4245-76-5

Basic information

• Product Name: 1-Methyl-3-nitroguanidine
• Synonyms: METHYLNITROGUANIDINE;1-methyl-3-nitroguanidine (contains ca. 25% water;Methylnnitroguanidine;1-Methyl-3-nitorguanidine;N'-Nitro-N-methylguanidine;1-METHYL-3-NITRO-1-NITROGUANIDINE;N-METHYL-N''-NITROGUANIDINE (WETTED WITH 25% WATER, CONTAINING 5G ON A DRY WEIGHT BASIS);N-Methyl-N'-nitroguanidine (wetted with ca. 25% Water, containing 5g and 25g on a dry weight basis respectively)
• CAS NO: 4245-76-5
• Molecular Formula: C₂H₆N₄O₂
• Molecular Weight: 118.09
• Product Categories: Guanidines;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 4245-76-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: 153-155 °C(lit.)
• Boiling Point: 220.6°C (rough estimate)
• Flash Point: 105.4 °C
• Appearance: /
• Density: 1.5428 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 2-8°C(protect from light)
• Solubility: very faint turbidity in hot Water
• PKA: 3.53±0.50(Predicted)
• Water Solubility: 14g/L at 25℃
• CAS DataBase Reference: 1-Methyl-3-nitroguanidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-3-nitroguanidine(4245-76-5)
• EPA Substance Registry System: 1-Methyl-3-nitroguanidine(4245-76-5)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36/37/38
• Safety Statements: 16-26-36/37/39-48
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• RTECS: MF4125000
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 4245-76-5(Hazardous Substances Data)

Usage

Uses

N-Methyl N-Nitroguanidine induces stomach adenocinoma in rats.

InChI:InChI=1/C2H7N4O2/c1-4-2(3)5-6(7)8/h1H3,(H,7,8)(H3,3,4,5)/q+1

Synthetic route

bromocyane (506-68-3) + methylamine (74-89-5) → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
Stage #1: bromocyane; methylamine In tetrahydrofuran at -10 - -5℃; for 1h; Stage #2: With ammonium nitrate In tetrahydrofuran at 130℃; for 8h; Stage #3: With sulfuric acid at -5 - 0℃; for 0.5h;	88.6%

methylamine (74-89-5) + cyanogen chloride (506-77-4) → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
Stage #1: methylamine; cyanogen chloride With sodium carbonate In tetrahydrofuran at -10 - -5℃; for 1h; Stage #2: With ammonium nitrate In tetrahydrofuran at 130℃; for 8h; Stage #3: With sulfuric acid at -5 - 0℃; for 0.5h;	86%

N-nitro-N'-methyl thiourea → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
With monomethanolamine In methanol at 20 - 80℃; for 4.75h; Temperature;	85%

nitroguanidine (556-88-7) + methylamine (74-89-5) → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
In water at 10 - 30℃; for 5h; Temperature; Reagent/catalyst; Sealed tube;	79.58%
at 60 - 70℃;

nitroguanidine (556-88-7) + methylamine hydrochloride (593-51-1) → N-methyl-N'-nitroguanidine (4245-76-5) + N',N''-dimethyl-N-nitroguanidine (101250-97-9)

Conditions	Yield
With potassium hydroxide

methyl-guanidine; sulfate (1866-88-2, 126979-75-7, 598-12-9) → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
With sulfuric acid; potassium nitrate

methyl nitrocarbamimidothioate (2986-25-6) + methylamine (74-89-5) → N-methyl-N'-nitroguanidine (4245-76-5)

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + nitric acid (7697-37-2) → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
at -40℃;

MNNG (6810-09-9) + nitric acid (7697-37-2) → N-methyl-N'-nitroguanidine (4245-76-5)

1-methylguanidine (471-29-4) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2) → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
at 25℃; Rate constant;
at 15 - 45℃; Equilibrium constant;

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + N-methylaniline (100-61-8) + ethanol <75 percent > → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
at 83℃;

N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7) + ethanol <95 percent > → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
bei laengerem Kochen;

methylguanidine nitrate → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
With sulfuric acid

N-methylguanidine nitrate (546-82-7) + concentrated H2SO4 → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
unter starker Kuehlung;

CYANAMID (420-04-2) + sulfuric acid (7664-93-9) + butan-1-ol (71-36-3) → N-methyl-N'-nitroguanidine (4245-76-5)

formaldehyd (50-00-0) + N-methyl-N'-nitroguanidine (4245-76-5) → 3-methyl-4-(nitromethylidene)-1,3,5-oxadiazinane

Conditions	Yield
With sulfuric acid; acetic acid at 70℃; for 9h;	98.5%

formaldehyd (50-00-0) + N-methyl-N'-nitroguanidine (4245-76-5) → 3,6-dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine (153719-38-1)

Conditions	Yield
With sulfuric acid; acetic acid In water at 46 - 78℃; for 14h; Temperature; Large scale;	85%
With acetic acid at 70℃; for 8h;

N-methyl-N'-nitroguanidine (4245-76-5) → N-methyl-N'-nitrosoguanidine (13830-58-5)

Conditions	Yield
With ethanol; ammonium chloride; zinc at 10 - 15℃;
With methanol; nickel under 88260.9 Torr;

N-methyl-N'-nitroguanidine (4245-76-5) → N-Methyl-N'-nitro-N-nitrosoguanidine (70-25-7)

Conditions	Yield
With nitric acid; sodium nitrite at 10℃;

N-methyl-N'-nitroguanidine (4245-76-5) → MNNG (6810-09-9)

Conditions	Yield
With nitric acid; acetic anhydride

N-methyl-N'-nitroguanidine (4245-76-5) → 1-Amino-3-methylguanidine (31106-59-9)

Conditions	Yield
With platinum(IV) oxide; acetic acid under 95616 Torr; Hydrogenation;

N-methyl-N'-nitroguanidine (4245-76-5) + ethyl acetoacetate (141-97-9) → 3,6-dimethyl-2-nitroamino-3H-pyrimidin-4-one (100114-70-3)

N-methyl-N'-nitroguanidine (4245-76-5) + methylamine (74-89-5) → 1,3,5-trimethyl-[1,3,5]triazinane-2,4,6-triylidenetriamine (34653-93-5) + N,N'-dimethyl-guanidine (3324-71-8)

Conditions	Yield
With water under 4927.9 Torr;

N-methyl-N'-nitroguanidine (4245-76-5) + methylamine (74-89-5) → N-Methylurea (598-50-5)

Conditions	Yield
With water

N-methyl-N'-nitroguanidine (4245-76-5) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → N-methyl-N'-nitro-N-(4-nitro-benzenesulfonyl)-guanidine

N-methyl-N'-nitroguanidine (4245-76-5) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → N-(N-acetyl-sulfanilyl)-N-methyl-N'-nitro-guanidine

N-methyl-N'-nitroguanidine (4245-76-5) + Sodium; (Z)-3-benzo[1,3]dioxol-5-yl-2-ethoxycarbonyl-propen-1-olate + 4-{[(2-aminoethyl)thio]methyl}-5-methylimidazole (38585-67-0) → SKF 93586 dihydrochloride (116608-85-6) + 2-<2-(5-methyl-4-imidazolylmethylthio)ethylamino>-1-methyl-5-(3,4-methylenedioxybenzyl)-4-pyrimidone dihydrochloride (116637-15-1)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

N-methyl-N'-nitroguanidine (4245-76-5) + aqueous sulfuric acid (72-81 percent ) → 1-methylguanidine (471-29-4)

Conditions	Yield
at 15 - 45℃; Rate constant; Hydrolysis;

N-methyl-N'-nitroguanidine (4245-76-5) + aqueous sulfuric acid (72-99 percent ) → 1-methylguanidine (471-29-4)

Conditions	Yield
at 15 - 45℃; Equilibrium constant; Hydrolysis;

N-methyl-N'-nitroguanidine (4245-76-5) + methylamine (74-89-5) → N,N'-dimethyl-guanidine (3324-71-8) + 1.3.5-trimethyl-isomelamine

Conditions	Yield
With carbon dioxide; water

methanol (67-56-1) + N-methyl-N'-nitroguanidine (4245-76-5) + Raney nickel → N-methyl-N'-nitrosoguanidine (13830-58-5)

Conditions	Yield
under 88260.9 Torr; Hydrogenation;

N-methyl-N'-nitroguanidine (4245-76-5) + ammonium chloride + water (7732-18-5) + zinc → N-methyl-N'-nitrosoguanidine (13830-58-5)

Conditions	Yield
at 10 - 15℃;

N-methyl-N'-nitroguanidine (4245-76-5) + ammonia (7664-41-7) + water (7732-18-5) + zinc → N-methyl-N'-nitrosoguanidine (13830-58-5)

Conditions	Yield
at 10 - 15℃;

Upstream product

• 1866-88-2 methyl-guanidine; sulfate 
• 556-88-7 nitroguanidine 
• 74-89-5 methylamine 
• 2986-25-6 methyl nitrocarbamimidothioate 
• 70-25-7 N-Methyl-N'-nitro-N-nitrosoguanidine 
• 7697-37-2 nitric acid 
• 6810-09-9 MNNG 
• 471-29-4 1-methylguanidine 
• 7664-93-9 sulfuric acid 
• 100-61-8 N-methylaniline 
• 546-82-7 N-methylguanidine nitrate 
• 506-68-3 bromocyane 
• 506-77-4 cyanogen chloride 
• 420-04-2 CYANAMID 

Downstream Products

• 13830-58-5 N-methyl-N'-nitrosoguanidine 
• 70-25-7 N-Methyl-N'-nitro-N-nitrosoguanidine 
• 6810-09-9 MNNG 
• 34653-93-5 1,3,5-trimethyl-[1,3,5]triazinane-2,4,6-triylidenetriamine 
• 3324-71-8 N,N'-dimethyl-guanidine 
• 598-50-5 N-Methylurea 
• 593-85-1 diguanidine carbonate 
• 74-89-5 methylamine 
• 153719-38-1 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine 
• 70-25-7 N-methyl-N''-nitro-N-nitrosoguanidine 
• 153719-38-1 3,6-dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazine-4-amine 
• 153719-38-1 3,6-dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine 
• 1294010-22-2 3-methyl-4-nitriminotetrahydro-1,3,5-oxadiazine 
• 136516-16-0 1,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine 

Relevant articles and documents

Process improvements for the preparation of insecticide clothianidin

This article describes the process improvements for the preparation of the insecticide clothianidin 1. (Z)-1-Methyl-N-nitro-5-propyl-1,3,5-triazinan-2- imine (9) which was obtained by Mannich reaction of (Z)-1-methyl-2- nitroguanidine (5) n-Propylamine an

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Method for preparing 1-methyl-3-nitroguanidine

The invention discloses a method for preparing 1-methyl-3-nitroguanidine. The method comprises the following steps: weighing of process water (mother liquor), methylamine and nitroguanidine, and stirring at a low temperature; gradient heating, heat preservation, and vacuum deamination; and reduction of the temperature of the system, centrifuging and filtering, reusing of the washing solution and the mother liquor, and drying for obtaining the 1-methyl-3-nitroguanidine. The method has the advantages of no acid, low reaction temperature, recyclability of ammonia gas generated by a byproduct, cycle use of the mother liquor and the washing solution, energy saving, environmental protection, white form of the finished product, improvement of the yield and purity, and great values in the field oflow-energy consumption green chemical engineering production.

A N-methyl-N ' nitroguanideine synthesis process

The invention belongs to the technical field of pesticide intermediates, and relates to a N-methyl-N'nitroguanidine synthesis process, which comprises: (1) pouring fuming nitric acid and concentrated sulfuric acid into a reaction bottle, and adding S-methyl isothiourea sulfate under a stirring condition; (2) after completing the reaction, adding ice, carrying out suction filtration, and carrying out vacuum drying to obtain N-nitro methylthiourea powder; (3) pouring methanol into the reaction bottle, adding the dried N-nitro methylthiourea, and adding a methylamine alcohol solution in a dropwise manner at a room temperature; and (4) carrying out a reaction for 3 h at a temperature of 80 DEG C, filtering while hot, cooling, carrying out suction filtration, and carrying out vacuum drying on the filter cake to obtain the N-methyl-N'nitroguanidine solid. According to the process, the reaction condition is optimized, the cost is saved, and the total yield is increased to 85%.