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591882

Sigma-Aldrich

(3R)-(−)-3-(1-Methyl-1H-indol-3-yl)butyraldehyde

98%

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About This Item

Empirical Formula (Hill Notation):
C13H15NO
CAS Number:
405873-05-4
Molecular Weight:
201.26
MDL number:
MFCD05664285
UNSPSC Code:
12352005
PubChem Substance ID:
24881358
NACRES:
NA.22

Quality Level

100

Assay

98%

optical activity

[α]20/D -6, c = 1% in chloroform

optical purity

ee: 99% (HPLC)

mp

55.5-59.5 °C (lit.)

SMILES string

C[C@H](CC=O)c1cn(C)c2ccccc12

InChI

1S/C13H15NO/c1-10(7-8-15)12-9-14(2)13-6-4-3-5-11(12)13/h3-6,8-10H,7H2,1-2H3/t10-/m1/s1

InChI key

OQWWHYBHQFZHLP-SNVBAGLBSA-N

Application

(3R)-(−)-3-(1-Methyl-1H-indol-3-yl)butyraldehyde can be used as a substrate in the synthesis of 2-alkyl cyclohexanone intermediates, applicable in the preparation of tricyclic steroid precursors.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A three-step route to a tricyclic steroid precursor
Taber DF and Sheth RB
The Journal of Organic Chemistry, 73(20), 8030-8032 (2008)
Can simple enones be useful partners for the catalytic stereoselective alkylation of indoles?
Bandini M, et al.
The Journal of Organic Chemistry, 69(22), 7511-7518 (2004)
Catalytic enantioselective conjugate addition of indoles to simple α, β-unsaturated ketones
Bandini M, et al.
Tetrahedron Letters, 44(31), 5843-5846 (2003)

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