181472-59-3

Basic information

• Product Name: Carbamic acid, (2-hydroxy-2-phenylpropyl)methyl-, 1,1-dimethylethyl ester
• CAS NO: 181472-59-3
• Molecular Formula: C15H23NO3
• Molecular Weight: 265.353
• Mol File: 181472-59-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Carbamic acid, (2-hydroxy-2-phenylpropyl)methyl-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (2-hydroxy-2-phenylpropyl)methyl-, 1,1-dimethylethyl ester(181472-59-3)
• EPA Substance Registry System: Carbamic acid, (2-hydroxy-2-phenylpropyl)methyl-, 1,1-dimethylethyl ester(181472-59-3)

Safety Data

• Hazardous Substances Data: 181472-59-3(Hazardous Substances Data)

Upstream product

• 16066-84-5 N-(tert-butoxycarbonyl)methylamine 
• 98-86-2 acetophenone 
• 189809-03-8 tert-butyl N-methyl-N-(tosylmethyl)carbamate 
• 39073-23-9 O-tert-butyl-N-(chloromethyl)-N-methyl carbamate 

Downstream Products

• 62432-74-0 3,5-dimethyl-5-phenyl-1,3-oxazolin-2-one 
• 5554-63-2 1-methyl-2-(dimethylamino)-1-phenylethanol 
• 6309-19-9 1-methyl-2-(methylamino)-1-phenylethanol 

Relevant articles and documents

α-Aminated methyllithium by DTBB-catalysed lithiation of a N- (chloromethyl) carbamate

The reaction of O-tert-butyl-N-(chloromethyl)-N-methyl carbamate (1) with lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 2.5 mol %) in the presence of different electrophiles [Me3SiCl, (i)BuCHO, (t)BuCHO, PhCHO, 4-MeOC6H4CHO, (CH2)4CO, MeCO(n)Pr, Et2CO, MeCO(CH2)2CH=CH2, PhCOMe, PhCO(n)Bu, Ph2CO] in THF at -78°C leads, after hydrolysis with water, to the expected functionalised carbamates 2. Carbamates 2 derived from carbonyl compounds are deprotected with hydrogen chloride (for aromatic aldehyde or ketone derivatives) or with a mixture of phenol and trimethylsilyl chloride (for aliphatic aldehyde derivatives) giving substituted 1,2-diols 4.

α-Nitrogenated organolithium compounds from N-(tosylmethyl)amides

Deprotonation of α-amido sulfones 7 with BunLi at -90°C followed by reaction with electrophiles leads, depending on the substitution on the amidic nitrogen to enamides 10 (secondary amides 7a,b) or functionalised α-amido sulfones 12 (tertiary amides 7c,d). Naphthalene-catalysed lithiation of tertiary α-amido sulfones 7c,d in the presence of electrophiles (Barbier conditions) at -78°C affords functionalised amides 13.