80404-34-8

Basic information

• Product Name: α,α-dideuterio-2-nitrobenzyl alcohol
• Synonyms: α,α-dideuterio-2-nitrobenzyl alcohol
• CAS NO: 80404-34-8
• Molecular Weight: 155.122
• Mol File: 80404-34-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: α,α-dideuterio-2-nitrobenzyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: α,α-dideuterio-2-nitrobenzyl alcohol(80404-34-8)
• EPA Substance Registry System: α,α-dideuterio-2-nitrobenzyl alcohol(80404-34-8)

Safety Data

• Hazardous Substances Data: 80404-34-8(Hazardous Substances Data)

Upstream product

• 610-14-0 2-nitrobenzyl chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 606-27-9 methyl 2-nitrobenzoate 

Downstream Products

• 50344-83-7 2-nitrobenzaldehyde-α-d₁ 
• 1643796-18-2 C₁₆H₁₂⁽²⁾HNO₂ 
• 1643796-19-3 C₁₆H₁₂⁽²⁾HNO₂ 
• 89650-54-4 2-nitro-<α-D>-styrene 
• 1643796-33-1 2-vinyl-d1-aniline 
• 1643796-05-7 benzyl (2-vinyl-d1-phenyl)carbamate 
• 945920-73-0 glutaric acid (4,5-dimethoxy-2-nitrobenzyl) ester (α,α-dideuterio-2-nitrobenzyl) ester 

Relevant articles and documents

Indole synthesis based on a modified koser reagent

A new metal-free method for the rapid and productive preparation of indoles has been developed. This process is based on sterically congested hypervalent iodine compounds of the family of Koser reagents, and iodosobenzene in combination with 2,4,5-tris-isopropylbenzene sulfonic acid provides the highest yields and fastest reaction times. This reagent alone promotes the chemoselective oxidative cyclization of 2-amino styrenes to indoles in high yields under mild conditions. Convenient route to indole: A fast, productive, and operationally simple indole synthesis was developed.

Isotope effects in photochemistry: Application to chromatic orthogonality

Equation Presented The main challenge in developing new wavelength-specific photolabile protecting groups is the rigorous control of the photolysis rate. This rate is controlled by two factors: the chromophore absorbance and the reaction quantum yield. Fine-tuning the properties by changing substituents or structural features is difficult, because both factors are independently affected. By the use of the kinetic isotope effect, we could tune the quantum yield without altering the absorbance, and hence control the overall reaction rate. We exemplified this approach with chromatically orthogonally protected diesters.

Photochemistry of (2-nitrophenyl)diazomethane studied by the matrix isolation technique. (Nitrophenyl)carbene to (carboxylphenyl)nitrene rearrangement by successive reduction of the nitro group with the carbenic center

Irradiation (λ > 350 nm) of (2-nitrophenyl)diazomethane (1) matrix-isolated in Ar at 10 K provided 2-nitrosobenzaldehyde (3) presumably as a result of intramolecular oxygen migration in (2-nitrophenyl)carbene (2). Upon further irradiation (λ > 350 nm), 3 was decomposed to give a mixture of 2,1-benzisoxazol-3(1H)-one (4) and carbonylcyclopentadiene imine (5) along with CO2. The oxazolone (4) underwent decarboxylation to give 5 upon irradiation with shorter wavelength light (λ > 300 nm) but not at longer wavelength (λ > 350 nm), suggesting 4 is not the direct precursor for 5 in the photolysis of 3. Irradiation (λ > 350 nm) of (4-n-butyl-2-nitrophenyl)diazomethane (1b) under similar conditions resulted in the formation of carbonyloximinocyclohexadienylidene (7) which then produced the oxazolone (4b) and the imine (5b) upon further irradiation, suggesting that a 1,4-biradical generated as a result of abstraction of H at the ortho position by the photoexcited nitroso group was involved in the reaction of 3 forming 4. (2-Carboxyphenyl)nitrene (9) generated by 1,4-OH shift in the 1,4-biradical was postulated as an intermediate leading to 5, and this was actually demonstrated by independent generation of 9 by the photolysis of 2-azidobenzoic acid (8).