102-36-3 Usage
Description
Isocyanic acid 3,4-dichlorophenyl ester, also known as 3,4-dichlorophenyl isocyanate, is a white to yellow low melting solid with chemical properties that make it a valuable chemical intermediate and component in organic synthesis. It is combustible and generally insoluble in water, with some reactivity.
Uses
Used in Chemical Synthesis:
Isocyanic acid 3,4-dichlorophenyl ester is used as a chemical intermediate for the synthesis of various compounds, including substituted urea derivatives, 1,5-disubstituted-2-thiobiuret derivatives, and methyl-labeled diuron. It is particularly useful in the preparation of these compounds due to its reactivity and versatility in organic synthesis.
Used in Pesticide Synthesis:
Isocyanic acid 3,4-dichlorophenyl ester is used as a key component in the synthesis of methyl-labeled diuron, a herbicide used in agriculture to control a wide range of broadleaf and grassy weeds. The ester's reactivity allows for the efficient preparation of this herbicide, contributing to its effectiveness in controlling unwanted plant growth.
Used in Pharmaceutical Synthesis:
Isocyanic acid 3,4-dichlorophenyl ester is used as a starting material in the synthesis of substituted urea derivatives, which have potential applications in the pharmaceutical industry. These derivatives can be further modified to create new drugs with various therapeutic properties.
Used in Organic Chemistry Research:
Isocyanic acid 3,4-dichlorophenyl ester is used as a reagent in the synthesis of 1,5-disubstituted-2-thiobiuret derivatives, which are of interest in organic chemistry research. The ester's unique properties allow for the exploration of new chemical reactions and the development of novel compounds with potential applications in various fields.
Used in the Synthesis of Chiral Compounds:
Isocyanic acid 3,4-dichlorophenyl ester is used in the synthesis of Rand S-isomers and RS-racemate of MBPU (3-(3,4-dichlorophenyl)-1,1-dimethylurea). The ability to produce these chiral compounds is important for the development of enantiomerically pure drugs, which can have different biological activities and may be more effective or have fewer side effects than their racemic counterparts.
Reactivity Profile
Isocyanates and thioisocyanates, such as Isocyanic acid 3,4-dichlorophenyl ester, 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.
Health Hazard
Strong irritant to tissue, especially eyes and mucous membranes
Fire Hazard
Inhalation of dust is poisonous; fire may produce irritating or poisonous gases.
Flammability and Explosibility
Notclassified
Potential Exposure
Those materials used as chemical
intermediates
Shipping
UN2250 Dichlorophenyl isocyanates, Hazard
Class: 6.1; Labels: 6.1-Poisonous materials.
Incompatibilities
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 theconcentration 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, and 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.
Waste Disposal
Combustion in an incinerator
equipped with afterburner and fume scrubber
Check Digit Verification of cas no
The CAS Registry Mumber 102-36-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 2 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 102-36:
(5*1)+(4*0)+(3*2)+(2*3)+(1*6)=23
23 % 10 = 3
So 102-36-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H3Cl2NO/c8-6-2-1-5(10-4-11)3-7(6)9/h1-3H
102-36-3Relevant articles and documents
COMBINED CARBONYLATION OF NITRO AND AZO COMPOUNDS IN THE SYNTHESIS OF ISOCYANATES
Manov-Yuvenskii, V. I.,Petrovskii, K. B.,Lapidus, A. L.
, p. 2486 - 2489 (1984)
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Kinetics and mechanism of hydrolysis of phenylureas
Salvestrini, Stefano,Di Cerbo, Paola,Capasso, Sante
, p. 1889 - 1893 (2002)
The hydrolysis of phenylureas has been found to be affected by temperature, pH and buffer concentration. Kinetic evidence suggests that the formation of phenylisocyanate, the initial product in the title reaction, occurs via an intermediate zwitterion. Depending on pH and buffer concentrations, the zwitterion can be produced through three parallel routes: at low pH, specific acid-general base catalysis, followed by slow deprotonation of a nitrogen atom by a general base; at high pH, specific basic-general acid catalysis, followed by slow protonation of a N atom by a general acid; at intermediate pH the reaction proceeds through a proton switch promoted by buffers. Bifunctional acid-base buffers such as HCO3-/CO32-, H2PO42- and CH3COOH/CH3COO- are very efficient catalysts. At high buffer concentration, as well as at pH 12, the breakdown of the zwitterion is rate-determining. The results are discussed in relation to recently published papers reporting different pathways.
INFLUENCE OF PYRIDINE AND COMPOUNDS OF VANADIUM, IRON, AND MOLIBDENUM ON THE CARBONYLATION OF AZO AND NITRO COMPOUNDS IN THE PRESENCE OF RhCl3-4H2O
Manov-Yuvenskii, V. I.,Petrovskii, K. B.,Lapidus, A. L.
, p. 546 - 549 (1983)
-
Synthesis process of 3,4-dichlorophenyl isocyanate
-
Paragraph 0026-0031, (2021/02/13)
The invention discloses a synthesis process of 3,4-dichlorophenyl isocyanate. The synthesis process comprises the following steps: adding 3,4-dichloroaniline and a solvent into a reaction kettle to obtain a 3,4-dichloroaniline solution while adding solid phosgene into the reaction kettle, and heating for dissolving; when the temperature of the reaction kettle reaches 60-100 DEG C, controlling thedripping speed through a DCS to start to dropwise add the 3,4-dichloroaniline solution in the step S1, so that 3,4-dichloroaniline and solid phosgene generate 3,4-dichloroaniline hydrochloride and 3,4-dichlorobenzene methylamino acyl chloride in a solvent medium; removing hydrogen chloride from the 3,4-dichlorobenzene methylamino acyl chloride obtained in S3 to obtain 3,4-dichlorophenyl isocyanate, and after dropwise adding is finished, carrying out reflux heat preservation for 1-3 h; and removing the acid-containing solvent at normal pressure, recycling, transferring the concentrated solutionto a rectifying still, and rectifying to obtain the product 3,4-dichlorophenyl isocyanate. According to the invention, green chemicals are used as production raw materials, so that potential safety hazards caused by phosgene leakage are reduced; and common chemical solid phosgene is adopted to replace virulent phosgene to serve as an acylation reagent, and a green degradable ester solvent is adopted as a reaction medium.
Disrupting the Conserved Salt Bridge in the Trimerization of Influenza A Nucleoprotein
Woodring, Jennifer L.,Lu, Shao-Hung,Krasnova, Larissa,Wang, Shih-Chi,Chen, Jhih-Bin,Chou, Chiu-Chun,Huang, Yi-Chou,Cheng, Ting-Jen Rachel,Wu, Ying-Ta,Chen, Yu-Hou,Fang, Jim-Min,Tsai, Ming-Daw,Wong, Chi-Huey
supporting information, p. 205 - 215 (2020/01/02)
Antiviral drug resistance in influenza infections has been a major threat to public health. To develop a broad-spectrum inhibitor of influenza to combat the problem of drug resistance, we previously identified the highly conserved E339?R416 salt bridge of the nucleoprotein trimer as a target and compound 1 as an inhibitor disrupting the salt bridge with an EC50 = 2.7 μM against influenza A (A/WSN/1933). We have further modified this compound via a structure-based approach and performed antiviral activity screening to identify compounds 29 and 30 with EC50 values of 110 and 120 nM, respectively, and without measurable host cell cytotoxicity. Compared to the clinically used neuraminidase inhibitors, these two compounds showed better activity profiles against drug-resistant influenza A strains, as well as influenza B, and improved survival of influenza-infected mice.