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Chemical Structure| 769960-94-3 Chemical Structure| 769960-94-3

Structure of 769960-94-3

Chemical Structure| 769960-94-3

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Product Details of [ 769960-94-3 ]

CAS No. :769960-94-3
Formula : C10H6N2S
M.W : 186.23
SMILES Code : S=C=NC1=CC2=C(C=CC=C2)C=N1
MDL No. :MFCD22557460
InChI Key :UGMQFWDSELPKKP-UHFFFAOYSA-N
Pubchem ID :57476565

Safety of [ 769960-94-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H317-H319-H330-H334-H335-H351-H412
Precautionary Statements:P201-P202-P260-P264-P271-P272-P273-P280-P284-P302+P352-P304+P340+P310-P305+P351+P338-P308+P313-P333+P313-P337+P313-P403+P233-P405-P501
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 769960-94-3 ]

* 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 [ 769960-94-3 ]

[ 769960-94-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 25475-67-6 ]
  • [ 6160-65-2 ]
  • [ 769960-94-3 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; N,N-dimethyl-formamide; at 65 - 70℃; for 1h; General Procedure A: Preparation of isothiocyanate 1,1 '-thiocarbonylimidazole (1.1 mmol) was added to a solution of amine (1 mmol) inTHF/DMF (2 mL, 1:1) and the reaction mixture was stirred at 65-70 0C for 1 h. The product thus formed, was used for further transformation without isolation.; Example 1; Synthesis of 2-(Isoquinolin-3-ylamino)-lH-benzimidazole-5-carboxylic acid benzothiazol-6- ylamide3-Isothiocyanatoisoquinoline was prepared from <strong>[25475-67-6]3-aminoisoquinoline</strong> (5 mmol) as described in general procedure A.The isothiocyanate from above was reacted with methyl 3,4-diaminobenzoate (5mmol) followed by cyclization using EDC as described in general procedure B to obtain 2- (Isoquinolin-3-ylamino)-lH-benzimidazole-5-carboxylic acid methyl ester. The ester was hydrolyzed to yield the corresponding carboxylic acid employing general procedure C. Benzothiazol-6-ylamine (0.25 mmol) was coupled with aforementioned carboxylic acid using HBTU employing general procedure D to provide 2-(Isoquinolm-3-ylammo)-lH- benzimidazole-5-carboxylic acid benzothiazol-6-ylamide. MS: m/z 437 (M+H)+.
  • 2
  • [ 25475-67-6 ]
  • [ 102368-13-8 ]
  • [ 769960-94-3 ]
YieldReaction ConditionsOperation in experiment
93% In dichloromethane; at 20℃; for 2h; Isoquinolin-3-amine (3.23 g, 22.4 mmol) was added to a solution of 1,1'-thiocarbonyldipyridin-2(1H)-one (5.20 g, 22.4 mmol) in dichloromethane (50 mL) at room temperature. The reaction was stirred for 2 h, then purified by flash chromatography on silica gel (0-10percent ethyl acetate in hexanes). Product fractions were combined and concentrated in vacuo to give 3-isothiocyanatoisoquinoline(3.9 g, 93 percent) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 9.12 (1 H, s), 8.00 (1 H, d, J=8.06 Hz), 7.69 - 7.85 (2 H, m), 7.58 - 7.68 (1 H, m), 7.50 (1 H, s). LCMS (method F) tR, 2.47 min, MH+ = 187.23
85% In dichloromethane; at 20℃; for 18h; Step A: 3-Isothiocyanatoisoquinoline To a solution of 1,1'-thiocarbonyldipyridin-2(1H)-one (0.805 g, 3.47 mmol) in dichloromethane at room temperature was added <strong>[25475-67-6]isoquinolin-3-amine</strong> (0.5 g, 3.47 mmol). The reaction was stirred at room temperature for 18 hours. The LC/MS showed the desired product peak a major peak. The deep orange solution was concentrated and filtered. The filtrate was purified by silica gel chromatography (0-40percent ethyl acetate-hexanes) to afford 4-isothiocyanato-6-(3-methoxyphenyl)pyrimidine (0.55 g, 2.96 mmol, 85percent yield) a white solid. LCMS R.T.=2.47; [M+H]+=187.23.
85% In dichloromethane; at 20℃; for 18h; EXAMPLE 4; (5S*,5'R*)-N-(isoquinolin~3-yl)-4^1-azaspiro[bicyclo[3.2 ]oamine; Step A: 3-Isothiocyanatoisoquinoline; To a solution of 1 , 1 '-thiocarbonyldipyridm-2(l H)-one (0.805 g, 3.47 mmol) in dichloromethane at room temperature was added <strong>[25475-67-6]isoquinolin-3-amine</strong> (0.5 g, 3.47 mmol). The reaction was stirred at room temperature for 18 hours. The LC/MS showed the desired product peak a major peak. The deep orange solution was concentrated and filtered. The filtrate was purified by silica gel cliromatography (0- 40percent ethyl acetate-hexanes) to afford 4-isothiocyanato-6-(3- methoxyphenyl)pyrimidine (0.55 g, 2.96 mmol, 85 percent yield) a white solid. LCMS R.T. - 2.47; [M+H]+ = 187.23.
85% In dichloromethane; at 20℃; for 18h; Step A: 3-IsothiocyanatoisoquinolineTo a solution of l, l'-thiocarbonyldipyridin-2(lH)-one (0.805 g, 3.47 mmol) in dichloromethane at room temperature was added isoquinolin-3 -amine (0.5 g, 3.47 mmol). The reaction was stirred at room temperature for 18 hours. The LC/MS showed the desired product peak a major peak. The deep orange solution was concentrated and filtered. The filtrate was purified by silica gel chromatography (0- 40percent ethyl acetate-hexanes) to afford 4-isothiocyanato-6-(3- methoxyphenyl)pyrimidine (0.55 g, 2.96 mmol, 85 percent yield) a white solid. LCMS R.T. = 2.47; [M+H]+ = 187.23.
85% In dichloromethane; at 20℃; for 18h; To a solution of 1,1'-thiocarbonyldipyridin-2(lH)one(0.805 g, 3.47 mmol) in dichloromethane at room temperature was added <strong>[25475-67-6]isoquinolin-3-amine</strong> (0.5 g, 3.47 mmol).The reaction was stirred at room temperature for 18 hours.The LC/MS showed the desired product peak a major peak.The deep orange solution was concentrated and filtered. Thefiltrate was purified by silica gel chromatography (0-40percentethyl acetate-hexanes) to afford 4-isothiocyanato-6-(3-methoxyphenyl)pyrimidine (0.55 g, 2.96 mmol, 85percent yield) a white solid.
In dichloromethane; at 20℃; for 18h; EXAMPLES 7, 7a, 7b; (3R*,4R*)-N-(Isoquinolin-3-yl)-4'H-l-azaspiro[bicyclo[2.2.1]heptane-3,5'-oxazol]-2' -amine; Step A: 3-Isothiocyanatoisoquinoli; To a solution of l,l'-thiocarbonyldipyridin-2(lH)-one (0.805 g, 3.47 mmol) in dichloromethane at room temperature was added isoquinolin-3 -amine (0.5 g, 3.47 mmol). The reaction was stirred at room temperature for 18 hours. The LC/MS showed the desired product peak a major peak. The deep orange solution was concentrated and filtered. The filtrate was purified by silica gel chromatography (0- 40percent ethyl acetate-hexanes) to afford 4-isothiocyanato-6-(3- methoxyphenyl)pyrimidine (0.55 g, 2.96 mmol, 85 percent yield) a white solid. LCMS R.T. = 2.47; [M+H]+ = 187.23.

  • 3
  • [ 25475-67-6 ]
  • [ 463-71-8 ]
  • [ 769960-94-3 ]
YieldReaction ConditionsOperation in experiment
62% In water; at 0 - 20℃; for 0.75h; [0069] To a mixture of <strong>[25475-67-6]isoquinolin-3-amine</strong> (0.2 g, 1.38 mmol) in water (5 mL) was added CSCl2 (0.1 mL, 1.52 mmol) slowly for a period of 5 min at 0° C., and the mixture was stirred for 40 min at rt. The reaction mixture was diluted with water and extracted with ether (2×50 mL). The combined ether layer was dried over Na2SO4 and concentrated under reduced pressure to give 0.158 g (62percent yield) of the titled compound which was used in the next step without further purification. [0070] 1H-NMR (400 MHz, DMSO-d6) delta (ppm) 7.73 (t, 1H, J=7.5 Hz), 7.85 (t, 1H, J=7.56 Hz), 7.90 (s, 1H), 7.99 (d, 1H, J=8.24 Hz), 8.19 (t, 1H, J=8.12 Hz), 9.26 (s, 1H).
 

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