Cyclopropylamine

Structural formula
General
Surname	Cyclopropylamine
other names	Cyclopropanamine ( IUPAC ); Aminocyclopropane;
Molecular formula	C 3 H 7 N
Brief description	colorless liquid
External identifiers / databases
EC number	212-142-2
ECHA InfoCard	100,011,038
PubChem	69828
ChemSpider	63025
Wikidata	Q1147604
properties
Molar mass	57.10 g mol −1
Physical state	liquid
density	0.82 g cm −3
Melting point	−10 ° C
boiling point	49-50 ° C
Vapor pressure	322 hPa (20 ° C)
solubility	soluble in water
Refractive index	1.4210 (20 ° C)
safety instructions
H and P phrases	H: 225-302-314
	P: 210-280-305 + 351 + 338-310
Thermodynamic properties
ΔH f 0	45.8 kJ / mol
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Cyclopropylamine ( cyclopropanamine according to IUPAC ) is a primary amine . The compound is liquid at room temperature and volatile because of its relatively low boiling point . Like many amines, cyclopropylamine has an ammonia to fishy odor.

properties

Chemical properties

Cyclopropylamine is an organic base and therefore forms with various acids such as. B. the hydrochloric acid salts of the type C ₃ H ₅ -NH ₃⁺ Cl ^- . The reactivity is strongly influenced by the nucleophilicity of nitrogen . It reacts, for example, with carboxylic acid halides to form amides and with aldehydes / ketones to form imines or, through reductive amination, to form corresponding secondary or tertiary amines.

The bond angles between carbon - atoms in the cyclopropyl ring is approximately 60 °, the bond distance of 151 pm is a single bond relatively short. Hence the ring is stretched and planar. These spatial properties are used, among other things, in pharmaceutical research for various purposes, for example as a “suitable” structural element for certain receptors .

use

Cyclopropylamine is used, among other things, in pharmaceutical chemistry as a starting material for the production of new active ingredients .

Biological importance

Cyclopropylamine as such has no biological significance for humans, animals or plants.

safety instructions

The connection is corrosive , so you should protect yourself with gloves. Storage and handling in well-ventilated rooms. The LD ₅₀ value is 445 mg / kg (rat, oral).

Individual evidence

↑ ^a ^b ^c Data sheet cyclopropylamine (PDF) from Merck , accessed on January 18, 2011.
↑ ^a ^b ^c ^d ^e ^f Datasheet Cyclopropylamine from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-132.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-24.

[merck-1] Data sheet cyclopropylamine (PDF) from Merck , accessed on January 18, 2011.

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f Datasheet Cyclopropylamine from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).

[CRC90_3_132-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-132.

[CRC90_5_24-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-24.