5-deazariboflavin

Base Information

• Chemical Name: 5-deazariboflavin
• CAS No.: 19342-73-5
• Molecular Formula: C18H21 N3 O6
• Molecular Weight: 375.381
• Mol file: 19342-73-5.mol

Synonyms:Pyrimido[4,5-b]quinoline-2,4(3H,10H)-dione,7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)- (8CI);Pyrimido[4,5-b]quinoline, D-ribitol deriv.; 5-Deazariboflavin;5-Deazariboflavine; NCI 0112202; NSC 112202

Chemical Property of 5-deazariboflavin

Chemical Property:

• Melting Point: 278-282 °C(Solv: water (7732-18-5))
• Boiling Point: °Cat760mmHg
• PKA: 5.79±0.20(Predicted)
• Flash Point: °C
• PSA: 148.67000
• Density: 1.57g/cm³
• LogP: -1.07020
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

5-Deazariboflavin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-Deazariboflavin, is the derivative of (-)-Riboflavin (R414995), known as vitamin B2 . 5-Deazariboflavin,is also utilized in photosensitized cleavage of thymine dimer, used in the study of the action of photoreactivation enzymes. It is also used in synthesis of 5-deazaflavin adenine dinucleotide (5-dFAD). 1-Deazariboflavin, is the derivative of (-)-Riboflavin (R414995), known as vitamin B2 .5-Deazariboflavin,is also utilized in photosensitized cleavage of thymine dimer, used in the study of the action of photoreactivation enzymes. It is also used in synthesis of 5-deazaflavin adenine dinucleotide (5-dFAD).

Technology Process of 5-deazariboflavin

There total 12 articles about 5-deazariboflavin 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: 96.0%

2',3',4',5'-tetra-O-acetyl-5-deazariboflavin (59389-72-9) → 5-deazariboflavin (19342-73-5)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 18h;

Reference yield:

4-amino-o-xylene (95-64-7) → 5-deazariboflavin (19342-73-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / sodium cyanoborohydride / methanol / 48 h / 65 °C

2: malononitrile / methanol / 48 h / Heating

3: 408 mg / pyridine / 1 h / 20 °C

4: 64 percent / phosphorus oxychloride / 0.75 h / 20 - 100 °C

5: methanol; ammonia

With pyridine; methanol; ammonia; sodium cyanoborohydride; trichlorophosphate; malononitrile; In methanol;

DOI:10.1021/jo049859f

Reference yield:

4-amino-o-xylene (95-64-7) → 5-deazariboflavin (19342-73-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 67.2 percent / ammonium chloride / methanol / 1 h / Heating

2: 75 percent / H₂ / 10 percent Pd/C / dimethylformamide / 1 h / 3102.9 Torr

3: 68 percent

4: 90 percent / perchloric acid / 2 h / 20 °C

5: 85 percent / POCl₃

6: 96 percent / anhydrous hydrogen chloride / methanol / 18 h / 20 °C

With hydrogenchloride; perchloric acid; ammonium chloride; hydrogen; trichlorophosphate; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

2',3',4',5'-tetra-O-acetyl-5-deazariboflavin

D-ribose

3,4-dimethyl-N-ribitylaniline

4-amino-o-xylene

Downstream raw materials:

7,8-dimethyl-10-(5-phosphono-L-ribitol-1-yl)-10H-pyrimido[4,5-b]quinoline-2,4-dione

5-deazaflavin adenine dinucleotide

Refernces

• 1、 Su, Qi,Boucher, Petrina A.,Rokita, Steven E.. "Conversion of a Dehalogenase into a Nitroreductase by Swapping its Flavin Cofactor with a 5-Deazaflavin Analogue". . p. 10862 - 10866. Retrieved 2017.
• 2、 Carlson, Erin E.,Kiessling, Laura L.. "Improved Chemical Syntheses of 1- and 5-Deazariboflavin". . p. 2614 - 2617. Retrieved 2007/10/03.