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Chemical Structure| 622-78-6 Chemical Structure| 622-78-6
Chemical Structure| 622-78-6

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Benzyl Isothiocyanate is a natural isothiocyanate with significant antibacterial and anticancer activity. It effectively inhibits the migration and invasion of cancer cells and also has some effects against bacterial infections.

Synonyms: Benzoylthiocarbimide; Isothiocyanic Acid Benzoyl Ester; Tromacaps

4.5 *For Research Use Only !

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Product Details of Benzyl isothiocyanate

CAS No. :622-78-6
Formula : C8H7NS
M.W : 149.21
SMILES Code : S=C=NCC1=CC=CC=C1
Synonyms :
Benzoylthiocarbimide; Isothiocyanic Acid Benzoyl Ester; Tromacaps
MDL No. :MFCD00004819
InChI Key :MDKCFLQDBWCQCV-UHFFFAOYSA-N
Pubchem ID :2346

Safety of Benzyl isothiocyanate

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H312-H332-H315-H319-H334-H335
Precautionary Statements:P280-P301+P312-P330-P302+P352-P312-P305+P351+P338
Class:6.1
UN#:2810
Packing Group:

Application In Synthesis of Benzyl isothiocyanate

* 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 [ 622-78-6 ]

[ 622-78-6 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 14779-17-0 ]
  • [ 622-78-6 ]
  • [ 5923-83-1 ]
  • 2
  • [ 926-39-6 ]
  • [ 622-78-6 ]
  • [ 5777-55-9 ]
  • 3
  • [ 30065-27-1 ]
  • [ 622-78-6 ]
  • C17H17N5OS2 [ No CAS ]
  • 4
  • [ 622-78-6 ]
  • [ 88088-95-3 ]
  • [ 130749-26-7 ]
  • 5
  • [ 39796-52-6 ]
  • [ 622-78-6 ]
  • N-1-benzyl-2-[(benzylamino)carbothioyl]aminoacetamide [ No CAS ]
  • 6
  • [ 63746-12-3 ]
  • [ 622-78-6 ]
  • 3-benzyl-6-(methoxycarbonyl)-2-thioxo-l,2,3,4-tetrahydroquinazolin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine;Heating / reflux; In Scheme 28, methyl [4-AMINOISOPHTHALATE] (2a) is treated with benzyl isothiocyanate, in a solvent such as pyridine or acetic acid, to give 3-benzyl-6- [(METHOXYCARBONYL)-2-THIOXO-1,] 2,3, 4-tetrahydroquinazolin-4-one (2b). This compound is heated, in a refluxing alcohol, in the presence of hydrazine hydrate to give the corresponding hydrazine which is in turn cyclized by reaction with a carboxylic acid derivative RCOOH (such as an acid chloride or an ortho ester). The 4-benzyl-7- (methoxycarbonyl)-4, 5-dihydrotriazolo [4,3-a] quinazolin-5-one (2d) obtained is N4-debenzylated using aluminum chloride in benzene, and the intermediate secondary lactam is then substituted with a halide, in the presence of a base such as cesium carbonate, in a solvent such as dimethylformamide. The N- substituted analogue obtained [(2F)] is then hydrolyzed, preferably in acidic medium, to give the corresponding acid (2g) which may be subsequently subjected to a coupling reaction of peptide type. The order of the steps in the above process may be modified for the synthesis of certain compounds. For example, when R2 is [PARA-CYANOBENZYL,] step 5 will be carried out last since the para-cyanobenzyl group would not withstand the conditions of step 6.
  • 7
  • 4-benzyl-3-hydroxy-5-mercapto-1,2,4-triazole [ No CAS ]
  • [ 13431-41-9 ]
  • [ 541-41-3 ]
  • [ 622-78-6 ]
  • [ 3034-48-8 ]
  • 4-benzyl-3-hydroxy-5-[(5-nitrothien-2-yl)mercapto]1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 7 4-benzyl-3-hydroxy-5-[(5-nitrothien-2-yl)mercapto]1,2,4-triazole (Compound 9) The title compound was prepared in a manner similar to that described in Example 5 starting with benzyl isothiocyanate. The intermediate 4-benzyl-3-thiosemicarbazide (1.81 g) was treated with ethyl chloroformate (1.09 g) as in Example 5. The reaction product 4-benzyl-3-hydroxy-5-mercapto-1,2,4-triazole (1.04 g) was reacted with 1.05 g of <strong>[3034-48-8]<strong>[3034-48-8]2-bromo-5-nitrothiazol</strong>e</strong> as in Example 5. Crystallization from ethanol and water gave 0.3 g of 4-benzyl-3-hydroxy-5-[(5-nitrothien-2-yl)mercapto]1,2,4-triazole, a yellow solid, MP 221°-224° C.
Example 7 4-benzyl-3-hydroxy-5-[(5-nitrothien-2-yl)mercapto]1,2,4-triazole (Compound 7) The title compound was prepared in a manner similar to that described in Example 5 starting with benzyl isothiocyanate. The intermediate 4-benzyl-3-thiosemicarbazide (1.81 g) was treated with ethyl chloroformate (1.09 g) as in Example 5. The reaction product 4-benzyl-3-hydroxy-5-mercapto-1,2,4-triazole (1.04 g) was reacted with 1.05 g of <strong>[3034-48-8]<strong>[3034-48-8]2-bromo-5-nitrothiazol</strong>e</strong> as in Example 5. Crystallization from ethanol and water gave 0.3 g of 4-benzyl-3-hydroxy-5-[(5-nitrothien-2-yl)mercapto]1,2,4-triazole, a yellow solid, MP 221-224° C.
  • 8
  • [ 622-78-6 ]
  • [ 53760-27-3 ]
  • [ 162781-26-2 ]
YieldReaction ConditionsOperation in experiment
39.0% With sodium hydroxide; In water; 4,4'-di(benzylthiocarbamoylamino)diphenylamine 4,4'-Diaminodiphenylamine sulfate (1.486 g, 5 mM) was dissolved in 100 ml of water, sodium hydroxide (0.40 g, 10 mM) was added and stirred, and extracted with 150 ml of ethyl acetate. The resulting ethyl acetate solution was thoroughly washed with water, dewatered, and vacuum concentrated to about 20 ml. Precipitated insoluble substances were filtered out, and 2 equivalents of benzylisothiocyanate (1.492 g, 10 mM) were added to the filtrate. The mixture was stirred at 80 C. for 30 minutes, after cooling, the reaction mixture was filtered, and washed with ethyl acetate/n-hexane to obtain 0.97 g (39.0% yield) of a pale pink crystal of compound A-21. Melting point: 179 C. 1 H-NMR (DMSO-d6) ppm delta=4.72 (4H, d, J=5.6, phi-CH2 -- x 2) delta=7.01-7.33 (18H, m, --C6 H4 -- x 2, C6 H5 -- x 2) delta=7.93 (2H, broad s, --CH2 NH-- x 2) delta=8.20 (1H, broad s, --NH--) delta=9.42 (2H, s, --NH-- x 2)
  • 9
  • 4-benzyl-3-hydroxy-5-mercapto-1,2,4-triazole [ No CAS ]
  • [ 13431-41-9 ]
  • [ 541-41-3 ]
  • [ 622-78-6 ]
  • [ 3034-48-8 ]
  • [ 186371-14-2 ]
YieldReaction ConditionsOperation in experiment
Example 7 4-benzyl-3-hydroxy-5-[(5-nitrothiazol-2-yl)mercapto]1,2,4-triazole (Compound 9) The title compound was prepared in a manner similar to that described in Example 5 starting with benzyl isothiocyanate. The intermediate 4-benzyl-3-thiosemicarbazide (1.81 g) was treated with ethyl chloroformate (1.09 g) as in Example 5. The reaction product 4-benzyl-3-hydroxy-5-mercapto-1,2,4-triazole (1.04 g) was reacted with 1.05 g of <strong>[3034-48-8]<strong>[3034-48-8]2-bromo-5-nitrothiazol</strong>e</strong> as in Example 5. Crystallization from ethanol and water gave 0.3 g of 4-benzyl-3-hydroxy-5-[(5-nitrothiazol-2-yl)mercapto]1,2,4-triazole, a yellow solid, MP 221°-224° C.
  • 10
  • [ 6761-52-0 ]
  • [ 622-78-6 ]
  • [ 1402083-77-5 ]
  • 11
  • [ 7210-76-6 ]
  • [ 622-78-6 ]
  • [ 1585956-65-5 ]
YieldReaction ConditionsOperation in experiment
60% With pyridine;Reflux; General procedure: To a solution of the thiazole 1 (0.93 g, 5 mmol) in pyridine (10 mL) was added the appropriate isothiocyanate (6 mmol). The reaction mixture was heated under reflux for 5-6 h then allowed to attain room temperature. Working up of the reaction mixture was carried out as described under 9a,b. Physicochemical and analytical data are recorded in Table 3. IR (cm-1): 3470-2935 (NH), 1730- 1718 (C=O), 982-958 (NCS).
  • 12
  • [ 538-28-3 ]
  • [ 622-78-6 ]
  • benzyl N-(benzylcarbamothioyl)carbamimidothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; In acetonitrile; at 20℃; for 16h; To a suspension of <strong>[538-28-3]S-benzylisothiourea hydrochloride</strong> (3 mmol) in acetonitrile were added benzyl isothiocyanate (3 mmol) and triethylamine (6.6 mmol), and stirred for 16 h at room temperature. The reaction mixture was concentrated under reduced pressure. Water was added to the crude mixture, and extracted with ethyl acetate. The combined organic layer was dried over MgSO4 and filtered. After removal of the solvent in vacuum, the residue was purified by column chromatography to afford the product (871 mg, 92percent).
  • 13
  • [ 20876-36-2 ]
  • [ 622-78-6 ]
  • 1-benzyl-3-(2-oxoindolin-5-yl)thiourea [ No CAS ]
  • 14
  • [ 622-78-6 ]
  • [ 27018-76-4 ]
  • C23H20N2O [ No CAS ]
 

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