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Neopentylamine

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Chemical compound
Neopentylamine
Names
IUPAC name 2,2-dimethylpropan-1-amine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.024.890 Edit this at Wikidata
EC Number
  • 227-378-1
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H13N/c1-5(2,3)4-6/h4,6H2,1-3H3Key: XDIAMRVROCPPBK-UHFFFAOYSA-N
SMILES
  • CC(C)(C)CN
Properties
Chemical formula C5H13N
Molar mass 87.166 g·mol
Appearance colorless liquid
Density 0.74 g/cm
Melting point −70 °C (−94 °F; 203 K)
Boiling point 80–82 °C (176–180 °F; 353–355 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Irritant, Flammable, Corrosive
GHS labelling:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H225, H302, H314
Precautionary statements P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P370+P378, P403+P235, P405, P501
Flash point -13
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N (what is  ?) Infobox references
Chemical compound

Neopentylamine is an organic compound with the molecular formula (CH3)3CCH2NH2. It is a colorless liquid. The molecule is the primary amine derivative of neopentane, (CH3)4C.

Like most alkyl amines, it degrades slowly in air.

Synthesis

Neopentylamine is prepared by the reaction of neopentyl alcohol with ammonia in the presence of a hydrogenation catalyst.

Use

It is a common building block. For example, some experimental drugs incorporate this amine.

References

  1. "Neopentylamine 5813-64-9 | Tokyo Chemical Industry UK Ltd". www.tcichemicals.com. Retrieved 2021-03-01.
  2. US 4495369, Werner, Friedrich; Blank, Heinz U. & Gramm, Gunther et al., "Process for the preparation of neopentylamine", published 1985-01-22, issued 1981-09-22, assigned to Bayer AG 
  3. "Neopentylamine Safety Data Sheet". Fisher Scientific. Retrieved March 1, 2021.
  4. Biamonte, Marco A.; Shi, Jiandong; Hong, Kevin; Hurst, David C.; Zhang, Lin; Fan, Junhua; Busch, David J.; Karjian, Patricia L.; Maldonado, Angelica A.; Sensintaffar, John L.; Yang, Yong-Ching; Kamal, Adeela; Lough, Rachel E.; Lundgren, Karen; Burrows, Francis J.; Timony, Gregg A.; Boehm, Marcus F.; Kasibhatla, Srinivas R. (2006). "Orally Active Purine-Based Inhibitors of the Heat Shock Protein 90". Journal of Medicinal Chemistry. 49 (2): 817–828. doi:10.1021/jm0503087. PMID 16420067.
  5. Fraser, Robert R.; Mansour, Tarek S. (1984). "Acidity measurements with lithiated amines: Steric reduction and electronic enhancement of acidity". The Journal of Organic Chemistry. 49 (18): 3442–3443. doi:10.1021/jo00192a059.
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