[ CAS No. 103262-35-7 ] {[proInfo.proName]}

Name: 103262-35-7|(2,3-Dihydrobenzofuran-5-yl)methanol|98%
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SKU: A134899
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Quality Control of [ 103262-35-7 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 103262-35-7 ]

CAS No. :	103262-35-7	MDL No. :	MFCD02169755
Formula :	C₉H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XQDNBMXUZGAWSZ-UHFFFAOYSA-N
M.W :	150.17	Pubchem ID :	2776158
Synonyms :

Safety of [ 103262-35-7 ]

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 [ 103262-35-7 ]

* 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 [ 103262-35-7 ]
Downstream synthetic route of [ 103262-35-7 ]

[ 103262-35-7 ] Synthesis Path-Upstream 1~2

1
[ 103262-35-7 ]
[ 196598-26-2 ]

Reference： [1] Patent: EP1199304, 2002, A1, . Location in patent: Referential example 80

2
[ 103262-35-7 ]
[ 7789-60-8 ]
[ 196598-26-2 ]

Reference： [1] Patent: US6034239, 2000, A,

[ 103262-35-7 ] Synthesis Path-Downstream 1~20

1
[ 55745-70-5 ]
[ 103262-35-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium borohydrid; In methanol;	Reference Example 79 (2,3-dihydrobenzofuran-5-yl)methanol To a solution of 2,3-dihydrobenzofuran-5-carbaldehyde (30.0 g, 0.202 mol) in methanol (150 mL) was added sodium borohydride (3.83 g, 0.101 mol) under ice-cooling. The mixture was stirred for 15 minutes at ambient temperature and then diluted with water. The product was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to afford the title compound (yield 27.6 g, 91%) as an oily product. NMR (CDCl3) delta: 1.67 (1H, s), 3.20 (2H, t, J 8.6 Hz), 4.57 (2H, t, J=8.6 Hz), 4.58 (2H, s), 6.76 (1H, d, J=8.0 Hz), 7.10 (1H, d, J=8.0 Hz), 7.22 (1H, s)

Reference： [1]Patent: EP1199304,2002,A1 .Location in patent: Referential example 79
[2]Journal of the Chemical Society,1956,p. 2455,246
[3]Patent: US6034239,2000,A

2
[ 103262-35-7 ]
[ 55745-68-1 ]

Reference： [1]Journal of the Chemical Society,1958,p. 4665,4668

3
2,3-dihydro-benzofuran-5-carboxylic acid ethyl ester [ No CAS ]
[ 103262-35-7 ]

Reference： [1]Journal of the Chemical Society,1958,p. 4665,4668

4
[ 496-16-2 ]
[ 103262-35-7 ]

Reference： [1]Journal of the Chemical Society,1956,p. 2455,246

5
[ 103262-35-7 ]
[ 196598-26-2 ]

Reference： [1]Patent: EP1199304,2002,A1 .Location in patent: Referential example 80
[2]Journal of the American Chemical Society,2022,vol. 144,p. 86 - 92

6
[ 103262-35-7 ]
[ 7789-60-8 ]
[ 196598-26-2 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Reference Example 80 5-bromomethyl-2,3-dihydrobenzofuran To a solution of <strong>[103262-35-7](2,3-dihydrobenzofuran-5-yl)methanol</strong> (29.0 g, 0.193 mol) in tetrahydrofuran (150 mL) was added phosphorous tribromide (34.8 g, 0.129 mol) under ice/salt-cooling. The mixture was stirred for 20 minutes and then poured into water. The mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and evaporated to afford the title compound (yield 27.6 g, 91%). m.p.: 57-60 C.; NMR (CDCl3) δ: 3.20 (2H, t, J=8.8 Hz), 4.51 (2H, s), 4.59 (2H, t, J=8.8 Hz), 6.73 (1H, d, J=8.2 Hz), 7.14 (1H, d, J=8.2 Hz), 7.24 (1H, s)

Reference： [1]Patent: US6034239,2000,A

7
[ 103262-35-7 ]
[ 124-63-0 ]
[ 55745-68-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; ethyl acetate;	Reference Example 14-1 (2,3-dihydrobenzo[b]furan-5-yl)methyl chloride To a solution of <strong>[103262-35-7](2,3-dihydrobenzo[b]furan-5-yl)methanol</strong> (1.5 g, 10 mmol) in dichloromethane (10 mL) were added under ice-cooling triethylamine (1.67 mL, 12 mmol) and methanesulfonyl chloride (0.85 mL, 10 mmol) and the mixture was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (1.6 g, 100%).

Reference： [1]Patent: EP1223170,2002,A1

8
[ 76429-73-7 ]
[ 103262-35-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; In tetrahydrofuran; methanol;	Reference Example 13-1 (2,3-dihydrobenzo[b]furan-5-yl)methanol To a solution of 2,3-dihydrobenzo[b]furan-5-carboxylic acid (1.64 g, 10 mmol) in tetrahydrofuran (10 mL) was added under ice-cooling lithium aluminum hydride (949 mg, 25 mmol) and the mixture was stirred at 60C for 1 h. The reaction mixture was stirred under ice-cooling and methanol and 1N hydrochloric acid were added. The precipitate was filtered off and the mother liquor was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (1.5 g, 100%).
	With lithium aluminium tetrahydride; In tetrahydrofuran; at -8 - 20℃; for 3.0h;	(1) Dissolve dihydrobenzofuran-5-carboxylic acid in anhydrous tetrahydrofuran to obtain solution A. Under temperature of -8 deg.C ~ -6 deg.C, Dropwise adding lithium aluminum hydride to solution A to obtain reaction system A, Warm reaction system A to room temperature uniformly, React for 3h under stirring conditions, Then placed in an ice-water bath to dropwise add ice-water to quench until no bubbles are generated. Add tetrahydrofuran solvent, wash the filtrate 3 times with dichloromethane, and then wash the filtrate with saturated brine. Filter and distill off the solvent under reduced pressure to obtain dihydrobenzofuran-5-methanol; where the mass-volume ratio of dihydrobenzofuran-5-carboxylic acid to anhydrous tetrahydrofuran in reaction system A is 1:20, The molar ratio of hydrobenzofuran-5-carboxylic acid to lithium aluminum hydride is 1: 2.5; the drop acceleration rate of lithium aluminum hydride is 1 g / min;

Reference： [1]Patent: EP1223170,2002,A1
[2]Patent: CN110357866,2019,A .Location in patent: Paragraph 0034; 0172-0176; 0185-0189

9
[ 103262-35-7 ]
[ 910114-60-2 ]
[ 1353585-35-9 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 24.0h;	To Cpd 8c (0.3 g, 1.07 mmol) in tetrahydrofuran was added <strong>[103262-35-7]2,3-dihydro-1-benzofuran-5-ylmethanol</strong> (0.16 g, 1.07 mmol), triphenylphosphine (0.57 g, 2.15 mmol) and diethyl azodicarboxylate (0.22 g, 1.29 mmol). The reaction was stirred at room temperature for 24 h. The reaction mixture was taken up in ethyl acetate, washed with water, and the phases were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting material was purified by normal phase chromatography using an ISCO automated system to give Cpd 8d.
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 24.0h;	To Cpd 8c (0.3 g, 1.07 mmol) in tθtrahydrofuran was added <strong>[103262-35-7]2,3-dihydro-1-benzofuran-5-ylmethanol</strong> (0.16 g, 1.07 mmol), triphenylphosphine (0.57 g, 2.15 mmol) and diethyl azodicarboxylate (0.22 g, 1.29 mmol). The reaction was stirred at room temperature for 24 h. The reaction mixture was taken up in ethyl acetate, washed with water, and the phases were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting material was purified by normal phase chromatography using an ISCO automated system to give Cpd 8d.
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 24.0h;	To Cpd 8c (0.3 g, 1.07 mmol) in tetrahydrofuran was added <strong>[103262-35-7]2,3-dihydro-1-benzofuran-5-ylmethanol</strong> (0.16 g, 1.07 mmol), triphenylphosphine (0.57 g, 2.15 mmol) and diethyl azodicarboxylate (0.22 g, 1.29 mmol). The reaction was stirred at room temperature for 24 h. The reaction mixture was taken up in ethyl acetate, washed with water, and the phases were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting material was purified by normal phase chromatography using an ISCO automated system to give Cpd 8d.

Reference： [1]Patent: US2008/269225,2008,A1 .Location in patent: Page/Page column 33
[2]Patent: WO2007/79214,2007,A2 .Location in patent: Page/Page column 94
[3]Patent: US2011/319400,2011,A1 .Location in patent: Page/Page column 33

10
[ 103262-35-7 ]
[ 944114-62-9 ]
C₂₁H₁₉F₂N₃O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;	To compound 18d (2.8 g, 8.9 mmol) in 100 mL of THF was added DIAD (2.1 mL, 10.7 mmol), triphenyl phosphine (17.8 mmol), and compound Xxa. The mixture was allowed to stir at rt under an atmosphere of Argon. The mixture was concentrated, diluted with EtOAc, and washed with water. The organic phase was partitioned, dried over MgSO4, filtered, and the filtrate was concentrated to a yellow oil. The oil was purified by reverse-phase chromatography to furnish compound XXb.
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;Inert atmosphere;	To compound 18d (2.8 g, 8.9 mmol) in 100 mL of THF was added DIAD (2.1 mL, 10.7 mmol), triphenyl phosphine (17.8 mmol), and <strong>[103262-35-7]2,3-dihydro-1-benzofuran-5-ylmethanol</strong>. The mixture was allowed to stir at rt under an atmosphere of Argon. The mixture was concentrated, diluted with EtOAc, and washed with water. The organic phase was partitioned, dried over MgSO4, filtered, and the filtrate was concentrated to a yellow oil. The oil was purified by reverse-phase chromatography to furnish compound 32a.

Reference： [1]Patent: WO2007/79214,2007,A2 .Location in patent: Page/Page column 129
[2]Patent: US2011/319400,2011,A1 .Location in patent: Page/Page column 49

11
[ 103262-35-7 ]
[ 944114-62-9 ]
C₂H₄F₂O*C₂₀H₁₉N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;	To compound 18d (2.8 g, 8.9 mmol) in 100 mL of THF was added DIAD (2.1 mL, 10.7 mmol), triphenyl phosphine (17.8 mmol), and compound Xxa. The mixture was allowed to stir at rt under an atmosphere of Argon. The mixture was concentrated, diluted with EtOAc, and washed with water. The organic phase was partitioned, dried over MgSO4, filtered, and the filtrate was concentrated to a yellow oil. The oil was purified by reverse-phase chromatography to furnish compound XXb.

Reference： [1]Patent: US2008/269225,2008,A1 .Location in patent: Page/Page column 50

12
[ 103262-35-7 ]
C₁₃H₁₅NO₂ [ No CAS ]
(2,3-dihydrobenzofuran-5-yl)methyl 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1693 - 1703

13
tert-butyl((2,3-dihydrobenzofuran-5-yl)methoxy)dimethylsilane [ No CAS ]
[ 103262-35-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 6057 - 6062

14
[ 103262-35-7 ]
[ 18162-48-6 ]
tert-butyl((2,3-dihydrobenzofuran-5-yl)methoxy)dimethylsilane [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 6057 - 6062

15
[ 103262-35-7 ]
[ 124-63-0 ]
C₁₀H₁₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃;	(2) Under the condition of 0 C, add dihydrobenzofuran-5-methanol from step (1) and triethylamine to a dichloromethane solvent, Stir for 5min, Then add methanesulfonyl chloride dropwise to obtain reaction system B, Reaction system B was stirred for 0.5 h,Water was added dropwise to quench, and then saturated brine was added, and extracted with dichloromethane. The organic phase was dried, filtered, and the solvent was distilled off under reduced pressure to obtain the mesylate. The molar ratio of amine and methylsulfonyl chloride is 1: 1.2: 3, and the mass-to-volume ratio g of dihydrobenzofuran-5-methanol to dichloromethane solvent is 1:20;

Reference： [1]Patent: CN110357866,2019,A .Location in patent: Paragraph 0034; 0177; 0185; 0190

16
[ 103262-35-7 ]
C₃₀H₂₇N₂O₂⁽¹⁺⁾*Br^(1-) [ No CAS ]

Reference： [1]Patent: CN110357866,2019,A

17
[ 103262-35-7 ]
3-(2-bromobenzyl)-1-((2,3-dihydrobenzofuran-5-yl)methyl) -5,6-dimethyl-1H-benzo[d]imidazol-3-ium bromide [ No CAS ]

Reference： [1]Patent: CN110357866,2019,A

18
[ 103262-35-7 ]
C₁₈H₁₈N₂O [ No CAS ]

Reference： [1]Patent: CN110357866,2019,A

19
[ 103262-35-7 ]
5-(2-(bromomethyl)-1,1,1-trifluorodecan-2-yl)-2,3-dihydrobenzofuran [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2022,vol. 144,p. 86 - 92

20
[ 103262-35-7 ]
[ 55745-70-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With acetic anhydride; acetic acid; In dimethyl sulfoxide; at 60℃; for 0.25h;Microwave irradiation; Green chemistry;	7a (0.67mmol, 0.1g), DMSO 2.05mL, Ac2O 1.43mL, AcOH 0.26mL were successively added to a 15mL microwave reaction tube, the microwave power was 150w, the heating temperature was 60C, and the reaction time was 15min.After cooling, NaHCO3 solution was added and stirred at room temperature for 30 min. Extract with ethyl acetate, collect the organic phase, and extract the aqueous phase with ethyl acetate 2-3 times.The organic phases were combined, washed with water in sequence, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the target product 7b (yield: 65%).

Reference： [1]Patent: CN114149297,2022,A .Location in patent: Paragraph 0007; 0044-0046

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H200	Unstable explosive
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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. 103262-35-7 ] {[proInfo.proName]}

Quality Control of [ 103262-35-7 ]

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Application In Synthesis of [ 103262-35-7 ]

[ 103262-35-7 ] Synthesis Path-Upstream 1~2

[ 103262-35-7 ] Synthesis Path-Downstream 1~20

Related Functional Groups of [ 103262-35-7 ]

Alcohols

Related Parent Nucleus of [ 103262-35-7 ]

Benzofurans

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[ 103262-35-7 ]

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[ 103262-35-7 ]