tert-Butyl (4-iodophenyl)carbamate

Name: tert-Butyl (4-iodophenyl)carbamate
Brand: ChemScene
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CAS No. 159217-89-7
Cat. No. CS-0041019
Purity≥98%
MDL No.MFCD03490497

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tert-Butyl (4-iodophenyl)carbamate|CS-0041019

Structure of 159217-89-7

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General Information

CAS No. 159217-89-7
Cat. No. CS-0041019
Purity ≥98%
MDL No. MFCD03490497
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₄INO₂
Molecular Weight 319.14
Synonym(s) tert-butyl N-(4-iodophenyl)carbamate
SMILES O=C(OC(C)(C)C)NC1=CC=C(I)C=C1

Description

tert-Butyl (4-iodophenyl)carbamate delivers a robust, bench-stable platform for installing iodinated aryl handles in late-stage functionalization. The carbamate moiety enables efficient deprotection under mild acidic conditions, while the para-iodo group supports diverse cross-coupling reactions, including Suzuki-Miyaura and Sonogashira transformations. This reagent combines high stability with predictable reactivity, simplifying synthetic workflows in medicinal chemistry and materials development.

Application

tert-Butyl (4-iodophenyl)carbamate serves as a stable, bench-ready precursor for the introduction of 4-iodophenylamine units in cross-coupling reactions. The carbamate group provides excellent protection of the amine functionality, enabling orthogonal reactivity in multi-step syntheses. Its iodide moiety facilitates reliable Suzuki, Stille, and Negishi couplings, offering high functional group tolerance and ease of purification. This compound functions as a key building block in the synthesis of biaryl scaffolds relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  540-37-4
- ~99%
- In-stock
  
  159217-89-7
References
- Jin, Yi; Zhou, Zu-Yu; Tian, Wei; Yu, Qiang; Long, Ya-Qiu Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 22 p. 5864 - 5869
Route2
- In-stock
  
  3422-01-3
- ~82%
- In-stock
  
  159217-89-7
References
- Gallo, Rafael D.C.; Ferreira, Irlon M.; Casagrande, Gleison A.; Pizzuti, Lucas; Oliveira-Silva, Diogo; Raminelli, Cristiano Tetrahedron Letters, 2012 , vol. 53, # 40 p. 5372 - 5375
Route3
- In-stock
  
  34619-03-9
- In-stock
  
  540-37-4
- ~90%
- In-stock
  
  159217-89-7
References
- Yokoyama, Akihiro; Maruyama, Takurou; Tagami, Kei; Masu, Hyuma; Katagiri, Kosuke; Azumaya, Isao; Yokozawa, Tsutomu Organic Letters, 2008 , vol. 10, # 15 p. 3207 - 3210

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS09
Signal Word : Warning	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H317-H410
Precautionary Statements : P261-P264-P270-P272-P273-P280-P302+P352-P330-P362+P364-P391-P501

Quality Control

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Computational Chemistry Data

TPSA 38.33
LogP 3.6382
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Iodide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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tert-Butyl (4-iodophenyl)carbamate

CAS No. 159217-89-7

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