Nitromethane
General
Systematic name	nitromethane
Other names	nitrocarbol
Molecular formula	CH3NO2
SMILES	C[N+]([O-])=O
Molar mass	61.04 g/mol
Appearance	colorless liquid
CAS number	[200-876-6]
Properties
Density and phase	1.138 g/cm3, liquid
Solubility in water	miscible
Melting point	-29 °C (? K)
Boiling point	100-103 °C (? K)
Acidity (pKa)	10.2
Viscosity	? cP at ? °C
Hazards
MSDS	External MSDS
Main hazards	Flammable, harmful
NFPA 704
Flash point	35 °C
R/S statement	R: R5 R10 R22 S: S41
RTECS number	PA9800000
Related compounds
Related nitro compounds	nitroethane
Related compounds	methyl nitrite methyl nitrate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Nitromethane is an organic compound with the chemical formula CH₃NO₂. It is the simplist organic nitro compound. It is a slightly viscous, highly polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent. As an intermediate in organic synthesis, it is used widely in the manufacture of pharmaceuticals, pesticides, explosives, fibers, and coatings. It also finds use as a racing fuel. Image File history File links Nitromethane2. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... A substance is soluble in a fluid if it dissolves in that fluid. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid. ... In chemistry and biochemistry, acid dissociation constant, the acidity constant, or the acid-ionization constant (Ka) is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ... The pitch drop experiment at the University of Queensland. ... The poise (P) is the cgs unit of viscosity, 1 P = 1 g·cm-1·s-1 The SI analog is 1 pascal second (Pa·s) = 1 kg·m-1·s-1 = 10 P. It is named after Jean Louis Marie Poiseuille. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Worker safety and health is the prevention and reduction of the number of occupational safety and health hazards at the places of employment, providing safe and healthful working conditions. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... The flash point of a fuel is the lowest temperature at which it can form an ignitable mix with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... Wikipedia does not yet have an article with this exact name. ... The chemical compound methyl nitrite is an Alkyl nitrite. ... Methyl nitrate has formula CH3NO3. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and gases containing carbon. ... Nitro compounds are organic compounds that contain one or more nitro functional groups (-NO2). ... Organic synthesis is the construction of organic molecules via chemical processes. ...

Reactions

The weak acidicity of nitromethane allows it to undergo reactions analogous to those of carbonyl compounds:

• Nitromethane can add to aldehydes in 1,2-addition in the nitroaldol reaction
• Nitromethane can act as a Michael donor, adding to α,β-unsaturated carbonyl compounds by 1,4-addition in the Michael reaction

An aldehyde is either a functional group consisting of a terminal carbonyl group or a compound containing a terminal carbonyl group. ... The Nitroaldol reaction or Henry reaction 1 is a aldol type reaction between an aldehyde and nitromethane. ... The Michael reaction is an intermolecular aldol reaction followed by a base catylized elimination reaction. ...

Use as an engine fuel

Nitromethane is used as a fuel in racing, particularly drag racing, to provide more power. In this context, it is commonly referred to as "nitro" or "top-fuel". A Top Fuel dragster, the ultimate in drag racing. ...

The oxygen in the molecular structure of nitromethane enables it to burn with much less atmospheric oxygen in comparison to hydrocarbons such as gasoline. Part of the oxygen needed for combustion is carried by nitromethane itself. 14.6 kg of air are needed to burn one kg of gasoline, but only 1.7 kg of air are needed to burn one kg of nitromethane. Since an engine’s cylinder can only contain a limited amount of air on each stroke, 8.7 times more nitromethane than gasoline can be burned in one stroke. However, nitromethane has a lower energy density. Gasoline provides 18,000 BTU/pound (42 MJ/kg). Nitromethane provides only 5,000 BTU/pound (12 MJ/kg). [1]. The net result is that nitromethane provides 2.4 times more power per stroke than gasoline. General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... The British thermal unit (BTU) is a non-metric unit of energy, used in the United States and, to a certain extent, the UK. The SI unit is the joule (J), which is used by most other countries. ... The joule (symbol: J) is the SI unit of energy, or work. ...

The flamefront of combusting nitromehane does not move as quickly as it does for gasoline, meaning that there is not enough time to burn all the nitromethane in the cylinder when the engine is running at high RPM. When the exhaust valves open, nitromethane flows out through the exhaust pipes where it is ignited producing the visible flames characteristic of dragsters and funny cars. Drag racing is a form of auto racing in which cars attempt to complete a fairly short, straight and level course in the shortest amount of time. ... Funny Car is an NHRA drag racing car class. ...

In addition, model aircraft and car fuel contains from 0% to 65% nitromethane. It has also been used as a model rocket fuel. Aircraft modeling or aeromodelling is a hobby that has been popular since the 1930s. ... Metal die-cast model of a Checker taxicab A model car is a toy which represents an automobile, generally reproducing the shapes of actually produced vehicles, as a small scale model. ...

Explosive properties

Nitromethane was not known to be an explosive until the 1950's. That's when a whole railroad tanker car of it exploded, leaving a huge crater. (See the Encyclopedida of Chemical Technology) Much testing later it was realized that nitromethane was a more energetic high explosive than TNT. However TNT has a higher velocity of detonation and brisanance (shattering power against hard targets). Both of these explosives are oxygen poor and some benefits are gained from mixing with an oxidisor; such as ammonium nitrate. One graphic example of this was the use of nitromethane and ammonium nitrate on the Alfred P. Murrah Federal Building at Oklahoma City. Pure nitromethane is a very insensitive explosive, but even so inhibitors may be used to reduce the hazards. The tank car explosion was speculated to be due to abidiatic compression, a hazard common to all liquid explosives. This is when small entrained air bubbles compress and superheat with rapid rises in pressure (gas-laws). It was thought that an operator rapidly snapped shut a valve creating a 'hammer-lock' pressure surge. Nitromethane can be sensitized by adding base as so to raise the pH. Avoid base contamination if increased explosive sensitivity is unwanted. If one desires more sensitity, then a small amount of a (basic) primary amine is mixed in. This renders nitromethane sensitive enouph to detonate with larger blasting caps and without (?) an intermediate booster. Purchasing nitromethane may bring unwanted attention if the final destiny of the chemical is questionable. Aerial view of Alfred P. Murrah building after bombing The Alfred P. Murrah Federal Building was a United States Government complex located in downtown Oklahoma City, Oklahoma on 200 N.W. 5th Street that was the target of the Oklahoma City bombing in 1995. ...