1-(bromomethyl)-4-nitrobenzene

• ChemBase ID: 85634
• Molecular Formular: C7H6BrNO2
• Molecular Mass: 216.03204
• Monoisotopic Mass: 214.95819044
• SMILES: BrCc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: BrCc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C7H6BrNO2/c8-5-6-1-3-7(4-2-6)9(10)11/h1-4H,5H2
• InChIKey: VOLRSQPSJGXRNJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(bromomethyl)-4-nitrobenzene
• IUPAC Traditional name: nitrobenzyl bromide; 4-nitrobenzyl bromide
• Synonyms: 4-Nitrobenzyl bromide; α-Bromo-4-nitrotoluene; 4-Nitrobenzyl bromide; alpha-Bromo-4-nitrotoluene; 1-(Bromomethyl)-4-nitrobenzene; 4-(Bromomethyl)nitrobenzene; 4-Nitrobenzyl bromide 98%; p-NITROBENZYL BROMIDE; 1-(Bromomethyl)-4-nitrobenzene; α-溴-4-硝基甲苯; 4-硝基苄溴; 4-硝基溴苄

Database IDs

• CAS Number: 100-11-8
• EC Number: 202-820-6
• MDL Number: MFCD00007373
• Beilstein Number: 742796
• PubChem SID: 162072750; 24897481
• PubChem CID: 66011

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.6859674
• LogD (pH = 7.4): 2.6859674
• Log P: 2.6859674
• Molar Refractivity: 45.2289 cm^3
• Polarizability: 16.891603 Å^3
• Polar Surface Area: 43.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 96-99 °C(lit.); 97-101°C; 97-101°C

Safety Information

• Storage Warning: Corrosive/Lachrymatory/Light Sensitive/Moisture Sensitive/Store under Argon
• RTECS: XS7967000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; 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

Product Information

• Purity: 97%; 97+%; 99%
• Linear Formula: O2NC6H4CH2Br

DETAILS

MP Biomedicals - 05205773

MP Biomedicals Rare Chemical collection

Sigma Aldrich - N13054

Packaging
25, 100 g in glass bottle

REFERENCES

• Has been used as a protecting reagent for the carboxyl group in peptide synthesis: Helv. Chim. Acta, 42, 972 (1959); see 4-Nitrobenzyl chloride, A15749, and Appendix 6. Has also been used in ?-lactam synthesis. Cleavage by sodium sulfide avoids hydrogenolysis problems otherwise encountered with these sulfur-containing nuclei: J. Org. Chem., 43, 1243 (1978).
• For the protection of alcohols, introduction of the group by the use of silver oxide has been recommended. Selective cleavage can be accomplished with DDQ (2,3-Dichloro-5,6-dicyanobenzoquinone, A11879) or by anodic oxidation. Many other benzyl-type protecting groups are unaffected by these conditions: Tetrahedron Lett., 31, 389 (1990). Indium metal in the presence of ammonium chloride is an effective deprotection system for 4-nitrobenzyl ethers and esters: J. Chem. Soc., Perkin 1, 955 (2001).