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Sigma-Aldrich

Cyclopropylamine

98%

Synonym(s):

Aminocyclopropane

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About This Item

Linear Formula:
C3H5NH2
CAS Number:
765-30-0
Molecular Weight:
57.09
Beilstein/REAXYS Number:
741858
EC Number:
212-142-2
MDL number:
MFCD00001301
UNSPSC Code:
12352100
PubChem Substance ID:
24847670
NACRES:
NA.22

vapor pressure

4.67 psi ( 20 °C)

Quality Level

200

assay

98%

form

liquid

autoignition temp.

527 °F

refractive index

n20/D 1.420 (lit.)

bp

49-50 °C (lit.)

density

0.824 g/mL at 25 °C (lit.)

SMILES string

NC1CC1

InChI

1S/C3H7N/c4-3-1-2-3/h3H,1-2,4H2

InChI key

HTJDQJBWANPRPF-UHFFFAOYSA-N

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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.

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Description
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Danger

Hazard Classifications

Acute Tox. 4 Oral - Flam. Liq. 2 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

33.8 °F - closed cup

flash_point_c

1 °C - closed cup

ppe

Faceshields, Gloves, Goggles

Certificates of Analysis (COA)

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(Cyclopropylmethyl)methylamine AldrichCPR

Sigma-Aldrich

CBR00064

(Cyclopropylmethyl)methylamine

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)
Coordination Mode vs. Anticancer Activity of the Platinum (II) Complexes Involving Sulfur-Containing Ylidenemalonate Ligands.
Sakai N, et al.
Bull. Korean Chem. Soc., 19(12), 1377-1379 (1998)
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
Bram Denolf et al.
Organic letters, 9(2), 187-190 (2007-01-16)
Treatment of novel chiral N-sulfinyl alpha-chloro ketimines with Grignard reagents resulted in the synthesis of chiral N-(1-substituted cyclopropyl)-tert-butanesulfinamides in acceptable to good yields and diastereoselectivity via 1,3-dehydrohalogenation and subsequent addition of the Grignard reagent to the intermediate cyclopropylideneamine. Only in
Soda Chanthamath et al.
Organic letters, 15(4), 772-775 (2013-01-31)
The Ru(II)-Pheox-catalyzed asymmetric cyclopropanation of vinylcarbamates with diazoesters resulted in the corresponding cyclopropylamine derivatives in high yield and excellent diastereoselectivity (up to 96:4) and enantioselectivity (up to 99% ee).
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