1-Deoxy-1-(6-phenylazo-3,4-xylidino)-D-ribitol

Base Information

• Chemical Name: 1-Deoxy-1-(6-phenylazo-3,4-xylidino)-D-ribitol
• CAS No.: 21037-26-3
• Molecular Formula: C19H25N3O4
• Molecular Weight: 359.425
• European Community (EC) Number: 244-163-8
• DSSTox Substance ID: DTXSID101189430
• Nikkaji Number: J191.740D
• Mol file: 21037-26-3.mol

Synonyms:21037-26-3;1-Deoxy-1-(6-phenylazo-3,4-xylidino)-D-ribitol;(2R,3S,4S)-5-(4,5-dimethyl-2-phenyldiazenylanilino)pentane-1,2,3,4-tetrol;1-Deoxy-1-[4,5-dimethyl-2-(phenylazo)phenylamino]-D-ribitol;3,4-Xylyl-6-phenylazo-D-ribitylamine;SCHEMBL10351519;DTXSID101189430;EINECS 244-163-8;1-Deoxy-1-{[4,5-dimethyl-2-(phenyldiazenyl)phenyl]amino}pentitol;1-(d-Ribosylamino)-3,4-dimethylphenyl-6-azobenzene;W-109183;1-[2-(Phenylazo)-4,5-dimethylanilino]-1-deoxy-D-ribitol;1-Deoxy-1-[[4,5-dimethyl-2-(2-phenyldiazenyl)phenyl]amino]-D-ribito

Chemical Property of 1-Deoxy-1-(6-phenylazo-3,4-xylidino)-D-ribitol

Chemical Property:

• Vapor Pressure: 1.08E-17mmHg at 25°C
• Melting Point: >170?C (dec.)
• Boiling Point: 648.3°Cat760mmHg
• Flash Point: 345.9°C
• PSA: 117.67000
• Density: 1.27g/cm³
• LogP: 2.27870
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Ethyl Acetate, Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 359.18450629
• Heavy Atom Count: 26
• Complexity: 431

Purity/Quality:

98%min ^*data from raw suppliers

3,4-Xylyl-6-phenylazo-D-ribitylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1C)N=NC2=CC=CC=C2)NCC(C(C(CO)O)O)O
• Isomeric SMILES: CC1=CC(=C(C=C1C)N=NC2=CC=CC=C2)NC[C@@H]([C@@H]([C@@H](CO)O)O)O
• Uses: Riboflavin intermediate.

Technology Process of 1-Deoxy-1-(6-phenylazo-3,4-xylidino)-D-ribitol

There total 12 articles about 1-Deoxy-1-(6-phenylazo-3,4-xylidino)-D-ribitol 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: 95.0%

N-ribityl-3,4-dimethylaniline (83916-71-6) + aniline (62-53-3) → N-ribityl-2-phenylazo-4,5-dimethylaniline (21037-26-3,113473-93-1)

Guidance literature:

aniline; With hydrogenchloride; In water; at 0 ℃; for 0.166667h;

With sodium nitrite; In water; at 0 ℃; for 0.5h;

N-ribityl-3,4-dimethylaniline; Further stages;

DOI:10.1021/acs.joc.6b00640

Reference yield:

benzenediazonium (2684-02-8) + 3,4-dimethyl-N-ribitylaniline (3051-94-3) → N-<3,4-dimethyl-6-(phenylazo)phenyl>-D-ribitylamine (21037-26-3) + N-<3,4-dimethyl-2-(phenylazo)phenyl>-D-ribitylamine (21037-25-2)

Guidance literature:

DOI:10.1021/ja01198a068 DOI:10.1002/hlca.19360190141

Reference yield:

benzenediazonium (2684-02-8) + L-ribo-5-(3.4-dimethyl-anilino)-1.2.3.4-tetraacetoxy-pentane (911650-71-0) → N-<3,4-dimethyl-6-(phenylazo)phenyl>-D-ribitylamine (21037-26-3) + N-<3,4-dimethyl-2-(phenylazo)phenyl>-D-ribitylamine (21037-25-2)

Guidance literature:

und Behandlung des Reaktionsprodukts mit Natriummethylat in Methanol;

DOI:10.1021/ja01198a068

upstream raw materials:

4-amino-o-xylene

D-ribose

N-ribityl-3,4-dimethylaniline

aniline

Downstream raw materials:

riboflavin

N-D-ribityl-4,5-dimethyl-1,2-phenylenediamine

1-N-D-ribitylamino-3,4-dimethyl-6-phenylazobenzene

riboflavin

Refernces

• 1、 Neti, Syam Sundar,Poulter, C. Dale. "Site-Selective Synthesis of 15N- and 13C-Enriched Flavin Mononucleotide Coenzyme Isotopologues". . p. 5087 - 5092. Retrieved 2016/07/06.