[ CAS No. 2941-62-0 ] {[proInfo.proName]}

Name: 2941-62-0|2-Methylbenzo[d]thiazol-6-amine|98%
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COA NMR CNMR HPLC LC-MS

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CAS No. :	2941-62-0	MDL No. :	MFCD00160076
Formula :	C₈H₈N₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HFUJOSYKJMNSFQ-UHFFFAOYSA-N
M.W :	164.23	Pubchem ID :	762831
Synonyms :

Safety of [ 2941-62-0 ]

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

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* 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 [ 2941-62-0 ]
Downstream synthetic route of [ 2941-62-0 ]

[ 2941-62-0 ] Synthesis Path-Upstream 1~2

1
[ 2941-62-0 ]
[ 4146-24-1 ]

Reference： [1] Yakugaku Zasshi, 1952, vol. 72, p. 739,742

2
[ 2941-62-0 ]
[ 5304-21-2 ]

Reference： [1] Yakugaku Zasshi, 1957, vol. 77, p. 1161,1163, 1164[2] Chem.Abstr., 1958, p. 6319

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Yield	Reaction Conditions	Operation in experiment
	With acetic acid
	With acetic acid In ethanol at 40℃;	5.4. General method for the synthesis of unsymmetric hydrazines (3b-3g, 3k-3p) [26] General procedure: To a solution of nitrosobenzene (0.5 g, 4.7 mmol) in glacial acetic acid (12 mL) and EtOH (3 mL), the appropriate amine (1.0 equiv) was added. The reaction mixture was stirred at 40 °C for overnight. Then, the mixture was poured into ice water and filtered to afford azobenzene crude product which was directly used for the next step without purification. The crude product was dissolved in a mixture of EtOH (25 mL) and H2O (25 mL), and ammonium chloride (1.26 g, 23.5 mmol, 5.0 equiv) was added at room temperature. Then zinc dust (916 mg, 14.1 mmol, 3.0 equiv) was added gradually. The reaction mixture was stirred at room temperature for overnight and then diluted by adding ethyl acetate and washed with 1M NaCl aqueous solution. Two layers were separated, and the aqueous layer was extracted with ethyl acetate three times. The combined organic layer was dried over MgSO4, filtered, and concentrated on rotary evaporator. The residue was purified by flash column chromatography to give the desired product.

Yield	Reaction Conditions	Operation in experiment
92%	With HCOONH₂ In tetrahydrofuran; methanol at 20℃; for 72h;
92%	With hydrogenchloride; iron In ethanol; water at 90℃; for 0.666667h; Sonication;
86%	With hydrogenchloride; iron In ethanol at 90℃; for 0.333333h; sonification;

83%	With hydrazine hydrate In ethanol for 0.5h; Heating;
80%	With iron(III) chloride; hydrazine hydrate In isopropyl alcohol	Reduction of 2-methyl-6-nitrobenzothiazole 3 with hydrazine hydrate in PriOH in the presence of ‘Norit’ activated carbon and iron trichloride gave amine 4 in 80% yield, mp 123-124 °C. UV (EtOH, λmax/nm): 223, 290. 1H NMR (CDCl3) δ: 2.75 (s, 3 H, Me), 3.78 (br. s,2 H, NH2), 6.78 (dd, 1H, H-5), 7.05 (br. s, 1H, H-7), 7.7 (d, 1H, H-4).
79.2%	With palladium 10% on activated carbon; ammonium formate In tetrahydrofuran; methanol at 20℃; for 60h;
77%	With ammonium formate; zinc In methanol at 20℃;
76%	With hydrogenchloride; tin(ll) chloride In methanol for 0.5h; Heating;
71%	With iron(II,III) oxide hydrate; hydrazine hydrate In tetrahydrofuran; ethanol at 60 - 65℃; for 2h;
56%	With sodium tetrahydroborate; iron(III) trifluoromethanesulfonate; ethanol at 20℃; Inert atmosphere; Green chemistry;
	With hydrogenchloride; tin
	With hydrogenchloride; tin(ll) chloride
	With hydrogenchloride; tin
	With hydrogenchloride; iron In ethanol; water Reflux;
	With hydrogenchloride; iron In ethanol; water for 24h; Reflux;
	With iron; acetic acid
	With water; iron In ethanol for 12h; Reflux;	1.5 5. Synthesis of Intermediate 7 Compound 6 (30mmol), iron powder (2.5g), solid sodium chloride, water (10mL) and ethanol (30mL) were sequentially added to a 100mL dry round-bottomed flask and refluxed for 12h.After hot filtration, the filter cake was washed three times with ethanol, the filtrate was combined, and the solvent was spin-dried to dry the crude product. The crude product was separated by column chromatography (mobile phase) to obtain compound 7.

Yield	Reaction Conditions	Operation in experiment
97%	With sodium carbonate In acetone 1.) 5-8 deg C, 5 min, 2.) 20-22 deg C, 1 h;
	In chloroform; water

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[ 2941-62-0 ] Synthesis Path-Upstream 1~2

[ 2941-62-0 ] Synthesis Path-Downstream 1~88