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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:
19777-66-3
Molecular Weight:
147.05
Beilstein:
5740936
MDL number:
MFCD00050706
UNSPSC Code:
12352116
PubChem Substance ID:
24865810
NACRES:
NA.22

Quality Level

100

Assay

99%

optical activity

[α]22/D −4°, c = 20 in H2O

mp

227-229 °C (lit.)

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stereochemical studies of adrenergic drugs. Optically active derivatives of imidazolines.
Miller DD, et al.
Journal of Medicinal Chemistry, 19(12), 1382-1384 (1976)
Optically active derivatives of imidazolines: a-Adrenergic blocking properties.
Hsu FL, et al.
Journal of Medicinal Chemistry, 23(11), 1232-1235 (1980)
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
K Hamana et al.
Microbios, 103(404), 43-51 (2000-10-18)
Cellular levels of diaminopropane, putrescine and cadaverine, and decarboxylase activities to produce these diamines in six species (16 strains) of Haemophilus and four species (5 strains) of Actinobacillus belonging to the family Pasteurellaceae of the gamma subclass of the class
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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