Ammonium salicylate

• CAS: 528-94-9
• Catalog Number: ACM528949
• Category: Main Products
• Molecular Weight: 155.15
• Molecular Formula: C₇H₉NO₃
• Synonyms: AMMONIUM SALICYLATE
• IUPAC Name: azanium;2-carboxyphenolate
• SMILES: C1=CC=C(C(=C1)C(=O)O)[O-].[NH4+]
• InChI Key: BOFZOTMTKBQRAB-UHFFFAOYSA-N
• Boiling Point: 336.3ºC at 760 mmHg
• Flash Point: 144.5ºC
• Appearance: white solid
• EC Number: 208-444-9
• Exact Mass: 155.05800
• Safety Description: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .; S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .

Case Study

Ammonium Salicylate as a Critical Enabler for High-Efficiency Synthesis of Sitagliptin

Steinhuebel, Dietrich, et al. Journal of the American Chemical Society 131.32 (2009): 11316-11317.

This case study examined the development of a direct asymmetric reductive amination process for manufacturing sitagliptin, focusing on the pivotal role of ammonium salicylate.
Key Findings
· Optimal Catalyst: Ru(OAc)2((R)-dm-segphos) was identified as the superior catalyst, delivering unprecedented >99% ee for the hydrogenation of the key enamine intermediate.
· Acid addition (e.g., AcOH, benzoic acid) was essential for Ru catalyst reactivity and high ee in the hydrogenation step, but promoted significant dimer byproduct (4) formation.
· Superior Performance of Salicylic Acid: Salicylic acid (pKa ≈ 3) effectively suppressed the dimer byproduct during hydrogenation, increasing the yield of the desired amine (2) to 75% while maintaining high ee.
· Ammonium Salicylate Breakthrough: Using ammonium salicylate (NH4SA) completely eliminated the dimer byproduct (4) in the hydrogenation step, yielding the desired amine (2) in 96% yield with 99.5% ee.
· Enabling Efficient One-Pot Synthesis: In the direct one-pot reductive amination of the β-keto amide (1), ammonium salicylate (5 equiv) proved superior to other ammonium salts (e.g., acetate), affording sitagliptin precursor 2 in 91% assay yield and 99.5% ee.
· Studies on the effects of excess ammonium salicylate have demonstrated a dual effect. In addition to shifting the equilibrium toward 3, it can also inhibit dimer formation and/or disrupt dimers, releasing products 2 and 3 for hydrogenation.

Custom Q&A

What is the molecular formula of ammonium salicylate?

The molecular formula of ammonium salicylate is C7H9NO3.

What are the synonyms for ammonium salicylate?

The synonyms for ammonium salicylate include AMMONIUM SALICYLATE, Benzoic acid, 2-hydroxy-, monoammonium salt, Wulpyrin, Salicyl-vasogen, and more.

What is the CAS number of ammonium salicylate?

The CAS number of ammonium salicylate is 528-94-9.

What is the IUPAC name of ammonium salicylate?

The IUPAC name of ammonium salicylate is azanium;2-carboxyphenolate.

What is the InChIKey of ammonium salicylate?

The InChIKey of ammonium salicylate is BOFZOTMTKBQRAB-UHFFFAOYSA-N.

What is the molecular weight of ammonium salicylate?

The molecular weight of ammonium salicylate is 155.15g/mol.

How many hydrogen bond donor counts are there in ammonium salicylate?

There are 2 hydrogen bond donor counts in ammonium salicylate.

How many hydrogen bond acceptor counts are there in ammonium salicylate?

There are 3 hydrogen bond acceptor counts in ammonium salicylate.

How many rotatable bond counts are there in ammonium salicylate?

There is 1 rotatable bond count in ammonium salicylate.

Is ammonium salicylate a canonicalized compound?

Yes, ammonium salicylate is a canonicalized compound.