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412562

Sigma-Aldrich

(S)-(−)-1,2-Diaminopropane dihydrochloride

99%

Synonym(s):

(S)-(−)-Propylenediamine dihydrochloride, (S)-1,2-Propanediamine dihydrochloride

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About This Item

Linear Formula:
CH3CH(NH2)CH2NH2·2HCl
CAS Number:
Molecular Weight:
147.05
Beilstein:
5740936
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

optical activity

[α]22/D −4°, c = 20 in H2O

mp

227-229 °C (lit.)

functional group

amine

SMILES string

Cl.Cl.C[C@H](N)CN

InChI

1S/C3H10N2.2ClH/c1-3(5)2-4;;/h3H,2,4-5H2,1H3;2*1H/t3-;;/m0../s1

InChI key

AEIAMRMQKCPGJR-QTNFYWBSSA-N

Application

(S)-(-)-1,2-Diaminopropane dihydrochloride may be used in the preparation of following chiral imidazoline derivatives, which show moderate α-adrenergic blocking activity:
  • (S)-(-)-4-methyl-2-(1-naphthylmethyl)imidazoline hydrochloride
  • (S)-(-)-2-benzyl-4-methylimidazoline picrate
  • (S )-(-)-2-[(2,6-dichlorophenyl)imino]-4-methylimidazolidine hydrochloride

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Optically active derivatives of imidazolines: a-Adrenergic blocking properties.
Hsu FL, et al.
Journal of Medicinal Chemistry, 23(11), 1232-1235 (1980)
Stereochemical studies of adrenergic drugs. Optically active derivatives of imidazolines.
Miller DD, et al.
Journal of Medicinal Chemistry, 19(12), 1382-1384 (1976)
Lorin A Thompson et al.
Bioorganic & medicinal chemistry letters, 21(22), 6909-6915 (2011-10-07)
The synthesis, evaluation, and structure-activity relationships of a set of related constrained diaminopropane inhibitors of BACE-1 are described. The full in vivo profile of an optimized inhibitor in both normal and P-gp deficient mice is compared with data generated in
Keisuke Maruyoshi et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(7), 1618-1626 (2009-01-09)
Endogenous polyamines, represented by putrescine, spermidine, and spermine, are known to exert their physiological functions by interacting with polyanionic biomolecules such as DNA, RNA, adenosine triphosphate (ATP), and phospholipids. Very few examples of conformation analysis have been reported for these
S A M Fathi et al.
Journal of hazardous materials, 164(1), 133-137 (2008-09-10)
Bis(5-bromo-2-hydroxybenzaldehyde)-1,2-propanediimine is synthesized by the reaction of 5-bromo-2-hydroxybenzaldehyde and 1,2-diaminopropane in ethanol. This ligand is used as a modifier of octadecyl silica disks for preconcentration of trace amounts of copper(II) ions, followed by nitric acid elution and flame atomic absorption

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