2-(bromomethyl)-4-nitrophenol

• ChemBase ID: 102528
• Molecular Formular: C7H6BrNO3
• Molecular Mass: 232.03144
• Monoisotopic Mass: 230.95310506
• SMILES: Oc1c(CBr)cc(cc1)[N+](=O)[O-]
• Canonical SMILES: BrCc1cc(ccc1O)[N+](=O)[O-]
• InChI: InChI=1S/C7H6BrNO3/c8-4-5-3-6(9(11)12)1-2-7(5)10/h1-3,10H,4H2
• InChIKey: KFDPCYZHENQOBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(bromomethyl)-4-nitrophenol
• IUPAC Traditional name: 2-(bromomethyl)-4-nitrophenol
• Synonyms: α-Bromo-4-nitro-o-cresol; Koshland Reagent I; 2-Bromomethyl-4-nitrophenol; Koshland I; 2-HYDROXY-5-NITROBENZYL BROMIDE; α-Bromo-4-nitro-o-cresol; Koshland’s Reagent I; 2-Hydroxy-5-nitrobenzyl bromide; α-溴-4-硝基邻甲酚; 2-溴甲基-4-硝基苯酚; Koshland 试剂 I; 2-羟基-5-硝基苄溴

Database IDs

• CAS Number: 772-33-8
• EC Number: 212-248-9
• MDL Number: MFCD00007340
• Beilstein Number: 1868798
• PubChem SID: 162088697; 24879845; 24850013
• PubChem CID: 13044

CALCULATED PROPERTIES

• Acid pKa: 6.7776985
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.3602483
• LogD (pH = 7.4): 1.6808807
• Log P: 2.382402
• Molar Refractivity: 48.214 cm^3
• Polarizability: 17.603182 Å^3
• Polar Surface Area: 66.05 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 144-149 °C; 144-149 °C(lit.)

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 34; R:34
• Safety Statements: 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95% (AT); 90%; 98%
• Linear Formula: HOC6H3(NO2)CH2Br

DETAILS

MP Biomedicals - 02102019

Yellow crystals
Purity: 98%
Protein modification reagent with high specificity for tryptophan.

Sigma Aldrich - 162906

Other Notes
Contains 2-hydroxy-5-nitrobenzyl alcohol
Packaging
5 g in glass bottle
Application
Reagent for sulfhydryl modification.1

Sigma Aldrich - 56011

Other Notes
For the modification of tryptophan residues in neutral and acid conditions1,2,3

REFERENCES

• Koshland, D.E. Jr., et al., J. Am. Chem. Soc. , 86 : 1450, (1964).
• Also see 2-Methoxy-5-nitrobenzyl bromide.