[ CAS No. 66826-78-6 ] {[proInfo.proName]}

Name: 66826-78-6|5-Bromo-2,3-dihydrobenzofuran|98%
Brand: Ambeed
SKU: A358371
Price: 9.0 USD
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Quality Control of [ 66826-78-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 66826-78-6 ]

Product Details of [ 66826-78-6 ]

CAS No. :	66826-78-6	MDL No. :	MFCD02677716
Formula :	C₈H₇BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UDWFSJAYXTXMLM-UHFFFAOYSA-N
M.W :	199.04	Pubchem ID :	2776159
Synonyms :

Calculated chemistry of [ 66826-78-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.49
TPSA :	9.23 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) :	-5.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	2.83
Log Po/w (WLOGP) :	2.38
Log Po/w (MLOGP) :	2.49
Log Po/w (SILICOS-IT) :	3.21
Consensus Log Po/w :	2.64

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.3
Solubility :	0.0995 mg/ml ; 0.0005 mol/l
Class :	Soluble
Log S (Ali) :	-2.68
Solubility :	0.414 mg/ml ; 0.00208 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.54
Solubility :	0.0567 mg/ml ; 0.000285 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.79

Safety of [ 66826-78-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 66826-78-6 ]

* 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 [ 66826-78-6 ]
Downstream synthetic route of [ 66826-78-6 ]

[ 66826-78-6 ] Synthesis Path-Upstream 1~16

1
[ 66826-78-6 ]
[ 23145-07-5 ]

Reference： [1] Heterocycles, 1997, vol. 45, # 9, p. 1657 - 1661

2
[ 496-16-2 ]
[ 66826-78-6 ]

Yield	Reaction Conditions	Operation in experiment
70.3%	With bromine In 1,4-dioxane; ethyl acetate	Preparation 94 To an ice-cooled dioxane (30 ml) was slowly added liquid bromine (2.66 g) and this mixture was stirred for 30 minutes at said temperature. To the mixture was added dropwise 2,3-dihydrobenzofuran (2 g), and the resulting mixture was stirred for 3 hours at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in AcOEt (50 ml) and the solution was washed with saturated aqueous NaHCO₃ solution and brine, and dried over MgSO₄. The solvent was evaporated to give an orange oil as a crude product. The crude product was purified on an SiO₂ column (hexane-AcOEt 20:1) to give 2.33 g of 5-bromo-2,3 dihydrobenzofuran as white crystals (yield 70.3percent). ¹H-NMR (300 MHz, CDCl₃, δ): 3.11(2H, t, J=11 Hz), 4.57(2H, t, J=11 Hz), 6.66(1H, d, J=8 Hz), 7.20(1H, d, J=8 Hz), 7.30(1H, s)
28%	at 10℃; for 1.16667 h;	To a chilled (10°C) solution of 10 g (83 mmol) of 2, 3-dihydrobenzofuran in 50 mL of acetic acid, 4 mL (78 mmol) of bromine in 6 mL of acetic acid was added dropwise over a 10 minute period. After 1 hour, the mixture was made basic by cautiously pouring the reaction mixture into saturated/solid aqueous sodium bicarbonate and stirring overnight. The mixture was then extracted with three 100 mL portions of EtOAc. The combined organic layers were washed with two 50 mL portions of saturated aqueous sodium bicarbonate, three 50 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated to afford a yellow oil. The oil was diluted with hexane and passed through a pad (600 mL funnel) of silica gel eluting with hexane to afford a white solid which was diluted with cold (dry ice-acetone) hexane and collected by filtration to afford 4.7 g (28percent) of the title compound as a white solid, m. p. 45°C- 48°C. The filtrate was concentrated to afford 5.1 g of 5-bromo-2, 3-dihydrobenzofuran which was 70percent pure.

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 16, p. 4313 - 4336
[2] Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1044 - 1047
[3] Synthesis, 1988, # 12, p. 950 - 952
[4] Patent: US6333324, 2001, B1,
[5] Patent: WO2003/82787, 2003, A1, . Location in patent: Page/Page column 137-138
[6] Synlett, 2005, # 18, p. 2837 - 2842
[7] Patent: US6235771, 2001, B1,
[8] Patent: WO2007/27917, 2007, A2, . Location in patent: Page/Page column 23-25
[9] Patent: EP1394147, 2004, A1, . Location in patent: Page 92

3
[ 377091-18-4 ]
[ 66826-78-6 ]

Reference： [1] Organic Letters, 2001, vol. 3, # 21, p. 3357 - 3360

4
[ 76429-66-8 ]
[ 66826-78-6 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 7, p. 1384 - 1388

5
[ 1435-52-5 ]
[ 66826-78-6 ]

Reference： [1] Organic Letters, 2001, vol. 3, # 21, p. 3357 - 3360

6
[ 377091-17-3 ]
[ 66826-78-6 ]

Reference： [1] Organic Letters, 2001, vol. 3, # 21, p. 3357 - 3360

7
[ 106-41-2 ]
[ 66826-78-6 ]

Reference： [1] Journal of the American Chemical Society, 1920, vol. 42, p. 163
[2] Journal of the American Chemical Society, 1920, vol. 42, p. 163

8
[ 34743-88-9 ]
[ 66826-78-6 ]

Reference： [1] Journal of the American Chemical Society, 1920, vol. 42, p. 163

9
[ 18800-30-1 ]
[ 66826-78-6 ]

Reference： [1] Journal of the American Chemical Society, 1920, vol. 42, p. 163

10
[ 615-58-7 ]
[ 66826-78-6 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 7, p. 1384 - 1388

11
[ 64010-12-4 ]
[ 66826-78-6 ]

Reference： [1] Synthesis, 1988, # 12, p. 950 - 952

12
[ 66826-78-6 ]
[ 68-12-2 ]
[ 55745-70-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 16, p. 4313 - 4336

13
[ 109-72-8 ]
[ 66826-78-6 ]
[ 55745-70-5 ]

Reference： [1] Patent: US6649643, 2003, B1,

14
[ 66826-78-6 ]
[ 40492-52-2 ]

Reference： [1] Synthesis, 1988, # 12, p. 950 - 952

15
[ 66826-78-6 ]
[ 227305-69-3 ]

Reference： [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 6, p. 1115 - 1118

16
[ 66826-78-6 ]
[ 121-43-7 ]
[ 227305-69-3 ]

Reference： [1] Patent: US6387931, 2002, B1,

[ 66826-78-6 ] Synthesis Path-Downstream 1~88

1
[ 34743-88-9 ]
[ 66826-78-6 ]

Reference： [1]Journal of the American Chemical Society,1920,vol. 42,p. 163

2
[ 496-16-2 ]
[ 66826-78-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With bromine; In dichloromethane; at 20℃; for 2.75h;	Dissolve 2,3-dihydrobenzofuran (1,5 g, 41.6 mmol) in dichloromethane (35 mL),Br2 (6.65 g, 41.6 mmol) was weighed and dissolved in dichloromethane (15 mL). The mixture was added dropwise to the above mixture within 45 minutes at room temperature, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, a saturated NaHSO3 solution (25 mL) was added to quench, and extracted with dichloromethane (15 mL × 3). The separated organic layer was washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure to obtain the target compound as a white solid 7.5 g, yield: 91%. This white solid was 5-bromo-2,3-dihydrobenzofuran (the compound 2).
70.3%	With bromine; In 1,4-dioxane; ethyl acetate;	Preparation 94 To an ice-cooled dioxane (30 ml) was slowly added liquid bromine (2.66 g) and this mixture was stirred for 30 minutes at said temperature. To the mixture was added dropwise 2,3-dihydrobenzofuran (2 g), and the resulting mixture was stirred for 3 hours at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in AcOEt (50 ml) and the solution was washed with saturated aqueous NaHCO3 solution and brine, and dried over MgSO4. The solvent was evaporated to give an orange oil as a crude product. The crude product was purified on an SiO2 column (hexane-AcOEt 20:1) to give 2.33 g of 5-bromo-2,3 dihydrobenzofuran as white crystals (yield 70.3%). 1H-NMR (300 MHz, CDCl3, delta): 3.11(2H, t, J=11 Hz), 4.57(2H, t, J=11 Hz), 6.66(1H, d, J=8 Hz), 7.20(1H, d, J=8 Hz), 7.30(1H, s)
28%	With bromine; acetic acid; at 10℃; for 1.16667h;	To a chilled (10C) solution of 10 g (83 mmol) of 2, 3-dihydrobenzofuran in 50 mL of acetic acid, 4 mL (78 mmol) of bromine in 6 mL of acetic acid was added dropwise over a 10 minute period. After 1 hour, the mixture was made basic by cautiously pouring the reaction mixture into saturated/solid aqueous sodium bicarbonate and stirring overnight. The mixture was then extracted with three 100 mL portions of EtOAc. The combined organic layers were washed with two 50 mL portions of saturated aqueous sodium bicarbonate, three 50 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated to afford a yellow oil. The oil was diluted with hexane and passed through a pad (600 mL funnel) of silica gel eluting with hexane to afford a white solid which was diluted with cold (dry ice-acetone) hexane and collected by filtration to afford 4.7 g (28%) of the title compound as a white solid, m. p. 45C- 48C. The filtrate was concentrated to afford 5.1 g of 5-bromo-2, 3-dihydrobenzofuran which was 70% pure.

	With bromine; sodium carbonate; In hexane; water;	Reference Example 69 To a mixture of 2,3-dihydrobenzofuran (11.06 g) and sodium carbonate (14.8 g) in hexane (100 ml) was added dropwise at 0 C. a solution of bromine (4.8 ml) in hexane (20 ml) for 1.5 hours, and the mixture was stirred at room temperature for 1 hour. To the mixture was added water, and the mixture was extracted with hexane. The organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give gray crystals of 5-bromo-2,3-dihydrobenzofuran (17.64 g). 1H-NMR (200 MHz, CDCl3) delta 3.20 (2H, t, J=8.8 Hz), 4.57 (2H, t, J=8.8 Hz), 6.66 (1H, d, J=8.4 Hz), 7.17-7.30 (2H, m).
	With N-Bromosuccinimide;zirconium(IV) chloride; In dichloromethane; at 20℃; for 1h;Conversion of starting material;	Bromination using NBS has been found to be applicable for use with a wide range of aromatic starting materials or substrates, as is EPO <DP n="25"/>summarized in Table 1 . For example, anisole can be brominated by use of 1 equivalent of NBS in the presence of 5 mol % of ZrCI4 at -78 0C to afford p- bromoanisole in 98% yield as sole product (Table 1 , Entry 1 ). However, in the absence of ZrCI4 the halogenation does not proceed, even at room temperature (Table 1 , Entry 1 ).[00111] All of the substrates shown in Table 1 were brominated to give the corresponding monobromo products in excellent yield and regioselectivity. In most cases, the reaction can proceed at very low temperature and no further purification is necessary. In addition. Table 1 reveals that the halogenation of the present invention is compatible with a variety of substituents.Table 1 ZrCI4 Catalyzed Bromination of Aromatic Compounds EPO <DP n="26"/>(5 mol %), CH2CI2 (4d See spectroscopic data for characterization.
	With N-Bromosuccinimide; In acetonitrile; at 20℃; for 3h;	[188.2] Dihydrobenzofuran (9.34 g) was dissolved in 130 ml of acetonitrile, 13.9 g of N-bromosuccinimide was added thereto and the mixture was stirred at room temperature for 3 hours. The solvent was evaporated, then the residue was dissolved in ethyl acetate and successively washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed, to give 15. 94 g of the title compound.1H-NMR(CDCl3) delta: 3.02 (t, J=8.8Hz, 2H) 4.57 (t, J=8.8Hz, 2H) 6.66 (d, J=8.0Hz, 1H) 7.12-7.21 (m, 1H) 7.28-7.29 (m, 1H)

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4313 - 4336
[2]Chemistry - A European Journal,2017,vol. 23,p. 1044 - 1047
[3]Synthesis,1988,p. 950 - 952
[4]Patent: CN110452201,2019,A .Location in patent: Paragraph 0019; 0021-0025
[5]Patent: US6333324,2001,B1
[6]Patent: WO2003/82787,2003,A1 .Location in patent: Page/Page column 137-138
[7]Synlett,2005,p. 2837 - 2842
[8]Patent: US6235771,2001,B1
[9]Patent: WO2007/27917,2007,A2 .Location in patent: Page/Page column 23-25
[10]Patent: EP1394147,2004,A1 .Location in patent: Page 92

3
[ 76429-66-8 ]
[ 66826-78-6 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 1384 - 1388

4
[ 66826-78-6 ]
[ 178419-47-1 ]
(R)-3'-(2,3-dihydrobenzo[b]furan-5-yl)spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin]-2'-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4374 - 4383

5
[ 66826-78-6 ]
5-(2,3-dihydro-benzofuran-5-yl)-7-(2-hydroxy-4-methoxy-phenyl)-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

6
[ 66826-78-6 ]
5-(2,3-dihydro-benzofuran-5-yl)-7-(2-hydroxy-4-methoxy-phenyl)-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

7
[ 66826-78-6 ]
5-(2,3-dihydro-benzofuran-5-yl)-7-[4-methoxy-2-(2-methyl-3-oxo-propyl)-phenyl]-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

8
[ 66826-78-6 ]
5-(2,3-dihydro-benzofuran-5-yl)-7-[2-(3-hydroxy-2-methyl-propyl)-4-methoxy-phenyl]-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

9
[ 66826-78-6 ]
7-[2-(3-acetoxy-2-methyl-propyl)-4-methoxy-phenyl]-5-(2,3-dihydro-benzofuran-5-yl)-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

10
[ 66826-78-6 ]
(5S,6R,7R)-5-(2,3-Dihydro-benzofuran-5-yl)-7-[2-(3-hydroxy-2-methyl-propyl)-4-methoxy-phenyl]-2-isopropylamino-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

11
[ 66826-78-6 ]
5-(2,3-dihydro-benzofuran-5-yl)-7-(4-methoxy-2-trifluoromethanesulfonyloxy-phenyl)-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

12
[ 66826-78-6 ]
7-[2-(3-acetoxy-2-methyl-propyl)-4-methoxy-phenyl]-5-(2,3-dihydro-benzofuran-5-yl)-1-oxy-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

13
[ 66826-78-6 ]
5-acetoxy-7-(2-benzyloxy-4-methoxy-phenyl)-5-(2,3-dihydro-benzofuran-5-yl)-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

14
[ 66826-78-6 ]
5-(2,3-dihydro-benzofuran-5-yl)-7-[2-(3-hydroxy-2-methyl-propyl)-4-methoxy-phenyl]-2-isopropylamino-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

15
[ 66826-78-6 ]
7-[2-(3-acetoxy-2-methyl-propyl)-4-methoxy-phenyl]-2-(benzoyl-isopropyl-amino)-5-(2,3-dihydro-benzofuran-5-yl)-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

16
[ 66826-78-6 ]
7-[2-(3-acetoxy-2-methyl-propyl)-4-methoxy-phenyl]-2-(benzoyl-isopropyl-amino)-5-(2,3-dihydro-benzofuran-5-yl)-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2139 - 2150

17
[ 1435-52-5 ]
[ 66826-78-6 ]

Reference： [1]Organic Letters,2001,vol. 3,p. 3357 - 3360

18
[ 377091-17-3 ]
[ 66826-78-6 ]

Reference： [1]Organic Letters,2001,vol. 3,p. 3357 - 3360

19
[ 66826-78-6 ]
[ 1027464-48-7 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

20
[ 66826-78-6 ]
[ 188109-85-5 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

21
[ 66826-78-6 ]
[ 188111-34-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

22
[ 66826-78-6 ]
[ 1025972-81-9 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

23
[ 66826-78-6 ]
[ 1026622-35-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

24
[ 66826-78-6 ]
[ 1027233-28-8 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

25
[ 66826-78-6 ]
2,3,6,7,8,9-Hexahydro-naphtho[1,2-b]furan-6-carbonyl chloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

26
[ 66826-78-6 ]
6-Hydroxy-2,3,6,7,8,9-hexahydro-naphtho[1,2-b]furan-6-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

27
[ 66826-78-6 ]
4-(2,3-Dihydro-benzofuran-6-yl)-4-oxo-butyric acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

28
[ 66826-78-6 ]
4-(2,3-Dihydro-benzofuran-6-yl)-4-oxo-butyric acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

29
[ 66826-78-6 ]
Methanesulfonic acid (R)-1-(2,3,6,7,8,9-hexahydro-naphtho[1,2-b]furan-6-yl)methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

30
[ 66826-78-6 ]
[ 152149-20-7 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

31
[ 66826-78-6 ]
[ 1026481-77-5 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

32
[ 66826-78-6 ]
[ 1026940-34-0 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

33
[ 66826-78-6 ]
[ 1027551-06-9 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

34
[ 66826-78-6 ]
[ 1053655-08-5 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

35
[ 66826-78-6 ]
[ 152149-19-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

36
[ 66826-78-6 ]
[ 1054718-62-5 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

37
[ 66826-78-6 ]
2-(2-Benzoyl-2,3-dihydro-1H-isoindol-5-yl)-N-((R)-5-methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-N-methyl-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

38
[ 66826-78-6 ]
[ 1053261-07-6 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

39
[ 66826-78-6 ]
(4R,5S,6S,7R)-1,3-Dibenzyl-4,7-bis-(2,3-dihydro-benzofuran-5-ylmethyl)-5,6-dihydroxy-[1,3]diazepan-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

40
[ 66826-78-6 ]
(3aS,4R,8R,8aS)-5,7-Dibenzyl-4,8-bis-(2,3-dihydro-benzofuran-5-ylmethyl)-2,2-dimethyl-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

41
[ 66826-78-6 ]
[ 1053254-59-3 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

42
[ 66826-78-6 ]
[ 188948-00-7 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

43
[ 66826-78-6 ]
(4R,5S,6S,7R)-4,7-Bis-(2,3-dihydro-benzofuran-5-ylmethyl)-5,6-dihydroxy-1,3-bis-(3-methylamino-benzyl)-[1,3]diazepan-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

44
[ 66826-78-6 ]
(4R,5S,6S,7R)-1,3-Bis-(3-acetyl-benzyl)-4,7-bis-(2,3-dihydro-benzofuran-5-ylmethyl)-5,6-dihydroxy-[1,3]diazepan-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

45
[ 66826-78-6 ]
[ 1053251-31-2 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

46
[ 66826-78-6 ]
[ 1053259-55-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

47
[ 66826-78-6 ]
C₃₉H₄₀N₄O₇ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

48
[ 66826-78-6 ]
(3aS,4R,8R,8aS)-4,8-Bis-(2,3-dihydro-benzofuran-5-ylmethyl)-2,2-dimethyl-5,7-bis-(3-nitro-benzyl)-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474

49
[ 66826-78-6 ]
[ 330195-80-7 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

50
[ 66826-78-6 ]
(2-Benzo[1,3]dioxol-5-yl-ethyl)-[(R)-1-(2,3,6,7,8,9-hexahydro-naphtho[1,2-b]furan-6-yl)methyl]-methyl-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

51
[ 66826-78-6 ]
[ 784119-78-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

52
[ 66826-78-6 ]
((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-[2-(2-trifluoromethanesulfonyl-2,3-dihydro-1H-isoindol-5-yl)-ethyl]-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

53
[ 64010-12-4 ]
[ 66826-78-6 ]

Reference： [1]Synthesis,1988,p. 950 - 952

54
[ 615-58-7 ]
[ 66826-78-6 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 1384 - 1388

55
[ 106-41-2 ]
[ 66826-78-6 ]

Reference： [1]Journal of the American Chemical Society,1920,vol. 42,p. 163
[2]Journal of the American Chemical Society,1920,vol. 42,p. 163

56
[ 66826-78-6 ]
[ 281678-73-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hexamethylenetetramine; In trifluoroacetic acid; at 50℃;	[188.3] <strong>[66826-78-6]5-Bromo-2,3-dihydrobenzo[b]furan</strong> (15.94 g) was dissolved in 200 ml of trifluoroacetic acid, and 22.5 g of hexamethylenetetramine was added thereto, and the mixture was stirred at 50C overnight. The solvent was evaporated, then the residue was dissolved in ethyl acetate and successively washed with water, a saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by silica gel column, to give 11.42 g of the title compound in the 4:1 hexane-ethyl acetate fraction.1H-NMR(CDCl3) delta: 3.26 (t, J=8.8Hz, 2H) 4.76 (t, J=8.8Hz, 2H) 7.49 (dt, J=1.2, 3.2Hz, 1H) 7.69 (dt, J=0.8, 2.8, 1H) 10.12 (s, 1H)

Reference： [1]Patent: EP1394147,2004,A1 .Location in patent: Page 92

57
[ 66826-78-6 ]
[ 121-43-7 ]
[ 227305-69-3 ]

Yield	Reaction Conditions	Operation in experiment
		PREPARATION 108 2,3-Dihydrobenzofuran-5-ylboronic Acid Obtained as a colourless solid (38%), m.p. >240 C.(decomp.), from <strong>[66826-78-6]5-bromo-2,3-dihydrobenzofuran</strong> (Synthesis, 1988, 952) and trimethyl borate, using the procedure of Preparation 101. delta(DMSOd6): 3.33 (t,2H), 4.48 (t,2H), 6.68 (d,1H), 7.56 (d,1H), 7.63 (s,1H), 7.70 (brs,2H).

Reference： [1]Patent: US6387931,2002,B1

58
[ 109-72-8 ]
[ 66826-78-6 ]
[ 55745-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide;	(i) Production of Ethyl 2,3-Dihydronaphtho[2,3-b]furan-6-carboxylate 5-Bromo-2,3-dihydrobenzofuran (38.86 g), which was prepared according to the literature (Alabaster, Ramon J. et al., Synthesis, 1988, vol. 12, pp950.), was dissolved in THF (300 mL) and cooled to -78 C. n-Butyl-lithium in hexane (1.6M; 160 mL) was added to the solution and stirred for 30 min. DMF (40 mL) was added to the mixture and was allowed to warm to room temperature. Water was added to the mixture and the solvent was evaporated. The residue was diluted with ethyl acetate, washed with water and brine, dried and concentrated to give crude product of 5-formyl-2,3-dihydrobenzofuran (28.47 g) as an oil.

Reference： [1]Patent: US6649643,2003,B1

59
[ 66826-78-6 ]
[ 106-93-4 ]
5-(2-methylallyl)-2,3-dihydrobenzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogenchloride; magnesium; In tetrahydrofuran; 2-methyl-3-bromo-1-propene;	A. 5-(2-Methylallyl)-2,3-dihydrobenzofuran A solution of <strong>[66826-78-6]5-bromo-2,3-dihydrobenzofuran</strong> (50 grams, 0.251 mole), and 1,2-dibromoethane (2.2 ml) in tetrahydrofuran (250 ml) was added dropwise to a stirred suspension of magnesium turnings (7.5 grams, 0.31 gram-atoms) in tetrahydrofuran (50 ml) over a period of 45 minutes. During the addition the reaction temperature was maintained at 30 C. The solution was cooled in an ice-bath and 3-bromo-2-methylpropene was added all at once. After stirring overnight, the reaction was quenched with cold 2% hydrochloric acid and the mixture was extracted with ether. Evaporation of solvent gave 5-(2-methylallyl)-2,3-dihydrobenzofuran as an oil (43.4 grams, 99%). M+ 174.

Reference： [1]Patent: US6319920,2001,B1

60
[ 66826-78-6 ]
palladium tetrakistriphenylphosphine [ No CAS ]
3-(2,3-dihydro-benzo[b]furan-5-yl)acrylic acid tert butyl ester [ No CAS ]
[ 1663-39-4 ]
[ 203505-84-4 ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid; triethylamine; trifluoroacetic acid; In n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;	EXAMPLE 7 3-(2,3-Dihydro-benzo[b]furan-5-yl)acrylic acid STR9 A mixture of <strong>[66826-78-6]5-bromo-2,3-dihydro-benzo[b]furan</strong> (9.95 g, 0.05 mol), tert-butyl acrylate (9.71 g, 0.075 mol), palladium tetrakistriphenylphosphine (200 mg, 0.2 mmol), triethylamine (11 ml) in N,N-dimethylformamide (40 ml) was heated at reflux temperature for 20 h under an atmosphere of nitrogen. The cooled reaction mixture was diluted with water (150 ml) and extracted with ethyl acetate (2*50 ml). The combined organic extracts were washed with water (50 ml), saturated aqueous ammonium chloride (20 ml), dried (MgSO4), filtered and evaporated in vacuo. The residue was recrystallized from heptane affording after drying 1.55 g 13%) of 3-(2,3-dihydro-benzo[b]furan-5-yl)acrylic acid tert butyl ester as a solid. To a solution of the above tert butyl ester (1.23 g, 5 mmol) in dichloromethane (10 ml) was added trifluoroacetic acid (2.5 ml) and the reaction mixture was stirred at room temperature for 20 h. The volatiles were evaporated in vacuo, the residue was dissolved in toluene (20 ml) and evaporated in vacuo (repeated three times) affording a crude product. The crude product was purified by column chromatography on silicagel (180 ml) using a mixture of ethyl acetate, heptane and formic acid (45:45:10) as eluent. This afforded 0.37 g which was recrystallized from ethyl acetate affording 0.16 g (16%) of the title compound as a solid. Calculated for C11 H10 O3: C, 69.46%; H, 5.30%. Found: C, 69.32%; H, 5.45%.

Reference： [1]Patent: US6043247,2000,A

Yield	Reaction Conditions	Operation in experiment
		4-[E,Z-2-(2,3-Dihydrobenzo[b]furan-5-yl)ethenyl]benzo[b]thiophene-2-carboxamidine hydrochloride A quantitative yield of 5-bromo-2,3-dihydrobenzofuran (418.0 mg, 0.21 mmol) was obtained from the reaction of 2,3-dihydrofuran (250.0 mg, 2.1 mmol) with Br2 (400.0 mg, 2.5 mmol) in CH2 Cl2 (5 mL) at 0 C. under N2. The reaction was diluted with CHCl3, washed with 10% sodium metabisulfite, water, saturated brine, dried (MgSO4), filtered and evaporated to dryness.

62
[ 66826-78-6 ]
[ 121-43-7 ]
2,3-dihydrobenzofuran-5-yl borate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; sulfuric acid; In tetrahydrofuran; hexane;	Working Example 57 (Production of Compound 56) Under argon atmosphere, to a solution of <strong>[66826-78-6]5-bromo-2,3-dihydrobenzofuran</strong> (17.64 g) in THF (150 ml) was added dropwise at -78 C. a solution of 1.6M n-butyllithium in hexane (60 ml), and the mixture was stirred for 1 hour. To the mixture was added dropwise a solution of trimethyl borate (30 ml) in THF (30 ml). The reaction mixture was allowed to gradually warm to room temperature, and the mixture was stirred at room temperature for 2 hours. To the mixture was added dropwise 10% sulfuric acid (100 ml), and the mixture was stirred for 30 minutes and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give colorless crystals, which were collected by filtration. The crystals were washed with diisopropylether to give colorless crystals of 2,3-dihydrobenzofuran-5-yl borate (8.28 g).

Reference： [1]Patent: US6235771,2001,B1

64
[ 66826-78-6 ]
[ 93-05-0 ]
N'-(2,3-dihydro-1-benzofuran-5-yl)-N,N-diethylbenzene-1,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃; for 48h;	Example 6; Preparation of N'-(2,3-dihydro-1-benzofuran-5-yl)-N,N-diethylbenzene-1,4-diamine; [Show Image] To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added N,N-diethyl-1,4-phenylenediamine (3.35 grams, 20.4 mmoles), <strong>[66826-78-6]5-bromo-2,3-dihydrobenzofuran</strong> (3.4 grams, 17.1 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.39 grams, 0.43 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (2.1 grams, 3.4 mmoles), sodium tert-butoxide (0.71 grams, 1.28 mmoles) and anhydrous toluene (90 mL). The contents of the flask were heated to 80C for two days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (200 mL). The combined organic layers were concentrated in vacuo to yield a dark blue oil. The oil was chromatographed on silica gel, eluting with a hexane/ethyl acetate gradient to afford 4.2 grams of the desired product as a brown oil. 1H NMR (CDCl3) delta 6.6-7.0 (m, 7H), 5.15 (bs, 1H), 4.5 (t, 2H), 3.05-3.2 (m, 6H), 1.1 (t, 6H).
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃; for 48h;	To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added N,N-diethyl-1,4-phenylenediamine (3.35 grams, 20.4 mmoles), <strong>[66826-78-6]5-bromo-2,3-dihydrobenzofuran</strong> (3.4 grams, 17.1 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.39 grams, 0.43 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (2.1 grams, 3.4 mmoles), sodium tert-butoxide (0.71 grams, 1.28 mmoles) and anhydrous toluene (90 mL). The contents of the flask were heated to 80 C. for two days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (200 mL). The combined organic layers were concentrated in vacuo to yield a dark blue oil. The oil was chromatographed on silica gel, eluting with a hexane/ethyl acetate gradient to afford 4.2 grams of the desired product as a brown oil. 1H NMR (CDCl3) delta 6.6-7.0 (m, 7H), 5.15 (bs, 1H), 4.5 (t, 2H), 3.05-3.2 (m, 6H), 1.1 (t, 6H).

Reference： [1]Patent: EP1801104,2007,A2 .Location in patent: Page/Page column 12-13
[2]Patent: US7501386,2009,B2 .Location in patent: Page/Page column 22

65
[ 66826-78-6 ]
tris(dibenzylideneacetone)dipalladium ⁽⁰⁾ [ No CAS ]
[ 93-05-0 ]
N'-(2,3-dihydro-1-benzofuran-5-yl)-N,N-diethylbenzene-1,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen; sodium t-butanolate; In toluene;	Example 6 Preparation of N'-(2,3-dihydro-1-benzofuran-5-yl)-N,N-diethylbenzene-1,4-diamine To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added N,N-diethyl-1,4-phenylenediamine (3.35 grams, 20.4 mmoles), <strong>[66826-78-6]5-bromo-2,3-dihydrobenzofuran</strong> (3.4 grams, 17.1 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.39 grams, 0.43 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (2.1 grams, 3.4 mmoles), sodium tert-butoxide (0.71 grams, 1.28 mmoles) and anhydrous toluene (90 mL). The contents of the flask were heated to 80 C. for two days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (200 mL). The combined organic layers were concentrated in vacuo to yield a dark blue oil. The oil was chromatographed on silica gel, eluding with a hexane/ethyl acetate gradient to afford 4.2 grams of the desired product as a brown oil. 1H NMR (CDCl3) delta 6.6-7.0 (m, 7H), 5.15 (bs, 1H), 4.5 (t, 2H), 3.05-3.2 (m, 6H), 1.1 (t, 6H).

Reference： [1]Patent: US2007/142246,2007,A1

66
[ 66826-78-6 ]
tris(dibenzylideneacetone)dipalladium ⁽⁰⁾ [ No CAS ]
[ 42933-43-7 ]
N-(2,3-dihydro-1-benzofuran-5-yl)-2,3-dihydro-1-benzofuran-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen; sodium t-butanolate; In toluene;	Example 3 Preparation of N-(2,3-dihydro-1-benzofuran-5-yl)-2,3-dihydro-1-benzofuran-5 -amine To a flask equipped with a magnetic stirrer, reflux condenser, and nitrogen inlet was added 2,3-dihydro-1-benzofuran-5-amine (4.53 grams, 33.3 mmoles, prepared as in Example 23 of U.S. Pat. No. 20040029932), <strong>[66826-78-6]5-bromo-2,3-dihydrobenzofuran</strong> (6.63 grams, 32.9 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.61 grams, 0.67 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (0.83 grams, 1.33 mmoles), sodium tert-butoxide (6.44 grams, 66.6 mmoles) and anhydrous toluene (60 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (200 mL). The combined organic layers were concentrated in vacuo to yield a dark yellow oil. The solid was chromatographed on silica gel, eluding with a hexane/ethyl acetate gradient. The resulting solid was recrystallized from ethanol to afford 1.8 grams of the desired product as a white solid. 1H NMR (CDCl3/D2O) delta 6.55-6.95 (m, 6H), 4.5 (t, 4H), 3.15 (t, 4H).

Reference： [1]Patent: US2007/142245,2007,A1

67
[ 66826-78-6 ]
[ 42933-43-7 ]
N-(2,3-dihydro-1-benzofuran-5-yl)-2,3-dihydro-1-benzofuran-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 72h;Heating / reflux;	Example 3 Preparation of N-(2,3-dihydro-1-benzofuran-5-yl)-2,3-dihydro-1-benzofuran-5-amine To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 2,3-dihydro-1-benzofuran-5-amine (4.53 grams, 33.3 mmoles, prepared as in Example 23 of), <strong>[66826-78-6]5-bromo-2,3-dihydrobenzofuran</strong> (6.63 grams, 32.9 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.61 grams, 0.67 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (0.83 grams, 1.33 mmoles), sodium tert-butoxide (6.44 grams, 66.6 mmoles) and anhydrous toluene (60 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (200 mL). The combined organic layers were concentrated in vacuo to yield a dark yellow oil. The solid was chromatographed on silica gel, eluding with a hexane/ethyl acetate gradient. The resulting solid was recrystallized from ethanol to afford 1.8 grams of the desired product as a white solid. 1H NMR (CDCl3/D2O) delta 6.55-6.95 (m, 6H), 4.5 (t, 4H), 3.15 (t, 4H).

Reference： [1]Patent: EP1801105,2007,A1 .Location in patent: Page/Page column 11-12

68
[ 66826-78-6 ]
[ 227305-69-3 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 1115 - 1118

69
[ 66826-78-6 ]
[ 1583-88-6 ]
[ 1111735-80-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	With 2-acetylcyclohexanone; caesium carbonate;copper(l) iodide; In N,N-dimethyl-formamide; at 120℃; for 1h;	Step 1: (2,3-Dihydro-benzofuran-5-yl)-[2-(4-fluoro-phenyl)-ethyl]-amine A mixture of 4-fluorophenethylamine (700 mg, 5.03 mmol), <strong>[66826-78-6]5-bromo-2,3-dihydro-benzofuran</strong> (1.00 g, 5.03 mmol), copper(I) iodide (48 mg, 0.25 mmol) and cesium carbonate (3.28 g, 10.1 mmol), DMF (1.4 mL) and 2-acetylcyclohexanone (133 mul, 1.01 mmol) was stirred for 1 h at 120 C. under a argon atmosphere. After cooling to ambient temperature it was diluted with TBME (15 mL) and washed twice with water (10 mL) and brine (10 mL). The aqueous layers were extracted with TBME (15 mL). The combined organic layers were dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 70:30) afforded the title compound (860 mg, 66%) as a light-brown oil. MS m/e: 258.1 [M+H]+.

Reference： [1]Patent: US2009/36422,2009,A1 .Location in patent: Page/Page column 96

70
[ 66826-78-6 ]
[ 55745-70-5 ]
[ 87901-66-4 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 4162 - 4166

71
[ 66826-78-6 ]
[ 74-88-4 ]
[ 76429-68-0 ]

Yield	Reaction Conditions	Operation in experiment
45%		To a chilled (-78C) solution of 5.2 g (26.12 mmol) of <strong>[66826-78-6]5-bromo-2,3-dihydrobenzofuran</strong> in anhydrous THF was added 13.4 mL (26.8 mmol) of a 2.0 M solution of 7c-BuLi in pentane. After 10 minutes, 4 mL (64.25 mmol) of iodomethane was added dropwise. After the addition, the cold bath was removed and the mixture stirred at room temperature. After 2 hours, the mixture was diluted with 40 mL of saturated aqueous ammonium chloride and extracted with three 30 mL portions of EtOAc. The combined organic layers were washed with three 30 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated to afford 3.7 g of a yellow oil. The oil was distilled (Kugelrohr) under vacuum at 70C-80C to afford 1.6 g (45%) of the title compound which was used without further purification.

Reference： [1]Patent: WO2003/82787,2003,A1 .Location in patent: Page/Page column 138

72
[ 66826-78-6 ]
[ 530-93-8 ]
[ 1254366-35-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium methanolate;dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In 1,4-dioxane; at 100℃; for 0.25h;Inert atmosphere; Reflux;	Bis(di-tert-butyl)phosphinoferrocene palladium dichloride (100 mg, 0.15 mmol, 2 mol %) and KOMe (0.63 g, 9 mmol) were placed in a dry flask under argon atmosphere. Dioxane (10 ml, dry) was added followed by the addition of 4-bromo benzodihydrofuran (1.6 g, 8 mmol dissolved in 5 ml dioxane (dry)). The flask was placed into an oil bath (100 C.). 2-Tetralone (1.18 g, 8 mmol dissolved in 10 ml dioxane (dry)) was added dropwise over period of 5 minutes while stirring. The resulting mixture was stirred for 10 minutes. The reaction was stopped when a control performed with TLC showed the complete consumption of 4-bromo benzodihydrofuran. The solution was cooled with an ice bath and HCl (1N, 10 ml) and 100 mL of water were added. Dichloromethane was added to this mixture. The organic phase was separated, and the water phase washed twice with dichloromethane. The combined organic phases were washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by flash column chromatography (hexane/ethyl acetate, 90-10?70-30). Only the 1-aryl-2-tetralone was isolated in 75% yield (1.59 g, 6.01 mmol), which crystallized while standing. 1H NMR (400 MHz, CDCl3) delta 7.33-7.17 (m, 3H), 7.01 (d, J=7.1, 1H), 6.93 (s, 1H), 6.77 (d, J=9.5, 1H), 6.69 (d, J=8.2, 1H), 4.66 (s, 1H), 4.53 (t, J=8.7, 2H), 3.22-2.92 (m, 4H), 2.80-2.47 (m, 2H). 13C NMR (101 MHz, CDCl3) delta 210.09, 159.35, 136.89, 136.83, 129.54, 129.45, 128.38, 127.86, 127.61, 127.17, 127.11, 125.21, 109.27, 71.36, 59.17, 36.89, 29.68, 28.21. GC-MS (EI): calculated for C18H16O2 264.32; m/z found 264.2. FT-IR (neat): 1678, 1487, 1280, 1230, 1074.

Reference： [1]Patent: US7829745,2010,B1 .Location in patent: Page/Page column 8

73
[ 217195-91-0 ]
[ 66826-78-6 ]
[ 609807-36-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6842 - 6851

74
[ 66826-78-6 ]
3-(4-bromophenyl)-4-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-4H-1,2,4-triazole [ No CAS ]
4-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		Example 744-[(35)-l-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-[4-(2,3-dihydro-l-benzofuran- 5-yl)phenyl]-4H-l ,2,4-triazoleA mixture of 3-(4-bromophenyl)-4-[(35)-l-(cyclopropylcarbonyl)-3- pyrrolidinyl]methyl} -4H- 1 ,2,4-triazole (100 mg, 0.266 mmol), PdCl2(dppf) (20 mg, 0.024 mmol), ¾zs(pinacolato)diboron (70 mg, 0.276 mmol), and KOAc (100 mg, 1.019 mmol) in 1,4-dioxane (2 mL) was purged with nitrogen and stirred at 110 C for 4 h. 5-Bromo-2,3- dihydro-l-benzofuran (60 mg, 0.301 mmol) and 2 M aq. K2C03 (1.0 mL) were added and the reaction mixture was stirred at 110 C for 1 h. The reaction mixture was cooled to room temperature and the 1,4-dioxane layer was filtered through a plug of Celite and Na2S04, rinsing with 1,4-dioxane (4 mL). The combined 1,4-dioxane layers were concentrated in vacuo and the residue was purified by reverse phase HPLC (20-50%) CH3CN/water with 0.1 % TFA). The desired fractions were collected, neutralized with saturated aq. NaHC03, extracted with CH2C12, and the organic layer was dried over Na2S04, filtered, and concentrated in vacuo to afford the title compound (45 mg, 41%) as a solid. MS(ES)+ m/e 415.2 [M+H]+.

Reference： [1]Patent: WO2012/37298,2012,A1 .Location in patent: Page/Page column 96

75
[ 66826-78-6 ]
[ 1332333-61-5 ]
[ 1332331-99-3 ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 100℃;Inert atmosphere; Sealed tube;	b) 5 - [(3S)- 1 -(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl} -4-[4-(2,3-dihydro- 1 - benzofuran-5-yl)-2-fluorophenyl]-2,4-dihydro-3H-l,2,4-triazol-3-oneA solution of 5-[(3S)-l-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-4-[2- fluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-2,4-dihydro-3H-l,2,4- triazol-3-one (0.351 mmol) in dioxane (1.5 mL) was treated with 5-bromo-2,3-dihydro-l- benzofuran (0.319 mmol), dichloro[l, -bis(diphenylphosphino)ferrocene]palladium(II)- dichloromethane adduct (18 mg), and 2M aq potassium carbonate (0.956 mmol). The reaction mixture was purged with nitrogen, sealed, and stirred at 100 C overnight. The reaction mixture was cooled to room temperature and was diluted with water (50 mL). The aqueous layer was acidified to pH ~4 using IN aq HC1 and was extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by reverse phase HPLC (20-50% acetonitrile/water + 0.1% NH4OH) to afford the title compound (29%). MS(ES)+ m/e 449.0 [M+H]+

Reference： [1]Patent: WO2011/103546,2011,A1 .Location in patent: Page/Page column 127

76
[ 66826-78-6 ]
[ 50448-95-8 ]
[ 1396789-95-9 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7480 - 7501

77
[ 66826-78-6 ]
[ 1447730-80-4 ]
[ 1447730-81-5 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10642 - 10645

78
[ 66826-78-6 ]
[ 1447730-80-4 ]
[ 1447730-82-6 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10642 - 10645

79
[ 66826-78-6 ]
[ 109-94-4 ]
[ 87901-66-4 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 14612 - 14630

80
[ 66826-78-6 ]
[bis(2,3-dihydrobenzofuran-5-yl)methyl]triphenylphosphonium tetrafluoroborate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 14612 - 14630

81
[ 66826-78-6 ]
C₁₀H₁₇BrZn*LiCl [ No CAS ]
(E)-5-(3-cyclohexylbut-2-en-1-yl)-2,3-dihydrobenzofuran [ No CAS ]
(Z)-5-(3-cyclohexylbut-2-en-1-yl)-2,3-dihydrobenzofuran [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 14098 - 14102
Angew. Chem.,2013,vol. 125,p. 14348 - 14352,5

82
[ 66826-78-6 ]
[ 201230-82-2 ]
[ 93-55-0 ]
[ 1581733-71-2 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 17926 - 17938

83
[ 66826-78-6 ]
[ 201230-82-2 ]
[ 2235-46-3 ]
3-(2,3-dihydrobenzofuran-5-yl)-N,N-diethyl-3-oxopropanamide [ No CAS ]

Reference： [1]IUBMB Life,2014,vol. 356,p. 3519 - 3524
[2]Advanced Synthesis and Catalysis,2014,vol. 356,p. 3519 - 3524

84
[ 66826-78-6 ]
[ 108-98-5 ]
[ 82102-37-2 ]
S-phenyl 2,3-dihydrobenzofuran-5-carbothioate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 11830 - 11840

85
[ 66826-78-6 ]
[ 4733-52-2 ]
C₁₆H₁₁BrO₅ [ No CAS ]
C₁₆H₁₁BrO₅ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4420 - 4423

86
[ 66826-78-6 ]
[ 17692-84-1 ]
4-bromo-2-(naphthalen-2-yl)-1-tosyl-1,2,2a,7a-tetrahydrobenzofuro[2,3-b]azete [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 6252 - 6255

87
[ 66826-78-6 ]
[ 656835-59-5 ]
4-bromo-2-(4-methoxyphenyl)-1-(naphthalen-2-ylsulfonyl)-1,2,2a,7a-tetrahydrobenzofuro[2,3-b]-azete [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 6252 - 6255

88
[ 288-13-1 ]
[ 66826-78-6 ]
1-(2’,3’-dihydrobenzofuran-5’-yl)-1H-pyrazole [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 1044 - 1047

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[ 66826-78-6 ]

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[ 66826-78-6 ]

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H304	May be fatal if swallowed and enters airways
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
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
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
Environmental hazards
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. 66826-78-6 ] {[proInfo.proName]}

Quality Control of [ 66826-78-6 ]

Related Doc. of [ 66826-78-6 ]

Product Details of [ 66826-78-6 ]

Calculated chemistry of [ 66826-78-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 66826-78-6 ]

Application In Synthesis of [ 66826-78-6 ]

[ 66826-78-6 ] Synthesis Path-Upstream 1~16

[ 66826-78-6 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 66826-78-6 ]

Bromides

Related Parent Nucleus of [ 66826-78-6 ]

Benzofurans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 66826-78-6 ]

Related Parent Nucleus of
[ 66826-78-6 ]