| Identification | More | [Name]
3,5-Dibromopyridine | [CAS]
625-92-3 | [Synonyms]
3,5-DIBROMOPYRIDINE
IFLAB-BB F1995-0190
TIMTEC-BB SBB003237
Pyridine, 3,5-dibromo-
3,5-Dibromopyridine,99%
3,5-Dibromopyridine, 98+%
3,5-dibormopyridine | [EINECS(EC#)]
210-916-4 | [Molecular Formula]
C5H3Br2N | [MDL Number]
MFCD00014634 | [Molecular Weight]
236.89 | [MOL File]
625-92-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Light-Yellow Solid | [Melting point ]
110-115 °C (lit.) | [Boiling point ]
222 °C | [density ]
2.0383 (rough estimate) | [refractive index ]
1.5800 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly, Heated), Methanol (Slightly) | [form ]
Needle-Like Crystals | [pka]
0.52±0.20(Predicted) | [color ]
White to light beige | [Water Solubility ]
Soluble in Chloroform and Methanol. Insoluble in water. | [Detection Methods]
GC,NMR | [BRN ]
108477 | [InChIKey]
SOSPMXMEOFGPIM-UHFFFAOYSA-N | [CAS DataBase Reference]
625-92-3(CAS DataBase Reference) | [NIST Chemistry Reference]
3,5-Dibromopyridine(625-92-3) | [EPA Substance Registry System]
625-92-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN2811 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333999 |
| Raw materials And Preparation Products | Back Directory | [Preparation Products]
5-methoxypyridin-3-amine-->5-Bromo-2-fluoro-3-methoxypyridine-->3-Amino-5-hydroxypyridine-->5-(BENZYLOXY)PYRIDIN-3-AMINE-->5-METHOXY-PYRIDINE-3-CARBALDEHYDE-->3-(BENZYLOXY)-5-BROMOPYRIDINE-->5-Bromopyridine-3-boronic acid-->3-Bromo-5-fluoropyridine-->3-Amino-5-bromopyridine-->3-BROMO-5-(METHYLTHIO)PYRIDINE-->2-(5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)propan-2-ol-->4,6-Di(4-carboxyphenyl)pyrimidine-->3-BroMo-5-(prop-1-en-2-yl)pyridine-->3,5-Difluoro-4-pyridinecarboxaldehyde-->3,5-Dibromo-4-cyanopyridine, 97%-->3,5-DIBROMOPYRIDINE 1-OXIDE-->5-BROMO-3-METHOXY-2-NITROPYRIDINE-->3,5-Dimethoxypyridine |
| Hazard Information | Back Directory | [Chemical Properties]
Light-Yellow Solid | [Uses]
3-Acetylamino-5-ethoxypyridine was prepared by converting 3, 5-dibromopyridine with sodium ethylate into 3-bromo-5-ethoxypyridine, allowing this substance to interact with ammonia and acetylating the aminoethoxypyridine thus formed with acetic anhydride. Lithiation of 3, 5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3, 5-dibromopyridines 2 in high yield. Ligand was prepared by a Pd(0)-catalyzed cross-coupling reaction of 3,5-dibromopyridine and 5-tributylstannyl-3,3?-bipyridine. The synthesis of 3, 5-bis (2-indolyl) pyridine and 3-[(2-indolyl)-5-phenyl] pyridine derivatives as includes Stille or Suzuki type reactions, which were realized on the 3,5-dibromopyridine. | [Application]
3,5-Dibromopyridine (3,5-DBP) can be used for:
(1) Spectroscopic analysis: FTIR and FT Raman spectra in the solid phase of 3,5-DBP and 3,5- dichloro-2,4,6-trifluoropyridine (3,5-DCTFP) were recorded in the regions of 4000-400 cm-1 and 3500-100 cm-1, respectively[1].
(2) Chemical reactions: 3,5-DBP can be reacted with phenyl isocyanate. chemoselective Staudinger-Phosphite reaction of 2,4,6-triazido-3,5-dibromopyridine azide moiety[2-3].
(3) Organic synthesis: Using 3,5-dibromopyridine as raw material can be used to prepare 3-acetamido-5-ethoxypyridine[4]. | [Definition]
ChEBI: 3,5-dibromopyridine is a dibromopyridine. | [General Description]
3,5-Dibromopyridine undergoes lithiation with lithium diisopropylamide and on subsequent reaction with electrophiles yields 4-alkyl-3,5-dibromopyridines. | [References]
[1] V. KRISHNAKUMAR R. J X. Density functional theory calculations and vibrational spectra of 3,5-dibromopyridine and 3,5-dichloro-2,4,6-trifluoropyridine[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2005. DOI:10.1016/j.saa.2004.03.038.
[2] SERGEI V. CHAPYSHEV Igor K Y Alexander V Chernyak. Chemoselective Staudinger-Phosphite Reaction on the Azido Groups of 2,4,6-Triazido-3,5-dibromopyridine[J]. Journal of Heterocyclic Chemistry, 2015. DOI:10.1002/jhet.2339.
[3] T. HISANO M. I Toshikazu Matsuoka. THE REACTION OF 3,5-DIBROMOPYRIDINE N-OXIDE WITH PHENYL ISOCYANATE[J]. ChemInform, 1974. DOI:10.1002/CHIN.197448358.
[4] H. J. HERTOG A. V D L A W M Falter. The reactivity of bromine atoms in brominated pyridines. The preparation of 3-acetylamino-5-ethoxypyridine from 3,5-dibromopyridine?[J]. Recueil des Travaux Chimiques des Pays-Bas, 1948. DOI:10.1002/RECL.19480670507. |
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