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180807

Sigma-Aldrich

(−)-cis-Myrtanylamine

98%

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About This Item

Empirical Formula (Hill Notation):
C10H19N
CAS Number:
73522-42-6
Molecular Weight:
153.26
MDL number:
MFCD00001349
UNSPSC Code:
12352116
PubChem Substance ID:
24850900
NACRES:
NA.22

Assay

98%

form

liquid

optical activity

[α]22/D −30.5°, neat

refractive index

n20/D 1.4877 (lit.)

bp

94-99 °C/27 mmHg (lit.)

density

0.915 g/mL at 25 °C (lit.)

SMILES string

CC1(C)[C@@]2([H])CC[C@](CN)([H])[C@@]1(C2)[H]

InChI

1S/C10H19N/c1-10(2)8-4-3-7(6-11)9(10)5-8/h7-9H,3-6,11H2,1-2H3/t7-,8-,9-/m0/s1

InChI key

SYJBFPCQIJQYNV-CIUDSAMLSA-N

Related Categories

Application

(-)-cis-Myrtanylamine may be used:
  • As a reactant to prepare N,N-bis((-)-cis-myrtanyl)butylene-2,3-diimine (BMDI), a bidentate diimine ligand that can form transition metal complexes for catalyzing asymmetric synthesis.
  • As a building block to prepare imidazole derivatives, which are potent and selective cannabinoid receptor (CB2) antagonists.
  • To prepare a chiral catalyst, which can catalyze asymmetric three-component Mannich reaction.

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

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

172.4 °F - closed cup

Flash Point(C)

78 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Efficient catalysts for asymmetric Mannich reactions.
Rachwalski M, et al.
Organic & Biomolecular Chemistry, 11(25), 4207-4213 (2013)
Synthesis of new chiral diimine palladium (II) and nickel (II) complexes bearing oxazoline-and myrtanyl-based nitrogen ligands. Crystal structure of the C 2-symmetric complex [{(1R, 2S)-inda-box} PdCl 2].
Abu-Surrah AS, et al.
Polyhedron, 21(1), 27-31 (2002)
Synthesis and SAR of novel imidazoles as potent and selective cannabinoid CB 2 receptor antagonists with high binding efficiencies.
Lange JHM, et al.
Bioorganic & Medicinal Chemistry Letters, 20(3), 1084-1089 (2010)
Marco Busnelli et al.
British journal of pharmacology, 177(2), 328-345 (2019-10-18)
Fenretinide, a synthetic retinoid derivative first investigated for cancer prevention and treatment, has been shown to ameliorate glucose tolerance, improve plasma lipid profile and reduce body fat mass. These effects, together with its ability to inhibit ceramide synthesis, suggest that

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