6-Nitroveratryl alcohol (HCID 66097)

Names & identifiers

Preferred name: 6-Nitroveratryl alcohol
IUPAC: (4,5-dimethoxy-2-nitrophenyl)methanol
English name: 4,5-Dimethoxy-2-nitrobenzyl alcohol
Molecular formula: C9H11NO5
Molecular weight: 213.19

Names & synonyms

1016-58-66-Nitroveratryl alcohol4,5-Dimethoxy-2-nitrobenzenemethanolEINECS 213-806-4DTXSID50144044RefChem:544108DTXCID00665354,5Dimethoxy2nitrobenzyl alcohol213-806-44,5-Dimethoxy-2-nitrobenzyl alcohol(4,5-dimethoxy-2-nitrophenyl)methanolBenzenemethanol, 4,5-dimethoxy-2-nitro-

Show more names

4,5- dimethoxy-2-nitro benzyl alchohol(4,5-Dimethoxy-2-nitro-phenyl)-methanolTIMTEC-BB SBB009964RARECHEM AL BD 0187LABOTEST-BB LT008477214,5-Dimethoxy-2-nitrobenzyL6-NITROVERATRYL ALCOHOL 98+%

MFCD000147012-nitro-4,5-dimethoxybenzyl alcohol(4,5-dimethoxy-2-nitrophenyl)methan-1-ol4,5-Dimethoxy-2-nitrobenzyl alcohol, 98%CS-0104904D4811EN300-1841144BCP11712

Database identifiers

CAS: 1016-58-6
PubChem CID: 66097
DTXSID: DTXSID50144044
EC Number: 213-806-4
Nikkaji: J217.140F

Properties

Computed structural properties

XLogP: 0.8
Topological polar surface area: 84.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 5
Rotatable bonds: 3
Heavy atoms: 15
Formal charge: 0
Complexity: 217

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)

Physical DescriptionBeige powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point: 145 · 145-148 °C (lit.)
Boiling point: 383.9 · 383.9±37.0 °C(Predicted)
Density: 1.307 · 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 · 13.59±0.10(Predicted)
color: White to Yellow to Green
Water Solubility: Soluble in water.
λmax: 400 nm · 400nm(CH3CN)(lit.)
Sensitive: Light Sensitive
BRN: 1880093 · 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 · 1016-58-6(CAS DataBase Reference)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 280 · P280-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
F: 8 · 8
HazardClass: IRRITANT
HS Code: 29094990 · 29094990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Hazard information

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]

Safety data

F: 8
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29094990
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 22-24/25
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Precautionary statements: P280-P305+P351+P338

Chemistry & industry

Applications · 3 items

Uses4,5-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.

Uses4,5-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-nitrobenzenebis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol, a photolabile protecting groupoptically-sensitive monomernitroveratryl (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-phenylcarbonate6-nitroveratryloxycarbonyl chloride (NVOCCl), a reagent used in the protection of amino function in amino sugars

General Description4,5-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).