2-Nitrobenzenemethan-d2-ol

Base Information

• Chemical Name: 2-Nitrobenzenemethan-d2-ol
• CAS No.: 80404-34-8
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 155.122
• DSSTox Substance ID: DTXSID701310920
• Mol file: 80404-34-8.mol

Synonyms:2-Nitrobenzenemethan-d2-ol;DTXSID701310920;80404-34-8

Chemical Property of 2-Nitrobenzenemethan-d2-ol

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 155.055146577
• Heavy Atom Count: 11
• Complexity: 143

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CO)[N+](=O)[O-]
• Isomeric SMILES: [2H]C([2H])(C1=CC=CC=C1[N+](=O)[O-])O

Technology Process of 2-Nitrobenzenemethan-d2-ol

There total 3 articles about 2-Nitrobenzenemethan-d2-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-nitrobenzyl chloride (610-14-0) → α,α-dideuterio-2-nitrobenzyl alcohol (80404-34-8)

Guidance literature:

2-nitrobenzyl chloride; With sodium borodeuteride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 24h;

With hydrogenchloride; In tetrahydrofuran; N,N-dimethyl-formamide; Further stages.;

DOI:10.1021/ol070820h

Reference yield: 93.0%

methyl 2-nitrobenzoate (606-27-9) → α,α-dideuterio-2-nitrobenzyl alcohol (80404-34-8)

Guidance literature:

With lithium aluminium deuteride; In diethyl ether; at 0 - 20 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201402661

Reference yield:

ortho-nitrobenzoic acid (552-16-9,104810-18-6) → α,α-dideuterio-2-nitrobenzyl alcohol (80404-34-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / thionyl chloride / toluene / 3 h / Heating

2.1: NaBD₄ / dimethylformamide; tetrahydrofuran / 24 h / 20 °C

2.2: 94 percent / aq. HCl / dimethylformamide; tetrahydrofuran

With thionyl chloride; sodium borodeuteride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol070820h

upstream raw materials:

methyl 2-nitrobenzoate

2-nitrobenzyl chloride

ortho-nitrobenzoic acid

Downstream raw materials:

2-nitrobenzaldehyde-α-d₁

glutaric acid (4,5-dimethoxy-2-nitrobenzyl) ester (α,α-dideuterio-2-nitrobenzyl) ester

C₁₆H₁₂⁽²⁾HNO₂

C₁₆H₁₂⁽²⁾HNO₂

Refernces

• 1、 Fang, Yuan-Qing,Lautens, Mark. "A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles". . p. 538 - 549. Retrieved 2008/09/17.
• 2、 Blanc, Aurelien,Bochet, Christian G.. "Isotope effects in photochemistry. 1. o-nitrobenzyl alcohol derivatives". . p. 7174 - 7175. Retrieved 2007/10/03.