1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene

Base Information

• Chemical Name: 1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene
• CAS No.: 53413-67-5
• Molecular Formula: C9H10BrNO4
• Molecular Weight: 276.087
• Hs Code.: 29093090
• European Community (EC) Number: 627-578-2
• DSSTox Substance ID: DTXSID40201579
• Nikkaji Number: J721.138D
• Wikidata: Q72468146
• Mol file: 53413-67-5.mol

Synonyms:1-(bromomethyl)-2-nitro-4,5-dimethoxybenzene;BMNDMB

Chemical Property of 1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene

Chemical Property:

• Vapor Pressure: 2.07E-05mmHg at 25°C
• Melting Point: 131-133 °C(lit.)
• Refractive Index: 1.571
• Boiling Point: 372.3 °C at 760 mmHg
• Flash Point: 179 °C
• PSA: 64.28000
• Density: 1.544 g/cm³
• LogP: 3.03010
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Lachrymatory
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 274.97932
• Heavy Atom Count: 15
• Complexity: 221

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,5-Dimethoxy-2-nitrobenzyl bromide 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 22-26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C(=C1)CBr)[N+](=O)[O-])OC
• Uses: 1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene is a useful research chemical. 4,5-Dimethoxy-2-nitrobenzyl bromide (DMNB bromide, 6-nitroveratryl bromide) is suitable reagent used in the synthesis of N-(4,5-dimethoxy-2-nitrobenzyl)vanillylamine which forms caged vanilloid. It may be used in the synthesis of the following:4-(4′,5′-dimethoxy-2-nitrobenzyloxy)benzaldehyde, a DMNB-caged aldehydeN-[4-[(4,5-dimethoxy-2-nitrobenzyl)oxy]-3-methoxybenzyl]acetamidecaged derivative of pyridostatin ([C]-PDS)photosensitive polyimide (PI-DMNB)caged β-ecdysone4-tert-butyldimethylsilyloxy-1-(2-deoxy-3,5-di-O-toluoyl-β-D-ribofuranosyl)-2-(6-nitroveratrylthio)-1H-benzimidazole, an intermediate in synthesis of phosphoramidite bearing 4-hydroxy-2-mercaptobenzimidazole (SBNV) nucleobasealkylation of dihydrofluorescein4-(4′,5′-Dimethoxy-2′-nitrobenzyloxy)benzaldehyde

Technology Process of 1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene

There total 4 articles about 1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene 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%

6-nitroveratryl alcohol (1016-58-6) → 6-nitroveratrylbromide (53413-67-5)

Guidance literature:

With phosphorus tribromide; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1039/c7cc04635a

Reference yield:

6-nitroveratraldehyde (20357-25-9) → 6-nitroveratrylbromide (53413-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / NaBH₄ / methanol / 1 h

2: 64.6 percent / PBr₃, pyridine / benzene / 24 h

With pyridine; sodium tetrahydroborate; phosphorus tribromide; In methanol; benzene;

DOI:10.1021/jo00292a038

Reference yield:

vanillin (121-33-5,8014-42-4) → 6-nitroveratrylbromide (53413-67-5)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / acetone / 17 h / Reflux

2: nitric acid / 2 h / 0 - 20 °C

3: sodium tetrahydroborate / ethanol / 4 h / 20 °C

4: phosphorus tribromide / dichloromethane / 20 °C / Inert atmosphere

With sodium tetrahydroborate; nitric acid; phosphorus tribromide; potassium carbonate; In ethanol; dichloromethane; acetone;

DOI:10.1039/c7cc04635a

upstream raw materials:

6-nitroveratryl alcohol

6-nitroveratraldehyde

vanillin

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

N-Boc-L-leucine (4,5-dimethoxy-2-nitro)benzyl ester

4,5-dimethoxy-2-nitrobenzyl (tert-butoxycarbonyl)-L-alaninate

1-<(4',5'-dimethoxy-2'-nitrophenyl)methyl> 5-tert-butyl N-(tert-butoxycarbonyl)glutamate

N,ω-(Boc)2-L-lysine (4,5-dimethoxy-2-nitro)benzyl ester

Refernces

• 1、 Rickhoff, Jonas,Cornelissen, Nicolas V.,Beuse, Thomas,Rentmeister, Andrea,Jan Ravoo, Bart. "Multiresponsive hydrogels and organogels based on photocaged cysteine". supporting information. p. 5913 - 5916. Retrieved 2021/06/18.
• 2、 Chaudhuri, Amrita,Venkatesh, Yarra,Das, Joyjyoti,Gangopadhyay, Moumita,Maiti, Tapas K.,Singh, N. D. Pradeep. "One- And Two-Photon-Activated Cysteine Persulfide Donors for Biological Targeting". . p. 11441 - 11449. Retrieved 2019/10/02.