| Identification | More | [Name]
3-BROMO-4-HYDROXYBENZONITRILE | [CAS]
2315-86-8 | [Synonyms]
2-BROMO-4-CYANOPHENOL
3-BROMO-4-HYDROXYBENZONITRILE
LABOTEST-BB LT01143437
TIMTEC-BB SBB005818
3-Bromo-4-hydroxybenzonitrile, 98+% | [EINECS(EC#)]
219-022-9 | [Molecular Formula]
C7H4BrNO | [MDL Number]
MFCD00143096 | [Molecular Weight]
198.02 | [MOL File]
2315-86-8.mol |
| Chemical Properties | Back Directory | [Appearance]
brown crystals or needles | [Melting point ]
155-159 °C(lit.)
| [Boiling point ]
271.1±25.0 °C(Predicted) | [density ]
1.79±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
6.30±0.18(Predicted) | [color ]
Off-White to Pale Beige | [BRN ]
2207020 | [InChI]
InChI=1S/C7H4BrNO/c8-6-3-5(4-9)1-2-7(6)10/h1-3,10H | [InChIKey]
HLHNOIAOWQFNGW-UHFFFAOYSA-N | [SMILES]
C(#N)C1=CC=C(O)C(Br)=C1 | [CAS DataBase Reference]
2315-86-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3276 | [WGK Germany ]
3
| [Hazard Note ]
Harmful | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29269090 | [Storage Class]
13 - Non Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
brown crystals or needles | [Uses]
3-Bromo-4-hydroxybenzonitrile is a reactant that has been used in the preparation of tetrazoles. | [Synthesis]
4-Hydroxybenzonitrile (III) (5.0 g, 0.042 mol) was dissolved in acetonitrile (50 mL) under nitrogen atmosphere. The reaction mixture was cooled to -15 °C and trifluoromethanesulfonic acid (CF3SO3H) (3.7 mL, 6.3 g, 0.042 mol) was slowly added. Maintaining the reaction temperature at -15 °C, N-bromosuccinimide (NBS) (8.2 g, 0.046 mol) was added in 6 additions in batches. After addition, the reaction mixture was returned to room temperature and continued to be stirred under nitrogen atmosphere for 4 h. The reaction process was monitored by thin-layer chromatography (TLC) (unfolding reagent: hexane/ethyl acetate = 75:25, detection method: UV and KMnO4 color development). When the raw materials were completely consumed, the reaction mixture was diluted with aqueous sodium carbonate (Na2CO3) and extracted with methyl tert-butyl ether (MTBE) (3 x 50 mL). The organic layers were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to give 3-bromo-4-hydroxybenzonitrile (IV) as a white solid (7.7 g, 93% yield).1H NMR (DMSO-d6, 300 MHz, 300 K): δ=8.04 (d, J=2.2Hz, 1H), 7.63 (dd, J=2.2Hz, 8.5Hz, 8.5 Hz. 1H), 7.04 (d, J=8.5Hz, 1H). | [References]
[1] Patent: US9181298, 2015, B2. Location in patent: Page/Page column 33; Sheet 8
[2] Journal of Organic Chemistry, 2005, vol. 70, # 11, p. 4267 - 4271
[3] Patent: WO2010/142653, 2010, A1. Location in patent: Page/Page column 14
[4] Patent: CN103333134, 2016, B. Location in patent: Paragraph 0101; 0102
[5] RSC Advances, 2014, vol. 4, # 49, p. 25898 - 25903 |
|
|