Cyclopropylamine Property

Melting point:

-50 °C

Boiling point:

49-50 °C (lit.)

Density 

0.824 g/mL at 25 °C (lit.)

vapor pressure 

4.67 psi ( 20 °C)

refractive index 

n20/D 1.420(lit.)

Flash point:

−14 °F

storage temp. 

Store below +30°C.

solubility 

Chloroform, Ethyl Acetate (Sparingly), Methanol (Slightly)

pka

pK1:9.10(+1) (25°C)

form 

Volatile Liquid

color 

Clear colorless

Specific Gravity

0.824

Water Solubility 

Miscible with water, ethanol,ether and chloroform.

Sensitive 

Lachrymatory

BRN 

741858

Stability:

Volatile

InChIKey

HTJDQJBWANPRPF-UHFFFAOYSA-N

LogP

0.070

CAS DataBase Reference

765-30-0(CAS DataBase Reference)

NIST Chemistry Reference

Cyclopropylamine(765-30-0)

EPA Substance Registry System

Cyclopropanamine (765-30-0)

Safety

Hazard Codes 

F,C,Xi

Risk Statements 

11-22-34-36/37

Safety Statements 

16-26-36/37/39-45-33-7/9

RIDADR 

UN 2733 3/PG 2

WGK Germany 

2

RTECS 

GZ0685500

Autoignition Temperature

527 °F

Hazard Note 

Extremely Flammable/Harmful/Corrosive/Lachrymatory

TSCA 

T

HazardClass 

3

PackingGroup 

II

HS Code 

29213099

Toxicity

LD50 orally in Rabbit: 445 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Cyclopropylamine Chemical Properties,Usage,Production

Chemical Properties

Cyclopropylamine is a colorless and transparent flammable liquid with volatility and ammonia odor. It is miscible with water, methanol, ethanol, benzene, toluene and other solvents.

Uses

Cyclopropylamine is used in the preparation of N-[4-(4-fluoro)phenyl-2-aminothiazol-5-yl]pyrimidin-2-yl-alkylamine derivatives. It is also used to prepare Pt(CPA)2(bismethylthiomethylenepropanedioate) and Pt(CPA)2(bisethylthiomethylenepropanedioate) complexes.

Definition

ChEBI: Cyclopropylamine is a primary aliphatic amine that consists of cyclopropane bearing a single amino substituent. It has a role as a mouse metabolite.

Application

Cyclopropylamine is mainly used in organic synthesis, pharmaceutical synthesis intermediates, and can be used in the synthesis of new antibacterial drugs ciprofloxacin products, such as the synthesis of ciprofloxacin, enrofloxacin, spafloxacin and other drugs. In addition, cyclopropylamine is also an important intermediate for the synthesis of pesticides, plant protection agents and herbicides, such as 2-chloro-4-6-cyclopropyl-s-triazine, cyprochlor, cyproterazine, cyprocyanine and other cyclopropanes class of pesticides.

Preparation

Cyclopropylamine is synthesized from 1,3-propanediol by bromination, cyanation, cyclization, amidation, and Hoffmann rearrangement. It is also synthesized with γ-butyrolactone and isopropanol by five steps of ring-opening esterification, cyclization, hydrolysis, acylation and Hofmann degradation.

Biochem/physiol Actions

Cyclopropylamine inactivates cytochrome P450 enzymes by a mechanism involving initial one-electron oxidation at nitrogen followed by scission of the cyclopropane ring leading to covalent modification of the enzyme. It is a mechanism-based inhibitor of quinoprotein methylamine dehydrogenase from Paracoccus denitrificans.

Purification Methods

It has been isolated as the benzamide m 100.6-101.0o (from aqueous EtOH). It forms a picrate m 149o (from EtOH/pet ether) from which the free base can be recovered using a basic ion-exchange resin and can then be distilled through a Todd column (p 11) using an automatic still head which only collects products boiling below 51o/atm. Polymeric materials if present will boil above this temperature. The hydrochloride has m 85-86o [Roberts & Chambers J Am Chem Soc 73 5030 1951, Jones J Org Chem 9 484 1944, Emmons J Am Chem Soc 79 6522 1957]. [Beilstein 12 IV 3.]