3-Amino-5,5-dimethylcyclohex-2-en-1-one

Name: 3-Amino-5,5-dimethylcyclohex-2-en-1-one
Brand: ChemScene
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CAS No. 873-95-0
Cat. No. CS-0199484
Molecule weight139.19
Purity≥98%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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3-Amino-5,5-dimethylcyclohex-2-en-1-one|CS-0199484

Structure of 873-95-0

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General Information

CAS No. 873-95-0
Cat. No. CS-0199484
Purity ≥98%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₃NO
Molecular Weight 139.19
Synonym(s) 3-Amino-5,5-dimethyl-2-cyclohexen-1-one
SMILES CC1(C)CC(=CC(=O)C1)N

Description

3-Amino-5,5-dimethylcyclohex-2-en-1-one features a conjugated enone system paired with a primary amine, enabling direct participation in nucleophilic additions and condensation reactions. The sterically hindered dimethyl groups stabilize the enone moiety under standard conditions, while the amino functionality facilitates downstream derivatization in synthetic sequences. This scaffold serves as a key intermediate in the construction of nitrogen-containing heterocycles and bioactive molecule frameworks.

Application

3-Amino-5,5-dimethylcyclohex-2-en-1-one serves as a versatile building block in medicinal chemistry, enabling access to nitrogen-containing heterocycles and functionalized carbocycles. Its enone functionality supports Michael additions and conjugate reductions, while the amino group offers direct derivatization potential. The dimethyl substitution enhances steric shielding and bench stability, facilitating purification and handling in multi-step syntheses.

Synthesis

Route1
- In-stock
  
  126-81-8
- ~99%
- In-stock
  
  873-95-0
References
- Bilbao, Estibaliz R.; Alvarado, Mario; Masaguer, Christian F.; Ravina, Enrique Tetrahedron Letters, 2002 , vol. 43, # 19 p. 3551 - 3554
Route2
- 3471-13-4
- ~96%
- In-stock
  
  873-95-0
References
- Baraldi, P. G.; Simoni, D.; Manfredini, S. Synthesis, 1983 , # 11 p. 902 - 903
Route3
- 99-61-6
- In-stock
  
  126-81-8
- In-stock
  
  100-06-1
- ~%
- 68063-55-8
- 1446490-97-6
- In-stock
  
  873-95-0
References
- Green Chemistry, , vol. 15, # 7 p. 1910 - 1924

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-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 43.09
LogP 1.2181
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Fatty ring compounds Other fatty ring compounds

Key Words

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3-Amino-5,5-dimethylcyclohex-2-en-1-one

CAS No. 873-95-0

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