Names | |
---|---|
Preferred IUPAC name Propane-1,2-diamine | |
Other names 1,2-Propanediamine | |
Identifiers | |
3D model (JSmol) | |
605274 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.001.051 |
EC Number |
|
25709 | |
MeSH | 1,2-diaminopropane |
PubChem CID | |
RTECS number |
|
UNII | |
UN number | 2258 |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C3H10N2 | |
Molar mass | 74.127 g·mol−1 |
Appearance | Colourless liquid |
Odor | Fishy, ammoniacal |
Density | 870 mg mL−1 |
Melting point | −37.1 °C; −34.9 °F; 236.0 K |
Boiling point | 119.6 °C; 247.2 °F; 392.7 K |
Vapor pressure | 1.9 Pa (at 20 °C) |
-58.1·10−6 cm3/mol | |
Refractive index (nD) | 1.446 |
Thermochemistry | |
Heat capacity (C) | 205.64 J K−1 mol−1 |
Std molar entropy (S | 247.27 J K−1 mol−1 |
Std enthalpy of formation (ΔfH⦵298) | −98.2–−97.4 kJ mol−1 |
Std enthalpy of combustion (ΔcH⦵298) | −2.5122–−2.5116 MJ mol−1 |
Hazards | |
GHS pictograms | |
GHS Signal word | Danger |
H226, H302, H312, H314 | |
P280, P305+351+338, P310 | |
Flash point | 34 °C (93 °F; 307 K) |
360 °C (680 °F; 633 K) | |
Explosive limits | 1.9–11.1% |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
|
Related compounds | |
Related alkanamines | |
Related compounds | 2-Methyl-2-nitrosopropane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
verify (what is ?) | |
Infobox references | |
1,2-Diaminopropane (propane-1,2-diamine) is organic compound with the formula CH3CH(NH2)CH2NH2. A colorless liquid, it is the simplest chiral diamine. It is used as a bidentate ligand in coordination chemistry.
Industrially, this compound is synthesized by the ammonolysis of 1,2-dichloropropane: [1]
This preparation allows for the use of waste chloro-organic compounds to form useful amines using inexpensive and readily available ammonia. [1]
The racemic mixture of this chiral compound may be separated into enantiomers by conversion into the diastereomeric tartaric acid ammonium salt. After purification of the diastereomer, the diamine can be regenerated by treatment of the ammonium salt with sodium hydroxide. [2] Alternate reagents for chiral resolution include N-p-toluenesulfonylaspartic acid, N-benzenesulfonylaspartic acid, or N-benzoylglutamic acid. [3]
1,2-Diaminopropane is used in the synthesis of N,N′-disalicylidene-1,2-propanediamine, a salen-type ligand, usually abbreviated as salpn, that is used as a metal deactivating additive in motor oils. [4]
In organic chemistry, amines (, UK also ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; see Category:Amines for a list of amines. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).
Hydroxylamine is an inorganic compound with the formula NH2OH. The pure material is a white, unstable crystalline, hygroscopic compound. However, hydroxylamine is almost always provided and used as an aqueous solution. It is used to prepare oximes, an important functional group. It is also an intermediate in biological nitrification. In biological nitrification, the oxidation of NH3 to hydroxylamine is mediated by the enzyme ammonia monooxygenase (AMO). Hydroxylamine oxidoreductase (HAO) further oxidizes hydroxylamine to nitrite.
Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is the simplest amide derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent. The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between acetone, which has two methyl (CH3) groups either side of the carbonyl (CO), and urea which has two amide (NH2) groups in those locations.
Samarium(III) chloride, also known as samarium trichloride, is an inorganic compound of samarium and chloride. It is a pale yellow salt that rapidly absorbs water to form a hexahydrate, SmCl3.6H2O. The compound has few practical applications but is used in laboratories for research on new compounds of samarium.
Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.
Iron(II) chloride, also known as ferrous chloride, is the chemical compound of formula FeCl2. It is a paramagnetic solid with a high melting point. The compound is white, but typical samples are often off-white. FeCl2 crystallizes from water as the greenish tetrahydrate, which is the form that is most commonly encountered in commerce and the laboratory. There is also a dihydrate. The compound is highly soluble in water, giving pale green solutions.
The phosphonium cation describes polyatomic cations with the chemical formula PR+
4. They are tetrahedral and generally colorless.
Phosphorus trichloride is a inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is a toxic and reacts violently with water to release hydrogen chloride.
DABCO (1,4-diazabicyclo[2.2.2]octane) is a bicyclic organic compound with the formula N2(C2H4)3. This colorless solid is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagent in polymerization and organic synthesis.
Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. Like diisopropylethylamine (Hünig's base), triethylamine is commonly employed, usually as a base, in organic synthesis.
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group R−N+
2X−
where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halogen.
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine readily reacts with moisture in humid air to produce a corrosive, toxic and irritating mist, to which even short exposures can cause serious damage to health (see safety). Ethylenediamine is the first member of the so-called polyethylene amines.
o-Phenylenediamine (OPD) is an organic compound with the formula C6H4(NH2)2. This aromatic diamine is an important precursor to many heterocyclic compounds. It is isomeric with m-phenylenediamine and p-phenylenediamine.
Hexamethylenediamine is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor. About 1 billion kilograms are produced annually.
Potassium tetrachloroplatinate(II) is the chemical compound with the formula K2PtCl4. This reddish orange salt is an important reagent for the preparation of other coordination complexes of platinum. It consists of potassium cations and the square planar dianion PtCl42−. Related salts are also known including Na2PtCl4, which is brown-colored and soluble in alcohols, and quaternary ammonium salts, which are soluble in a broader range of organic solvents.
1-Methylimidazole or N-methylimidazole is an aromatic heterocyclic organic compound with the formula CH3C3H3N2. It is a colourless liquid that is used as a specialty solvent, a base, and as a precursor to some ionic liquids. It is a fundamental nitrogen heterocycle and as such mimics for various nucleoside bases as well as histidine and histamine.
1,2-Diphenyl-1,2-ethylenediamine, DPEN, is an organic compound with the formula H2NCHPhCHPhNH2, where Ph is phenyl (C6H5). DPEN exists as three stereoisomers: meso and two enantiomers S,S- and R,R-. The chiral diastereomers are used in asymmetric hydrogenation. Both diastereomers are bidentate ligands.
In chemistry, the sulfonamide functional group (also spelled sulphonamide) is -S(=O)2-NH2, a sulfonyl group connected to an amine group. Relatively speaking this group is unreactive. The amine center is no longer basic. The S-N bond is cleaved only with difficulty. Because of the rigidity of the functional group, sulfonamides are typically crystalline. For this reason, the formation of a sulfonamide is a classic method to convert an amine into a crystalline derivative which can be identified by its melting point. Many important drugs contain the sulfonamide group.
Ammonium hexachloroiridate(IV) is the inorganic compound with the formula (NH4)2[IrCl6]. This dark brown solid is the ammonium salt of the iridium(IV) complex [IrCl6]2−. It is a commercially important iridium compound one of the most common complexes of iridium(IV). A related but ill-defined compound is iridium tetrachloride, which is often used interchangeably.
Salpn is the common name for a chelating ligand, properly called N,N′-bis(salicylidene)-1,2-propanediamine, used as a motor oil additive.