ChemicalBook > CAS DataBase List > 4,5-DIMETHOXY-2-NITROBENZYL BROMIDE

4,5-DIMETHOXY-2-NITROBENZYL BROMIDE

Product Name: 4,5-DIMETHOXY-2-NITROBENZYL BROMIDE
CAS No.: 53413-67-5
Chemical Name: 4,5-DIMETHOXY-2-NITROBENZYL BROMIDE
Synonyms: 6-NITROVERATRYL BROMIDE;1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene;-4,5-dimethoxy-2-nitrobenzene;4,5-dimenoxy-2-nitrobenzyl bromide;3,4-Dimethoxy-6-nitrobenzyl bromide;4,5-DIMETHOXY-2-NITROBENZYL BROMIDE;4,5-Dimethoxy-2-nitrobenzyl bromide 95%;4,5-Dimethoxy-2-nitro-1-bromomethylbenzene;1-(bromomethyl)-2-nitro-4,5-dimethoxybenzene;Benzene, 1-(bromomethyl)-4,5-dimethoxy-2-nitro-
CBNumber: CB4762285
Molecular Formula: C9H10BrNO4
Formula Weight: 276.08
MOL File: 53413-67-5.mol

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4,5-DIMETHOXY-2-NITROBENZYL BROMIDE Property

Melting point:: 131-133 °C (lit.)
Boiling point:: 372.3±37.0 °C(Predicted)
Density: 1.544
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
form: Crystalline Powder or Needles
color: Yellow to brown
Sensitive: Lachrymatory
InChI: InChI=1S/C9H10BrNO4/c1-14-8-3-6(5-10)7(11(12)13)4-9(8)15-2/h3-4H,5H2,1-2H3
InChIKey: UEKFEYNZISYRRH-UHFFFAOYSA-N
SMILES: C1(CBr)=CC(OC)=C(OC)C=C1[N+]([O-])=O

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Safety

Hazard Codes: C
Risk Statements: 34
Safety Statements: 22-26-27-36/37/39-45
RIDADR: UN 3261 8/PG 2
WGK Germany: 3
HazardClass: 8
PackingGroup: III
HS Code: 29093090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 392855
Product name: 4,5-Dimethoxy-2-nitrobenzyl bromide
Purity: 97%
Packaging: 1g
Price: $121.6
Updated: 2025/07/31

Sigma-Aldrich

Product number: 392855
Product name: 4,5-Dimethoxy-2-nitrobenzyl bromide
Purity: 97%
Packaging: 5g
Price: $507
Updated: 2025/07/31

Biosynth Carbosynth

Product number: FB139514
Product name: 4,5-Dimethoxy-2-nitrobenzyl bromide
Packaging: 250mg
Price: $75
Updated: 2021/12/16

SynQuest Laboratories

Product number: 4754-9-00
Product name: 4,5-Dimethoxy-2-nitrobenzyl bromide
Purity: 95%
Packaging: 1g
Price: $125
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB139514
Product name: 4,5-Dimethoxy-2-nitrobenzyl bromide
Packaging: 1g
Price: $180
Updated: 2021/12/16

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4,5-DIMETHOXY-2-NITROBENZYL BROMIDE Chemical Properties,Usage,Production

Uses

1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene is a useful research chemical.

Uses

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 aldehyde
N-[4-[(4,5-dimethoxy-2-nitrobenzyl)oxy]-3-methoxybenzyl]acetamide
caged derivative of pyridostatin ([C]-PDS)
photosensitive polyimide (PI-DMNB)
caged β-ecdysone
4-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 (SB^NV) nucleobase
alkylation of dihydrofluorescein
4-(4′,5′-Dimethoxy-2′-nitrobenzyloxy)benzaldehyde

General Description

4,5-Dimethoxy-2-nitrobenzyl bromide (DMNBB, 1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene) is a 4,5-dimethoxy-2-nitrobenzyl derivative. 4,5-Dimethoxy-2-nitrobenzyl (DMNB) group of DMNBB is used as a photolabile protecting group in caging technology to develop pro-drugs. Synthesis of 1-(bromomethyl)-4,5-dimethoxy-2-nitrobenzene by using 6-nitroveratraldehyde as starting reagent has been reported.

Synthesis

1016-58-6

53413-67-5

Step 1: A tetrahydrofuran (THF, 100 mL) solution of phosphorus tribromide (27.1 g, 100.0 mmol) was added slowly and dropwise through a dosing funnel to a stirring solution of 4,5-dimethoxy-2-nitrobenzenemethanol (10.7 g, 50.0 mmol) in THF (200 mL) under nitrogen protection. The reaction mixture was stirred overnight and the THF was removed by distillation under reduced pressure.The residue was partitioned with saturated aqueous sodium bicarbonate (NaHCO3) to separate the organic layer. The organic layer was subsequently washed with saturated aqueous NaHCO3 and dried with anhydrous magnesium sulfate (MgSO4). After filtration, the filtrate was concentrated to give a dark yellow oil. The oil was purified by silica gel column chromatography (SiO2, elution gradient: hexane/ethyl acetate from 4:1 to 3:1). Concentration of the product-containing eluate gave 11.8 g of 1-(bromomethyl)-4,5-dimethoxy-2-nitrobenzene as a bright yellow solid in 86% yield.

References

[1] Chemical Communications, 2017, vol. 53, # 68, p. 9470 - 9473
[2] Patent: WO2017/95704, 2017, A1. Location in patent: Page/Page column 58
[3] Journal of Organic Chemistry, 1990, vol. 55, # 5, p. 1585 - 1589
[4] Photochemical and Photobiological Sciences, 2012, vol. 11, # 3, p. 548 - 555
[5] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 125 - 136

4,5-DIMETHOXY-2-NITROBENZYL BROMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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4,5-DIMETHOXY-2-NITROBENZYL BROMIDE Suppliers

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53413-67-5, 4,5-DIMETHOXY-2-NITROBENZYL BROMIDERelated Search:

3-(BROMOMETHYL)PHENOL 3-METHOXYBENZYL BROMIDE 2-(bromomethyl)-Benzenamine 4-Methoxybenzyl bromide 4,5-DIMETHOXY-2-NITROBENZYL BROMIDE 4-AMINOCATECHOL HBR 4-Methoxy-2-nitrobenzyl bromide 2-Nitrobenzyl bromide 4-(BROMOMETHYL)PHENOL 3,4-DIMETHOXYBENZYL BROMIDE 2-(BROMOMETHYL)-4-METHOXY-1-NITROBENZENE

4,5-DIMETHOXY-2-NITROBENZYL BROMIDE

6-NITROVERATRYL BROMIDE

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

4,5-Dimethoxy-2-nitrobenzyl bromide 95%

1-(bromomethyl)-2-nitro-4,5-dimethoxybenzene

4,5-dimenoxy-2-nitrobenzyl bromide

3,4-Dimethoxy-6-nitrobenzyl bromide

4,5-Dimethoxy-2-nitro-1-bromomethylbenzene

-4,5-dimethoxy-2-nitrobenzene

JR-13611, 1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene, 97%

Benzene, 1-(bromomethyl)-4,5-dimethoxy-2-nitro-

53413-67-5

O2NC6H2OCH32CH2Br

Organic Building Blocks

Nitrogen Compounds

Nitro Compounds

Building Blocks