Hydrogen

General Information:

Structure:

CAS Number: 1333-74-0

Molecular Weight: 2.02 g/mol

Appearance: Colorless gas

Common Uses:

Reagent for the reduction of nitro groups to amines

Procedure excerpt:

. . . the SM (15.0 g, 67.5 mmol) in MeOH (400 mL). The flask was repeatedly evacuated and flushed with H2 gas. The resulting mixture was allowed to warm to RT and . . .

[full procedure]

Reagent for the reduction of nitriles to amines

Procedure excerpt:

A mixture of the SM (45 mg, 0.12 mmol) and Pd/C (5 mg) in 4:1 THF/NH4OH (2.5 mL) was stirred under H2 at RT for 1 h. The reaction mixture was filtered, concentrated, and . . .

[full procedure]

Reagent for the reduction of alkenes to alkanes

Procedure excerpt:

To a solution of the SM (2.4 g, 9.4 mmol) in EtOH (20 mL) was added PtO2 (10%, 200 mg). The mixture was stirred for 1 h under a H2 atmosphere. The catalyst was filtered . . .

[full procedure]

Reagent for the reduction of alkynes to alkanes

Procedure excerpt:

. . . the SM (100 mg, 0.385 mmol) in EtOH was degassed by bubbling argon for 2 min. Pd/C (10% wt, 41 mg) was added and the reaction mixture atmosphere was changed to H2 . . .

[full procedure]

Reagent for the benzyl deprotections

Procedure excerpt:

. . . purged with N2 and 10% Pd/C (0.30 g) was added. The reaction was hydrogenated on a Parr shaker apparatus under 40 psi H2 for 30 min. The mixture was filtered . . .

[full procedure]

Reagent for Cbz deprotections

Procedure excerpt:

To a solution of the SM (7.5 g, 23 mmol) in MeOH (300 mL) was added 10% Pd/C (2 g). The reaction mixture was hydrogenated in a Parr apparatus at RT under 40 psi H2. . . .

[full procedure]

Safety:

Hydrogen (H2) is a highly flammable gas.

References:

1) Patent Reference: WO2011014535, page 40, (17.3 MB)

2) Patent Reference: WO2016011390, page 152, (20.2 MB)

3) Patent Reference: WO2015089337, page 183, (17.5 MB)

4) UK Pat App GB2463151A, page 121

5) Patent Reference: WO2012069948, page 53, (3.9 MB)

6) Patent Reference: WO2014177977, page 86, (6.0 MB)

7) Wikipedia: Hydrogen (link)

8) www.sigmaaldrich.com: Hydrogen (link)