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

4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL

Product Name
4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL
CAS No.
1016-58-6
Chemical Name
4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL
Synonyms
(4,5-Dimethoxy-2-nitro-phenyl)-methanol;TIMTEC-BB SBB009964;RARECHEM AL BD 0187;LABOTEST-BB LT00847721;6-NITROVERATRYL ALCOHOL;4,5-Dimethoxy-2-nitrobenzyL;6-NITROVERATRYL ALCOHOL 98+%;2-Nitro-4,5-dimethoxybenzyl alcohol;4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL;4,5-Dimethoxy-2-nitrobenzenemethanol
CBNumber
CB9392243
Molecular Formula
C9H11NO5
Formula Weight
213.19
MOL File
1016-58-6.mol
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4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL Property

Melting point:
145-148 °C (lit.)
Boiling point:
383.9±37.0 °C(Predicted)
Density 
1.307±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
form 
powder to crystal
pka
13.59±0.10(Predicted)
color 
White to Yellow to Green
Water Solubility 
Soluble in water.
λmax
400nm(CH3CN)(lit.)
Sensitive 
Light Sensitive
BRN 
1880093
InChI
1S/C9H11NO5/c1-14-8-3-6(5-11)7(10(12)13)4-9(8)15-2/h3-4,11H,5H2,1-2H3
InChIKey
WBSCOJBVYHQOFB-UHFFFAOYSA-N
SMILES
COc1cc(CO)c(cc1OC)[N+]([O-])=O
CAS DataBase Reference
1016-58-6(CAS DataBase Reference)
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
F 
8
HazardClass 
IRRITANT
HS Code 
29094990
Storage Class
11 - Combustible Solids
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

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

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
392847
Product name
4,5-Dimethoxy-2-nitrobenzyl alcohol
Purity
98%
Packaging
10g
Price
$373.35
Updated
2025/07/31
TCI Chemical
Product number
D4811
Product name
4,5-Dimethoxy-2-nitrobenzyl Alcohol
Purity
>98.0%(GC)
Packaging
1g
Price
$59
Updated
2025/07/31
TCI Chemical
Product number
D4811
Product name
4,5-Dimethoxy-2-nitrobenzyl Alcohol
Purity
>98.0%(GC)
Packaging
5g
Price
$178
Updated
2025/07/31
TRC
Product number
D470698
Product name
4,5-Dimethoxy-2-nitrobenzyl Alcohol
Packaging
500mg
Price
$75
Updated
2021/12/16
TRC
Product number
D470698
Product name
4,5-Dimethoxy-2-nitrobenzyl Alcohol
Packaging
50mg
Price
$45
Updated
2021/12/16
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4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powde

Uses

4,5-Dimethoxy-2-nitrobenzyl alcohol, is used as Reagent for the protection of alcohols, etc., as ethers which can be cleaved by photolysis involving intramolecular rearrangement to derivatives of o-nitrosobenzaldehyde, which are readily cleaved by hydrolysis. It is also used as photochemical protecting groups in organic synthesis. It is also used as a pharmaceutical intermediate.

Uses

4,5-Dimethoxy-2-nitrobenzyl alcohol (6-nitroveratryl alcohol) is suitable reagent used in the synthesis of 4,5-dimethoxy-2-nitrobenzyl methacrylate, a photolabile monomer and 2-(4-((4-(4,5-dimethoxy-2-nitrobenzyloxy)phenyl)cyclohexylidene)methyl)phenoxy)-N,N-dimethylethanamine, a caged cyclofen-OH ligand.

It may be used in the synthesis of the following:

  • 1-[[(chlorocarbonyl)oxy]methyl]-4,5-dimethoxy-2-nitrobenzene
  • bis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol, a photolabile protecting group
  • optically-sensitive monomer
  • nitroveratryl (NV) protected α-hydroxyacetic acid (αG) (NV-αG-OH), required in the preparation of nitroveratryl (NV) protected cyanomethyl (CM) ester of α-hydroxyacetic acid (αG) (NV-αG-CM)
  • 4,5-dimethoxy-2-nitrobenzyl p-nitro-phenylcarbonate
  • 6-nitroveratryloxycarbonyl chloride (NVOCCl), a reagent used in the protection of amino function in amino sugars

General Description

4,5-Dimethoxy-2-nitrobenzyl alcohol (6-Nitroveratryl Alcohol) is 2-nitrobenzyl alcohol derivative. It has been reported to be one of the oxidation products of veratryl (3,4-dimethoxybenzyl) alcohol by lignin peroxidase (isolated from Phanerochaete chrysosporium).

Synthesis

20357-25-9

1016-58-6

Step (a): sodium borohydride (7.6 g, 199 mmol) was slowly added to a solution of 4,5-dimethoxy-2-nitrobenzaldehyde (20.0 g, 95 mmol) in a solvent mixture of methanol/dichloromethane (800 mL; 3:1) at 0 °C. The reaction mixture was stirred at room temperature overnight before the reaction was quenched by the addition of water. The organic layer was separated, washed sequentially with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane as eluent) afforded the pure product 4,5-dimethoxy-2-nitrobenzyl alcohol (19.7 g, 92 mmol) as a yellow solid in 99% yield.

References

[1] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 453 - 462
[2] Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2434 - 2441
[3] Tetrahedron, 1997, vol. 53, # 39, p. 13449 - 13472
[4] Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5567 - 5577
[5] Chemical Communications, 2017, vol. 53, # 68, p. 9470 - 9473

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

Raw materials

Preparation Products

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4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL Suppliers

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View Lastest Price from 4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL 1016-58-6
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-06
Henan Bao Enluo International TradeCo.，LTD
Product
4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL 1016-58-6
Price
US $50.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
10000MT
Release date
2023-08-10
Career Henan Chemical Co
Product
4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL 1016-58-6
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100kg
Release date
2019-07-12

1016-58-6, 4,5-DIMETHOXY-2-NITROBENZYL ALCOHOLRelated Search:

Methyl 2-nitro-3,4,5-trimethoxybenzoate 4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL 6-NITROVERATRYL CHLOROFORMATE 4-[4-(1-Hydroxyethyl)-2-Methoxy-5-nitrophenoxy]butanoic Acid ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE Methyl 4,5-dimethoxy-2-nitrobenzoate D-ribo-Hexanoic acid, 3-deoxy-, γ-lactone 2-Nitrobenzyl alcohol GLUTAMATE, CAGED 4,5-DIMETHOXY-2-NITROBENZYL ADENOSINE 3',5'-CYCLICMONOPHOSPHATE 4-(4-HYDROXYMETHYL-2-METHOXY-5-NITROPHENOXY)BUTYRIC ACID (4,5-DIMETHOXY-2-NITRO-PHENYL)-PHENYL-METHANOL 3,4,5-TRIMETHOXY-2-NITROBENZOIC ACID D-LUCIFERIN 1-(4,5-DIMETHOXY-2-NITROPHENYL)ETHYL ESTER ARACHIDONIC ACID 1-(4,5-DIMETHOXY-2-NITROPHENYL)ETHYL ESTER ADENOSINE 5'-TRIPHOSPHATE, P3-(1-(4,5-DIMETHOXY-2-NITROPHENYL)ETHYL) ESTER, DISODIUM SALT A-23187, 1-(4,5-DIMETHOXY-2-NITROPHENYL)ETHYL ESTER 4-BROMO A-23187, 1-(4,5-DIMETHOXY-2-NITROPHENYL)ETHYL ESTER

  • RARECHEM AL BD 0187
  • TIMTEC-BB SBB009964
  • LABOTEST-BB LT00847721
  • 6-NITROVERATRYL ALCOHOL
  • 4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL
  • 4,5-Dimethoxy-2-nitrobenzyl alcohol 98%
  • 6-NITROVERATRYL ALCOHOL 98+%
  • (4,5-Dimethoxy-2-nitro-phenyl)-methanol
  • 2-Nitro-4,5-dimethoxybenzenemethanol
  • 2-Nitro-4,5-dimethoxybenzyl alcohol
  • 4,5-Dimethoxy-2-nitrobenzenemethanol
  • 4,5-Dimethoxy-2-nitrobenzyl alcohol, 98+%
  • 4,5-Dimethoxy-2-nitrobenzyL
  • Benzenemethanol, 4,5-dimethoxy-2-nitro-
  • 4,5- dimethoxy-2-nitro benzyl alchohol
  • 1016-58-6
  • C9H11N05
  • O2NC6H2OCH32CH2OH
  • Alcohols
  • Building Blocks
  • C9 to C30
  • Oxygen Compounds
  • Organic Building Blocks
  • Benzhydrols, Benzyl & Special Alcohols
  • Alcohols
  • Building Blocks
  • C9 to C10
  • Chemical Synthesis
  • Organic Building Blocks
  • Oxygen Compounds