472654
N-Boc-2-aminoacetaldehyde
95%
Synonym(s):
tert-Butyl N-(2-oxoethyl)carbamate
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About This Item
Linear Formula:
HCOCH2NHCO2C(CH3)3
CAS Number:
Molecular Weight:
159.18
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
95%
Quality Level
assay
95%
refractive index
n20/D 1.455 (lit.)
functional group
aldehyde, amine
storage temp.
−20°C
SMILES string
CC(C)(C)OC(=O)NCC=O
InChI
1S/C7H13NO3/c1-7(2,3)11-6(10)8-4-5-9/h5H,4H2,1-3H3,(H,8,10)
InChI key
ACNRTYKOPZDRCO-UHFFFAOYSA-N
Gene Information
human ... CTSK(1513)
General description
N-Boc-2-aminoacetaldehyde is an organic building block. It reacts with Horner-Wadsworth-Emmons (HWE) reagent to afford γ-aminobutyric acid (GABA)-derived α-keto amide/ester units.
Application
N-Boc-2-aminoacetaldehyde may be employed in the following:
- As a starting reagent in the total synthesis of (+)-negamycin.
- Synthesis of (E)-ethyl 4-((tert-butoxycarbonyl)amino)but-2-enoate.
- Synthesis of 2,2′-bipyridine.
A building block in the synthesis of a protected pyrroloproline.
α-Methylenation of this amino aldehyde proceeds in a quick and efficient manner using a recently reported protocol involving formaldehyde and catalysis by either pyrrolidine proprionic acid or the dipeptide L-Pro-β-Ala.
Also used in a three-component synthesis of pyrrolidines involving 1,3-dipolar cycloaddition.
Also used in a three-component synthesis of pyrrolidines involving 1,3-dipolar cycloaddition.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Gloves, type N95 (US)
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Anniina Erkkilä et al.
The Journal of organic chemistry, 71(6), 2538-2541 (2006-03-11)
A rapid and extremely convenient method for alpha-methylenation of aldehydes with aqueous formaldehyde is described. Two optimal catalytic systems are presented that allow short reaction times and afford the functionalized products in good to excellent yields (up to 99%) and
Anna Turetsky et al.
Scientific reports, 4, 4782-4782 (2014-04-25)
A number of Bruton's tyrosine kinase (BTK) inhibitors are currently in development, yet it has been difficult to visualize BTK expression and pharmacological inhibition in vivo in real time. We synthesized a fluorescent, irreversible BTK binder based on the drug
Diethyl [3-Cyano-2-Oxo-3-(Triphenylphosphoranylidene) propyl] phosphonate: A Useful Horner-Wadsworth-Emmons Reagent for alpha-Keto (Cyanomethylene)-triphenylphosphoranes from Carbonyl Compounds.
Lee K.
Bull. Korean Chem. Soc., 28(10), 1641-1641 (2007)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 472654-25G | 04061833490358 |
| 472654-1G | 04061825585482 |
| 472654-5G | 04061832360683 |