1,3-Diaminopropane: Difference between revisions
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| ImageName = Skeletal formula of 1,3-diaminopropane |
| ImageName = Skeletal formula of 1,3-diaminopropane |
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| PIN = Propane-1,3-diamine |
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| OtherNames = {{Unbulleted list|Propandiamine|1,3-Propylenediamine|Trimethylenediamine|3-Aminopropylamine |
| OtherNames = {{Unbulleted list|Propandiamine|1,3-Propylenediamine|Trimethylenediamine|3-Aminopropylamine |
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| CASNo = 109-76-2 |
| CASNo = 109-76-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = CB3ISL56KG |
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| PubChem = 428 |
| PubChem = 428 |
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| ChemSpiderID = 415 |
| ChemSpiderID = 415 |
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'''1,3-Diaminopropane''', also known as {{Not a typo|trimethylenediamine}}, is a simple [[diamine]] with the formula |
'''1,3-Diaminopropane''', also known as {{Not a typo|trimethylenediamine}}, is a simple [[diamine]] with the formula H<sub>2</sub>N(CH<sub>2</sub>)<sub>3</sub>NH<sub>2</sub>. A colourless liquid with a fishy odor, it is soluble in water and many polar organic solvents. It is isomeric with [[1,2-diaminopropane]]. Both are building blocks in the synthesis of [[heterocycle]]s, such as those used in [[textile finishing]], and [[coordination complex]]es. It is prepared by the amination of [[acrylonitrile]] followed by [[hydrogenation]] of the resulting [[aminopropionitrile]].<ref name=Ullmann>Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. {{doi|10.1002/14356007.a02_001}}</ref> |
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The potassium salt was used in the [[alkyne zipper reaction]].<ref>{{cite journal | author = C. A. Brown and A. Yamashita | title = Saline hydrides and superbases in organic reactions. IX. Acetylene zipper. Exceptionally facile contrathermodynamic multipositional isomeriazation of alkynes with potassium 3-aminopropylamide | year = 1975 | journal = [[J. Am. Chem. Soc.]] | volume = 97 | issue = 4 | pages = 891–892 | doi = 10.1021/ja00837a034 |
The potassium salt was used in the [[alkyne zipper reaction]].<ref>{{cite journal | author = C. A. Brown and A. Yamashita | title = Saline hydrides and superbases in organic reactions. IX. Acetylene zipper. Exceptionally facile contrathermodynamic multipositional isomeriazation of alkynes with potassium 3-aminopropylamide | year = 1975 | journal = [[J. Am. Chem. Soc.]] | volume = 97 | issue = 4 | pages = 891–892 | doi = 10.1021/ja00837a034}}</ref> |
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Known uses of 1,3- |
Known uses of 1,3-diaminopropane are in the synthesis of [[piroxantrone]] and [[losoxantrone]]. |
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== Safety== |
== Safety== |
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1,3-Diaminopropane is toxic on skin exposure with an LD50 of 177 mg kg<sup>−1</sup> (dermal, rabbit) |
1,3-Diaminopropane is toxic on skin exposure with an {{LD50}} of 177 mg kg<sup>−1</sup> (dermal, rabbit) |
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==References== |
==References== |
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Latest revision as of 19:38, 27 October 2022
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| Names | |
|---|---|
| Preferred IUPAC name
Propane-1,3-diamine | |
Other names
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| Identifiers | |
3D model (JSmol)
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| 3DMet | |
| 605277 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.367 |
| EC Number |
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| 1298 | |
| KEGG | |
| MeSH | trimethylenediamine |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 2922 |
CompTox Dashboard (EPA)
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| Properties | |
| C3H10N2 | |
| Molar mass | 74.127 g·mol−1 |
| Appearance | Colourless liquid |
| Odor | Fishy, ammoniacal |
| Density | 0.888 g mL−1 |
| Melting point | −12.00 °C; 10.40 °F; 261.15 K |
| Boiling point | 140.1 °C; 284.1 °F; 413.2 K |
| log P | −1.4 |
| Vapor pressure | <1.1 kPa or 11.5 mm Hg(at 20 °C) |
| -58.1·10−6 cm3/mol | |
Refractive index (nD)
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1.458 |
| Hazards | |
| GHS labelling: | |
  
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| Danger | |
| H226, H302, H310, H314 | |
| P280, P302+P350, P305+P351+P338, P310 | |
| NFPA 704 (fire diamond) | |
| Flash point | 51 °C (124 °F; 324 K) |
| 350 °C (662 °F; 623 K) | |
| Explosive limits | 2.8–15.2% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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| Related compounds | |
Related alkanamines
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Related compounds
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2-Methyl-2-nitrosopropane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,3-Diaminopropane, also known as trimethylenediamine, is a simple diamine with the formula H2N(CH2)3NH2. A colourless liquid with a fishy odor, it is soluble in water and many polar organic solvents. It is isomeric with 1,2-diaminopropane. Both are building blocks in the synthesis of heterocycles, such as those used in textile finishing, and coordination complexes. It is prepared by the amination of acrylonitrile followed by hydrogenation of the resulting aminopropionitrile.[1]
The potassium salt was used in the alkyne zipper reaction.[2]
Known uses of 1,3-diaminopropane are in the synthesis of piroxantrone and losoxantrone.
Safety
[edit]1,3-Diaminopropane is toxic on skin exposure with an LD50 of 177 mg kg−1 (dermal, rabbit)
References
[edit]- ^ Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
- ^ C. A. Brown and A. Yamashita (1975). "Saline hydrides and superbases in organic reactions. IX. Acetylene zipper. Exceptionally facile contrathermodynamic multipositional isomeriazation of alkynes with potassium 3-aminopropylamide". J. Am. Chem. Soc. 97 (4): 891–892. doi:10.1021/ja00837a034.