1338338-67-2

Basic information

• Product Name: C₉H₁₂⁽¹⁸⁾O
• Synonyms: C₉H₁₂⁽¹⁸⁾O
• CAS NO: 1338338-67-2
• Molecular Weight: 138.194
• Mol File: 1338338-67-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₉H₁₂⁽¹⁸⁾O(CAS DataBase Reference)
• NIST Chemistry Reference: C₉H₁₂⁽¹⁸⁾O(1338338-67-2)
• EPA Substance Registry System: C₉H₁₂⁽¹⁸⁾O(1338338-67-2)

Safety Data

• Hazardous Substances Data: 1338338-67-2(Hazardous Substances Data)

Upstream product

• 102-93-2 3-phenylpropionamide 
• 10264-11-6 N‐butyl‐3‐phenylpropanamide 
• 18859-19-3 N,N-diethyl-3-phenylpropanamide 
• 30076-98-3 (3,3-dimethoxypropyl)benzene 

Downstream Products

• 1381884-62-3 C₁₅H₂₂O⁽¹⁸⁾O 
• 98511-61-6 ⁽¹⁸⁾O-triphenylphosphine oxide 

Relevant articles and documents

Highly chemoselective reduction of amides (primary, secondary, tertiary) to alcohols using SmI2/amine/H2O under mild conditions

Highly chemoselective direct reduction of primary, secondary, and tertiary amides to alcohols using SmI2/amine/H2O is reported. The reaction proceeds with C-N bond cleavage in the carbinolamine intermediate, shows excellent functional group tolerance, and delivers the alcohol products in very high yields. The expected C-O cleavage products are not formed under the reaction conditions. The observed reactivity is opposite to the electrophilicity of polar carbonyl groups resulting from the nX → πC=O (X = O, N) conjugation. Mechanistic studies suggest that coordination of Sm to the carbonyl and then to Lewis basic nitrogen in the tetrahedral intermediate facilitate electron transfer and control the selectivity of the C-N/C-O cleavage. Notably, the method provides direct access to acyl-type radicals from unactivated amides under mild electron transfer conditions.