94838-55-8 | 4-(N-Boc-aminomethyl)aniline

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$8.00	$5.00
250mg	98%	in stock	$9.00	$7.00
1g	98%	in stock	$12.00	$9.00
5g	98%	in stock	$46.00	$33.00
10g	98%	in stock	$81.00	$57.00
25g	98%	in stock	$144.00	$101.00
100g	98%	in stock	$481.00	$337.00

Description

• Catalog Number: AB48411
• Chemical Name: 4-(N-Boc-aminomethyl)aniline
• CAS Number: 94838-55-8
• Molecular Formula: C12H18N2O2
• Molecular Weight: 222.2835
• MDL Number: MFCD03001716
• SMILES: O=C(OC(C)(C)C)NCc1ccc(cc1)N

Computed Properties

• Complexity: 228
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 16
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 4
• XLogP3: 1.7

Upstream Synthesis Route

The upstream synthesis of 4-(N-Boc-aminomethyl)aniline typically involves the following steps:

1. **Nitration of Toluene**: Start with toluene as your base compound. Subject it to nitration using nitric acid and sulfuric acid to introduce a nitro group, yielding 4-nitrotoluene.

2. **Catalytic Hydrogenation**: Convert the nitro group to an amino group through catalytic hydrogenation of 4-nitrotoluene over a palladium on carbon (Pd/C) catalyst at elevated pressures of hydrogen gas to form 4-(aminomethyl)toluene (also known as 4-methylbenzenemethanamine).

3. **Protection of Amino Group**: Protect the amino group by reacting the 4-(aminomethyl)toluene with di-tert-butyl dicarbonate (Boc2O) in the presence of a base such as triethylamine. This step affords 4-(N-Boc-aminomethyl)toluene.

4. **Oxidative Dealkylation**: Lastly, remove the methyl group on the benzene ring through oxidative dealkylation using an oxidizing agent like ceric ammonium nitrate (CAN) or oxygen in the presence of a catalyst (like cobalt acetate) in an acidic aqueous media, resulting in the desired product: 4-(N-Boc-aminomethyl)aniline.

Each step should be followed by adequate purification techniques such as recrystallization, column chromatography or distillation to achieve the desired purity of intermediates and the final compound.