tert-Butyl 2-bromo-3-fluorobenzylcarbamate

Name: tert-Butyl 2-bromo-3-fluorobenzylcarbamate
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CAS No. 2201101-20-2
Cat. No. CS-0565719
Purity≥96%
MDL No.None

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tert-Butyl 2-bromo-3-fluorobenzylcarbamate|CS-0565719

Structure of 2201101-20-2

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General Information

CAS No. 2201101-20-2
Cat. No. CS-0565719
Purity ≥96%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₅BrFNO₂
Molecular Weight 304.16
Synonym(s) None
SMILES O=C(NCC1=C(Br)C(F)=CC=C1)OC(C)(C)C

Description

tert-Butyl 2-bromo-3-fluorobenzylcarbamate features a bromo-fluoro-substituted benzyl scaffold with a bench-stable carbamate protecting group. This bifunctional intermediate enables direct coupling in late-stage diversification, where the bromine serves as a site for palladium-catalyzed cross-coupling and the fluorine modulates electronic properties. The tert-butyl carbamate facilitates easy deprotection under mild acidic conditions, streamlining access to functionalized anilines.

Application

tert-Butyl 2-bromo-3-fluorobenzylcarbamate serves as a versatile building block for the synthesis of fluorinated arylamines, enabling efficient Suzuki-Miyaura and Buchwald-Hartwig coupling reactions. The ortho-bromo and meta-fluoro substituents provide complementary reactivity for sequential functionalization, while the tert-butyl carbamate group offers excellent stability and straightforward deprotection under mild acidic conditions. Its bench-stable solid form facilitates handling and purification in multi-step synthetic sequences.

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

TPSA 38.33
LogP 3.6129
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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tert-Butyl 2-bromo-3-fluorobenzylcarbamate

CAS No. 2201101-20-2

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