Chemistry:Neopentylamine

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Short description: Chemical compound
Neopentylamine
Neopentylamine-2D-skeletal.svg
Names
IUPAC name
2,2-dimethylpropan-1-amine
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 227-378-1
UNII
Properties
C5H13N
Molar mass 87.166 g·mol−1
Appearance colorless liquid
Density 0.74 g/cm3
Melting point −70 °C (−94 °F; 203 K)
Boiling point 80–82 °C (176–180 °F; 353–355 K)
Hazards
Main hazards Irritant, Flammable, Corrosive
GHS pictograms GHS02: FlammableGHS05: CorrosiveGHS07: Harmful
GHS Signal word Danger
H225, H302, H314
P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+312, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P330, P363, P370+378, P403+235, P405, P501
Flash point -13
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[1]

Synthesis

Neopentylamine is prepared by the reaction neopentanol with ammonia.[2]

Use

It is a common building block.[3] For example, some experimental drugs incorporate this amine.[4][5]

References

  1. "Neopentylamine 5813-64-9 | Tokyo Chemical Industry UK Ltd.". https://www.tcichemicals.com/GB/en/p/N0505. 
  2. Werner, Friedrich; Heinz U. Blank & Gunther Gramm et al., "Process for the preparation of neopentylamine", US patent 4495369, published 1985-01-22, issued 1981-09-22
  3. "Neopentylamine Safety Data Sheet". https://www.fishersci.com/store/msds?partNumber=AC173690250&productDescription=NEOPENTYLAMINE%2C+97%25+25ML&vendorId=VN00032119&countryCode=US&language=en. 
  4. Biamonte, Marco A.; Shi, Jiandong; Hong, Kevin; Hurst, David C.; Zhang, Lin; Fan, Junhua; Busch, David J.; Karjian, Patricia L. et al. (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.