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%
Product Name
N-Boc-2-aminoacetaldehyde, 95%
InChI
1S/C7H13NO3/c1-7(2,3)11-6(10)8-4-5-9/h5H,4H2,1-3H3,(H,8,10)
SMILES string
CC(C)(C)OC(=O)NCC=O
InChI key
ACNRTYKOPZDRCO-UHFFFAOYSA-N
assay
95%
refractive index
n20/D 1.455 (lit.)
functional group
aldehyde
amine
storage temp.
−20°C
Quality Level
Gene Information
human ... CTSK(1513)
Related Categories
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.
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.
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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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
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
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)
Efficient total synthesis of (+)-negamycin, a potential chemotherapeutic agent for genetic diseases.
Yoshio Hayashi et al.
Chemical communications (Cambridge, England), (20)(20), 2379-2381 (2008-05-14)
Herein, we describe an efficient strategy for the total synthesis of (+)-negamycin using commercially available achiral N-Boc-2-aminoacetaldehyde as starting material with 42% overall yield for a limited number of steps.
The Journal of Organic Chemistry, 70, 10869-10869 (2005)
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