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HomeProduct name listCyclopropylamine

Cyclopropylamine

Synonym(s):Aminocyclopropane;Cyclopropylamine

  • CAS NO.:765-30-0
  • Empirical Formula: C3H7N
  • Molecular Weight: 57.09
  • MDL number: MFCD00001301
  • EINECS: 212-142-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-24 19:19:26
Cyclopropylamine Structural

What is Cyclopropylamine?

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.

The Uses of Cyclopropylamine

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.

What are the applications of Application

Cyclopropylamine is inactivates cytochrome P450 enzymes

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.

What are the applications of 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.]

Properties of Cyclopropylamine

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
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 information for Cyclopropylamine

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Corrosion
Corrosives
GHS05
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H225:Flammable liquids
H302:Acute toxicity,oral
H314:Skin corrosion/irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233:Keep container tightly closed.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Cyclopropylamine

InChIKey HTJDQJBWANPRPF-UHFFFAOYSA-N

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