(5-Amino-2-nitrophenyl)methanol

Name: (5-Amino-2-nitrophenyl)methanol
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CAS No. 77376-03-5
Cat. No. CS-0312383
Purity≥97%
MDL No.MFCD00036068

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(5-Amino-2-nitrophenyl)methanol|CS-0312383

Structure of 77376-03-5

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General Information

CAS No. 77376-03-5
Cat. No. CS-0312383
Purity ≥97%
MDL No. MFCD00036068
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₈N₂O₃
Molecular Weight 168.15
Synonym(s) 5-Amino-2-nitrobenzyl alcohol
SMILES OCC1=CC(N)=CC=C1[N+]([O-])=O

Description

This amino-nitrobenzyl alcohol integrates a reactive hydroxymethyl group with an electron-deficient aromatic core, enabling straightforward conjugation and functionalization. The para-substituted scaffold supports efficient derivatization under mild conditions, making it valuable for bioconjugation and probe synthesis.

Application

(5-Amino-2-nitrophenyl)methanol serves as a versatile building block for heterocyclic synthesis and functionalized aromatic systems. The molecule combines an amino group ortho to a nitro function with a benzylic alcohol, enabling sequential transformations such as reduction, coupling, or cyclization. Its bench-stable nature and compatibility with standard protecting group strategies facilitate reliable use in multi-step synthetic sequences for medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  13280-60-9
- ~83%
- In-stock
  
  77376-03-5
References
- Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic Chemistry - A European Journal, 2006 , vol. 12, # 26 p. 6865 - 6879
Route2
- 1079039-46-5
- ~74%
- In-stock
  
  77376-03-5
References
- Serafinowski, Pawel J.; Garland, Peter B. Organic and Biomolecular Chemistry, 2008 , vol. 6, # 18 p. 3284 - 3291
Route3
- 123306-29-6
- ~%
- In-stock
  
  77376-03-5
References
- Fourneau; de Lestrange Bulletin de la Societe Chimique de France, 1933 , vol. <4> 53, p. 330,332

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

TPSA 89.39
LogP 0.6693
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Alcohol

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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(5-Amino-2-nitrophenyl)methanol

CAS No. 77376-03-5

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