404586-94-3

Basic information

• Product Name: BOC-1-TERT-BUTOXY-1,2-DIHYDROISOQUINOLIN
• Synonyms: 1-tert-Butoxy-2-butoxycarbonyl-1,2-dihydroisoquinoline, BBDI;BBDI
• CAS NO: 404586-94-3
• Molecular Formula: C₁₈H₂₅NO₃
• Molecular Weight: 303.4
• Mol File: 404586-94-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 112-116 °C
• Boiling Point: 412.9°C at 760 mmHg
• Flash Point: 203.5°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 5.01E-07mmHg at 25°C
• Refractive Index: 1.543
• PKA: -2.58±0.40(Predicted)
• CAS DataBase Reference: BOC-1-TERT-BUTOXY-1,2-DIHYDROISOQUINOLIN(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-1-TERT-BUTOXY-1,2-DIHYDROISOQUINOLIN(404586-94-3)
• EPA Substance Registry System: BOC-1-TERT-BUTOXY-1,2-DIHYDROISOQUINOLIN(404586-94-3)

Safety Data

• Hazard Codes: T,N,Xn
• Statements: 25-36/37/38-50/53-22
• Safety Statements: 26-36/37-45-60-61
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 404586-94-3(Hazardous Substances Data)

Usage

Uses

A versatile tert-butoxycarbonylation protecting reagent for a variety of acidic substrates including phenols, amine hydrochlorides, carboxylic acids, N-protected amino acids, thiols, sulfonamides, and imides.

InChI:InChI=1/C18H25NO3/c1-17(2,3)21-15-14-10-8-7-9-13(14)11-12-19(15)16(20)22-18(4,5)6/h7-12,15H,1-6H3

Upstream product

• 119-65-3 isoquinoline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 156281-11-7 tert-butyl (4-(hydroxymethyl)phenyl)carbonate 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 
• 95932-39-1 carbonic acid 4-aminophenyl ester tert-butyl ester 
• 95932-40-4 tert-butyl (4-((tert-butoxycarbonyl)oxy)phenyl)carbamate 
• 53639-33-1 benzoic tert-butylcarbonic anhydride 
• 2845-66-1 N-(tert-butoxycarbonyl)benzenesulfonamide 
• 6627-89-0 tert-butyl phenyl carbonate 
• 404586-95-4 4-(tert-butoxycarbonyloxy)methoxybenzene 
• 36760-43-7 O-(tert-butyl) S-phenyl thiocarbonate 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 104060-23-3 tert-butyl N-[4-(2-hydroxyethyl)phenyl]carbamate 
• 54840-15-2 4-N-tert-butoxycarbonylaminophenol 

Relevant articles and documents

Enantioselective Dearomative Arylation of Isoquinolines

The C1-substituted tetrahydroisoquinolines and 1,2-dihydroisoquinoline constitute an important group and are interesting structural motifs found in many natural products and pharmaceuticals. In this context, a phosphoric-acid-catalyzed enantioselective dearomative arylation of isoquinolines was realized, providing the chiral dihydroisoquinolines with indole substituents at the C1-position in good results (up to >99% yield and 97% ee). The reaction features mild reaction conditions and operational simplicity, which make it an attractive approach to the discovery of biologically interesting α-indolisoquinolines.

Synthesis of acylsilanes by copper(I)-catalyzed addition of silicon nucleophiles onto acid derivatives

The transition metal-catalyzed transfer of silicon nucleophiles onto various electrophiles has recently gained considerable attention, due to the now readily available silicon pro-nucleophiles such as silylboronates. Our interest lies in the addition of such species to acid derivatives for the generation of acylsilanes. We report herein an efficient method to synthesize these compounds, starting from easy-to-form anhydrides, with very good yields. Copyright

A novel tert-butoxycarbonylation reagent: 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI)

The use of 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) as a tert-butoxycarbonylation reagent for acidic proton-containing substrates such as phenols, aromatic and aliphatic amines hydrochlorides, and aromatic carboxylic acids in the absence of a base is described. The reactions proceed chemoselectively in high yield under mild conditions.