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

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

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

• 75-15-0 carbon disulfide 
• 6336-01-2 3-n-butyl-1-phenylthiourea 
• 463-71-8 thiophosgene 
• 109-73-9 N-butylamine 
• 60448-30-8 N-butylthioformamide 
• 400-59-9 N-butyl-2,2,2-trifluoroacetamide 
• 20465-03-6 diethyl N-butylphosphoramidate 
• 2769-64-4 n-butyl isonitrile 
• 56134-96-4 ethyl butyldithiocarbamate 
• 628-05-7 1-nitropentane 
• 17356-08-0 thiourea 
• 4669-59-4 bis(diethylamino)dimethylsilane 
• 109-46-6 1,3-dibutylthiourea 
• 96989-50-3 di-2-pyridyl thionocarbonate 

Downstream Products

• 7501-78-2 9-butyl-1,3-dimethyl-8-thio-uric acid 
• 1119-49-9 N-butylacetamide 
• 99987-73-2 N-butyl-N'-(4-nitro-phenyl)-thiourea 
• 91194-23-9 N-butyl-N'-(4-sulfamoyl-phenyl)-thiourea 
• 21198-52-7 4-Butyl-2-methyl-thiosemicarbazid 
• 34021-80-2 N-(4-amino-phenyl)-N'-butyl-thiourea 
• 6629-59-0 1-n-Dodecyl-3-n-butyl-2-thioharnstoff 
• 91953-36-5 N-butyl-N'-(N,N-dimethyl-sulfanilyl)-thiourea 
• 1792-17-2 N,N'-di-n-butylurea 
• 1516-32-1 N-butylthiourea 
• 109-73-9 N-butylamine 
• 6610-31-7 4-butyl-3-thiosemicarbazide 
• 4932-55-2 N-(4-methylphenylsulfonyl)-N'-butylthiourea 
• 93334-98-6 1,1,2-Trimethyl-4-n-butyl-thiosemicarbazid 

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.

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

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.

Iron-promoted one-pot approach: Synthesis of isothiocyanates

We have established a facile and versatile synthesis for the construction of isothiocyanates from their respective amines in the presence of an eco-friendly, inexpensive, easily available Iron catalyst under mild conditions. This reaction provides the target products through the formation of thiocarbamate salt as an intermediate. Both aromatic amines and aliphatic amines provided the respective target products in moderate to high yield under optimized reaction conditions. However, electron withdrawing substituents were difficult to give target product at room temperature, whereas, they obtained final products in good yield at moderate temperature. In addition, mechanistic studies were revealed that the synthetic route involved iron based subsequent reactions of addition and removal of sulfur.

Preparation method of isothiocyano compound

The invention discloses a preparation method of an isothiocyano compound. An ammonium thiocyanate, sodium thiocyanate or potassium thiocyanate water solution and a halide are used as raw materials, and an isothiocyano compound is synthesized under the action of a phase transfer catalyst. The requirements that the thiocyanate radical in each batch of reaction is excessive by 10% and the yield is high are met, the purpose that the concentration of thiocyanic acid in wastewater is very low is realized, complex wastewater treatment equipment and treatment operation are avoided, and environmental protection pressure is reduced. The preparation method is a green preparation method, and solves the problems of extremely difficult degradation and high biotoxicity of thiocyanate-containing wastewater in conventional isothiocyano compound production. The method is simple to operate and is suitable for industrial production.

One-pot three-component tandem reaction: Synthesis of aryl/alkyl cyanamides libraries and their further conversion into tetrazole derivatives

We have developed methodology for the synthesis of aryl/alkyl cyanamides from amines in one-pot four steps reaction using cheap, readily available and air stable copper source as catalyst under mild reaction conditions. We have also studied the application of cyanamides. In this connection, we could construct aryl tetrazolamine from cyanamides using click reaction.

Synthesis of novel dithiocarbamates and xanthates using dialkyl azodicarboxylates: S–N bond formation

A one?pot three?component route for the synthesis of a novel category of dithiocarbamates or xanthates is developed by a reaction of in-situ generated dithiocarbamic acids or xanthates with dialkyl azodicarboxylates under mild and catalyst-free conditions. The reaction is characterized by a wide scope, high efficiency and straightforward isolation protocol. The synthetic utility of the dithiocarbamates and xanthates was demonstrated on the preparation of symmetrical and unsymmetrical thioureas, isothiocyanates, and thiocarbamates.

T3P - A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates

A number of alkyl, aryl and bifunctional isothiocyanates are obtained in moderate to high yields (41-94%) in a two-step, one-pot reaction of the parent primary amines or their salts with carbon disulfide, followed by reaction of the thus formed dithiocarbamates with T3P (propane phosphonic acid anhydride) as a new and efficient desulfurating agent.

A novel one-pot synthesis of isothiocyanates and cyanamides from dithiocarbamate salts using environmentally benign reagent tetrapropylammonium tribromide

A highly efficient and simple protocol for the synthesis of isothiocyanates and cyanamides from their respective amines in the presence of a mild, efficient, and non-toxic reagent tetrapropylammonium tribromide is described. High environmental acceptability of the reagents, cost effectiveness and high yields are the important attributes of this methodology.