545872

Sigma-Aldrich

(R)-(+)-Aminoglutethimide

97%

Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
Molecular Weight:
232.28
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

optical activity

[α]20/D +160°, c = 1 in methanol

mp

115.5-119.5 °C (lit.)

SMILES string

CC[C@@]1(CCC(=O)NC1=O)c2ccc(N)cc2

InChI

1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)/t13-/m1/s1

InChI key

ROBVIMPUHSLWNV-CYBMUJFWSA-N

Gene Information

Related Categories

Application

(R)-(+)-Aminoglutethimide can be used:
  • As a building block for the development of cephalosporin based prodrug for antibody-directed enzyme prodrug therapy (ADEPT).
  • To prepare (R)-3-ethyl-3-(4-(3,4,5-trimethoxybenzylamino)phenyl)piperidine-2,6-dione by reacting with 3,4,5-trimethoxybenzylamine via deaminative coupling reaction.
  • To synthesize (R)-2-fluoro-2-(4-methoxyphenyl)-N-(R)-(+)-aminoglutethimide by enantioselective α-fluorination.

Packaging

500 mg in amber glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

hazcat

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

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Combining asymmetric catalysis with natural product functionalization through enantioselective α-fluorination
E Jeremy, et al.
The Journal of Organic Chemistry, 75(3), 969-971 (2010)
Toward the development of a cephalosporin-based dual-release prodrug for use in ADEPT
Grant JW and Smyth TP
The Journal of Organic Chemistry, 69(23), 7965-7970 (2004)
Synthesis of symmetric and unsymmetric secondary amines from the ligand-promoted ruthenium-catalyzed deaminative coupling reaction of primary amines
Arachchige PT K, et al.
The Journal of Organic Chemistry, 83(9), 4932-4947 (2018)

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