20532-34-7|Benzo[b]thiophen-5-ylmethanol| Ambeed

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Quality Control of [ 20532-34-7 ] Purity: 97% SDS Specification

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Product Details of [ 20532-34-7 ]

CAS No. :	20532-34-7
Formula :	C₉H₈OS
M.W :	164.22
SMILES Code :	OCC1=CC=C2C(C=CS2)=C1
MDL No. :	MFCD04972640
InChI Key :	JSYSQUAJOCDMJW-UHFFFAOYSA-N
Pubchem ID :	2795446

Safety of [ 20532-34-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 20532-34-7 ]

* 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.

Downstream synthetic route of [ 20532-34-7 ]

[ 20532-34-7 ] Synthesis Path-Downstream 1~38

1
[ 20532-34-7 ]
[ 74-88-4 ]
[ 96803-56-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium hydroxide; In dimethyl sulfoxide;	Step A Preparation of 5-Methoxymethylbenzo [b]thiophene To a stirred mixture of powdered KOH (18.9 g, 0.336 mol) in dimethylsulfoxide (100 ml) was added <strong>[20532-34-7]5-hydroxymethylbenzo[b]thiophene</strong> (13.8 g, 0.084 mol) in 25 ml of dimethylsulfoxide. Then methyl iodide (23.9 g, 0.168 mol) was added dropwise at ambient temperature over several minutes. Stirring was continued for 11/2 hours. The mixture was filtered, diluted with water (150 ml) and extracted with methylene chloride (200 ml) in three portions. The combined extracts were washed with water, dried over anhydrous Na2 SO4, filtered and concentrated in vacuo. This gave 14.1 g of amber liquid. Distillation gave 10.47 g of colorless liquid, b.p. 2.2 mm Hg 110-111 C. (Yield 70%).

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2548 - 2554.
[2]Patent: US4668697,1987,A .

2
[ 10133-22-9 ]
[ 20532-34-7 ]
[ 10133-30-9 ]
sodium; benzo[<i>b</i>]thiophen-5-yl-methanesulfonate [ No CAS ]

References: [1]Synthetic Communications,2003,vol. 33,p. 627 - 632.

3
[ 20532-34-7 ]
[ 96803-63-3 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2548 - 2554.

4
[ 20532-34-7 ]
[ 96803-58-6 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2548 - 2554.

5
[ 20532-34-7 ]
[ 96803-57-5 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2548 - 2554.

6
[ 20532-34-7 ]
[ 96803-59-7 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2548 - 2554.

7
[ 20532-34-7 ]
[ 96803-62-2 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2548 - 2554.

8
[ 20532-34-7 ]
[ 96803-11-1 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2548 - 2554.

9
[ 20532-34-7 ]
[ 96803-60-0 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2548 - 2554.

11
[ 20532-34-7 ]
[ 10133-30-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With manganese(IV) oxide; In benzene; for 12.0h;	a) benzorblthiophene-5-carbaldehvde; <n="178"/>Benzo[b]thiophen-5-ylmethanol (311 mg, 1.89 mmol) was dissolved in anhydrous benzene (20 niL). MnO2 (1317 mg, 15.2 mmol) was added and the reaction was stirred for 12 h. The solution was filtered through celite and the filter cake was washed with ethyl acetate (50 mL). The filtrate was concentrated under vacuum to give the product (284 mg, 92%) as an off-white solid: 1H NMR (400 MHz, OMSOd6) delta 10.09 (s, IH), 8.46-8.45 (m, IH), 8.21 (d, J= 8.4 Hz, IH), 7.94 (d, J= 5.6 Hz, IH), 7.81 (dd, J= 8.4, 1.2 Hz, IH), 7.66 (d, J= 5.6 Hz, IH).
570 mg	With manganese(IV) oxide; In dichloromethane; at 20℃;	To a solution of <strong>[20532-34-7]benzo[b]thiophen-5-ylmethanol</strong> (LXX) (1 g, crude) in DCM (20 mL) was added manganese oxide (6.36 g, 0.07 mol). The mixture was stirred at room temperature overnight. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (PE: EtOAc=10:1) to give benzo[b]thiophene-5-carbaldehyde (LXXI) as an orange solid. (570 mg, 3.51 mmol, 68.9% yield for 2 steps)1H NMR (DMSO-d6, 400 MHz) delta ppm 7.68 (d, J=5.2 Hz, 1H), 7.85 (d, J=8.4 Hz, 1H), 7.95 (d, J=5.2 Hz, 1H), 8.23 (d, J=8.4 Hz, 1H), 8.48 (s, 1H), 10.11 (s, 1H); ESIMS found C9H6OS m/z 163.0 (M+H)

References: [1]Patent: WO2007/53131,2007,A2 .Location in patent: Page/Page column 176-177.
[2]Patent: US2014/243349,2014,A1 .Location in patent: Paragraph 1750; 1754.

12
[ 20532-34-7 ]
[ 10133-22-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; for 1.0h;Inert atmosphere;	(5-Bromomethyl)benzo[b]thiophene (15b). To a stirred solution of <strong>[20532-34-7]benzo[b]thiophen-5-ylmethanol</strong> (14b) (100 mg, 0.61 mmol) in dry dichloromethane (15 mL) and under argon, PPh3 (290 mg, 1.09 mmol) and then CBr4 (240 mg, 0.73 mmol) were added. After stirring for 1 h, diethyl ether was added and the resulting precipitate was filtered and washed with diethyl ether. The solvents were removed under reduced pressure and the crude residue was purified by flash chromatography eluting with (10:90) diethyl ether/hexanes to afford bromide 15b (129 mg, 93%) as a white amorphous solid. 1H NMR (250 MHz, CDCl3) delta 7.86 (m, 2H, 2*ArH), 7.49 (d, 1H, J=5.5 Hz, ArH), 7.39 (d, 1H, J=8.7 Hz, ArH), 7.33 (d, 1H, J=5.5 Hz, ArH) and 4.66 (s, 2H, CH2O) ppm. 13 C NMR (63 MHz, CDCl3) delta 139.7 (C), 139.7 (C), 133.8 (C), 127.4 (CH), 125.2 (CH), 123.9 (CH), 123.7 (CH), 122.8 (CH) and 34.1 (CH2) ppm. MS (CI) m/z (%) 227 and 229 (MH+). HRMS calcd for C9H3S79Br (MH+): 226.9530; found, 226.9532.

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 191 - 200.
[2]Patent: US2011/313032,2011,A1 .Location in patent: Page/Page column 23.

13
[ 4923-87-9 ]
[ 20532-34-7 ]

References: [1]Patent: US2014/243349,2014,A1 .

14
[ 2060-63-1 ]
[ 20532-34-7 ]

References: [1]Patent: US2014/243349,2014,A1 .

15
[ 2060-64-2 ]
[ 20532-34-7 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃;Inert atmosphere;	To a solution of benzo[b]thiophene-5-carboxylic acid (LXIX) (0.9 g, 5.1 mmol) in THF (20 mL) was added LAH (0.28 g, 7 mmol) in portions at 0 C. under nitrogen atmosphere. The reaction was quenched by water, washed with 20% aq. NaOH (4 mL) and extracted with EtOAc. The EtOAc phase was concentrated in vacuo to give the crude benzo[b]thiophen-5-ylmethanol (LXX) as yellow solid. (1 g, used without further purification) ESIMS found C9H8OS m/z 165.0 (M+H).

References: [1]Patent: US2014/243349,2014,A1 .Location in patent: Paragraph 1750; 1753.

16
[ 20532-34-7 ]
methyl 3-(4-((3-(2-methylphenyl)benzo[b]thiophen-5-yl)methoxy)phenyl)-propanoate [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .

17
[ 20532-34-7 ]
3-[4-[[3-(2-methylphenyl)benzo[b]thiophen-5-yl]methoxy]phenyl] propanoic acid [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .

18
[ 20532-34-7 ]
(3S)-3-[4-[[3-(2-methylphenyl)benzo[b]thiophen-5-yl]methoxy]phenyl]hex-4-ynoic acid [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .
[3]Patent: US2017/291908,2017,A1 .

19
[ 20532-34-7 ]
C₃₀H₂₈O₄S [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .

20
[ 20532-34-7 ]
ethyl 2-(1-(4-((3-bromobenzo[b]thiophen-5-yl)methoxy)phenyl)-3-oxocyclobutyl)acetate [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .

21
[ 20532-34-7 ]
ethyl 2-(1-(4-((3-(4-(2-ethoxyethoxy)-2-methylphenyl)benzo[b]thiophen-5-yl)methoxy)phenyl)-3-oxocyclobutyl)acetate [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .

22
[ 20532-34-7 ]
2-(1-(4-((3-(4-(2-ethoxyethoxy)-2-methylphenyl)benzo[b]thiophen-5-yl)methoxy)phenyl)-3-oxocyclobutyl)acetic acid [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .

23
[ 20532-34-7 ]
ethyl 2-(1-(4-((3-(4-((1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy)-2-methylphenyl)benzo[b]thiophen-5-yl)methoxy)phenyl)-3-oxocyclobutyl)acetate [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .

24
[ 20532-34-7 ]
ethyl 2-(3-oxo-1-(4-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-yl)methoxy)phenyl)cyclobutyl)acetate [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .

25
[ 20532-34-7 ]
5-(bromomethyl)-3-(2-methylphenyl)benzo[b]thiophene [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .
[3]Patent: US2017/291908,2017,A1 .

26
[ 20532-34-7 ]
ethyl 3-(6-((3-(2-methylphenyl)benzo[b]thiophen-5-yl)methoxy)pyridin-3-yl)hex-4-ynoate [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .

27
[ 20532-34-7 ]
5-hydroxymethyl-3-(2-methylphenyl)benzo[b]thiophene [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .
[3]Patent: US2017/291908,2017,A1 .

28
[ 20532-34-7 ]
3-bromo-5-(bromomethyl)-1-benzothiophene [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .
[3]Patent: US2017/291908,2017,A1 .

29
[ 20532-34-7 ]
ethyl 3-[6-[(3-bromo-1-benzothiophen-5-yl)methoxy]pyridin-3-yl]hex-4-ynoate [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .
[3]Patent: US2017/291908,2017,A1 .

30
[ 20532-34-7 ]
5-(chloromethyl)-3-(2-methylphenyl)benzo[b]thiophene [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .

31
[ 20532-34-7 ]
3-bromo-5-hydroxymethylbenzothiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With N-Bromosuccinimide; In tetrahydrofuran; at 20℃; for 3.0h;Inert atmosphere; Cooling with ice;	(A) To an ice-cooled solution of <strong>[20532-34-7]5-hydroxymethylbenzothiophene</strong> (1.45 g; 8.83 mmol) in THF (15 mL) was added NBS (1.73 g; 9.71 mmol) under an argon atmosphere. The resulting solution was allowed to warm to rt and stirring was continued for 3 h. The reaction was then concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 0-20% EtOAc in heptanes to afford 3-bromo-5- hydroxymethylbenzothiophene (968 mg, 45%) as a white solid. 1H NMR (CDCl3) G: 7.78 - 7.88 (m, 2H), 7.46 (s, 1H), 7.43 (d, J = 9.6 Hz, 1H), 4.86 (d, J = 5.8 Hz, 2H), 1.84 (t, J = 5.8 Hz, 1H).
45%	With N-Bromosuccinimide; In tetrahydrofuran; at 20℃; for 3.0h;Cooling with ice; Inert atmosphere;	(A) To an ice-cooled solution of <strong>[20532-34-7]5-hydroxymethylbenzothiophene</strong> (1.45 g; 8.83 mmol) in THF (15 mL) was added NBS (1.73 g; 9.71 mmol) under an argon atmosphere. The resulting solution was allowed to warm to rt and stirring was continued for 3 h. The reaction was then concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 0-20% EtOAc in heptanes to afford 3-bromo-<strong>[20532-34-7]5-hydroxymethylbenzothiophene</strong> (968 mg, 45%) as a white solid. 1H NMR (CDCl3) delta: 7.78-7.88 (m, 2H), 7.46 (s, 1H), 7.43 (d, J=9.6 Hz, 1H), 4.86 (d, J=5.8 Hz, 2H), 1.84 (t, J=5.8 Hz, 1H).
45%	With N-Bromosuccinimide; In tetrahydrofuran; at 20℃; for 3.0h;Inert atmosphere; Cooling with ice;	(A) To an ice-cooled solution of <strong>[20532-34-7]5-hydroxymethylbenzothiophene</strong> (1.45 g; 8.83 mmol) in THF (15 mL) was added NBS (1.73 g; 9.71 mmol) under an argon atmosphere. The resulting solution was allowed to warm to rt, with stirring continued for another 3 h. The reaction was then concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 0-20% EtOAc in heptanes to afford 3-bromo-<strong>[20532-34-7]5-hydroxymethylbenzothiophene</strong> (968 mg, 45%) as a white solid. 1H NMR (CDCl3) delta: 7.78-7.88 (m, 2H), 7.46 (s, 1H), 7.43 (d, J=9.6 Hz, 1H), 4.86 (d, J=5.8 Hz, 2H), 1.84 (t, J=5.8 Hz, 1H)

References: [1]Patent: WO2016/57731,2016,A1 .Location in patent: Page/Page column 88.
[2]Patent: US2017/290800,2017,A1 .Location in patent: Paragraph 0449.
[3]Patent: US2017/291908,2017,A1 .Location in patent: Paragraph 0334.

32
[ 20532-34-7 ]
(3S)-ethyl 3-(4-((3-(2-methylphenyl)benzo[b]thiophen-5-yl)methoxy)phenyl)hex-4-ynoate [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .

33
[ 20532-34-7 ]
(3R)-ethyl 3-(6-((3-(2-methylphenyl)benzo[b]thiophen-5-yl)methoxy)pyridin-3-yl)hex-4-ynoate [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .
[3]Patent: US2017/291908,2017,A1 .

34
[ 20532-34-7 ]
(3RS)-methyl 3-(4-((3-(2-methylphenyl)benzo[b]thiophen-5-yl)methoxy)phenyl)hex-4-ynoate [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .

35
[ 20532-34-7 ]
3-(4-((3-(2-methylphenyl)benzo[b]thiophen-5-yl)methoxy)phenyl)hex-4-ynoic acid [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .

36
[ 20532-34-7 ]
5-hydroxymethyl-3-(2,6-dimethylphenyl)benzo[b]thiophene [ No CAS ]

References: [1]Patent: WO2016/57731,2016,A1 .
[2]Patent: US2017/290800,2017,A1 .

37
[ 20532-34-7 ]
[ 5241-64-5 ]
benzo[b]thiophen-5-ylmethyl D-tryptophanate hydrochloride [ No CAS ]

References: [1]ChemMedChem,2016,p. 1924 - 1935.

38
[ 20532-34-7 ]
[ 5241-64-5 ]
benzo[b]thiophen-5-ylmethyl (tert-butoxycarbonyl)-D-tryptophanate [ No CAS ]

References: [1]ChemMedChem,2016,p. 1924 - 1935.

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Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation

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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

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CAS No.: 20532-34-7

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CAS No.: 20532-34-7

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Product Details of [ 20532-34-7 ]

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Application In Synthesis of [ 20532-34-7 ]

[ 20532-34-7 ] Synthesis Path-Downstream 1~38

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