[ CAS No. 20061-46-5 ] {[proInfo.proName]}

Name: 20061-46-5|2-Methyl-5-benzothiazolecarboxaldehyde|98%
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Quality Control of [ 20061-46-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 20061-46-5 ]

Product Details of [ 20061-46-5 ]

CAS No. :	20061-46-5	MDL No. :	MFCD02690143
Formula :	C₉H₇NOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PONNYPGVGULWMI-UHFFFAOYSA-N
M.W :	177.22	Pubchem ID :	2308820
Synonyms :

Safety of [ 20061-46-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 20061-46-5 ]

* 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 [ 20061-46-5 ]
Downstream synthetic route of [ 20061-46-5 ]

[ 20061-46-5 ] Synthesis Path-Upstream 1~12

1
[ 20061-46-5 ]
[ 24851-69-2 ]

Reference： [1] Patent: EP1445249, 2004, A1, . Location in patent: Page 132

2
[ 32770-97-1 ]
[ 20061-46-5 ]

Yield	Reaction Conditions	Operation in experiment
0.65 g	With sodium hydrogencarbonate; Dess-Martin periodane In dichloromethane at 20℃; for 2 h;	To a stirred solution of (2-methylbenzo[d]thiazol-5-yl)methanol (0.6 g, 3.35 mmol) in dry DCM (6 mL), NaHCO₃ (1.12 g, 13.4 mmol) followed by Dess-Martin periodinane (2.84 g, 6.70 mmol) were added and the reaction mixture was stirred at rt for 2 h. It was diluted with DCM (50 mL) and washed with water (15 mL), 10percent NaHCO₃ solution (15 mL), brine (15 mL) and dried over Na₂SO₄.The title product was obtained after evaporation of the solvents. Yield: 99percent (0.65 g, brown liquid). ¹ H NMR (400 MHz, DMSO-d₆): δ 10.12 (s, 1H), 8.25(s, 1H), 7.80-7.79 (m, 2H), 2.86 (s, 3H). LCMS: (Method A) 178.0 (M+H), Rt. 2.84 min, 81.57percent (Max).

Reference： [1] Angewandte Chemie - International Edition, 2006, vol. 45, # 47, p. 7942 - 7948
[2] J. Gen. Chem. USSR (Engl. Transl.), 1964, vol. 34, p. 3852 - 3856[3] Zhurnal Obshchei Khimii, 1964, vol. 34, p. 3801 - 3806
[4] Synthetic Communications, 2002, vol. 32, # 11, p. 1647 - 1652
[5] Patent: WO2016/30443, 2016, A1, . Location in patent: Page/Page column 98

3
[ 95-26-1 ]
[ 20061-46-5 ]

Reference： [1] Patent: EP2261221, 2010, A1, . Location in patent: Page/Page column 26

4
[ 125872-96-0 ]
[ 20061-46-5 ]

Reference： [1] Patent: US2011/112149, 2011, A1, . Location in patent: Page/Page column 21-22

5
[ 24851-69-2 ]
[ 20061-46-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2006, vol. 45, # 47, p. 7942 - 7948
[2] Patent: WO2016/30443, 2016, A1,
[3] Patent: WO2017/31325, 2017, A1,

6
[ 96-99-1 ]
[ 20061-46-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2006, vol. 45, # 47, p. 7942 - 7948
[2] Synthetic Communications, 2002, vol. 32, # 11, p. 1647 - 1652
[3] Patent: WO2016/30443, 2016, A1,

7
[ 646-06-0 ]
[ 1006-99-1 ]
[ 20061-46-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 25, p. 7191 - 7194[2] Angew. Chem., 2017, vol. 129, # 25, p. 7297 - 7300,4

8
[ 32770-98-2 ]
[ 20061-46-5 ]

Reference： [1] Synthetic Communications, 2002, vol. 32, # 11, p. 1647 - 1652

9
[ 35350-37-9 ]
[ 20061-46-5 ]

Reference： [1] Synthetic Communications, 2002, vol. 32, # 11, p. 1647 - 1652

10
[ 74-11-3 ]
[ 20061-46-5 ]

Reference： [1] Synthetic Communications, 2002, vol. 32, # 11, p. 1647 - 1652

11
[ 1006-99-1 ]
[ 20061-46-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 25, p. 7191 - 7194[2] Angew. Chem., 2017, vol. 129, # 25, p. 7297 - 7300,4

12
[ 20061-46-5 ]
[ 924727-12-8 ]
[ 16251-45-9 ]

Reference： [1] Angewandte Chemie - International Edition, 2006, vol. 45, # 47, p. 7942 - 7948

[ 20061-46-5 ] Synthesis Path-Downstream 1~7

1
[ 32770-97-1 ]
[ 20061-46-5 ]

Yield	Reaction Conditions	Operation in experiment
94.7%	With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine In dichloromethane at 23℃; for 2h;
	With chromium(VI) oxide In acetic acid Heating;
	With pyridinium chlorochromate

0.65 g

With sodium hydrogencarbonate; Dess-Martin periodane In dichloromethane at 20℃; for 2h;

26.3 Step 3: 2-methylbenzo[d]thiazole-5-carbaldehyde To a stirred solution of (2-methylbenzo[d]thiazol-5-yl)methanol (0.6 g, 3.35 mmol) in dry DCM (6 mL), NaHCO3 (1.12 g, 13.4 mmol) followed by Dess-Martin periodinane (2.84 g, 6.70 mmol) were added and the reaction mixture was stirred at rt for 2 h. It was diluted with DCM (50 mL) and washed with water (15 mL), 10% NaHCO3 solution (15 mL), brine (15 mL) and dried over Na2SO4.The title product was obtained after evaporation of the solvents. Yield: 99% (0.65 g, brown liquid). 1 H NMR (400 MHz, DMSO-d6): δ 10.12 (s, 1H), 8.25(s, 1H), 7.80-7.79 (m, 2H), 2.86 (s, 3H). LCMS: (Method A) 178.0 (M+H), Rt. 2.84 min, 81.57% (Max).

Reference： [1]Klar, Ulrich; Buchmann, Bernd; Schwede, Wolfgang; Skuballa, Werner; Hoffmann, Jens; Lichtner, Rosemarie B. [Angewandte Chemie - International Edition, 2006, vol. 45, # 47, p. 7942 - 7948]
[2]Zubarovskii,V.M.; Khodot,G.P. [Journal of general chemistry of the USSR, 1964, vol. 34, p. 3852 - 3856][Zhurnal Obshchei Khimii, 1964, vol. 34, p. 3801 - 3806]
[3]Xu, Ju-Hua; Li, Yu-Liang; Zhu, Dao-Ben [Synthetic Communications, 2002, vol. 32, # 11, p. 1647 - 1652]
[4]Current Patent Assignee: ASCENEURON SA - WO2016/30443, 2016, A1 Location in patent: Page/Page column 98

2
(4S,5R)-4-methyl-5-phenyl-3-acetyl-2-oxazolidinone [ No CAS ]
[ 20061-46-5 ]
[ 924727-12-8 ]
(4S,5R,3'R)-4-methyl-5-phenyl-3-[3'-(2-methylbenzothiazol-5-yl)-3'-hydroxy-2'-oxopropyl]-2-oxazolidinone [ No CAS ]
[ 16251-45-9 ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 7942 - 7948

3
[ 24851-69-2 ]
[ 20061-46-5 ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 7942 - 7948
[2]Patent: WO2016/30443,2016,A1
[3]Patent: WO2017/31325,2017,A1

4
[ 96-99-1 ]
[ 20061-46-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: Na₂S / 0.33 h / Heating 1.2: 77.6 percent / acetic acid / 0.33 h / Heating 2.1: lithium aluminum hydride / tetrahydrofuran / 2 h / Heating 3.1: 94.7 percent / SO₃*pyridine; DMSO; triethylamine / CH₂Cl₂ / 2 h / 23 °C
	Multi-step reaction with 5 steps 1: Na₂S₂ 2: zinc / acetic acid 3: lithium aluminum hydride / diethyl ether / -40 °C 4: pyridinium chlorochromate
	Multi-step reaction with 3 steps 1.1: sodium sulfide / 0.33 h / Reflux 1.2: 0.33 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

Reference： [1]Klar, Ulrich; Buchmann, Bernd; Schwede, Wolfgang; Skuballa, Werner; Hoffmann, Jens; Lichtner, Rosemarie B. [Angewandte Chemie - International Edition, 2006, vol. 45, # 47, p. 7942 - 7948]
[2]Xu, Ju-Hua; Li, Yu-Liang; Zhu, Dao-Ben [Synthetic Communications, 2002, vol. 32, # 11, p. 1647 - 1652]
[3]Current Patent Assignee: ASCENEURON SA - WO2016/30443, 2016, A1

5
[ 32770-98-2 ]
[ 20061-46-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminum hydride / diethyl ether / -40 °C 2: pyridinium chlorochromate

Reference： [1]Xu, Ju-Hua; Li, Yu-Liang; Zhu, Dao-Ben [Synthetic Communications, 2002, vol. 32, # 11, p. 1647 - 1652]

6
[ 20061-46-5 ]
[ 24851-69-2 ]

Yield	Reaction Conditions	Operation in experiment
		3.83 g of silver nitrate was dissolved in 10 ML of water, to which a solution of 1.81 g of sodium hydroxide in 10 ML of water was added dropwise and then a solution of 2.00 g of 2-methyl-1,3-benzothiazole-5-carbaldehyde in 20 ML of tetrahydrofuran was added dropwise at room temperature, and this solution was stirred for 30 minutes at the same temperature.. The reaction mixture was filtered through Celite, and 6M hydrochloric acid was added to the filtrate to adjust its PH value to 3.5 followed by addition of ethyl acetate, and then the organic phase was separated therefrom.. After the resultant organic phase was washed with a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure.. The resultant residue was dissolved in 30 ML of methylene chloride, to which 20 muL of N,N-dimethylformamide and 1.5 ML of oxalyl chloride were added successively, and this solution was stirred for 30 minutes at room temperature.. The reaction mixture, to which 20 ML of methanol was added dropwise, was stirred for 30 minutes at room temperature, and after water was added thereto, the PH value of this mixture was adjusted to 7 with a 5M solution of sodium hydroxide in water, and then the organic phase was separated therefrom.. After the resultant organic phase was washed with a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 1.90 g of methyl 2-methyl-1,3-benzothiazole-5-carboxylate as light yellow solid. NMR(400MHz,CDCl3) delta value: 2.87(3H,s), 3.97(3H,s), 7.88(1H,d,J=8.4Hz), 8.03(1H,dd,J=8.4,1.6Hz), 8.61(1H,d,J=1.6Hz)

Reference： [1]Patent: EP1445249,2004,A1 .Location in patent: Page 132

7
[ 646-06-0 ]
[ 1006-99-1 ]
5-(1,3-dioxolan-4-yl)-2-methylbenzo[d]thiazole [ No CAS ]
[ 20061-46-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: 1,3-DIOXOLANE; 2-methyl-5-chloro-benzothiazole With potassium phosphate; (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine for 0.166667h; Glovebox; Stage #2: With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate at 23℃; for 72h; Sealed tube; Irradiation; Stage #3: With hydrogenchloride In water; acetone at 23℃;

Reference： [1]Nielsen, Matthew K.; Shields, Benjamin J.; Liu, Junyi; Williams, Michael J.; Zacuto, Michael J.; Doyle, Abigail G. [Angewandte Chemie - International Edition, 2017, vol. 56, # 25, p. 7191 - 7194][Angew. Chem., 2017, vol. 129, # 25, p. 7297 - 7300]

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[ 20061-46-5 ]

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[ CAS No. 20061-46-5 ] {[proInfo.proName]}

Quality Control of [ 20061-46-5 ]

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Application In Synthesis of [ 20061-46-5 ]

[ 20061-46-5 ] Synthesis Path-Upstream 1~12

[ 20061-46-5 ] Synthesis Path-Downstream 1~7

Related Functional Groups of [ 20061-46-5 ]

Aldehydes

Related Parent Nucleus of [ 20061-46-5 ]

Benzothiazoles

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Inquiry

Related Functional Groups of
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Related Parent Nucleus of
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