59-89-2

Basic information

• Product Name: N-NITROSOMORPHOLINE
• Synonyms: 4-nitroso-morpholin;4-Nitrosomorpholine;Morpholine, N-nitroso-;Morpholine,4-nitroso-;nci-c02164;nitrosomorpholineisopac;NMOR;N-Nitrosomorfolin
• CAS NO: 59-89-2
• Molecular Formula: C₄H₈N₂O₂
• Molecular Weight: 116.12
• EINECS: 200-659-6
• Product Categories: Nitrosamine;pharmacetical;Alpha Sort;N;NA - NI;N-OAlphabetic;Volatiles/ Semivolatiles;Mutagenesis Research Chemicals;Nitric Oxide Reagents
• Mol File: 59-89-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 29°C
• Boiling Point: 225℃
• Flash Point: 29 °C
• Appearance: yellow crystals or gold liquid
• Density: 1.2829 (rough estimate)
• Refractive Index: 1.4880 (estimate)
• Storage Temp.: 2-8°C
• PKA: -5.72±0.20(Predicted)
• Water Solubility: Completely soluble in water
• Stability: Stability Stable, but light-sensitive. Combustible. Incompatible with strong oxidizing agents. Refrigerate, store in the dark.
• Merck: 14,6640
• CAS DataBase Reference: N-NITROSOMORPHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-NITROSOMORPHOLINE(59-89-2)
• EPA Substance Registry System: N-NITROSOMORPHOLINE(59-89-2)

Safety Data

• Hazard Codes: Xn,T,F
• Statements: 22-40-39/23/24/25-23/24/25-11
• Safety Statements: 36/37-45-16-7
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: QE7525000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 59-89-2(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystals or gold liquid

Uses

Different sources of media describe the Uses of 59-89-2 differently. You can refer to the following data:
1. N-Nitrosomorpholine, a frequently used genotoxic model carcinogen. Toxicogenomic analysis of N-Nitrosomorpholine induced changes in rat liver.
2. Solvent for polyacrylonitrile; present during rubber manufacturing

Definition

ChEBI: A nitrosamine that is morpholine in which the hydrogen attached to the nitrogen is replaced by a nitroso group. A carcinogen and mutagen, it is found in snuff tobacco.

Synthesis Reference(s)

Synthetic Communications, 22, p. 2607, 1992 DOI: 10.1080/00397919208021659

General Description

Yellow crystals. Golden liquid with many crystals at 68°F.

Air & Water Reactions

Water soluble.

Reactivity Profile

N-NITROSOMORPHOLINE is incompatible with strong oxidizing agents .

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition N-NITROSOMORPHOLINE emits toxic fumes of nitrogen oxides.

Fire Hazard

Flash point data for N-NITROSOMORPHOLINE are not available; however, N-NITROSOMORPHOLINE is probably combustible.

Biochem/physiol Actions

Tumor initiator in rodent liver, trachea, nasal cavity, esophagus, kidney, lung, and thyroid.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Moderately toxic by inhalation. Human mutation data reported. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx. See also N-NITROSO COMPOUNDS.

Carcinogenicity

N-Nitrosomorpholine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

InChI:InChI=1/C4H8N2O2/c7-6-4-3-5-1-2-8-4/h4-5H,1-3H2

Upstream product

• 1116-54-7 N-nitrosodiethanolamine 
• 110-91-8 morpholine 
• 128767-05-5 benzo-1,2,3,4-tetrazine 1,3-dioxide 
• 4164-32-3 N-nitromorpholine 
• 78657-44-0 (Z)-1-morpholino-2-phthalimido-diazen-1-oxid 
• 45508-78-9 4-methylene-morpholinium 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 10311-10-1 1-bromo-2-nitrosooxy-ethane 
• 563-70-2 bromonitromethane 
• 544-16-1 n-Butyl nitrite 
• 543-67-9 n-propyl nitrite 
• 5625-90-1 4-(morpholinomethyl)morpholine 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 4319-49-7 1-aminomorpholine 
• 110-91-8 morpholine 
• 57902-11-1 N,N'-bis(morpholino)diazene 
• 61578-30-1 N-Nitroso-3,3,5,5-tetradeutero-morpholin 

Relevant articles and documents

Release of nitrosating species in the course of reduction of benzo-1,2,3,4-tetrazine 1,3-dioxides.

[reaction: see text] The reduction of benzo-1,2,3,4-tetrazine 1,3-dioxides (BTDOs) 1 with Na(2)S(2)O(4) or SnCl(2) is suggested to proceed via intermediate N-nitrosobenzotriazoles 3 to afford benzotriazoles 2. The (15)N-labeling experiments exhibit that t

Reactions of Secondary Nitramines with Tributyltin Hydride and Tris(trimethylsilyl)silane

The reactions of secondary nitramines (N-nitroamines) with tributyltin hydride or tris(trimethylsilyl)silane have been investigated under free radical conditions.Reactions of nitramines with tributyltin radicals gave mostly the denitration products (secondary amines) whilst reactions with tris(trimethylsilyl)silyl radicals afforded almost exclusively nitrosamines (N-nitrosoamines).

Transfer of the Nitroso Group in Water/AOT/Isooctane Microemulsions: Intrinsic and Apparent Reactivity

The kinetics of the transfer of the nitroso group from N-methyl-N-nitroso-p-toluenesulfonamide to each of seven secondary amines (piperazine, N-methylbenzylamine, piperidine, dimethylamine, morpholine, pyrrolidine, and diisopropylamine) was studied using a wide variety of water/AOT/isooctane microemulsions as reaction media.The diverse kinetic behavior of the various amines can be explained quantitatively on the basis of a single model taking into account the distribution of the amine among the aqueous and isooctane phases and their mutual interface; the reaction itself always takes place at the interface.The relative reactivities of the amines are discussed in comparison with the order observed in water.