tert-Butyl (4-bromo-3-cyano-7-fluorobenzo[b]thiophen-2-yl)carbamate

Name: tert-Butyl (4-bromo-3-cyano-7-fluorobenzo[b]thiophen-2-yl)carbamate
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CAS No. 2649788-79-2
Cat. No. CS-0356856
Purity≥97%
MDL No.MFCD34566926

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tert-Butyl (4-bromo-3-cyano-7-fluorobenzo[b]thiophen-2-yl)carbamate|CS-0356856

Structure of 2649788-79-2

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General Information

CAS No. 2649788-79-2
Cat. No. CS-0356856
Purity ≥97%
MDL No. MFCD34566926
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₂BrFN₂O₂S
Molecular Weight 371.22
Synonym(s) None
SMILES O=C(OC(C)(C)C)NC1=C(C#N)C2=C(Br)C=CC(F)=C2S1

Description

tert-Butyl (4-bromo-3-cyano-7-fluorobenzo[b]thiophen-2-yl)carbamate features a sterically hindered tert-butyl carbamate protecting group paired with electron-deficient aryl halide and nitrile functionalities. This combination enables direct coupling in Pd-catalyzed cross-coupling reactions, offering robust stability under standard conditions. The fluorine substituent enhances metabolic resistance and modulates electronic properties for downstream functionalization in medicinal chemistry applications.

Application

tert-Butyl (4-bromo-3-cyano-7-fluorobenzo[b]thiophen-2-yl)carbamate serves as a versatile building block for the synthesis of fluorinated benzo[b]thiophene scaffolds. The molecule combines bromo, cyano, and fluoro substituents with a bench-stable carbamate group, enabling orthogonal functionalization in late-stage diversification. It facilitates palladium-catalyzed cross-coupling reactions, supports nucleophilic substitution at the bromo site, and maintains compatibility with standard protecting group strategies in medicinal chemistry workflows.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

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Computational Chemistry Data

TPSA 62.12
LogP 5.02158
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Benzothiophene compounds

Key Words

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tert-Butyl (4-bromo-3-cyano-7-fluorobenzo[b]thiophen-2-yl)carbamate

CAS No. 2649788-79-2

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