5843-42-5

Basic information

• Product Name: METHYL ISOCYANATOFORMATE
• Synonyms: METHYL ISOCYANATOFORMATE;Carbomethoxyisocyanate;methyl carbonisocyanatidoate
• CAS NO: 5843-42-5
• Molecular Formula: C₃H₃NO₃
• Molecular Weight: 101.06
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 5843-42-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 97 °C(lit.)
• Flash Point: 87 °F
• Appearance: /
• Density: 1.251 g/mL at 25 °C(lit.)
• Vapor Pressure: 30.4mmHg at 25°C
• Refractive Index: n20/D 1.413(lit.)
• Storage Temp.: ?20°C
• CAS DataBase Reference: METHYL ISOCYANATOFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL ISOCYANATOFORMATE(5843-42-5)
• EPA Substance Registry System: METHYL ISOCYANATOFORMATE(5843-42-5)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/21/22-36/37/38-42
• Safety Statements: 16-26-36/37
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 5843-42-5(Hazardous Substances Data)

Usage

Description

METHYL ISOCYANATOFORMATE, also known as methyl carbonisocyanatidate, is an organic building block that contains an isocyanate group. METHYL ISOCYANATOFORMATE is characterized by its ability to form stable carbamates and is widely used in various chemical reactions and applications due to its unique properties.

Uses

Used in Pharmaceutical Industry:
METHYL ISOCYANATOFORMATE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form stable carbamates makes it a valuable building block for the development of new drugs and drug candidates.
Used in Agrochemical Industry:
In the agrochemical industry, METHYL ISOCYANATOFORMATE is used as a precursor for the synthesis of various pesticides and insecticides. Its reactivity and ability to form carbamates contribute to the development of effective and targeted pest control solutions.
Used in Polymer Industry:
METHYL ISOCYANATOFORMATE is utilized as a monomer in the production of polyurethanes and other polymers. Its isocyanate group allows for the formation of urethane linkages, which are essential for the creation of durable and versatile polymer materials.
Used in Research and Development:
METHYL ISOCYANATOFORMATE is employed as a research chemical in various scientific studies and experiments. Its unique properties and reactivity make it an interesting compound for exploring new chemical reactions and developing innovative applications.

InChI:InChI=1/C3H3NO3/c1-7-3(6)4-2-5/h1H3

Upstream product

• 19245-23-9 cyano-μ-imido-dicarbonic acid dimethyl ester 
• 1118-02-1 trimethylsilyl isocyanate 
• 79-22-1 methyl chloroformate 
• 79-37-8 oxalyl dichloride 
• 598-55-0 methyl carbamate 

Downstream Products

• 87343-81-5 4-phenyl-allophanic acid methyl ester 
• 122916-47-6 (Dimethoxy-phosphoryl)-phenyl-aminocarbonyl)-carbamic acid methyl ester 
• 66389-76-2 tert-butyl methyl iminodicarboxylate 
• 927837-64-7 methyl trans-pent-2-enyl imidodicarbonate 
• 1173206-38-6 tert-butyl 4-[5-(4-{[(methoxycarbonyl)carbamoyl]amino}phenyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]piperidine-1-carboxylate 
• 69200-74-4 1-(3,4-dimethoxyphenyl)-3-methoxycarbonylurea 
• 14739-06-1 4-(2-hydroxy-4,6-di-piperidin-1-yl-phenyl)-[1,3]oxazet-2-one 
• 17218-84-7 4-(2,4-bis-dimethylamino-6-hydroxy-phenyl)-[1,3]oxazet-2-one 
• 37895-15-1 C₁₁H₁₃NO₆ 
• 83308-57-0 1-(4'-nitrobenzenesulfonyl)-3-methoxycarbonyl urea 

Relevant articles and documents

Hydroxyamination of olefins using Br-n-(co2me)2

The hydroxyamination reagent Br-N-(CO2Me)2 underwent Markovnikov addition to various olefins in the presence of catalytic BF3·OEt2 and provides efficient access to aminoalcohols. The reaction provided the trans-1-bromo, 2-N-bis-carbamate adduct stereoisomer in all cases. The resulting adduct underwent cyclization to give an oxazolidinone, which could be readily hydrolyzed to an oxazolidin-2-one or an amino alcohol.

Direct observation of methoxycarbonylnitrene

The simplest alkoxycarbonylnitrene, CH3OC(O)N, has been generated through laser (266 and 193 nm) photolysis of CH3OC(O)N3 and CH3OC(O)NCO and subsequently characterized by IR (15N, D-labelling) and EPR (|D/hc| = 1.66 cm-1 and |E/hc| = 0.020 cm-1) spectroscopy in cryogenic matrices. Two conformers of the nitrene, with the CH3 group being in syn or anti configuration to the CO bond, have been unambiguously identified. Further UV light irradiation (365 nm) of the nitrene results in isomerization to CH3ONCO, completing the frequently explored mechanism for the Curtius-rearrangement of CH3OC(O)N3.

Revealing CSA Tensors and Hydrogen Bonding in Methoxycarbonyl Urea: A combined 13C, 15N and 13C14N 2 Dipolar Chemical Shift NMR and DFT Study

Methoxycarbonyl urea (MCU), a potential long-term nitrogen fertilizer, is studied by 13C and 15N dipolar chemical shift NMR spectroscopy and ab initio calculations. Employing a combination of dipolar chemical shift NMR, selective isotope labeling and ab initio gas phase calculations, possible molecular structures and chemical shielding tensors of all 15N nuclei and of two out of the three 13C nuclei were revealed. Four possible stable configurations of the molecule with different energies were found in the calculations. The CSA tensors were calculated for these configurations. While the calculated 13C(urea) CSA tensor orientation of the configuration with the lowest energy is in good agreement with the experimental tensor orientation, there are pronounced differences between calculated and experimental tensor eigenvalues. These differences are a clear indication of the presence of intermolecular hydrogen bonds in the experimental sample, which are neglected in the gas phase calculations. Four different possible orientations of the experimental 13C(urea) CSA tensor exist, due to symmetry. This ambiguity is solved by comparison with results from GIAO calculations of the 13C CSA tensor, employing the minimum energy configuration (EEZ). It is found that the orientation, where δ11 points approximately in direction of N(imide), δ22 approximately in direction of the C=O bond, and δ33 is oriented perpendicular to the molecular frame, is adopted in the molecule.