125504
Cyclopropylamine
98%
Synonym(s):
Aminocyclopropane
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About This Item
Linear Formula:
C3H5NH2
CAS Number:
Molecular Weight:
57.09
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-142-2
Beilstein/REAXYS Number:
741858
MDL number:
Assay:
98%
Form:
liquid
refractive index
n20/D 1.420 (lit.)
bp
49-50 °C (lit.)
density
0.824 g/mL at 25 °C (lit.)
InChI key
HTJDQJBWANPRPF-UHFFFAOYSA-N
InChI
1S/C3H7N/c4-3-1-2-3/h3H,1-2,4H2
SMILES string
NC1CC1
vapor pressure
4.67 psi ( 20 °C)
assay
98%
form
liquid
autoignition temp.
527 °F
Quality Level
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Application
Cyclopropylamine(CPA) has been used in the synthesis of N-[4-(4-fluoro)phenyl-2-aminothiazol-5-yl]pyrimidin-2-yl-alkylamine derivatives. It has been used in the synthesis of Pt(CPA)2(bismethylthiomethylenepropanedioate) and Pt(CPA)2(bisethylthiomethylenepropanedioate) complexes.
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.
signalword
Danger
Storage Class
3 - Flammable liquids
wgk
WGK 2
flash_point_f
33.8 °F - closed cup
flash_point_c
1 °C - closed cup
ppe
Faceshields, Gloves, Goggles
hcodes
Hazard Classifications
Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B
Regulatory Information
危险化学品
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Dapeng Sun et al.
FEBS letters, 517(1-3), 172-174 (2002-06-14)
Cyclopropylamine is a mechanism-based inhibitor of the quinoprotein methylamine dehydrogenase (MADH) from Paracoccus denitrificans. The resulting inactivation is accompanied by the formation of a covalent cross-link between the alpha and beta subunits of MADH. The results of site-directed mutagenesis studies
Synthesis and Antifungal Activity of 5-[2-(Alkylamino) pyrimidin-4-yl]-4-phenylthiazol-2-cycloalkylamine Derivatives on Phytophthora capsici.
Nam Sw, et al.
J. Korean Chem. Soc., 54(3), 395-402 (2011)
David J Aitken et al.
Organic & biomolecular chemistry, 9(21), 7517-7524 (2011-09-23)
The Kulinkovich-de Meijere reaction between an unsaturated Grignard reagent and a chiral amide takes place with a high trans stereoselectivity and provides a convenient access to non-racemic trans cyclopropylamines. These compounds are transformed in four steps into the corresponding N-protected
Fluorinated phenylcyclopropylamines as inhibitors of monoamine oxidases.
Thomas C Rosen et al.
Chembiochem : a European journal of chemical biology, 5(8), 1033-1043 (2004-08-10)
Mark E Scott et al.
The Journal of organic chemistry, 73(21), 8154-8162 (2008-10-10)
This manuscript describes a highly selective iodide-mediated, tandem Mannich/cyclization to afford trans-2,3-disubstituted pyrrolidines from methylenecyclopropyl amides in good to excellent yields and selectivities. The reaction scope has been drastically expanded to include a wide array of aromatic, heteroaromatic and alpha,beta-unsaturated
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