4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butanoic acid

• ChemBase ID: 152858
• Molecular Formular: C13H17NO7
• Molecular Mass: 299.27658
• Monoisotopic Mass: 299.10050189
• SMILES: CC(c1cc(c(cc1[N+](=O)[O-])OCCCC(=O)O)OC)O
• Canonical SMILES: COc1cc(C(O)C)c(cc1OCCCC(=O)O)[N+](=O)[O-]
• InChI: InChI=1S/C13H17NO7/c1-8(15)9-6-11(20-2)12(7-10(9)14(18)19)21-5-3-4-13(16)17/h6-8,15H,3-5H2,1-2H3,(H,16,17)
• InChIKey: DUIJUTBRRZCWRD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butanoic acid
• IUPAC Traditional name: 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butanoic acid
• Synonyms: 4-[4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy]butanoic Acid; Hydroxyethyl photolinker; 4-[4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyric acid; 羟乙基光偶联剂; 4-[4-(1-羟乙基)-2-甲氧基-5-硝基苯氧基]丁酸

Database IDs

• CAS Number: 175281-76-2
• MDL Number: MFCD01318869
• Beilstein Number: 7717635
• PubChem SID: 24879281; 162247001
• PubChem CID: 3437287

CALCULATED PROPERTIES

• Acid pKa: 3.0735114
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.1443652
• LogD (pH = 7.4): -2.2144175
• Log P: 1.25077
• Molar Refractivity: 73.0828 cm^3
• Polarizability: 27.748936 Å^3
• Polar Surface Area: 121.81 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 161-164°C (dec.); 163-166 °C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C13H17NO7

DETAILS

Sigma Aldrich - 55262

Other Notes
Photolabile linker which can be bound to amino- and hydroxymethyl resins. Synthesis of sensitive acids1,2
Packaging
1 g in glass bottle

Toronto Research Chemicals - H825255

Used for preparation of photolabile linking groups for use in solid phase synthesis.

REFERENCES

• Jay, S., et al.: Nat. Biotechnol., 27, 543 (2009)
• Lin, C., et al.: Pharm. Res., 26, 631 (2009)
• Reed, J., et al.: Langmuir, 25, 36 (2009)