365441-87-8

Basic information

• Product Name: Carbamic acid, (2-methylpropyl)-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, (2-methylpropyl)-, 1,1-dimethylethyl ester (9CI);tert-butyl isobutylcarbamate
• CAS NO: 365441-87-8
• Molecular Formula: C₉H₁₉NO₂
• Molecular Weight: 173.25266
• Product Categories: N-BOC
• Mol File: 365441-87-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, (2-methylpropyl)-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (2-methylpropyl)-, 1,1-dimethylethyl ester (9CI)(365441-87-8)
• EPA Substance Registry System: Carbamic acid, (2-methylpropyl)-, 1,1-dimethylethyl ester (9CI)(365441-87-8)

Safety Data

• Hazardous Substances Data: 365441-87-8(Hazardous Substances Data)

Upstream product

• 34619-03-9 tert-butyldicarbonate 
• 78-81-9 isobutylamine 
• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 
• 13734-41-3 t-Boc-L-valine 
• 66389-76-2 tert-butyl methyl iminodicarboxylate 
• 271600-32-9 [2-methyl-1-(toluene-4-sulfonyl)-propyl]-carbamic acid tert-butyl ester 
• 4248-19-5 tert-butyl carbazate 
• 503-74-2 3-methylbutyric acid 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1610605-58-7 tert-butyl isobutyl(4-(trifluoromethyl)phenethyl-1,2,2-D₃)carbamate 
• 1873-29-6 isobutyl isocyanate 
• 112753-91-0 N-isobutyl-3-phenylpropionamide 
• 5705-57-7 N-isobutyl-benzamide 
• 130457-35-1 N-Boc-2-amino-3-methyl-butyronitrile 
• 1067679-06-4 (2-chloro-6-styryl-pyrimidin-4-yl)-isobutyl-carbamic acid tert-butyl ester 

Relevant articles and documents

A strategy for generating alkyl radicals from aliphatic esters and lactones via sequential hydrolysis and photoinduced decarboxylation

Sequential hydrolysis and photoinduced decarboxylation of methyl aliphatic esters lead to efficient generation of alkyl radicals under mild conditions. The generated alkyl radicals react with a variety of reagents to produce addition, reduction, and substitution products. In addition, the new tin and halogen free process for alkyl radical generation is applicable to a variety of aliphatic esters including those of dipeptides, steroids, saccharides, and lactones.

Ligand-controlled α- And β-arylation of acyclic N-boc amines

The palladium-catalyzed ligand-controlled arylation of α-zincated acyclic amines, obtained by directed α-lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α-arylated Boc-protected amines, more flexible N-phenylazole-based phosphine ligands induced major β-arylation through migrative cross-coupling. All manner of control: The arylation of α-zincated acyclic Boc-protected amines was selectively performed at the α- or β-position in a ligand-controlled manner. α-Arylation occurs by direct reductive elimination of the α-palladated intermediate whereas β-arylation involves palladium migration along the alkyl chain. Boc=tert-butoxycarbonyl.

Decarboxylative reduction of free aliphatic carboxylic acids by photogenerated cation radical

The decarboxylation of free carboxylic acids was effected by a photogenerated cation radical of phenanthrene to yield the reduction product in the presence of a thiol, which provides an alternative method to the Barton decarboxylation procedure for aliphatic acids such as N-Boc amino acids. The Royal Society of Chemistry.

Boc-protected amines via a mild and efficient one-pot curtius rearrangement

(Chemical Equation Presented) The reaction of a carboxylic acid with di-tert-butyl dicarbonate and sodium azide allowed the formation of an acyl azide intermediate, which undergoes a Curtius rearrangement in the presence of tetrabutylammonium bromide and zinc(II) triflate. The trapping of the isocyanate derivative in the reaction mixture led to the desired tert-butyl carbamate in high yields at low temperature. These reaction conditions are compatible with a variety of substrates, including malonate derivatives, which provide access to protected amino acids.

An expedient transformation of alcohols into N-Boc-amines

t-Butyl methyl iminodicarbonate (3) can be easily alkylated with primary or secondary alcohols under Mitsunobu conditions (DIAD, TPP) to give the corresponding N-alkyl iminodicarbonates. Partial deprotection of the latter with methanolic potassium hydroxi

Reductive BOC-amination of aldehydes

Base-assisted elimination-reduction of α-amidoalkyl sulfones with sodium borohydride proceeds in tetrahydrofuran at room temperature leading to the corresponding BOC-amines in good yields.