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75-52-5

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Basic Information
CAS No.: 75-52-5
Name: Nitromethane
Article Data: 163
Molecular Structure:
Molecular Structure of 75-52-5 (Nitromethane)
Formula: CH3NO2
Molecular Weight: 61.0403
Synonyms: Nitromethane [UN1261] [Flammable liquid];Nitrometan (Polish);Nitromethane(Methyl Nitrobenzene);Nitrometan;methane, nitro-;Nitrocarbol;Nitrometan [Polish];
EINECS: 200-876-6
Density: 1.055 g/cm3
Melting Point: -29 °C
Boiling Point: 85.1 °C at 760 mmHg
Flash Point: 35 °C
Solubility: 9.5 g/100 mL (20 °C ) in water
Appearance: clear liquid
Hazard Symbols: HarmfulXn,FlammableF,IrritantXi
Risk Codes: 5-10-22
Safety: 41
Transport Information: UN 1261 3/PG 2
PSA: 45.82000
LogP: 0.41610
Synthetic route
75-17-2

formaldoxime

75-52-5

nitromethane

Conditions
ConditionsYield
With dihydrogen peroxide; triethylamine In tert-butyl alcohol at 60℃; under 6000.6 Torr;96.5%
77-78-1

dimethyl sulfate

75-52-5

nitromethane

Conditions
ConditionsYield
With sodium carbonate; sodium nitrite In water at 30℃; for 3h; Reagent/catalyst; Temperature;84%
With sodium nitrite In water at 60℃;75%
With water; sodium carbonate; sodium nitrite zuletzt bei 120grad;
75-76-3

tetramethylsilane

A

75-52-5

nitromethane

B

420-56-4

trimethylsilyl fluoride

Conditions
ConditionsYield
With nitronium tetrafluoborate In sulfolane at 80℃; for 2h; Product distribution; Mechanism; other alkyl- and allylsilanes; other temperature, var. solvents;A 80%
B n/a
2009-83-8

6-chloro-1-hexanol

2483-57-0

methyl 2-nitroacetate

A

75-52-5

nitromethane

B

124-38-9

carbon dioxide

C

6-chlorohexyl 2-nitroacetate

Conditions
ConditionsYield
With di(n-butyl)tin oxide at 100℃; for 1.5h; Sealed tube; Inert atmosphere;A n/a
B n/a
C 76%
111-87-5

octanol

2483-57-0

methyl 2-nitroacetate

A

75-52-5

nitromethane

B

124-38-9

carbon dioxide

C

octyl 2-nitroacetate

Conditions
ConditionsYield
With di(n-butyl)tin oxide at 100℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere;A n/a
B n/a
C 69%
74-88-4

methyl iodide

A

75-52-5

nitromethane

B

624-91-9

methyl nitrite

Conditions
ConditionsYield
With tetrabutylammonium nitrite In chloroform-d1 at 20℃;A 67%
B 28 % Spectr.
With silver(I) nitrite
With silver nitrate
6032-29-7

(+/-)-2-pentanol

2483-57-0

methyl 2-nitroacetate

A

75-52-5

nitromethane

B

124-38-9

carbon dioxide

C

s-pentyl 2-nitroacetate

Conditions
ConditionsYield
With di(n-butyl)tin oxide at 100℃; for 1.5h; Sealed tube; Inert atmosphere;A n/a
B n/a
C 66%
2483-57-0

methyl 2-nitroacetate

107-18-6

allyl alcohol

A

75-52-5

nitromethane

B

124-38-9

carbon dioxide

C

221116-46-7

allyl 2-nitroacetate

Conditions
ConditionsYield
With di(n-butyl)tin oxide at 100℃; for 1.5h; Sealed tube; Inert atmosphere;A n/a
B n/a
C 66%
64-17-5

ethanol

2483-57-0

methyl 2-nitroacetate

A

626-35-7

nitroacetic acid ethyl ester

B

75-52-5

nitromethane

C

124-38-9

carbon dioxide

Conditions
ConditionsYield
With di(n-butyl)tin oxide at 100℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere;A 61%
B n/a
C n/a
66-27-3

Methyl methanesulfonate

A

75-52-5

nitromethane

B

624-91-9

methyl nitrite

Conditions
ConditionsYield
With tetrabutylammonium nitrite In chloroform-d1 at 20℃;A 60%
B 29 % Spectr.
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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 100 ppm
ACGIH TLV: TWA 20 ppm; Confirmed Animal Carcinogen with Unknown Relevance to Humans
DFG MAK: 100 ppm (250 mg/m3)
DOT Classification:  3; Label: Flammable Liquid

Analytical Methods

For occupational chemical analysis use NIOSH: Nitromethane, 2527.

 

Specification

The Nitromethane, with the CAS registry number 75-52-5, is also known as Methane, nitro-. It belongs to the product categories of Organics; Analytical Chemistry; Solvents for HPLC & Spectrophotometry; Solvents for Spectrophotometry; Analytical Reagents for General Use; I-N, Puriss p.a.; Puriss p.a.; Reagent Grade Solvents; Reagent Semi-Bulk Solvents; Reagent Solvents; Spectrophotometric Grade Solvents; Spectrophotometric Grade Solvents; Reagent Plus(R) Solvent Grade Products; ReagentPlus(R) Solvents; Chromasolv for HplcSolvents; Chromasolv Solvents (Hplc, LC-MS); Chromasolv(R) Hplc Grade Solvents; Alpha Sort; N-O; Volatiles/ Semivolatiles; ACS Grade Solvents; ACS GradeSemi-Bulk Solvents; ACS Grade Solvents; Amber Glass Bottles; Carbon Steel Cans with NPT Threads; Solvent Bottles. Its EINECS registry number is 200-876-6. This chemical's molecular formula is CH3NO2 and molecular weight is 61.04. Its IUPAC name is called nitromethane. What's more, this chemical's classification code is Tumor data.

Physical properties of Nitromethane: (1)#H bond acceptors: 3; (2)Index of Refraction: 1.358; (3)Molar Refractivity: 12.7 cm3; (4)Molar Volume: 57.8 cm3; (5)Surface Tension: 25.9 dyne/cm; (6)Density: 1.055 g/cm3; (7)Flash Point: 35 °C; (8)Enthalpy of Vaporization: 31.2 kJ/mol; (9)Boiling Point: 85.1 °C at 760 mmHg; (10)Vapour Pressure: 78.6 mmHg at 25°C.

Preparation of Nitromethane: this chemical is produced industrially by treating propane with nitric acid at 350–450 °C (622–842 °F). In addition, it can be prepared in other methods that are of instructional value. The reaction of sodium chloroacetate with sodium nitrite in aqueous solution produces this compound:

ClCH2COONa + NaNO2 + H2O → CH3NO2 + NaCl + NaHCO3

Uses of Nitromethane: The principal use of nitromethane is as a stabilizer for chlorinated solvents, which are used in dry cleaning, semiconductor processing, and degreasing. It is also used most effectively as a solvent or dissolving agent for acrylate monomers, such as cyanoacrylates. In organic synthesis nitromethane is employed as a one carbon building block. In more specialized organic synthesis, nitromethane serves as a Michael donor, adding to α,β-unsaturated carbonyl compounds via 1,4-addition in the Michael reaction. In a minor application, nitromethane is used as a fuel in racing, particularly drag racing, as well as for rockets and model airplanes and commonly referred to in this context as "nitro". Nitromethane can also be used as a monopropellant, i.e., a fuel that burns without added oxygen. The following equation describes this process:

2 CH3NO2 → 2 CO + 2 H2O + H2 + N2

When you are using this chemical, please be cautious about it. This chemical is harmful if swallowed. In addition, it is highly flammable and irritant. If heating may cause an explosion. In case of fire and/or explosion do not breathe fumes.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C[N+](=O)[O-]
(2)InChI: InChI=1S/CH3NO2/c1-2(3)4/h1H3
(3)InChIKey: LYGJENNIWJXYER-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 800mg/kg (800mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
AMA Archives of Industrial Health. Vol. 11, Pg. 102, 1955.
dog LDLo oral 125mg/kg (125mg/kg) KIDNEY, URETER, AND BLADDER: CHANGES IN BOTH TUBULES AND GLOMERULI

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"
AMA Archives of Industrial Health. Vol. 11, Pg. 102, 1955.
guinea pig LCLo inhalation 5000ppm/3H (5000ppm)   Journal of Industrial Hygiene and Toxicology. Vol. 22, Pg. 315, 1940.
monkey LCLo inhalation 1000ppm (1000ppm)   Industrial Medicine. Vol. 16, Pg. 441, 1947.
mouse LCLo inhalation 18gm/m3/2H (18000mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 93, 1982.
mouse LD50 intraperitoneal 110mg/kg (110mg/kg)   Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 10(6), Pg. 53, 1976.
mouse LD50 oral 950mg/kg (950mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 32(9), Pg. 9, 1967.
rabbit LCLo inhalation 5000ppm/6H (5000ppm)   Journal of Industrial Hygiene and Toxicology. Vol. 22, Pg. 315, 1940.
rabbit LD skin > 2gm/kg (2000mg/kg)   National Technical Information Service. Vol. OTS0516767,
rabbit LDLo intravenous 750mg/kg (750mg/kg)   AMA Archives of Industrial Health. Vol. 11, Pg. 102, 1955.
rabbit LDLo oral 750mg/kg (750mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ATAXIA
Journal of Industrial Hygiene and Toxicology. Vol. 22, Pg. 315, 1940.
rat LCLo inhalation 12750mg/m3/1H (12750mg/m3)   National Technical Information Service. Vol. OTS0516767,
rat LD50 oral 940mg/kg (940mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 32(9), Pg. 9, 1967.
rat LDLo intraperitoneal 1500mg/kg (1500mg/kg)   Bulletin de la Societe de Pharmacie de Lille. Vol. (1), Pg. 29, 1973.