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483761

Sigma-Aldrich

Boc-L-prolinal

97%

Synonym(s):

(S)-N-Boc-pyrrolidine-2-carboxaldehyde, N-(tert-Butoxycarbonyl)-L-prolinal

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About This Item

Empirical Formula (Hill Notation):
C10H17NO3
CAS Number:
Molecular Weight:
199.25
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

optical activity

[α]20/D −101°, c = 0.66 in chloroform

reaction suitability

reaction type: Boc solid-phase peptide synthesis

refractive index

n20/D 1.462 (lit.)

bp

211 °C (lit.)

density

1.063 g/mL at 25 °C (lit.)

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

[H]C(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C

InChI

1S/C10H17NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h7-8H,4-6H2,1-3H3/t8-/m0/s1

InChI key

YDBPZCVWPFMBDH-QMMMGPOBSA-N

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Application

Key building block for norsecurinine-type alkaloids and isaindigotidione carboskeleton.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

135.0 °F - closed cup

Flash Point(C)

57.2 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Ramon Alibés et al.
Organic letters, 6(11), 1813-1816 (2004-05-21)
The syntheses of securinine and (-)-allonorsecurinine have been achieved starting from easily available alpha-amino acid derivatives and using as key steps a RCM and a Heck reaction for the formation of rings D and C, respectively. [reaction: see text]
Tetrahedron Letters, 45, 2985-2985 (2004)

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