supported BEMP (786 mg, 1.547 mmol) and <strong>[184970-28-3]4-bromo-2-(bromomethyl)-1-methoxybenzene</strong> (500 mg, 1.786 mmol). The mixture was heated in a microwave synthesizer at 90 C. for 3 hours. The reaction mixture was filtered, rinsed alternatively by dichloromethane and methanol. The filtrate was concentrated to give a reddish orange residue, which was purified by silica chromatography to obtain a white powder (700 mg, 85% yield). 1H NMR (500 MHz, CDCl3) delta 7.56-7.50 (m, 2H), 7.34-7.29 (m, 2H), 6.81 (d, J=8.1 Hz, 1H), 6.66 (d, J=8.5 Hz, 1H), 4.47 (s, 2H), 3.88 (s, 2H), 3.71 (s, 3H), 2.78 (t, J=6.7 Hz, 2H), 1.82 (t, J=6.7 Hz, 2H), 1.38 (s, 9H), 1.34 (s, 6H).LRMS [ESI, MH-] m/z calcd for C25H33BrNO6S 554.12, found 554.1.

Reference： [1]Patent: US2011/207772,2011,A1 .Location in patent: Page/Page column 9-10

50
[ 14804-31-0 ]
[ 184970-28-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 95℃; for 3h;	A mixture of 4-bromo-1-methoxy-2-methylbenzene (1.0 eq) in CCl4 (0.3M), NBS (1.1 eq), and AIBN (0.2 eq) was stirred at 95 C. for 3 h. Then the mixture was filtered and the filtration was concentrated under reduced pressure to give the crude product, which was purified by column chromatography on a silica gel (eluent: PE) to give the title compound as a white solid.

Reference： [1]Organic Letters,2013,vol. 15,p. 4194 - 4197
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 3402 - 3410
[3]Patent: US2018/155298,2018,A1 .Location in patent: Paragraph 1052; 1053

51
[ 184970-28-3 ]
[ 144649-99-0 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4194 - 4197

52
[ 184970-28-3 ]
[ 40530-18-5 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4194 - 4197

53
[ 184970-28-3 ]
[ 876918-26-2 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4194 - 4197

54
[ 184970-28-3 ]
[ 1139901-88-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4194 - 4197

55
[ 184970-28-3 ]
febuxostat [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4194 - 4197

56
[ 184970-28-3 ]
[ 25016-01-7 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 3402 - 3410

57
[ 184970-28-3 ]
[ 24524-08-1 ]

Reference： [1]Patent: US2018/155298,2018,A1

58
[ 184970-28-3 ]
[ 24524-13-8 ]

Reference： [1]Patent: US2018/155298,2018,A1

59
[ 184970-28-3 ]
5-(5-bromo-2-methoxybenzyl)-N₄-butyl-6-methylpyrimidine-2,4-diamine [ No CAS ]

Reference： [1]Patent: US2018/155298,2018,A1

60
[ 141-97-9 ]
[ 184970-28-3 ]
[ 24523-97-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of ethyl 3-oxobutanoate (1.2 eq) in anhydrous THF (0.5M) at 0 C. was added portion-wise 60% NaH (1.3 eq). After stirring for 10 min, a solution of <strong>[184970-28-3]4-bromo-2-(bromomethyl)-1-methoxybenzene</strong> (1.0 eq) in THF (0.8M) was added dropwise into the above mixture over 10 min. Then the resulting mixture was stirred at 70 C. for 16 h, water was added and extracted with EtOAc. The combined organic phase was dried over Na2SO4, concentrated under reduced pressure. The residue was purified by column chromatography on a silica gel (eluent: PE/EA=100:1 to 10:1) to give the title compound as yellow oil.

Reference： [1]Patent: US2018/155298,2018,A1 .Location in patent: Paragraph 1052; 1054

61
(2S,3R,4S,5S)-2-ethyl 1-isopropyl 3-(tert-butyl)-4-hydroxy-5-phenylpyrrolidine-1,2-dicarboxylate [ No CAS ]
[ 184970-28-3 ]
(2S,3R,4S,5S)-2-ethyl 1-isopropyl 4-((5-bromo-2-methoxybenzyl)oxy)-3-(tert-butyl)-5-phenylpyrrolidine-1,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In N,N-dimethyl-formamide; for 0.533333h;Cooling with ice;	Example 38D (2S,3R,4S,5S)-2-ethyl 1-isopropyl 4-((5-bromo-2-methoxybenzyl)oxy)-3-(tert-butyl)-5-phenylpyrrolidine-1,2-dicarboxylate Example 38C (36 mg, 0.095 mmol) and <strong>[184970-28-3]4-bromo-2-(bromomethyl)-1-methoxybenzene</strong> (53.4 mg, 0.191 mmol) were dissolved in dry dimethylformamide (0.5 mL). After cooling in an ice bath, potassium 2-methylpropan-2-olate (0.200 mL, 0.200 mmol) solution was added dropwise over 2 minutes. After 30 minutes, the reaction was acidified with 1M aqueous HCl (10 drops) and warmed to room temperature. The mixture was concentrated and loaded onto a 12 g silica gel column and eluted with 5-100% ethyl acetate/heptanes over 20 minutes to provide (2S,3R,4S,5S)-2-ethyl 1-isopropyl 4-((5-bromo-2-methoxybenzyl)oxy)-3-(tert-butyl)-5-phenylpyrrolidine-1,2-dicarboxylate (57 mg, 0.099 mmol, 104% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.56 (dd, J=7.1, 1.6 Hz, 2H), 7.26-7.13 (m, 4H), 6.81-6.74 (m, 2H), 4.99 (d, J=6.0 Hz, 1H), 4.65 (dt, J=12.4, 6.2 Hz, 1H), 4.35 (d, J=3.2 Hz, 1H), 4.24-4.17 (m, 2H), 4.14 (qd, J=7.1, 2.6 Hz, 2H), 3.88 (dd, J=12.9, 0.9 Hz, 1H), 3.68-3.63 (m, 3H), 2.44 (t, J=2.9 Hz, 1H), 1.20 (t, J=7.1 Hz, 3H), 1.06 (d, J=6.2 Hz, 3H), 1.00 (s, 9H), 0.92 (d, J=7.5 Hz, 3H); MS (APCI+) m/z 577 (M+H)+.

Reference： [1]Patent: US2018/99932,2018,A1 .Location in patent: Paragraph 1658

62
[ 184970-28-3 ]
3-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-4-methoxybenzonitrile [ No CAS ]

Reference： [1]Patent: US2018/155298,2018,A1

63
[ 184970-28-3 ]
N4-butyl-5-(2-methoxy-5-(2H-tetrazol-5-yl)benzyl)-6-methylpyrimidine-2,4-diamine formic acid salt [ No CAS ]

Reference： [1]Patent: US2018/155298,2018,A1

64
[ 184970-28-3 ]
N4-butyl-5-(2-methoxybenzyl)-6-methylpyrimidine-2,4-diamine [ No CAS ]

Reference： [1]Patent: US2018/155298,2018,A1

65
[ 184970-28-3 ]
3-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-4-methoxybenzenesulfonyl chloride [ No CAS ]

Reference： [1]Patent: US2018/155298,2018,A1

66
[ 184970-28-3 ]
3-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-4-methoxybenzenesulfonic acid [ No CAS ]

Reference： [1]Patent: US2018/155298,2018,A1

67
[ 184970-28-3 ]
N⁴-butyl-5-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-6-methylpyrimidine-2,4-diamine [ No CAS ]

Reference： [1]Patent: US2018/155298,2018,A1

68
[ 184970-28-3 ]
(3-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-4-methoxyphenyl)boronic acid formic acid salt [ No CAS ]

Reference： [1]Patent: US2018/155298,2018,A1

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{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H221	Flammable gas
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H223	Flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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H336	May cause drowsiness or dizziness
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H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 184970-28-3 ] {[proInfo.proName]}

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[ 184970-28-3 ] Synthesis Path-Upstream 1~4

[ 184970-28-3 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 184970-28-3 ]

Aryls

Bromides

Ethers

Benzyl bromides

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[ 184970-28-3 ]