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
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 | n |
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) |
Flame Flammables GHS02 Corrosion Corrosives GHS05 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 |
Abamectin manufacturer
JSK Chemicals
Virchow Groups
Pallav Chemicals And Solvents Pvt Ltd
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