[ CAS No. 76429-69-1 ]

Name: 76429-69-1|5-Chloro-2,3-dihydrobenzofuran|98%
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Quality Control of [ 76429-69-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 76429-69-1 ]

SDS Specification

Alternatived Products of [ 76429-69-1 ]

Product Details of [ 76429-69-1 ]

CAS No. :	76429-69-1	MDL No. :	MFCD01566475
Formula :	C₈H₇ClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PEYYQHYMRUDUOH-UHFFFAOYSA-N
M.W :	154.59	Pubchem ID :	592964
Synonyms :

Calculated chemistry of [ 76429-69-1 ]

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 :	40.8
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) :	-5.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	2.77
Log Po/w (WLOGP) :	2.27
Log Po/w (MLOGP) :	2.33
Log Po/w (SILICOS-IT) :	3.17
Consensus Log Po/w :	2.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.99
Solubility :	0.159 mg/ml ; 0.00103 mol/l
Class :	Soluble
Log S (Ali) :	-2.62
Solubility :	0.371 mg/ml ; 0.0024 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.29
Solubility :	0.0795 mg/ml ; 0.000514 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.63

Safety of [ 76429-69-1 ]

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

Application In Synthesis of [ 76429-69-1 ]

* 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 [ 76429-69-1 ]
Downstream synthetic route of [ 76429-69-1 ]

[ 76429-69-1 ] Synthesis Path-Upstream 1~7

1
[ 121767-82-6 ]
[ 695-96-5 ]
[ 76429-69-1 ]
[ 106-48-9 ]

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

2
[ 496-16-2 ]
[ 76429-69-1 ]

Reference： [1] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7529 - 7537
[2] Synlett, 2005, # 18, p. 2837 - 2842
[3] Patent: WO2007/27917, 2007, A2, . Location in patent: Page/Page column 26

3
[ 76429-65-7 ]
[ 76429-69-1 ]

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

4
[ 23145-05-3 ]
[ 76429-69-1 ]

Reference： [1] Patent: US5262430, 1993, A,

5
[ 121767-82-6 ]
[ 695-96-5 ]
[ 76429-69-1 ]
[ 106-48-9 ]

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

6
[ 695-96-5 ]
[ 76429-69-1 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 7, p. 1384 - 1388
[2] Chemistry - A European Journal, 2014, vol. 20, # 47, p. 15334 - 15338

7
[ 115997-75-6 ]
[ 76429-69-1 ]

Reference： [1] Tetrahedron, 1989, vol. 45, # 12, p. 3769 - 3774

[ 76429-69-1 ] Synthesis Path-Downstream 1~29

1
[ 76429-65-7 ]
[ 76429-69-1 ]

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

2
[ 121767-82-6 ]
[ 695-96-5 ]
[ 76429-69-1 ]
[ 106-48-9 ]

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

3
[ 115997-75-6 ]
[ 76429-69-1 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 3769 - 3774

4
[ 496-16-2 ]
[ 76429-69-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide;zirconium(IV) chloride; In dichloromethane; at 20℃; for 12.0h;Conversion of starting material;	Chlorination using NCS has been found to be applicable for use with a wide range of aromatic starting materials or substrates, as is shown in Table 2. All the substrates treated with 1 equivalent of NCS and 5 mole % of ZrCU afforded the corresponding chlorinated compounds. The reaction at room temperature afforded a high yield of chlorinated product with high regioselectivity. In some cases, a small amount of regioisomers (Entry 3) or dichlorinated products (Entries 4 and 5) were observed.Table 2 ZrCIj Catalyzed Chlorination of Aromatic Compounds by NCS2-CI : 4-CI (13: 87)b EPO <DP n="27"/>1 -CI : 1 ,4-di-CI(83: 17)ba Reaction conditions. Substrate (0.5 mmol), NCS (0.5 mmol), ZrCI4 (5 mol %), CH2CI2 (4 mL). b Determined by 1H NMR. c See spectroscopic data for characterization.
2.28 g	With N-chloro-succinimide; acetic acid; In acetonitrile; at 10 - 35℃; for 48.0h;	a) 5-chloro-2,3-dihydrobenzofuran A mixture of 2,3-dihydrobenzofuran (2.00 g), NCS (2.70 g), acetic acid (2.0 mL) and acetonitrile (20 mL) was stirred at room temperature for 2 days. The reaction mixture was diluted with a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.28 g). 1H NMR (300 MHz, DMSO-d6) delta 3.18 (2H, t, J=8.8 Hz), 4.54 (2H, t, J=8.7 Hz), 6.76 (1H, dd, J=8.5, 0.3 Hz), 7.10 (1H, ddt, J=8.4, 2.3, 0.8 Hz), 7.27 (1H, dt, J=2.1, 1.1 Hz).

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 7529 - 7537
[2]Synlett,2005,p. 2837 - 2842
[3]Patent: WO2007/27917,2007,A2 .Location in patent: Page/Page column 26
[4]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 1164; 1165

5
[ 695-96-5 ]
[ 76429-69-1 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 1384 - 1388
[2]Chemistry - A European Journal,2014,vol. 20,p. 15334 - 15338

6
[ 76429-69-1 ]
sodium thiosulfate [ No CAS ]
[ 134402-21-4 ]

Yield	Reaction Conditions	Operation in experiment
2.55 g (92%)	With bromine; In acetic acid;	5-chloro-7-bromo-2,3-dihydrobenzofuran (34) To a stirred solution of (33) (1.84 g, 11.93 mmol) in acetic acid (10 ml) at 0 C., was slowly added a solution of bromine (1.24 ml, 24 mmol) in acetic acid (5 ml). The reaction mixture was stirred at room temperature for 4.5 h. A 10% sodium thiosulphate solution (70 ml) was added and the mixture stirred for 10 min. The bulk of the solvent was evaporated in vacuo. The resulting oil was dissolved in ether (50 ml), washed with water (20 ml), saturated NaHCO2 (215 ml), brine (115 ml), dried Na2 SO4 and evaporated in vacuo to give 2.55 g (92%) of (34) as a oil. 1 H-NMR (80 MHz, CDCl3) delta 7.18 (s, 1H), 7.00 (s, 1H), 4.60 (t, 2H), 3.21 (t, 2H).

Reference： [1]Patent: US5262430,1993,A

7
[ 23145-05-3 ]
[ 76429-69-1 ]

Yield	Reaction Conditions	Operation in experiment
1.84 g (91%)	Rh/C; In ethanol;	5-chloro-2,3-dihydrobenzofuran (33) 5-Chloro-benzofurane (2 g, 13.11 mmol) in dry EtOH (20 ml) was hydrogenated over 10% Rh/C (251 mg) catalyst at room temperature under atmospheric pressure. When H2 absorption ceased the catalyst was filtered off and the filtrate was concentrated in vacuo to give 1.84 g (91%) of (33) as a colourless solid. 1 H-NMR (80 MHz, CDCl3) delta 7.00 (d, 2H, J=8.53 Hz), 6.62 (d, 1H, J=8.53), 4.5 (t, 2H), 3.11 (t, 2H).

Reference： [1],2020,p. 2124 - 2130
[2]Patent: US5262430,1993,A

8
[ 76429-69-1 ]
5-chloro-7-nitro-2,3-dihydro-1-benzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.9 g (40.5%)	With nitric acid; In water;	a) To a stirred and cooled mixture of 32 nil of sulfuric acid and 14 ml of water there were added 17 g of <strong>[76429-69-1]2,3-dihydro-5-chlorobenzofuran</strong>, while keeping the temperature at 25 C. After cooling to 0 C., there were added dropwise 14 ml of nitric acid. Stirring and cooling at 0 C. was continued for 44 hours. The reaction mixture was diluted with water (temp. <10 C.) and stirred for 15 min. The precipitate was filtered off, washed with water and recrystallized from a mixture of ethyl acetate and hexane (30:70), yielding 8.9 g (40.5%) of 5-chloro-2,3-dihydro-7-nitrobenzofuran (interm. 3).
	With sulfuric acid; nitric acid; acetic acid; at 100℃; for 0.75h;	Intermediate 10: 5-chloro-7-nitro-2,3-dihydro-1 -benzofuran; To a mixture of <strong>[76429-69-1]5-chloro-2,3-dihydro-1-benzofuran</strong> (prepared by the method of :Ramon J. Alabaster*, Ian F. Cottrell, Hugh Marley, Stanley H. B. Wright Synthesis (1988), (12), 950-952) (4.3g) in glacial acetic acid (20ml) and concentrated sulphuric acid (4ml) at 1000C was added concentrated nitric acid (1.57ml) and glacial acetic acid (1 ml). After forty five minutes, the mixture was allowed to cool and dissolved in dichloromethane (250ml). The organic layer was washed with water (250ml), 1 M ammonium hydroxide (250ml) and water (250ml) and then dried (MgSO4) and evaporated. The solid was dissolved in dichloromethane and applied to a column and the column eluted to afford the title compound as a yellow solid (3.4g).
	With sulfuric acid; nitric acid; In acetic acid; at 100℃; for 0.75h;	To a mixture of 5-chloro-2,3-dihydro-l-benzofuran (prepared by the method of : Ramon J. Alabaster*, Ian F. Cottrell, Hugh Marley, Stanley H. B. Wright Synthesis (1988), (12), 950-952) (4.3g) in glacial acetic acid (20ml) and concentrated sulphuric acid (4ml) at 1000C was added concentrated nitric acid (1.57ml) and glacial acetic acid (ImI). After forty five minutes, the mixture was allowed to cool and dissolved in dichloromethane (250ml). The organic layer was washed with water (250ml), IM ammonium hydroxide (250ml) and water (250ml) and then dried (MgSO/i) and evaporated. The solid was dissolved in dichloromethane and applied to a column and the column eluted to afford the title compound as a yellow solid (3.4g).

Reference： [1]Patent: US5407961,1995,A
[2]Patent: WO2007/88168,2007,A1 .Location in patent: Page/Page column 42
[3]Patent: WO2008/116816,2008,A1 .Location in patent: Page/Page column 227

Yield	Reaction Conditions	Operation in experiment
		PREPARATION 29 5-Chloro-2,3-dihydrobenzo[b]furan Pd/C (5%, 12.2 g.) in 400 ml. of acetic acid was prehydrogenated at atmospheric pressure and 25 C. Title compound of the preceding Preparation (6.1 g.) in 100 ml. of acetic acid was added and hydrogenation continued until slightly more than 1 equivalent of hydrogen had been consumed. Catalyst was recovered by filtration over diatomaceous earth. The filtrate was neutralized with saturated potassium carbonate and extracted with four 200 ml. portions of ether. The combined extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. The oil was chromatographed on 400 g. of silica gel using hexane-3% ether as eluant, 15 ml. fractions and tlc monitoring. Pure product fractions 70-90 were combined and evaporated to yield title product [2.15 g.; oil; Rf 0.32 (hexane); m/e 156/154]. By the same procedure the other benzofuran of the preceding Preparation is converted to 5-fluoro-2,3-dihydrobenzo[b]furan.
		PREPARATION 20 5-Chloro-2,3-dihydrobenzo[b]furan Pd/C (5%, 12.2 g.) in 400 ml. of acetic acid was prehydrogenated at atmospheric pressure and 25 C. Title compound of the preceding Preparation (6.1 g.) in 100 ml. of acetic acid was added and hydrogenation continued until slightly more than 1 equivalent of hydrogen had been consumed. Catalyst was recovered by filtration over diatomaceous earth. The filtrate was neutralized with saturated potassium carbonate and extracted with four 200 ml. portions of ether. The combined extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. The oil was chromatographed on 400 g. silica gel using hexane-3% ether as eluant, 15 ml. fractions and tlc monitoring. Pure product fractions 70-90 were combined and evaporated to yield title product [2.15 g.; oil; Rf 0.32 (hexane); m/e 156/154]. By the same procedure, the other benzofurans of the preceding Preparation are converted to 5-fluoro-2,3-dihydrobenzo[b]furan and 6-chloro-2,3-dihydrobenzo[b]furan.

10
2-(2-bromo-4-chlorophenoxy)ethyl 4-methylbenzenesulfonate [ No CAS ]
[ 76429-69-1 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 15334 - 15338

11
[ 76429-69-1 ]
7-({8-[2-methoxy-4-trifluoromethylphenyl]quinazolin-2-yl}amino)-N-(piperidin-4-yl)-2,3-dihydro-1-benzofuran-4-carboxamide [ No CAS ]