tert-Butyl 4-(4-hydroxyphenyl)piperazine-1-carboxylate

Name: tert-Butyl 4-(4-hydroxyphenyl)piperazine-1-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 158985-25-2
Cat. No. CS-0020067
Purity≥97%
MDL No.MFCD04115060

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tert-Butyl 4-(4-hydroxyphenyl)piperazine-1-carboxylate|CS-0020067

Structure of 158985-25-2

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General Information

CAS No. 158985-25-2
Cat. No. CS-0020067
Purity ≥97%
MDL No. MFCD04115060
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₂N₂O₃
Molecular Weight 278.35
Synonym(s) 1-tert-Butoxycarbonyl-4-(4-hydroxyphenyl)piperazine; 4-(4-Hydroxyphenyl)piperazine-1-carboxylic acid tert-butyl ester; ; N-Boc-4-(4-hydroxyphenyl)piperazine
SMILES O=C(N1CCN(C2=CC=C(O)C=C2)CC1)OC(C)(C)C

Description

tert-Butyl 4-(4-hydroxyphenyl)piperazine-1-carboxylate features a piperazine core functionalized with a para-hydroxyphenyl group and a tert-butyl ester, delivering a bench-stable, moisture-tolerant scaffold for medicinal chemistry. This compound integrates readily into diverse synthetic routes, enabling efficient access to bioactive molecules through straightforward deprotection or coupling reactions.

Application

tert-Butyl 4-(4-hydroxyphenyl)piperazine-1-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient access to piperazine-based scaffolds. The pendant phenolic hydroxyl group permits direct derivatization via etherification or esterification, while the tert-butyl carbamate facilitates mild deprotection under acidic conditions. Its stability, ease of purification, and compatibility with diverse reaction conditions make it ideal for iterative synthesis workflows and API development.

Synthesis

Route1
- In-stock
  
  56621-48-8
- In-stock
  
  24424-99-5
- ~99%
- In-stock
  
  158985-25-2
References
- BRISTOL-MYERS SQUIBB PHARMA COMPANY Patent: WO2008/83056 A2, 2008 ; Location in patent: Page/Page column 51 ;
Route2
- In-stock
  
  56621-48-8
- In-stock
  
  34619-03-9
- ~%
- In-stock
  
  158985-25-2
References
- GLAXO GROUP LIMITED Patent: WO2004/35556 A1, 2004 ; Location in patent: Page 20 ; WO 2004/035556 A1
Route3
- In-stock
  
  470478-90-1
- ~%
- In-stock
  
  158985-25-2
References
- Scott, James S.; Birch, Alan M.; Brocklehurst, Katy J.; Broo, Anders; Brown, Hayley S.; Butlin, Roger J.; Clarke, David S.; Davidsson, Oejvind; Ertan, Anne; Goldberg, Kristin; Groombridge, Sam D.; Hudson, Julian A.; Laber, David; Leach, Andrew G.; MacFaul, Philip A.; McKerrecher, Darren; Pickup, Adrian; Schofield, Paul; Svensson, Per H.; Soerme, Pernilla; Teague, Joanne Journal of Medicinal Chemistry, 2012 , vol. 55, # 11 p. 5361 - 5379

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 : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 53.01
LogP 2.4493
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Phenol

Building Blocks Skeleton Aliphatic heterocycle compounds Piperazine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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tert-Butyl 4-(4-hydroxyphenyl)piperazine-1-carboxylate

CAS No. 158985-25-2

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