[ CAS No. 40422-70-6 ]

Name: 40422-70-6|1-Bromo-3-(2-bromoethyl)benzene|96%
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Quality Control of [ 40422-70-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 40422-70-6 ]

Product Details of [ 40422-70-6 ]

CAS No. :	40422-70-6	MDL No. :	MFCD07784359
Formula :	C₈H₈Br₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZDWCLHJHUMKCQS-UHFFFAOYSA-N
M.W :	263.96 g/mol	Pubchem ID :	14361216
Synonyms :

Calculated chemistry of [ 40422-70-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.79
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-5.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.67
Log Po/w (XLOGP3) :	4.07
Log Po/w (WLOGP) :	3.39
Log Po/w (MLOGP) :	4.12
Log Po/w (SILICOS-IT) :	3.84
Consensus Log Po/w :	3.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.35
Solubility :	0.0117 mg/ml ; 0.0000444 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.77
Solubility :	0.0444 mg/ml ; 0.000168 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.91
Solubility :	0.00323 mg/ml ; 0.0000122 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.91

Safety of [ 40422-70-6 ]

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 [ 40422-70-6 ]

* 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 [ 40422-70-6 ]
Downstream synthetic route of [ 40422-70-6 ]

[ 40422-70-6 ] Synthesis Path-Upstream 1~4

1
[ 2039-86-3 ]
[ 40422-70-6 ]

Reference： [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5622 - 5626

2
[ 28229-69-8 ]
[ 40422-70-6 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2007, vol. 50, # 3, p. 183 - 188
[2] Synthesis, 2006, # 18, p. 3085 - 3091

3
[ 75-25-2 ]
[ 765-46-8 ]
[ 40422-70-6 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 6.1, p. 935 - 937[2] Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 6, p. 1197 - 1199

4
[ 1878-67-7 ]
[ 40422-70-6 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2007, vol. 50, # 3, p. 183 - 188

[ 40422-70-6 ] Synthesis Path-Downstream 1~50

1
[ 78-82-0 ]
[ 40422-70-6 ]
[ 917-54-4 ]
[ 109757-57-5 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 91 - 92

2
[ 75-25-2 ]
[ 765-46-8 ]
[ 40422-70-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1992,vol. 28,p. 935 - 937
Zhurnal Organicheskoi Khimii,1992,vol. 28,p. 1197 - 1199

5
[ 64723-45-1 ]
lithium bromide [ No CAS ]
[ 40422-70-6 ]

Reference： [1]Journal of the American Chemical Society,1957,vol. 79,p. 3710

6
[ 40422-70-6 ]
[ 57186-65-9 ]

Reference： [1]Synthesis,2006,p. 3085 - 3091

7
[ 40422-70-6 ]
[ 2039-86-3 ]

Reference： [1]Synthesis,2006,p. 3085 - 3091
[2]Synthesis,2006,p. 3085 - 3091

8
[ 28229-69-8 ]
[ 40422-70-6 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2007,vol. 50,p. 183 - 188
[2]Synthesis,2006,p. 3085 - 3091
[3]Green Chemistry,2019,vol. 21,p. 4324 - 4328

9
[ 56346-57-7 ]
[ 40422-70-6 ]
[ 1000885-75-5 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2007,vol. 50,p. 183 - 188

10
[ 1878-67-7 ]
[ 40422-70-6 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2007,vol. 50,p. 183 - 188

11
[ 40422-70-6 ]
[ 439856-34-5 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2007,vol. 50,p. 183 - 188

12
[ 40422-70-6 ]
[ 109757-66-6 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 91 - 92

13
[ 615535-22-3 ]
[ 40422-70-6 ]
C₁₈H₁₇BrN₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 90℃; for 4.5h;	Example 158 Stannane 108A (80.8 mg, 0.2120 mmol), dibromide P26 (132.8 mg,-0. 4869 mmol), PdCl2 (Ph3P) 2 (13.0, 0.0185 mmol), KF (27.5 mg, 0.4733 mmol) and DMF (2.6 mL) were sequentially added into a vial. Nitrogen was bubbled through the heterogeneous mixture for about a minute ; it was heated at 90C for 4.5 h and allowed to cool to rt. The solvent was removed in vacuo and a silica gel mesh was prepared and submitted to flash chromatography (50-60 % EtOAc/hexanes) to afford impure Example 158 (33 mg).

Reference： [1]Patent: WO2003/84959,2003,A1 .Location in patent: Page/Page column 144

14
[ 6374-91-0 ]
[ 40422-70-6 ]
[ 1020264-96-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3118 - 3124

15
[ 40422-70-6 ]
[ 1202932-45-3 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorosulfonic acid; at 0 - 20℃;	Example 46 4-Bromo-2-(2-bromo-ethyl)-benzenesulfonyl chloride Chlorosulfonic acid (17 mL) was added dropwise to 1-bromo-3-(2-bromo-ethyl)-benzene (5 g, 19 mmol) at 0 C. The mixture was stirred at 0 C. for 1 h then an additional 3 h at rt. The mixture was poured into an ice-water slowly and extracted with methylene chloride, and the combined organic layers were evaporated under reduced pressure to give 4.3 g of crude 4-Bromo-2-(2-bromo-ethyl)-benzenesulfonyl chloride which was used directly for next reaction. MS (ESI) 342.9 (M-Cl+OH)-.
	With chlorosulfonic acid; at 0 - 20℃;	Example 18; 4-Bromo-2-(2-bromo-ethyl)-benzenesulfonyl chlorideChlorosulfonic acid (17 mL) was added dropwise to 1-bromo-3-(2-bromo-ethyl)-benzene (5 g, 19 mmol) at 0 C. The mixture was stirred at 0 C. for 1 h then an additional 3 h at rt. The mixture was poured into an ice-water slowly and extracted with methylene chloride, and the combined organic layers were evaporated under reduced pressure to give 4.3 g of crude 4-Bromo-2-(2-bromo-ethyl)-benzenesulfonyl chloride which was used directly for next reaction. MS (ESI) 342.9 (M-Cl+OH)-.

Reference： [1]Patent: US2010/4231,2010,A1 .Location in patent: Page/Page column 83
[2]Patent: US2010/16302,2010,A1 .Location in patent: Page/Page column 40

16
[ 1034917-42-4 ]
[ 40422-70-6 ]
[ 1352576-03-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7440 - 7446

17
[ 40422-70-6 ]
[ 1382354-46-2 ]
[ 1382354-32-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5760 - 5773

18
[ 40422-70-6 ]
2-(2',6'-dimethoxy-[1,1'-biphenyl]-3-yl)-N,N-dimethylethanamine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4574 - 4581

19
[ 40422-70-6 ]
[ 1034142-44-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4574 - 4581

20
[ 40422-70-6 ]
[ 74-89-5 ]
[ 785032-26-0 ]

Yield	Reaction Conditions	Operation in experiment
12%	With caesium carbonate; In water; N,N-dimethyl-formamide; for 1h;Reflux;	To a solution of 3-bromophenethylbromide (1 g, 3.83 mmol) in DMF (10 mL) was added 40% aqueous methylamine (2.97 mL, 38.3 mmol), followed by Cs2CO3 (1.625 g, 5 mmol). After the reaction mixture was refluxed for 1 h, it was cooled to room temperature and the solvent was removed. The residue was dissolved in ethyl acetate (30 mL), and the organic layer was washed with water (3 × 20 mL) and dried over Na2SO4. The solvent was removed in vacuo, and the oily residue was further purified using flash column chromatography (CHCl3/MeOH 5:2) yielding in 2 (100 mg, 12%) as a colorless liquid. 1H NMR (300 MHz, CDCl3): delta 7.26-7.23 (m, 2H, ArH), 7.06-7.04 (m, 2H, ArH), 2.78-2.74 (m, 4H), 2.30 (s, 3H, NCH3); TLC Rf: 0.2 (CHCl3/MeOH 5:2); GC-MS (EI) m/z (% rel Int.): 214 (100.0 [M]+), rt: 7.240 min (full analytical data are reported in27).

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4574 - 4581

21
[ 40422-70-6 ]
[ 17356-08-0 ]
C₉H₁₁BrN₂S*BrH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 2h;Reflux;	General procedure: Thiourea (7 mmol) was dissolved in 13.5 mL ethanol and the appropriate alkylbromide (7 mmol) was added. The mixture was stirred and heated under reflux for 2 h after which the reaction became homogenous. The reaction was allowed to cool to room temperature and the ethanol solvent was removed under reduced pressure. A solution of NaOH (10.5 mmol) in 8.75 mL water was added to the residue, and the reaction mixture was heated under reflux (120 C) for 2 h. The reaction was subsequently cooled to room temperature and aqueous H2SO4 (15%) was added. The mercaptan separated as oil droplets and was extracted to diethylether (30 mL). The organic phase was washed twice with water, dried over anhydrous Na2SO4 and removed under reduced pressure. This yielded the desired mercaptans which were used without further purification for the synthesis of 1, 3 and 4.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 7040 - 7050

22
[ 40422-70-6 ]
[ 1415676-45-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 7040 - 7050

23
[ 40422-70-6 ]
[ 1267473-59-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 7040 - 7050

24
[ 40422-70-6 ]
[ 768-60-5 ]
[ 1449689-91-1 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 12532 - 12535
[2]Chemical Communications,2014,vol. 50,p. 12915 - 12918

25
[ 40422-70-6 ]
[ 172484-94-5 ]

Reference： [1]Organic Process Research and Development,2002,vol. 6,p. 525 - 532

26
[ 40422-70-6 ]
4-(pyrrolidin-1-yl)-1-(3-(2-(pyrrolidin-1-yl)ethyl)phenyl)piperidine trifluoroacetate [ No CAS ]

Reference： [1]MedChemComm,2013,vol. 4,p. 1501 - 1507

27
[ 123-75-1 ]
[ 40422-70-6 ]
[ 1225280-80-7 ]

Reference： [1]MedChemComm,2013,vol. 4,p. 1501 - 1507

28
2,4,6-trimethyl-N-((3'-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)methyl)benzenesulfonamide [ No CAS ]
[ 40422-70-6 ]
[ 1613028-81-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 85℃; for 2h;Microwave irradiation;	A mixture of 2,4,6-trimethyl-N-((3'-(methylsulfonyl)-[l, r-biphenyl]-4- yl)methyl)benzenesulfonamide (0.443 g, 1 mmol), K2CO3 (0.276 g, 2 mmol), and l-bromo-3-(2-bromoethyl)benzene (0.792 g, 3 mmol) in anhydrous acetonitrile (5 ml) was heated to 85 C for 2 h under microwave irradiation. The white powder was filtered off, the solvent was evaporated and the mixture was dissolved in ethyl acetate and extracted with brine. The organic phase was separated, dried over anhydrous MgS04, filtered and concentrated in vacuo. The remaining crude residue was purified by flash chromatography on silica gel (ethyl acetate/hexanes) to obtain the title compound as white sharp needles (88% based on recovery of the starting materials); FontWeight="Bold" FontSize="10" H NMR (400 MHz, Chloroform-

Reference： [1]Patent: WO2014/85453,2014,A2 .Location in patent: Page/Page column 37-38

29
[ 40422-70-6 ]
[(E)-methyl 3-(2-oxo-1,2-dihydropyridin-3-yl)acrylate] [ No CAS ]
(E)-methyl 3-(1-(3-bromophenethyl)-2-oxo-1,2-dihydropyridin-3-yl)acrylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3512 - 3521

30
[ 40422-70-6 ]
[(E)-methyl 3-(2-oxo-1,2-dihydropyridin-3-yl)acrylate] [ No CAS ]
[ 1257335-71-9 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3512 - 3521

31
[ 40422-70-6 ]
[ 109838-85-9 ]
(2S,5R)-2-(3-bromophenethyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41.38%		To a 100 mL three neck round bottomed flask under nitrogen atmosphere, (R)-2- isopropyl-3,6-dimethoxy -2,5- dihydropyrazine (4 g, 21.7 mmol) was dissolved in dry THF (28 mL) and cooled to -78 C. To this reaction mixture, 1.6 M solution of n-BuLi in hexanes (16.28 mL, 26 mmol) was added dropwise at -78 C and stirred at same temperature for 15 minutes. After 15 minutes, l-bromo-3- (2-bromoethyl)benzene (5.73 g, 21.7 mmol) in dry THF (13 mL) was added dropwise at -78 C and stirred at -78 C for 1 h followed by stirring at room temperature (rt) for 3 h. The reaction was monitored by TLC using ethyl acctatc hcxancs (0.3:9.7) as a mobile phase. After completion of the reaction, reaction mixture was quenched with saturated ammonium chloride solution (75 mL) and extracted using ethyl acetate (3 x 100 mL). Combined organic layer was dried over sodium sulphate and concentrated to give crude which was purified by flash column purification with 1-3 % ethyl acetate in hexanes to yield 3.3 g of (2S,5R)-2-(3-bromophenethyl)-5- isopropyl-3, 6-dimethoxy-2,5-dihydropyrazine (41.38% yield).
3.3 g	With n-butyllithium; In tetrahydrofuran; at 20℃; for 3h;Inert atmosphere;	To a 100 ml three neck round bottomed flask under nitrogen atmosphere, (R)-2- isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (4 g, 21.7 mmol) was dissolved in dry THF (28 ml) and cooled to -78 C. To this reaction mixture, 1 .6 M solution of n-BuLi in hexanes (16.3 ml, 26 mmol) was added dropwise at -78 C and stirred for 15 minutes. A solution of l-bromo-3- (2-bromoethyl)benzene (5.73 g, 21 .7 mmol) in dry THF (13 ml) was added dropwise at -78 C and stirred for 1 h followed by stirring at rt for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted using ethyl acetate. The combined organic layer was dried over sodium sulfate and concentrated and purified by flash column purification with 1 -3 % ethyl acetate in hexanes to yield 3.3 g of (2S,5R)-2-(3-bromophenethyl)-5-isopropyl- 3,6-dimethoxy-2,5-dihydropyrazine.

Reference： [1]Patent: WO2019/99576,2019,A1 .Location in patent: Paragraph 0200
[2]Patent: WO2015/195950,A1 .Location in patent: Page/Page column 66;67
Patent: ,2015, .Location in patent: Page/Page column 66;67

32
[ 40422-70-6 ]
3-(2-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl)benzaldehyde [ No CAS ]

Reference： [1]Patent: WO2015/195950,A1
Patent: ,2015,
[2]Patent: WO2019/99576,2019,A1

33
[ 40422-70-6 ]
methyl (S)-2-amino-4-(3-formylphenyl)butanoate [ No CAS ]

Reference： [1]Patent: WO2015/195950,A1
Patent: ,2015,
[2]Patent: WO2019/99576,2019,A1

34
[ 40422-70-6 ]
methyl (S)-4-(3-formylphenyl)-2-((2S,3R)-3-hydroxy-2-(5-methylisoxazole-3-carboxamido)butanamido)butanoate [ No CAS ]