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193836

Sigma-Aldrich

3-Methoxy-4-nitrobenzyl alcohol

99%

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About This Item

Linear Formula:
CH3OC6H3(NO2)CH2OH
CAS Number:
80866-88-2
Molecular Weight:
183.16
EC Number:
279-593-5
MDL number:
MFCD00007098
UNSPSC Code:
12352100
PubChem Substance ID:
24851617
NACRES:
NA.22

Assay

99%

form

solid

mp

95-97 °C (lit.)

SMILES string

COc1cc(CO)ccc1[N+]([O-])=O

InChI

1S/C8H9NO4/c1-13-8-4-6(5-10)2-3-7(8)9(11)12/h2-4,10H,5H2,1H3

InChI key

AADYWCBPJZAJNU-UHFFFAOYSA-N

Application

3-Methoxy-4-nitrobenzyl alcohol was used in the synthesis of:
  • 3-methoxy-4-nitrobenzyl azide
  • new aryl azides, (Z)-1-(3′-azido-4′-methoxyphenyl)-2-(3″,4″,5″-trimethoxyphenyl)ethane and (Z)-1-(4′-azido-3′-methoxyphenyl)-2-(3″,4″,5″-trimethoxyphenyl)ethane, potentially useful photoaffinity labeling reagents for tubulin
  • 3-methoxy-4-nitrobenzaldehyde via oxidation
  • 4-[3-(2-methylphenyl)ureido]-3-methoxybenzylchloride, required for syntheses of trifluoromethyl-substituted hydantoins

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Trifluoromethyl-substituted hydantoins, versatile building blocks for rational drug design.
Wehner V, et al.
Tetrahedron, 60(19), 4295-4302 (2004)
Jeewoo Lee et al.
Journal of medicinal chemistry, 46(14), 3116-3126 (2003-06-27)
Isosteric replacement of the phenolic hydroxyl group in potent vanilloid receptor (VR1) agonists with the alkylsulfonamido group provides a series of compounds which are effective antagonists to the action of the capsaicin on rat VR1 heterologously expressed in Chinese hamster
K G Pinney et al.
Bioorganic & medicinal chemistry, 8(10), 2417-2425 (2000-11-01)
Two new aryl azides, (Z)-1-(3'-azido-4'-methoxyphenyl)-2-(3",4",5"-trimethoxyphenyl)ethene 9 and (Z)-1-(4'-azido-3'-methoxyphenyl)-2-(3",4",5"-trimethoxyphenyl)ethene 5, modeled after the potent antitumor, antimitotic agent combretastatin A-4 (CA-4), have been prepared by chemical synthesis as potentially useful photoaffinity labeling reagents for the colchicine site on beta-tubulin. Aryl azide 9
Can we predict reactivity for aromatic nucleophilic substitution with [18F] fluoride ion?
Rengan R, et al.
Journal of Labelled Compounds & Radiopharmaceuticals, 33(7), 563-572 (1993)

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