N -methyl- N -nitrosourea

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of N-methyl-N-nitrosourea
General
Surname N -methyl- N -nitrosourea
other names
  • N -nitroso- N -methylurea
  • Nitrosomethylurea
Molecular formula C 2 H 5 N 3 O 2
Brief description

colorless to yellowish needles

External identifiers / databases
CAS number 684-93-5
EC number 211-678-4
ECHA InfoCard 100.010.618
PubChem 12699
Wikidata Q3023727
properties
Molar mass 103.08 g mol −1
Physical state

firmly

density

1.58 g cm −3

Melting point

123 ° C (decomposition)

solubility

14.4 g l −1 in water (24 ° C)

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable 06 - Toxic or very toxic 08 - Dangerous to health

danger

H and P phrases H: 228-301-350-360D
P: 201-210-301 + 310-308 + 313
Toxicological data

110 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N -Methyl- N -nitrosourea is an unstable N - nitroso derivative of urea , which belongs to the group of nitrosoureas .

Presentation and extraction

The compound is made up of urea, methylamine and sodium nitrite . First, N- methylurea is obtained in a substitution reaction . The target compound results from a subsequent acid nitrosation.

N-methyl N-nitrosourea synthesis 01.svg

properties

N -Methyl- N -nitrosourea is a crystalline solid that tends to decompose spontaneously. This can occur even when the compound is stored at room temperature. The decomposition occurs as a self-accelerating reaction. Contact with alkali hydroxides, dichloromethane or friction with metal spatulas can also trigger decomposition. The decomposition products found were methyl isocyanate , nitrogen and water . Slow decomposition results in N , N , N -trimethylcyanuric acid .

use

The compound can be used to make diazomethane . Because of the instability of the compound, however, other starting compounds such as N -methyl- N -nitroso- p -toluenesulfonamide , which are also not carcinogenic, are preferred today.

Diazomethane synthesis 01.svg

Individual evidence

  1. ↑ a b c d e f g Lutz Roth, Ursula Weller-Schäferbarthold: Hazardous chemical reactions. 69th supplementary delivery, ecomed-Verlag 2013.
  2. ↑ a b c d e Entry on N-methyl-N-nitrosourea in the GESTIS substance database of the IFA , accessed on March 23, 2018(JavaScript required) .
  3. ↑ F. Arndt: Nitrosomethylurea In: Organic Syntheses . 15, 1935, p. 48, doi : 10.15227 / orgsyn.015.0048 ; Coll. Vol. 2, 1943, p. 461 ( PDF ).
  4. ↑ F. Brogli, P. Grimm, M. Meyer, H. Zubler: Hazards of self-accelerating reactions. In: Swiss Chem. 3, 1981, 3a.
  5. ↑ F. Arndt: Diazomethan In: Organic Syntheses . 15, 1935, p. 3, doi : 10.15227 / orgsyn.015.0003 ; Coll. Vol. 2, 1943, p. 165 ( PDF ).