592-82-5

Basic information

• Product Name: BUTYL ISOTHIOCYANATE
• Synonyms: Butane, 1-isothiocyanato-;BUTYL ISOTHIOCYANATE(RG);butyl isorhodanate;butyl isorhodanide;butyl isosulfocyanate;butyl isosulfocyanide;butyl isthiocyanide;BUTYLBORONICACID
• CAS NO: 592-82-5
• Molecular Formula: C₅H₉NS
• Molecular Weight: 115.2
• EINECS: 209-770-4
• Product Categories: Organics;Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates
• Mol File: 592-82-5.mol
• Article Data: 41

Chemical Properties

• Melting Point: 115 °C
• Boiling Point: 70-71 °C35 mm Hg(lit.)
• Flash Point: 66 °C
• Appearance: /
• Density: 0.955 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.19mmHg at 25°C
• Refractive Index: n20/D 1.5(lit.)
• Water Solubility: Insoluble in water.
• Sensitive: Moisture Sensitive
• BRN: 906839
• CAS DataBase Reference: BUTYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: BUTYL ISOTHIOCYANATE(592-82-5)
• EPA Substance Registry System: BUTYL ISOTHIOCYANATE(592-82-5)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34-42
• Safety Statements: 23-26-36/37-39-45
• RIDADR: UN 1693 6.1/PG 2
• WGK Germany: 3
• RTECS: NX8420500
• F: 3-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 592-82-5(Hazardous Substances Data)

Usage

Description

BUTYL ISOTHIOCYANATE is an isothiocyanate compound with a butyl group attached to the nitrogen. It is a clear, colorless to yellow liquid with a strong irritating green aroma. It is a natural product found in various plants, such as Capparis spinosa, Brassica carinata, and Eutrema japonicum. It has a role as a hapten and is known for its horseradish and vegetative cabbage-like taste with rooty, wasabi, radish-like notes, and a biting and metallic aftertaste.

Uses

Used in Chemical Synthesis:
BUTYL ISOTHIOCYANATE is used as a reagent in the synthesis and characterization of various compounds, such as Poly(N-Propargylthiourea) and 2-Aminobenzothiazoles. It is also used in the synthesis process via Copper (I)-Catalyzed Cross-Coupling with part-per-million catalyst loadings.
Used in Aquatic Toxicity and Reactivity Studies:
BUTYL ISOTHIOCYANATE is utilized in the TETRATOX assay for aquatic toxicity data and in abiotic thiol assays for reactivity data. These studies help understand the compound's impact on aquatic life and its potential interactions with other chemicals.
Used in Molecular Switch Immobilization:
BUTYL ISOTHIOCYANATE has been used as a capping reagent to immobilize the functionalized derivative of Oregon Green 514, a molecular switch, on a preformed amino self-assembled monolayer. This application is significant in the field of molecular electronics and sensing.
Used in Flavor and Fragrance Industry:
BUTYL ISOTHIOCYANATE is used as a flavoring agent for its slightly pungent, rooty mustard, horseradish, and wasabi-like aroma with sulfurous onion and garlic notes and a tropical nuance. It is also used in the fragrance industry for its strong and distinctive scent.
Used in Agricultural Industry:
As the main component of the volatile oil of Capparis spinosa, BUTYL ISOTHIOCYANATE is used in the agricultural industry for its natural pest repellent properties, helping to protect crops from pests and diseases.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 1970, 1974 DOI: 10.1021/jo00927a049

InChI:InChI=1/C5H9NS/c1-2-3-4-6-5-7/h2-4H2,1H3

Upstream product

• 56134-96-4 ethyl butyldithiocarbamate 
• 75-15-0 carbon disulfide 
• 109-73-9 N-butylamine 
• 60448-30-8 N-butylthioformamide 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 103-72-0 phenyl isothiocyanate 
• 22296-07-7 C₅H₁₀NS₂^(1-) 
• 109-65-9 1-bromo-butane 
• 333-20-0 potassium thioacyanate 
• 51034-33-4 N-n-butyl dithiocarbamic acid Potassium Salt 
• 85600-01-7 N'-butyl-N,N-dimethylacetimidamide 
• 144446-80-0 C₅H₁₁NS₂*C₆H₁₅N 
• 18879-99-7 N-butyldithiocarbamic acid 
• 4669-59-4 bis(diethylamino)dimethylsilane 

Downstream Products

• 91194-23-9 N-butyl-N'-(4-sulfamoyl-phenyl)-thiourea 
• 77523-94-5 N-benzimidazol-2-ylmethyl-N'-n-butyl-thiourea 
• 13906-07-5 3-butyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one 
• 69180-86-5 1-{4-[(butyl-thiocarbamoyl)-sulfamoyl]-phenyl}-5-methyl-1H-pyrazole-3-carboxylic acid 
• 88290-02-2 C₃₂H₃₄N₄O₅S₂ 
• 79491-02-4 1-phenyl-5-butyl-2,4-dithiobiuret 
• 78794-37-3 C₂₁H₂₄N₄O₂S₂ 
• 1792-17-2 N,N'-di-n-butylurea 
• 693-64-1 N,N'-di-n-butylcarbodiimide 
• 108168-84-9 4-n-butyl-5-(n-butylimino)-1,2,4-ditjiazolidine-3-one 
• 108168-85-0 2,4-dibutyl-1,2,4-thiadiazolidine-3-thione-5-one 
• 2769-64-4 n-butyl isonitrile 
• 321898-65-1 1-butyl-3-{3-[(3-butyl-thioureido)-methyl]-2-hydroxy-benzyl}-thiourea 
• 354119-70-3 5-((E)-3,4,5-trimethoxybenzylidene)-3-n-butyl-1-methyl-2-thiohydantoin 

Relevant articles and documents

Diaryl-substituted thiosemicarbazone: A potent scaffold for the development of New Delhi metallo-β-lactamase-1 inhibitors

The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has become an emerging public health threat. Inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. A potent scaffold, diaryl-substituted thiosemicarbazone, was constructed and assayed with metallo-β-lactamases (MβLs). The obtained twenty-six molecules specifically inhibited NDM-1 with IC50 0.038–34.7 μM range (except 1e, 2e, and 3d), and 1c is the most potent inhibitor (IC50 = 0.038 μM). The structure-activity relationship of synthetic thiosemicarbazones revealed that the diaryl-substitutes, specifically 2-pyridine and 2-hydroxylbenzene improved inhibitory activities of the inhibitors. The thiosemicarbazones exhibited synergistic antimycobacterial actions against E. coli-NDM-1, resulted a 2–512-fold reduction in MIC of meropenem, while 1c restored 16–256-, 16-, and 2-fold activity of the antibiotic on clinical isolates ECs, K. pneumonia and P. aeruginosa harboring NDM-1, respectively. Also, mice experiments showed that 1c had a synergistic antibacterial ability with meropenem, reduced the bacterial load clinical isolate EC08 in the spleen and liver. This work provided a highly promising scaffold for the development of NDM-1 inhibitors.

Novel method for preparing isothiocyanate

The invention relates to a novel method for preparing isothiocyanate. The method comprises the following steps: adding organic primary amine and benzene isothiocyanate into a high-boiling-point solvent, stirring under the condition of nitrogen protection, keeping the reaction temperature at 100-150 DEG C or heating and refluxing, reacting for 1-9 hours under the condition of normal pressure, afterthe reaction is finished, cooling the reaction solution, removing the solvent through vacuum rotary evaporation, and purifying the concentrate through silica gel column chromatography to obtain isothiocyanate. The method has the following advantages that: 1) the raw materials of organic primary amine and benzene isothiocyanate used in the invention are common chemical raw materials, especially benzene isothiocyanate is cheap and easily available, 2) the reaction conditions are mild, the safety is high, the temperature is generally 100-150 DEG C, and the reaction is carried out under normal pressure, and 3) the method has the advantages of simple technological process and post-treatment, easiness in operation, low cost, high product purity and good industrial application prospect.