111-36-4 Usage
Application
Butyl isocyanate is the important raw material or intermediate that has widely applied? in the synthesis of pharmaceutical, pesticide and dyestuff products, such as benzimidazole fungicides, sulfonylurea herbicides, and benomyl.
Butyl isocyanate is typical catalyst for the synthesis of the sulfonylurea herbicides, such as chlorsulfuron, sulfometuron, metsulfuron-methyl, and chlorimuron-ethyl, by treating the different groups substituted sulfonamide with phosgene in the presence of butyl isocyanate. Moreover, butyl isocyanate is also an intermedia for the synthesis of sulfonylurea.A number of novel sulfonylurea derivatives with sugar lowering activity, such as glibenclamide, tolbutamide, chlorpropamide and other hypoglycemic sulfonylurea agents also could be synthesized by using butyl isocyanate as synthetic intermediate.
Chemical Properties
Different sources of media describe the Chemical Properties of 111-36-4 differently. You can refer to the following data:
1. Colorless to faintly yellow liquid
2. Colorless, flammable liquid.
Uses
Different sources of media describe the Uses of 111-36-4 differently. You can refer to the following data:
1. n-Butyl isocyanate is used as an acylatingagent in the Friedel–Crafts reaction to produce amide.
2. Reagent in organic synthesis.
Definition
ChEBI: An isocyanate having a butyl group attached to the nitrogen.
Synthesis Reference(s)
The Journal of Organic Chemistry, 28, p. 2076, 1963 DOI: 10.1021/jo01043a030
General Description
A clear, colorless liquid with a pungent odor. Flash point 68°F. Very toxic by ingestion, and may also be toxic by skin absorption and inhalation. Vapors heavier than air. Less dense than water and insoluble in water. Produces toxic oxides of nitrogen during combustion.
Air & Water Reactions
Highly flammable. Extremely slow decomposition by water. Less dense than water and insoluble in water.
Reactivity Profile
Isocyanates and thioisocyanates are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].
Hazard
Strong irritant to eyes and skin.
Health Hazard
Different sources of media describe the Health Hazard of 111-36-4 differently. You can refer to the following data:
1. n-Butyl isocyanate exhibits low inhalationtoxicity and relatively higher oral toxicity.This is in contrast to the aromatic isocyanates. The toxic effects are nausea, dyspnea, insomnia, coughing, and chest pain.Such symptoms, however, are much lessmarked than those of methyl isocyanate.LC50 value, inhalation (mice): 680 mg/m3LD50 value, oral (mice): 150 mg/kgThere is no report of any carcinogenic orteratogenic study of this compound.
2. TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
Flammability and Explosibility
Highlyflammable
Safety Profile
A poison by ingestion
and intravenous routes. Mddly toxic by
inhalation. A powerful irritant to eyes, skin,
and mucous membranes. A flammable
liquid. See also CYANATES and
NITROGEN MONOXIDE.
Potential Exposure
N-Butyl isocyanate is used as a
reagent in organic synthesis; used as intermediates in production of pharmaceuticals, carbamate and urea insecticides, and fungicides. It is also used in the production of
sulfonylurea antidiabetic drugs
Shipping
UN2485 n-Butyl isocyanate, Hazard Class: 6.1;
Labels: 6.1—Poison Inhalation Hazard, 3—Flammable
liquid. Hazard, Inhalation Hazard Zone B. PGI.
Incompatibilities
Vapor may form explosive mixture with
air. Isocyanates are highly flammable and reactive with
many compounds, even with themselves. Incompatible with
oxidizers (chlorates, nitrates, peroxides, permanganates,
perchlorates, chlorine, bromine, fluorine, etc.); contact may
cause fires or explosions. Reaction with moist air, water or
alcohols may form amines and insoluble polyureas and
react exothermically, releasing toxic, corrosive or flammable gases, including carbon dioxide; and, at the same time,
may generate a violent release of heat increasing the concentration of fumes in the air. Incompatible with amines,
aldehydes, alkali metals, ammonia, carboxylic acids, caprolactum, alkaline materials, glycols, ketones, mercaptans,
hydrides, organotin catalysts, phenols, strong acids, strong
bases, strong reducing agents such as hydrides, urethanes,
ureas. Elevated temperatures or contact with acids, bases,
tertiary amines, and acylchlorides may cause explosive
polymerization. Contact with metals may evolve flammable
hydrogen gas. Attacks some plastics, rubber and coatings.
May accumulate static electrical charges, and may cause
ignition of its vapors
Waste Disposal
Dispose of contents and container to an approved waste disposal plant. Use a licensed
professional waste disposal service to dispose of this material. Caution: this chemical is highly flammable with a low
flash point (,20C). Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator
equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed.
Check Digit Verification of cas no
The CAS Registry Mumber 111-36-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 111-36:
(5*1)+(4*1)+(3*1)+(2*3)+(1*6)=24
24 % 10 = 4
So 111-36-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H4BrNO/c8-6-1-3-7(4-2-6)9-5-10/h1-4H
111-36-4Relevant articles and documents
Comparing hydrazine-derived reactive groups as inhibitors of quinone-dependent amine oxidases
Burke, Ashley A.,Severson, Elizabeth S.,Mool, Shreya,Solares Bucaro, Maria J.,Greenaway, Frederick T.,Jakobsche, Charles E.
, p. 496 - 503 (2017)
Lysyl oxidase has emerged as an important enzyme in cancer metastasis. Its activity has been reported to become upregulated in several types of cancer, and blocking its activity has been shown to limit the metastatic potential of various cancers. The small-molecules phenylhydrazine and β-aminopropionitrile are known to inhibit lysyl oxidase; however, issues of stability, toxicity, and poorly defined mechanisms limit their potential use in medical applications. The experiments presented herein evaluate three other families of hydrazine-derived compounds–hydrazides, alkyl hydrazines, and semicarbazides–as irreversible inhibitors of lysyl oxidase including determining the kinetic parameters and comparing the inhibition selectivities for lysyl oxidase against the topaquinone-containing diamine oxidase from lentil seedlings. The results suggest that the hydrazide group may be a useful core functionality that can be developed into potent and selective inhibitors of lysyl oxidase and eventually find application in cancer metastasis research.
Trifluoroacetic anhydride-catalyzed oxidation of isonitriles by DMSO: A rapid, convenient synthesis of isocyanates
Le, Hoang V.,Ganem, Bruce
, p. 2584 - 2585 (2011)
A smooth and efficient oxidation of isonitriles to isocyanates by sulfoxides is catalyzed by trifluoroacetic anhydride. With use of DMSO as the oxidant and 5 mol·% TFAA (dichloromethane, -60 to 0 °C), the process is complete in a few minutes, forming dimethyl sulfide as the only byproduct. The newly formed isocyanates may be used directly or isolated in high purity by solvent evaporation.
Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions
Hong, Wan Pyo,Tran, Van Hieu,Kim, Hee-Kwon
, p. 15890 - 15895 (2021/05/19)
A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.
Ebsulfur as a potent scaffold for inhibition and labelling of New Delhi metallo-β-lactamase-1 in vitro and in vivo
Su, Jianpeng,Liu, Jiayun,Chen, Cheng,Zhang, Yuejuan,Yang, Kewu
supporting information, p. 192 - 201 (2018/12/02)
The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has grown into an emerging threat, labelling and inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. Here, we report a potent covalent scaffold, ebsulfur, for targeting the protein in vitro and in vivo. Enzymatic kinetic study indicated that eighteen ebsulfurs gained except 1a–b and 1f inhibited NDM-1, exhibiting an IC50 value ranging of 0.16–9 μM, and 1g was found to be the best, dose- and time-dependent inhibitor with an IC50 of 0.16 μM. Also, these ebsulfurs effectively restored the antibacterial activity of cefazolin against E. coli expressing NDM-1, and the best effect was observed to be from 1g, 1i and 1n, resulting in an 256-fold reduction in MIC of the antibiotic at a dose of 16 μg/mL. The equilibrium dialysis study implied that the ebsulfur disrupted the coordination of one Zn(II) ion at active site of NDM-1. Labelling of NDM-1 using a constructed fluorescent ebsulfur Ebs-R suggested that the inhibitor covalently bound to the target through SDS-PAGE analysis in vitro. Also, labelling NDM-1 in living E. coli cells with Ebs-R by confocal microscopic imaging showed the real-time distribution change process of intracellular recombinant protein NDM-1. Moreover, the cytotoxicity of these ebsulfurs against L929 mouse fibroblastic cells was tested, and their capability to restore antibacterial activity of antibiotic against clinical strains E. coli EC08 producing NDM-1 was determined. The ebsulfur scaffold proposed here is valuable for development of the covalent irreversible inhibitors of NDM-1, and also for labelling the target in vitro and in vivo.
