N-Nitroso-N-methylurea supplier

Name
1-Methyl-1-nitrosourea
EINECS 211-678-4
CAS No. 684-93-5
Article Data42
CAS DataBase
Density 1.46 g/cm³
Solubility Soluble. <0.1 g/100 mL at 18 C
Melting Point 119-124°C
Formula C₂H₅N₃O₂
Boiling Point 164.3 °C at 760 mmHg
Molecular Weight 103.081
Flash Point 53.1 °C
Transport Information UN 1325 4.1/PG 2
Appearance Off-white to pale yellow solid
Safety 53-45-24/25-22
Risk Codes 45-46-61-11-25
Molecular Structure
Hazard Symbols F; T
Synonyms 1-methyl-1-nitroso-urea;Urea,1-methyl-1-nitroso- (6CI,8CI);1-Methyl-1-nitrosourea;1-Nitroso-1-methylurea;MNU;Methylnitrosourea;N-Nitroso-N-methylcarbamide;N-Nitroso-N-methylurea;NMH;NMM;NMU;NSC 23909;Nitrosomethylurea;
PSA 75.76000
LogP 0.37860

Synthetic route

: 598-50-5
N-Methylurea

: 684-93-5
1-methyl-1-nitrosourea

Conditions

Conditions	Yield
With dinitrogen tetroxide impregnated on activated charcoal In dichloromethane at 20℃; for 4h;	90%
With cross-linked polyvinylpyrrolidone*N2O4; dinitrogen tetraoxide In dichloromethane at 20℃; for 3.33333h;	89%
With hydrogenchloride; sodium nitrite In 2-methyltetrahydrofuran; diethyl ether; water at 25℃; under 6000.6 Torr; for 1.3h; Flow reactor;	83%

: 57-13-6
urea

: 74-89-5
methylamine

: 684-93-5
1-methyl-1-nitrosourea

Conditions

Conditions	Yield
Stage #1: urea; methylamine With hydrogenchloride In water for 3h; Reflux; Stage #2: With sodium nitrite at 0 - 20℃;	70%
With hydrogenchloride In water at -15 - 110℃;

: 1-methylurea nitrite

: 684-93-5
1-methyl-1-nitrosourea

Conditions

Conditions	Yield
With sulfuric acid; water at 0℃;	51%

: 623-59-6
N-acetyl-N'-methylurea

: 684-93-5
1-methyl-1-nitrosourea

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite
Stage #1: N-acetyl-N'-methylurea With hydrogenchloride at 100℃; for 0.0666667h; Stage #2: With sodium nitrite cooling; Further stages.;	8 g
Stage #1: N-acetyl-N'-methylurea With hydrogenchloride In water at 100℃; for 0.2h; Stage #2: With sodium nitrite In water Cooling with ice;	9 g

: 590-28-3
potassium cyanate

: 593-51-1
methylamine hydrochloride

: 684-93-5
1-methyl-1-nitrosourea

: 593-51-1
methylamine hydrochloride

: 57-13-6
urea

: 684-93-5
1-methyl-1-nitrosourea

Conditions

Conditions	Yield
With water bei Siedetemperatur und anschliessende Umsetzung mit NaNO2 und verd. H2SO4 unter Kuehlung;
Stage #1: methylamine hydrochloride; urea In water at 105℃; for 3.5h; Stage #2: With sodium nitrite In water at 40℃; for 0.25h; Stage #3: With sulfuric acid In tetrahydrofuran; water at 0 - 5℃; for 2h;
Stage #1: methylamine hydrochloride; urea In water at 105℃; for 3.5h; Stage #2: With sodium nitrite In water at 40℃; for 0.25h;

: 33868-17-6
Methylnitrosocyanamid

: 684-93-5
1-methyl-1-nitrosourea

Conditions

Conditions	Yield
With sulfuric acid In dichloromethane

nitrate methylurea: nitrate methylurea

: 684-93-5
1-methyl-1-nitrosourea

Conditions

Conditions	Yield
With water; sodium nitrite

: 7732-18-5
water

: 598-11-8
methyluronium nitrate

sodium nitrite: sodium nitrite

: 684-93-5
1-methyl-1-nitrosourea

...Expand

: 60-35-5
acetamide

: 684-93-5
1-methyl-1-nitrosourea

Conditions

Conditions	Yield
Stage #1: acetamide With bromine; sodium hydroxide In water at 100℃; Stage #2: With hydrogenchloride at 100℃; for 0.002h; Stage #3: With sodium nitrite In water Cooling with ice;	9 g

: 684-93-5
1-methyl-1-nitrosourea

: 18467-77-1
dikegulac

: 52507-90-1
methyl 2,3:4,6-di-O-isopropylidene-α-L-xylo-2-hexulofuranosonate

Conditions

Conditions	Yield
With potassium hydroxide 1.) ether, ice-bath cooling, 2 min, 2.) methanol, gently warming;	100%

: 684-93-5
1-methyl-1-nitrosourea

: 611-71-2
(R)-Mandelic Acid

: 20698-91-3
(R)-methyl mandelate

Conditions

Conditions	Yield
With potassium hydroxide In diethyl ether; water at 0℃; for 0.25h;	100%

: 684-93-5
1-methyl-1-nitrosourea

: 19835-38-2
1-adamantylacetyl chloride

: 27174-66-9
1-diazo-3-(1-adamantyl)-2-propanone

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With potassium hydroxide In diethyl ether at 0℃; for 0.25h; Inert atmosphere; Stage #2: 1-adamantylacetyl chloride In diethyl ether at 0 - 20℃; Inert atmosphere;	100%

: 684-93-5
1-methyl-1-nitrosourea

: 1513-60-6
ethyl 4,4,4-trifluoro-3-(trifluoromethyl)crotonate

: 390388-85-9
4-ethoxycarbonyl-3,3-bis(trifluoromethyl)-2-pyrazoline

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With potassium hydroxide In diethyl ether at 0℃; Stage #2: ethyl 4,4,4-trifluoro-3-(trifluoromethyl)crotonate In diethyl ether at 20℃; for 1h;	99%

: 684-93-5
1-methyl-1-nitrosourea

: 5123-55-7
Nα-phthaloyl-L-phenylalanine

: 14380-85-9
(S)-methyl 2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

Conditions

Conditions	Yield
With potassium hydroxide In diethyl ether; water	99%

: 684-93-5
1-methyl-1-nitrosourea

: 3-(benzofuran-2-yl)isoxazol-5(4H)-one

: 3-(benzofuran-2-yl)-5-methoxyisoxazole

Conditions

Conditions	Yield
With potassium hydroxide In diethyl ether; water for 0.5h;	99%

: 177949-92-7
(E)-4,4,5,5-tetramethyl-2-(3-methylbut-1-en-1-yl)-1,3,2-dioxaborolane

: 684-93-5
1-methyl-1-nitrosourea

: rac-trans-2-[2-isopropylcyclopropyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With potassium hydroxide In diethyl ether; water for 0.0833333h; Cooling with ice; Stage #2: (E)-4,4,5,5-tetramethyl-2-(3-methylbut-1-en-1-yl)-1,3,2-dioxaborolane With palladium diacetate In diethyl ether; water Cooling with ice;	99%
With palladium diacetate; potassium hydroxide In diethyl ether; water at 20℃;	99%

: 684-93-5
1-methyl-1-nitrosourea

: 36911-54-3
spiro<2.4>hepta-4,6-diene 2,6>deca-3,8-diene)-10-spirocyclopropane>

: 139537-61-4
dispiro2,6.08,10>undec-4-ene-12',1''-cyclopropane>

Conditions

Conditions	Yield
With potassium hydroxide; bis(benzonitrile)palladium(II) dichloride In dichloromethane at 10℃; for 0.333333h;	98%

: 684-93-5
1-methyl-1-nitrosourea

: undecacyclo[10.9.0.01,5.02,13.02,19.03,7.06,11.08,13.012,16.014,18.017,21]henicosane-4-anti-carboxylic acid

: methyl undecacyclo[10.9.0.01,5.02,13.02,19.03,7.06,11.08,13.012,16.014,18.017,21]henicosane-4-anti-carboxylate

Conditions

Conditions	Yield
With potassium hydroxide In diethyl ether; dichloromethane; water for 2h;	98%

: 498-66-8
norborn-2-ene

: 684-93-5
1-methyl-1-nitrosourea

: 5744-22-9
exo-3,4-diazatricyclo[5.2.1.02,6]dec-3-ene

Conditions

Conditions	Yield
With potassium hydroxide In diethyl ether; water at -5℃; for 1h;	98%

: 2-But-2-ynyl-2-[(E)-3-((1S,2R)-2-carboxy-cyclopropyl)-allyl]-malonic acid dimethyl ester

: 684-93-5
1-methyl-1-nitrosourea

: dimethyl trans-2-but-2-ynyl-2-[3-(2-methoxycarbonyl-cyclopropyl)-allyl]-malonate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With potassium hydroxide In diethyl ether; water at 0℃; Stage #2: 2-But-2-ynyl-2-[(E)-3-((1S,2R)-2-carboxy-cyclopropyl)-allyl]-malonic acid dimethyl ester In diethyl ether Further stages.;	98%

: 684-93-5
1-methyl-1-nitrosourea

: C28H28O12S2

: C29H30O12S2

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With potassium hydroxide Stage #2: C28H28O12S2	98%

: 684-93-5
1-methyl-1-nitrosourea

: 15042-01-0
5,6-O-isopropylidene-L-ascorbic acid

: 58650-92-3
5,6-O-isopropylidene-3-O-methyl-L-ascorbic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol at -20℃;	97%

: 684-93-5
1-methyl-1-nitrosourea

: 760179-31-5
1-(1-fluorovinyl)-1-methylcyclopropane

: 1-fluoro-1-(1-methylcyclopropyl)cyclopropane

Conditions

Conditions	Yield
With potassium hydroxide; palladium(II) acetylacetonate In dichloromethane; pentane	97%

: 684-93-5
1-methyl-1-nitrosourea

: 182156-01-0
2-[1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-succinic acid 1-ethyl ester

: 182156-02-1
2-[1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-succinic acid 1-ethyl ester 4-methyl ester

Conditions

Conditions	Yield
With triethylamine In various solvent(s) for 48h; Ambient temperature;	96%

: 684-93-5
1-methyl-1-nitrosourea

: (4R,7S,9S,E)-9-(benzyloxy)-7-hydroxy-4-(methoxymethoxy)dec-2-enoic acid

: (4R,7S,9S,E)-methyl-9-(benzyloxy)-7-hydroxy-4-(methoxymethoxy)dec-2-enoate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With potassium hydroxide In diethyl ether at 0℃; for 0.166667h; Stage #2: (4R,7S,9S,E)-9-(benzyloxy)-7-hydroxy-4-(methoxymethoxy)dec-2-enoic acid In diethyl ether for 0.166667h;	96%

: 684-93-5
1-methyl-1-nitrosourea

: 762-42-5
dimethyl acetylenedicarboxylate

: 603-35-0
triphenylphosphine

: dimethyl 2-(methyl{[(nitrosomethyl)amino]carbonyl}amino)-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions

Conditions	Yield
In hexane; ethyl acetate at 20℃; for 1.5h;	95%

...Expand

: 684-93-5
1-methyl-1-nitrosourea

: 18942-46-6
N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine

: 541-41-3
chloroformic acid ethyl ester

: 1120344-81-1
[(R)-3-diazo-1-(4-methoxy-benzylsulfanylmethyl)-2-oxo-propyl]-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine; chloroformic acid ethyl ester With 4-methyl-morpholine In tetrahydrofuran at -25℃; for 1h; Stage #2: 1-methyl-1-nitrosourea With potassium hydroxide In tetrahydrofuran; diethyl ether; water at -25 - 20℃; for 3h;	95%

...Expand

: 684-93-5
1-methyl-1-nitrosourea

: 84-79-7
Lapachol

: 17241-45-1
2-methoxylapachol

Conditions

Conditions	Yield
With potassium hydroxide at 0℃; Inert atmosphere;	95%

: 684-93-5
1-methyl-1-nitrosourea

: 5-bromo-1-nitro-2-propoxy-3-vinylbenzene

: 5-bromo-1-cyclopropyl-3-nitro-2-propoxybenzene

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With sodium hydroxide In diethyl ether; water at 0℃; for 0.25h; Stage #2: 5-bromo-1-nitro-2-propoxy-3-vinylbenzene With palladium diacetate In diethyl ether; dichloromethane at 0℃; for 1h;	95%

: 684-93-5
1-methyl-1-nitrosourea

: 914257-11-7
amphidinin B

: 1269803-21-5
dimethyl ester of amphidinin B

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With sodium hydroxide In water Stage #2: amphidinin B In diethyl ether at 0℃; Inert atmosphere;	94%

: 684-93-5
1-methyl-1-nitrosourea

: 203661-69-2
tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

: 1250994-14-9
tert-butyl 2-oxo-8-azaspiro[4.5]decane-8-carboxylate

Conditions

Conditions	Yield
With potassium hydroxide In 2-methyltetrahydrofuran; methanol	93%

: 684-93-5
1-methyl-1-nitrosourea

: 634606-12-5
4-(5-iodo-2-formyl-3-methyl-1H-4-pyrrolyl)butanoic acid

: 634606-13-6
methyl 4-(5-iodo-2-formyl-3-methyl-1H-4-pyrrolyl)butanoate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With potassium hydroxide In diethyl ether at 0℃; for 0.166667h; Stage #2: 4-(5-iodo-2-formyl-3-methyl-1H-4-pyrrolyl)butanoic acid In methanol; diethyl ether for 0.166667h;	90%

: 684-93-5
1-methyl-1-nitrosourea

: 1371608-84-2
(R)-2-(4-cyano-3-(trifluoromethyl)phenylamino)-3-hydroxypropanoic acid

: 1371608-85-3
(R)-methyl-2-(4-cyano-3-(trifluoromethyl)phenylamino)-3-hydroxypropanoate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With potassium hydroxide In diethyl ether Stage #2: (R)-2-(4-cyano-3-(trifluoromethyl)phenylamino)-3-hydroxypropanoic acid In tetrahydrofuran; diethyl ether at 0℃; for 1h;	90%

: 684-93-5
1-methyl-1-nitrosourea

: 2,3-diethyl-7-isobutyl-8-methyl-(10H)-dipyrrin-1-one-9-carboxylic acid

: 2,3-diethyl-7-isobutyl-8-methyl-9-carbomethoxy-(10H)-dipyrrin-1-one

Conditions

Conditions	Yield
Stage #1: 1-methyl-1-nitrosourea With potassium hydroxide In diethyl ether; water at 0℃; Stage #2: 2,3-diethyl-7-isobutyl-8-methyl-(10H)-dipyrrin-1-one-9-carboxylic acid In methanol; diethyl ether; water at 20℃; for 0.583333h;	90%

: 684-93-5
1-methyl-1-nitrosourea

: 1093262-44-2
4-chloro-N-({4-chloro-3-[(3-cyano-5-ethenylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

: 1093262-46-4
4-chloro-N-({4-chloro-3-[(3-cyano-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Conditions

Conditions	Yield
With potassium hydroxide; palladium diacetate In diethyl ether; dichloromethane; water at 0℃; for 1h;	90%

: 684-93-5
1-methyl-1-nitrosourea

: 356-77-4
1,1,2,2-tetrafluoro-3-vinylcyclobutane

: 3-cyclopropyl-1,1,2,2-tetrafluorocyclobutane

Conditions

Conditions	Yield
With palladium(II) acetylacetonate In potassium hydroxide; dichloromethane at 5 - 8℃;	89%

: 684-93-5
1-methyl-1-nitrosourea

: 697-14-3
2-chloro-1,1,2-trifluoro-3-vinylcyclobutane

: 2-chloro-3-cyclopropyl-1,1,2-trifluorocyclobutane

Conditions

Conditions	Yield
With palladium(II) acetylacetonate In potassium hydroxide; dichloromethane; pentane at 5 - 8℃;	89%

: 684-93-5
1-methyl-1-nitrosourea

: 4-(prop-2-yn-1-yl)-3-(quinolin-2-yl)isoxazol-5-ol

: 5-methoxy-4-(prop-2-yn-1-yl)-3-(quinolin-2-yl)isoxazole

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; diethyl ether; water	89%

N-Nitroso-N-methylurea 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. 56.(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) ; Human Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 17 ,1978,p. 227.(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 . 17 ,1978,p. 227.(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) , IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 1 ,1972,p. 125.(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) . EPA Genetic Toxicology Program. Community Right-To-Know List. Reported in EPA TSCA Inventory.

N-Nitroso-N-methylurea Specification

N-Methyl-N-nitrosourea(CAS NO.684-93-5) is a highly reliable carcinogen, mutagen, and teratogen. NMU is an alkylating agent, and exhibits its toxicity by transferring its methyl group to nucleobases in nucleic acids. It is used as precursor of diazomethane. It has a cytotoxicity effect. This product contains an undetermined amount of water. N-Methyl-N-nitrosourea is teratogenic and embryotoxic, resulting in craniofacial (cleft palate) and skeletal defects, increased fetal resorption, and fetal growth retardation.

Physical properties about N-Nitroso-N-methylurea are: (1)ACD/LogP: -0.302; (2)ACD/LogD (pH 5.5): -0.30; (3)ACD/LogD (pH 7.4): -0.30; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 16.32; (7)ACD/KOC (pH 7.4): 16.32; (8)#H bond acceptors: 5; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.545; (12)Molar Refractivity: 22.2 cm³; (13)Molar Volume: 70.241 cm³; (14)Polarizability: 8.801 10-24cm³; (15)Surface Tension: 61.148998260498 dyne/cm; (16)Density: 1.468 g/cm³; (17)Flash Point: 53.143 °C; (18)Enthalpy of Vaporization: 40.078 kJ/mol; (19)Boiling Point: 164.26 °C at 760 mmHg; (20)Vapour Pressure: 1.98300004005432 mmHg at 25°C

When you are using this chemical, please be cautious about it as the following:
1. Avoid exposure - obtain special instruction before use;
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
3. Avoid contact with skin and eyes;
4. Do not breathe dust;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C2H5N3O2/c1-5(4-7)2(3)6/h1H3,(H2,3,6);
(2)InChIKey=ZRKWMRDKSOPRRS-UHFFFAOYSA-N;
(3)SmilesN(C(N)=O)(N=O)C

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
hamster	LD50	subcutaneous	113mg/kg (113mg/kg)		British Journal of Cancer. Vol. 29, Pg. 359, 1974.
hamster	LDLo	intravenous	42mg/kg (42mg/kg)		Journal of Pathology and Bacteriology. Vol. 92, Pg. 35, 1966.
mammal (species unspecified)	LD50	intravenous	110mg/kg (110mg/kg)		Gann Monograph on Cancer Research. Vol. 17, Pg. 107, 1975.
mammal (species unspecified)	LD50	oral	110mg/kg (110mg/kg)		Gann Monograph on Cancer Research. Vol. 17, Pg. 107, 1975.
mouse	LD50	intraperitoneal	144mg/kg (144mg/kg)		Cancer Research. Vol. 30, Pg. 11, 1970.
rat	LD50	intraperitoneal	110mg/kg (110mg/kg)		Nature. Vol. 222, Pg. 1064, 1969.
rat	LD50	intravenous	108mg/kg (108mg/kg)		Naunyn-Schmiedebergs Archiv fuer Pharmakologie und Experimentelle Pathologie. Vol. 257, Pg. 296, 1967.
rat	LD50	oral	110mg/kg (110mg/kg)		Zeitschrift fuer Krebsforschung. Vol. 69, Pg. 103, 1967.
rat	LDLo	implant	30mg/kg (30mg/kg)	KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Chemico-Biological Interactions. Vol. 5, Pg. 139, 1972.

Product Name

1-Methyl-1-nitrosourea

Synthetic route

N-Nitroso-N-methylurea Consensus Reports

N-Nitroso-N-methylurea Specification

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