[ CAS No. 106429-07-6 ] {[proInfo.proName]}

Name: 106429-07-6|(2-Aminobenzo[d]thiazol-6-yl)methanol|95%
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Quality Control of [ 106429-07-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 106429-07-6 ]

CAS No. :	106429-07-6	MDL No. :	MFCD11976758
Formula :	C₈H₈N₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LPMULTSCZSOABY-UHFFFAOYSA-N
M.W :	180.23	Pubchem ID :	13821540
Synonyms :

Safety of [ 106429-07-6 ]

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

Application In Synthesis of [ 106429-07-6 ]

* 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.

Downstream synthetic route of [ 106429-07-6 ]

[ 106429-07-6 ] Synthesis Path-Downstream 1~8

1
[ 50850-93-6 ]
[ 106429-07-6 ]

Yield	Reaction Conditions	Operation in experiment
67%		[1069] Step 2: (2-aminobenzo[d]thiazol-6-yl)methanol[1070] To a solution of ethyl 2-aminobenzo[d]thiazol-6-carboxylate (10.10 g, 45.44 mmol) prepared in Step 1 in THF (320 mL) was added portionwise LAH (7.59 g, 199.94 mmol) at 0 ?. The reaction mixture was stirred at room temperature for 7 hours. Water (8.0 mL), 20% sodium hydroxide (8.0 mL), and water (24 mL) were sequentially added to the reaction mixture, which was then stirred for 2 hours. The resulting solid was filtered and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The resulting solid was suspended with diethyl ether, filtered, and then dried under reduced pressure to give 5.52 g of the titled compound as a white solid (Yield: 67%).
67%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 7h;	Step 2: (2-aminobenzo[d]thiazol-6-yl)methanol To a solution of ethyl 2-aminobenzo[d]thiazol-6-carboxylate (10.10 g, 45.44 mmol) prepared in Step 1 in THF (320 mL) was added portionwise LAH (7.59 g, 199.94 mmol) at 0 C. The reaction mixture was stirred at room temperature for 7 hours. Water (8.0 mL), 20% sodium hydroxide (8.0 mL), and water (24 mL) were sequentially added to the reaction mixture, which was then stirred for 2 hours. The resulting solid was filtered and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The resulting solid was suspended with diethyl ether, filtered, and then dried under reduced pressure to give 5.52 g of the titled compound as a white solid (Yield: 67%).
52%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 24h;	The ester (1.0 g, 4.5 mmol) was dissolved in anhydrous THF and the RB flask was cooled to 0 C. Then LiAlH4 was added slowly and the flask was stirred at 0 C. for additional 10 min. The flask was then stirred at room temperature for 24 h. The reaction was then cooled, quenched with methanol, NH4Cl Rochelle's salt and diluted with ethyl acetate (10 mL). The organic layer was separated and the aqueous layer was extracted with additional ethyl acetate (3×10 mL). The organic layers were combined, dried over Na2SO4 and concentrated under vacuo on a rotary evaporator to obtain a yellow solid. The crude product was purified via gradient silica gel column chromatography using a mixture of CH2Cl2 and methanol (100:1 to 5:1) to obtain the desired alcohol as yellow solid (420 mg, 52%). The alcohol (420 mg, 2.33 mmol) was dissolved in a mixture of CH2Cl2 and methanol (5:1) and MnO2 (81 mg, 9.32 mmol). The mixture was then stirred at room temperature for 48 h following which additional amount of MnO2 (40 mg) was added after TLC showed incompletion of the reaction. The mixture was stirred for additional 24 h and then filtered through a whatman filter paper (grade 8) and the filtrate was concentrated under vacuo on a rotary evaporator to obtain the desired aldehyde as a yellow solid (400 mg, 95%). 1H NMR (500 MHz, CDCl3): delta 7.57 (d, J=0.9 Hz, 1H), 7.35-7.46 (m, 1H), 7.25 (dd, J=8.2, 1.8 Hz, 1H), 6.45 (br s, 1H), 4.53 (s, 2H), 4.0 (br s, 1H). 13C NMR (125 MHz, CDCl3): delta 167.6, 150.5, 134.9, 130.6, 125.1, 119.4, 117.7, 64.2. 2-aminobenzo[d]thiazole-6-carbaldehyde: 1H NMR (500 MHz, CDCl3): delta 9.81 (s, 1H), 8.01 (d, J=1.5 Hz, 1H), 7.70 (dd, J=8.2, 1.5 Hz, 1H), 7.42 (d, J=8.5 Hz, 1H), 3.70 (br s, 1H). 13C NMR (125 MHz, CDCl3): delta 191.3, 164.5, 157.1, 130.3, 128.7, 122.6, 118.0

52%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 4h;	Commercially available ester 1 (1.0g, 4.5mmol) was dissolved in anhydrous THF and the RB flask was cooled to 0C. Then LiAlH4 was added slowly and the flask was stirred at 0C for additional 10min. The flask was then stirred at room temperature for 24h. The reaction was then cooled, quenched with methanol, NH4Cl Rochelle's salt and diluted with ethyl acetate (10ml). The organic layer was separated and the aqueous layer was extracted with additional ethyl acetate (3×10ml). The organic layers were combined, dried over Na2SO4 and concentrated under vacuo on a rotary evaporator to obtain a yellow solid. The crude product was purified via gradient silica gel column chromatography using a mixture of CH2Cl2 and methanol (100:1 to 5:1) to obtain the desired alcohol as yellow solid 2 (420mg, 52%). (0009) 1H NMR (500MHz, CDCl3): delta 7.57 (d, J=0.9Hz, 1H), 7.35-7.46 (m, 1H), 7.25 (dd, J=8.2, 1.8Hz, 1H), 6.45 (br s, 1H), 4.53 (s, 2H), 4.0 (br s, 1H). (0010) 13C NMR (125MHz, CDCl3): delta 167.6, 150.5, 134.9, 130.6, 125.1, 119.4, 117.7, 64.2,.
46%		EXAMPLE l; 6-(4-(4-fluorophenyI)oxazol-5-yl)-N-(2-morpholinoethyl)benzo[d]thiazoI-2-amine; 1. (2-aminobenzo[d]thiazol-6-yl)methanoI[00149]; To a solution of ethyl 2-aminobenzo[d]thiazole-6-carboxylate (5.05 g, 22.7 mmol, 1.0 eq.) in THF (60 mL) under nitrogen at 00C was added LAH (IM, THF; 100 mL, 100 mmol, 4.4 eq.) over 20 min. After 6.5 h, ice was added, and the solution was stirred overnight. The precipitate was filtered and rinsed with EtOAc. The filtrate was concentrated in vacuo to give a solid which was triturated with Et2O to give (2- aminobenzo[d]thiazol-6-yl)methanol as a yellow solid (1.90 g, 46% yield).
25.5 g (63%)	With sodium chloride; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; water; toluene;	(a) 2-Amino-6-hydroxymethylbenzothiazole (1a) 50 g (0.225 mol) of ethyl 2-aminobenzothiazole-6-carboxylate are suspended in 1,000 ml of THF, cooled to -70 C., and 562.5 ml (0.675 mol) of diisobutylaluminum hydride (DIBAL, 20% strength in toluene, 1.2 molar) are slowly added dropwise under nitrogen. The reaction solution is stirred at -70 C. to -40 C. overnight and then without cooling for a further 3 hours. Then it is cooled to -70 C., 61.5 ml of water are added dropwise (vigorous exothermic reaction), and the mixture is allowed to reach room temperature. 305 ml of saturated sodium chloride solution are added, and the mixture is stirred at 20 C. for 1 hour. Precipitated aluminum hydroxide is filtered off with suction and washed with THF, and the filtrate is evaporated to dryness (36 g). The residue is dissolved in boiling ethanol, some insolubles are filtered off, and the filtrate is evaporated to dryness. Yield: 25.5 g (63%).

Reference： [1]Patent: WO2013/43001,2013,A1 .Location in patent: Paragraph 1069; 1070
[2]Patent: US2015/11528,2015,A1 .Location in patent: Paragraph 0601
[3]Patent: US2014/309427,2014,A1 .Location in patent: Paragraph 0149; 0150
[4]European Journal of Pharmacology,2019,vol. 862
[5]Patent: WO2007/16392,2007,A2 .Location in patent: Page/Page column 34; 45
[6]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1874 - 1879
[7]Patent: US4748163,1988,A

2
[ 106429-07-6 ]
[ 106429-08-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With manganese(IV) oxide; In methanol; dichloromethane; at 20℃; for 72h;	The ester (1.0 g, 4.5 mmol) was dissolved in anhydrous THF and the RB flask was cooled to 0 C. Then LiAlH4 was added slowly and the flask was stirred at 0 C. for additional 10 min. The flask was then stirred at room temperature for 24 h. The reaction was then cooled, quenched with methanol, NH4Cl Rochelle's salt and diluted with ethyl acetate (10 mL). The organic layer was separated and the aqueous layer was extracted with additional ethyl acetate (3×10 mL). The organic layers were combined, dried over Na2SO4 and concentrated under vacuo on a rotary evaporator to obtain a yellow solid. The crude product was purified via gradient silica gel column chromatography using a mixture of CH2Cl2 and methanol (100:1 to 5:1) to obtain the desired alcohol as yellow solid (420 mg, 52%). The alcohol (420 mg, 2.33 mmol) was dissolved in a mixture of CH2Cl2 and methanol (5:1) and MnO2 (81 mg, 9.32 mmol). The mixture was then stirred at room temperature for 48 h following which additional amount of MnO2 (40 mg) was added after TLC showed incompletion of the reaction. The mixture was stirred for additional 24 h and then filtered through a whatman filter paper (grade 8) and the filtrate was concentrated under vacuo on a rotary evaporator to obtain the desired aldehyde as a yellow solid (400 mg, 95%). 1H NMR (500 MHz, CDCl3): delta 7.57 (d, J=0.9 Hz, 1H), 7.35-7.46 (m, 1H), 7.25 (dd, J=8.2, 1.8 Hz, 1H), 6.45 (br s, 1H), 4.53 (s, 2H), 4.0 (br s, 1H). 13C NMR (125 MHz, CDCl3): delta 167.6, 150.5, 134.9, 130.6, 125.1, 119.4, 117.7, 64.2. 2-aminobenzo[d]thiazole-6-carbaldehyde: 1H NMR (500 MHz, CDCl3): delta 9.81 (s, 1H), 8.01 (d, J=1.5 Hz, 1H), 7.70 (dd, J=8.2, 1.5 Hz, 1H), 7.42 (d, J=8.5 Hz, 1H), 3.70 (br s, 1H). 13C NMR (125 MHz, CDCl3): delta 191.3, 164.5, 157.1, 130.3, 128.7, 122.6, 118.0
95%	With manganese(IV) oxide; In dichloromethane; at 20℃; for 72h;	The alcohol 2 (420mg, 2.33mmol) was dissolved in a mixture of CH2Cl2 and methanol (5:1) and MnO2 (81mg, 9.32mmol). The mixture was then stirred at room temperature for 48h following which additional amount of MnO2 (40mg) was added after TLC showed incompletion of the reaction. The mixture was stirred for additional 24h and then filtered through a whatman filter paper (grade 8) and the filtrate was concentrated under vacuo on a rotary evaporator to obtain the desired aldehyde as a yellow solid 3 (400mg, 95%). (0012) 1H NMR (500MHz, CDCl3): delta 9.81 (s,1H), 8.01 (d, J=1.5Hz, 1H), 7.70 (dd, J=8.2, 1.5Hz, 1H), 7.42 (d, J=8.5Hz, 1H), 3.70 (br s, 1H). (0013) 13C NMR (125MHz, CDCl3): delta 191.3, 164.5, 157.1, 130.3, 128.7, 122.6, 118.0.
87%	With manganese(IV) oxide; In tetrahydrofuran;	2. 2-aminobenzo[d]thiazole-6-carbaIdehyde[00150]; To a solution of <strong>[106429-07-6](2-aminobenzo[d]thiazol-6-yl)methanol</strong> (1.90 g, 10.5 mmol, 1.0 eq.) in THF (75 mL) under nitrogen was added MnO2 (14 g, 161 mmol, 15.3 eq.). After stirring overnight, the reaction solution was filtered through Celite and rinsed with. THF. The filtrate was concentrated in vacuo to give 2- aminobenzo[d]thiazole-6-carbaldehyde as a yellow solid (1.64 g, 87% yield).

74 g (68%)

In tetrahydrofuran;

(b) 2-Aminobenzothiazole-6-carboxaldehyde (1b) 110.5 g (0.613 mol) of 1a are stirred in 200 ml of THF with 319.8 g (3.678 mol) of manganese (IV) oxide at room temperature for 3 days. The reaction mixture is filtered, the residue on the filter is washed with THF, and the filtrate is evaporated in vacuo. Yield: 74 g (68%). C8 H6 N2 OS (178.1). NMR (DMSO): delta=7.48 (d, J=7.5 Hz, 1H), 7.8 (d, J=7.5 Hz, 1H), 8.08 (s, 2H), 8.26 (s, 1H), 9.92 (s, 1H) ppm.

Reference： [1]Patent: US2014/309427,2014,A1 .Location in patent: Paragraph 0149; 0150
[2]European Journal of Pharmacology,2019,vol. 862
[3]Patent: WO2007/16392,2007,A2 .Location in patent: Page/Page column 34; 45
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1874 - 1879
[5]Patent: US4748163,1988,A

3
[ 106429-07-6 ]
[ 874-60-2 ]
[ 1428621-69-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With dmap; triethylamine; In tetrahydrofuran; at 80℃; for 4h;	[1071] Step 3: N-(6-(hydroxymethyl)benzo[d]thiazol-2(3H)-ylidene)-4-methylbenzamide [1072] To a solution of <strong>[106429-07-6](2-aminobenzo[d]thiazol-6-yl)methanol</strong> (5.34 g, 29.63 mmol) in tetrahydrofuran (300 mL), were added triethylamine (6.16 mL, 44.45 mmol), 4,4-dimethylaminopyridine (362 mg, 2.963 mmol), and p-toluoyl chloride (5.48 mL, 41.48 mmol). The reaction mixture was stirred at 80 ? for 4 hours. A 3N sodium hydroxide solution (20 mL) was added to the reaction mixture, which was then stirred at room temperature overnight. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and then evaporated. Isopropyl ether was added to the resulting residue and then filtered. The resulting solid was dried under reduced pressure to give 4.84 g of the titled compound as a white solid (Yield: 55%).[1073] 1H NMR (DMSO-d6, 400 MHz); 8.02 (d, 2H), 7.89 (s, 1H), 7.71 (d, 1H), 7.36 (m, 3H), 5.34 (brs, 1H), 4.59 (s, 2H), 2.50 (s, 1H), 2.38 (s, 3H)
55%	With dmap; triethylamine; In tetrahydrofuran; at 80℃; for 4h;	Step 3: N-(6-(hydroxymethyl)benzo[d]thiazol-2(3H)-ylidene)-4-methylbenzamide To a solution of <strong>[106429-07-6](2-aminobenzo[d]thiazol-6-yl)methanol</strong> (5.34 g, 29.63 mmol) in tetrahydrofuran (300 mL), were added triethylamine (6.16 mL, 44.45 mmol), 4,4-dimethylaminopyridine (362 mg, 2.963 mmol), and p-toluoyl chloride (5.48 mL, 41.48 mmol). The reaction mixture was stirred at 80 C. for 4 hours. A 3N sodium hydroxide solution (20 mL) was added to the reaction mixture, which was then stirred at room temperature overnight. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and then evaporated. Isopropyl ether was added to the resulting residue and then filtered. The resulting solid was dried under reduced pressure to give 4.84 g of the titled compound as a white solid (Yield: 55%). 1H NMR (DMSO-d6, 400 MHz); 8.02 (d, 2H), 7.89 (s, 1H), 7.71 (d, 1H), 7.36 (m, 3H), 5.34 (brs, 1H), 4.59 (s, 2H), 2.50 (s, 1H), 2.38 (s, 3H)

Reference： [1]Patent: WO2013/43001,2013,A1 .Location in patent: Paragraph 1071; 1072; 1073
[2]Patent: US2015/11528,2015,A1 .Location in patent: Paragraph 0602-0603

4
[ 94-09-7 ]
[ 106429-07-6 ]

Reference： [1]Patent: WO2013/43001,2013,A1
[2]Patent: US2015/11528,2015,A1

5
[ 106429-07-6 ]
[ 1428621-70-8 ]

Reference： [1]Patent: WO2013/43001,2013,A1

6
[ 106429-07-6 ]
[ 1428621-68-4 ]

Reference： [1]Patent: WO2013/43001,2013,A1
[2]Patent: US2015/11528,2015,A1

7
[ 106429-07-6 ]
(2S,4R,5R)-5-(((2-aminobenzo[d]thiazol-6-yl)methyl)amino)-2-(bis(4-fluorophenyl)methyl)tetrahydro-2H-pyran-4-ol [ No CAS ]

Reference： [1]Patent: US2014/309427,2014,A1
[2]European Journal of Pharmacology,2019,vol. 862

8
[ 106429-07-6 ]
(2S,4R,5R)-5-(((2-aminobenzo[d]thiazol-6-yl)methyl)amino)-2-(bis(4-fluorophenyl)methyl)tetrahydro-2H-pyran-4-ol trihydrochloride [ No CAS ]

Reference： [1]European Journal of Pharmacology,2019,vol. 862

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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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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. 106429-07-6 ] {[proInfo.proName]}

Quality Control of [ 106429-07-6 ]

Related Doc. of [ 106429-07-6 ]

Product Details of [ 106429-07-6 ]

Safety of [ 106429-07-6 ]

Application In Synthesis of [ 106429-07-6 ]

[ 106429-07-6 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 106429-07-6 ]

Alcohols

Amines

Related Parent Nucleus of [ 106429-07-6 ]

Benzothiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 106429-07-6 ]

Related Parent Nucleus of
[ 106429-07-6 ]