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1-Methyl-3-nitro-1-nitrosoguanidine
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Name

1-Methyl-3-nitro-1-nitrosoguanidine

 EINECS 200-730-1
CAS No. 70-25-7 Density 1.7979 (rough estimate)
PSA 114.37000 LogP 0.32950
Solubility Reacts violently Melting Point 118 ºC (dec.)
Formula C2H5 N5 O3 Boiling Point 267.16°C (rough estimate)
Molecular Weight 147.093 Flash Point 120.541oC
Transport Information UN 1325 Appearance yellow to pink crystals
Safety Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Poison by ingestion, intraperitoneal, and intravenous routes. Moderately toxic by subcutaneous route. Experimental reproductive effects. Human mutation data reported. An explosive sensitive to heat or impact. Flammable when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits very toxic fumes of NOx. See also N-NITROSO COMPOUNDS. Risk Codes R45;R20;R36/38;R51/53   
Molecular Structure Molecular Structure of 70-25-7 (1-Methyl-3-nitro-1-nitrosoguanidine) Hazard Symbols
Synonyms

Guanidine,1-methyl-3-nitro-1-nitroso- (6CI,8CI); 1-Methyl-1-nitroso-2-nitroguanidine;1-Methyl-1-nitroso-3-nitroguanidine; 1-Methyl-3-nitro-1-nitrosoguanidine;1-Nitroso-3-nitro-1-methylguanidine; MNNG; Methylnitronitrosoguanidine;N-Methyl-N-nitroso-N'-nitroguanidine; N-Methyl-N1-nitro-N-nitrosoguanidine;N-Methyl-N'-nitro-N-nitrosoguanadine; N-Methyl-N'-nitro-N-nitrosoguanidine;N-Methyl-nitroso-N'-nitroguanidine; N-Nitroso-N-methyl-N'-nitroguanidine;N-Nitroso-N-methylnitroguanidine; N-Nitroso-N'-nitro-N-methylguanidine; NSC9369; NTG; Nitrosoguanidine

Article Data 4

1-Methyl-3-nitro-1-nitrosoguanidine Synthetic route

4245-76-5

N-methyl-N'-nitroguanidine

70-25-7

N-Methyl-N'-nitro-N-nitrosoguanidine

Conditions
ConditionsYield
With nitric acid; sodium nitrite at 10℃;
70-25-7

N-Methyl-N'-nitro-N-nitrosoguanidine

400736-91-6

(2E,4E)-5-Bromo-2,4-dimethyl-penta-2,4-dienoic acid

400736-94-9

(2E,4E)-5-bromo-2,4-dimethyl-penta-2,4-dienoic acid methyl ester

Conditions
ConditionsYield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether at 0℃; for 0.25h;
Stage #2: (2E,4E)-5-Bromo-2,4-dimethyl-penta-2,4-dienoic acid In diethyl ether		99%
70-25-7

N-Methyl-N'-nitro-N-nitrosoguanidine

1009365-40-5

C17H21FO3

1009367-58-1

methyl 2-(9-(4-fluorophenyl)-3-hydroxybicyclo[3.3.1]nonan-9-yl)acetate

Conditions
ConditionsYield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; for 0.0833333h;
Stage #2: C17H21FO3 In diethyl ether; dichloromethane at 0℃; for 0.166667h;		99%
70-25-7

N-Methyl-N'-nitro-N-nitrosoguanidine

15647-47-9

5-benzoylaminopentanoic acid

17079-25-3

methyl N-benzoyl-5-aminopentanoate

Conditions
ConditionsYield
With sodium hydroxide In methanol; diethyl ether at 0℃;99%
70-25-7

N-Methyl-N'-nitro-N-nitrosoguanidine

1310810-17-3

trans-methyl 4-(4-bromophenyl)but-2-enoate

trans-methyl 2-(4-bromobenzyl)cyclopropanecarboxylate

Conditions
ConditionsYield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether at 0℃; for 0.25h;
Stage #2: trans-methyl 4-(4-bromophenyl)but-2-enoate With palladium diacetate In tetrahydrofuran; diethyl ether at 20℃; for 1h;		98%
70-25-7

N-Methyl-N'-nitro-N-nitrosoguanidine

(4aR,6S,8S,8aR)-6-(3-azidopropoxy)-2,2-di-tert-butyl-8-(((4aR,6R,7S,8S,8aR)-2,2-di-tert-butyl-7,8-bis((tert-butyldimethylsilyl)oxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)oxy)tetrahydropyrano[3,2-d][1,3,2]dioxasilin-7(6H)-one

(2S,4a’R,6’S,8’S,8a’R)-6’-(3-azidopropoxy)-2’,2’-di-tert-butyl-8’-(((4aR,6R,7S,8S,8aR)-2,2-di-tert-butyl-7,8-bis((tert-butyldimethylsilyl)oxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)oxy)tetrahydro-6’H-spiro[oxirane-2,7’-pyrano[3,2-d][1,3,2]dioxasiline]

Conditions
ConditionsYield
With potassium hydroxide In diethyl ether; ethanol; water for 0.166667h; Inert atmosphere;98%
70-25-7

N-Methyl-N'-nitro-N-nitrosoguanidine

110916-46-6

Mrz 2/138

N-[2-(3,5-dimethyl-1-adamantyl)ethyl]-nitroguanidine

Conditions
ConditionsYield
In diethyl ether; water at 22℃; for 1.5h;96.5%
In diethyl ether; water at 20 - 22℃; for 0.5h;96.5%
70-25-7

N-Methyl-N'-nitro-N-nitrosoguanidine

(E)-methyl 4-(4-((3-phenoxybenzyl)oxy)bicyclo[2.2.1]heptan-1-yl)but-2-enoate

methyl 2-((4-((3-phenoxybenzyl)oxy)bicyclo[2.2.1]heptan-1-yl)methyl)cyclopropanecarboxylate

Conditions
ConditionsYield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With palladium diacetate; potassium hydroxide In diethyl ether; water at 0℃; for 0.333333h;
Stage #2: (E)-methyl 4-(4-((3-phenoxybenzyl)oxy)bicyclo[2.2.1]heptan-1-yl)but-2-enoate With palladium diacetate In tetrahydrofuran at 0 - 20℃; for 1h;		95%
70-25-7

N-Methyl-N'-nitro-N-nitrosoguanidine

89232-30-4

(2E)-N-benzylbut-2-enamide

N-benzyl-2-methylcyclopropanecarboxamide

Conditions
ConditionsYield
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With water; potassium hydroxide In diethyl ether at 0℃; for 0.25h;
Stage #2: (2E)-N-benzylbut-2-enamide With palladium diacetate In tetrahydrofuran; diethyl ether at 20℃; for 1h;		94%
70-25-7

N-Methyl-N'-nitro-N-nitrosoguanidine

N-benzoyl-N-((E)-2-butenyl)-5-aminopentanoic acid

methyl N-benzoyl-N-((E)-2-butenyl)-5-aminopentanoate

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether at 0℃;94%

1-Methyl-3-nitro-1-nitrosoguanidine Chemical Properties

Molecular Formula: C2H5N5O3
Molar mass: 147.09 g/mol
Structure of 1-Methyl-3-nitro-1-nitrosoguanidine(70-25-7):
                                     
Synonyms of 1-Methyl-3-nitro-1-nitrosoguanidine(70-25-7):1-METHYL-3-NITRO-1-NITROSOGUANIDINE;MNNG;N-METHYL-N'-NITRO-N-NITROSOGUANIDINE;N-METHYL-N-NITROSO-N'-NITROGUANIDINE;DIAZOMETHANE PRECURSOR;1-Methyl-1-Nitroso-3-nitroguanidine;1-methyl-3-nitro-1-nitroso-guanidin;1-nitroso-3-nitro-1-methylguanidine
Water solubility:  Reacts violently
Melting point: 118°C (dec.)
storage temp:0-6°C
Stability of 1-Methyl-3-nitro-1-nitrosoguanidine(70-25-7):  Unstable. Heat, light and moisture sensitive. May explode if stored in sealed ampules. Highly flammable. Incompatible with aqueous solutions, bases, acids, oxidizing agents, reducing agents. Alkaline hydrolysis releases toxic and explosive gases. Reacts violently with water. May detonate under impact.
Appearance:  yellow to pink crystals

1-Methyl-3-nitro-1-nitrosoguanidine Toxicity Data With Reference

1.   

dnd-hmn:fbr 20 µmol/L

   ENMUDM    Environmental Mutagenesis. 7 (1985),267.
2.   

sce-hmn:hla 300 nmol/L

   CRNGDP    Carcinogenesis. 5 (1984),593.
3.   

ivn-rat TDLo:25 mg/kg (15D preg):ETA,TER

   KFIZAO    Kyoto-furitsu Ika Daigaku Zasshi. Journal of the Kyoto Prefectural School of Medicine. 84 (1975),23.
4.   

orl-rat LD50:90 mg/kg

   ZKKOBW    Zeitschrift fuer Krebsforschung und Klinische Onkologie. 91 (1978),183.
5.   

scu-rat LD50:420 mg/kg

   ZEKBAI    Zeitschrift fuer Krebsforschung. 69 (1967),103.
6.   

ivn-rat LD50:80 mg/kg

   EJCAAH    European Journal of Cancer. 16 (1980),395.
7.   

ipr-mus LD50:66 mg/kg

   JJIND8    JNCI, Journal of the National Cancer Institute. 62 (1979),911.
8.   

ivn-mus LD50:37,300 µg/kg

   NCISP*    National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program, Bethesda, MD 20205 JAN86 .
9.   

orl-ham LD50:1070 mg/kg

   CALEDQ    Cancer Letters (Shannon, Ireland). 4 (1978),241.

1-Methyl-3-nitro-1-nitrosoguanidine Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 248.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 ,1974,p. 183.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

1-Methyl-3-nitro-1-nitrosoguanidine Safety Profile

Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Poison by ingestion, intraperitoneal, and intravenous routes. Moderately toxic by subcutaneous route. Experimental reproductive effects. Human mutation data reported. An explosive sensitive to heat or impact. Flammable when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits very toxic fumes of NOx. See also N-NITROSO COMPOUNDS.
Hazard Codes:T,N,N,T
Risk Statements:
20:  Harmful by inhalation
36:  Irritating to the eyes
38:  Irritating to the skin
45:  May cause cancer
51:  Toxic to aquatic organisms
53:  May cause long-term adverse effects in the aquatic environment
Safety Statements:
 45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
53:  Avoid exposure - obtain special instruction before use
61:  Avoid release to the environment. Refer to special instructions safety data sheet

1-Methyl-3-nitro-1-nitrosoguanidine Standards and Recommendations

DOT Classification of 1-Methyl-3-nitro-1-nitrosoguanidine(70-25-7):  EXPLOSIVE 1.1A; Label: EXPLOSIVE 1.1A
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