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ALD00034

Sigma-Aldrich

(S)-tert-Butyl 1-(chloromethyl)-5-hydroxy-1H-benzo[e]indole-3(2H)-carboxylate

95% (HPLC)

Synonym(s):

N-Boc-seco-CBI

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About This Item

Empirical Formula (Hill Notation):
C18H20ClNO3
CAS Number:
130007-86-2
Molecular Weight:
333.81
UNSPSC Code:
12352200
PubChem Substance ID:
329772532
NACRES:
NA.22

Assay

95% (HPLC)

form

powder

optical activity

[α]/D -89.0, c = 0.05% in chloroform

storage temp.

−20°C

SMILES string

OC1=C2C(C=CC=C2)=C3C(N(C(OC(C)(C)C)=O)C[C@H]3CCl)=C1

InChI

1S/C18H20ClNO3/c1-18(2,3)23-17(22)20-10-11(9-19)16-13-7-5-4-6-12(13)15(21)8-14(16)20/h4-8,11,21H,9-10H2,1-3H3/t11-/m1/s1

InChI key

DGPQGWRHSMFTSW-LLVKDONJSA-N

Application

N-Boc-CBI best used as its seco precursor (seco-N-Boc-CBI) is a simple alkylation subunit analog of that found in the naturally occurring antitumor agents the duocarmycins, yatakemycin, and CC-1065, which act by sequence selective DNA alkylation.

Other Notes

Design, Synthesis, and Evaluation of Duocarmycin O-Amino Phenol Prodrugs Subject to Tunable Reductive Activation

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H410

Precautionary Statements

P273 - P501

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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