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2,5-Dibromopyridine

HCID 69353
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
624-28-2
Standard SMILES
Brc1ccc(Br)nc1
InChIKey
ZHXUWDPHUQHFOV-UHFFFAOYSA-N
Molecular formula
C5H3Br2N
Average molar mass
236.89 g/mol
Monoisotopic mass
234.8632233

Names & identifiers

Preferred name
2,5-Dibromopyridine
IUPAC
2,5-dibromopyridine
English name
2,5-Dibromopyridine
Molecular formula
C5H3Br2N
Molecular weight
236.89

Names & synonyms

2,5-Dibromopyridine624-28-2Pyridine, 2,5-dibromo-EINECS 210-839-6(2,5-DBrPyr)DTXSID00211452NSC 76597RefChem:82777DTXCID00133943210-839-6ZHXUWDPHUQHFOV-UHFFFAOYSA-N2,5-dibromo-pyridine
Show more names
Dibromopyridine5-DibroMop2,5-DBr-Py5-DibroMopyridine2,5-Dibrompyridin2,5 dibromopyrdine
2,5-DIBROMOPYRIDINMFCD00006221NSC-765972,5-Dibromo Pyridine67987-57-93,6-DIBROMOPYRIDINENSC765972,5-dibrompyridine

Database identifiers

CAS
624-28-2
PubChem CID
69353
DTXSID
DTXSID00211452
UNII
V4W4Z4K29X
EC Number
210-839-6
Nikkaji
J79.763D

Properties

Computed structural propertiesFilling in

XLogP
2.6
Topological polar surface area
12.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
8
Formal charge
0
Complexity
76.8

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Pyridines
Physical DescriptionDark brown powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
92 · 92-95 °C (lit.)
Boiling point
235 °C · 235 °C / 772mmHg
Density
2.0383 · 2.0383 (rough estimate)
refractive index
1.58 · 1.5800 (estimate)
Flash point
62 ℃ · 62℃
storage temp.
Inert atmosphere,Room Temperature
solubility
Chloroform (Slightly), Methanol (Slightly)
pka
-1.57 · -1.57±0.10(Predicted)
form
Crystalline Powder
color
Almost white or light beige to brown
Water Solubility

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: No longer Valid Update: 17-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30054

2,5-Dibromopyridine: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin and strong eye irritant; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
ridadr
UN2811
hs_code
29333999
risk_code
36/37/38-20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
26-37/39-36/37/39-36

Chemistry & industry

Applications · 2 items

DescriptionPyridine and its derivatives are distributed widely by nature. Many plant constituents are as contain pyridine ring compounds in the structure of alkaloids, etc.; they are the bases producing many vital compounds and are indispensable raw materials during medicine, agricultural chemicals, dyestuff, tension-active agents, rubber ingredients, fodder additives, foodstuff additives, tackiness agents, etc. are produced.2,5-dibromo pyridine is an important intermediate of organic synthesis and is mainly used in medicine intermediate, organic synthesis, and organic solvent, can also be applicable to aspects such as DYE PRODUCTION, pesticide production and spices. Selective monolithiation of 2,5-dibromopyridine at either the 2-position or the 5-position is reported. Solvent and concentration strongly influence the selectivity. Coordinating solvents and higher concentration favour the 5-position, while non-coordinating solvents and lower concentration favour the 2-position[1].

Uses2,5-Dibromopyridine (cas# 624-28-2) is a compound useful in organic synthesis.

Preparation methods · 1 item

PreparationTo synthesize 2,5-dibromopyridine, follow these steps:Add 2-amino-5-bromopyridine (13.0 kg) into a water-cooled solution at 10 °C.Slowly add 47% aqueous hydrogen bromide (37 L) to the mixture.Introduce liquid bromine (11 L) into the mixture.Maintain the reaction temperature below 10 °C.Prepare a solution of NaNO2 (16.1 kg) and H2O (19 L) and add it dropwise to the mixture while keeping the temperature between 0-5 °C.Stir the reaction mixture for 30 minutes.Treat the mixture with a solution of NaOH (28.0 kg) in water (30 L) at a controlled rate below 20-25 °C.Extract the reaction mixture with diethyl ether (3 × 40 L).Dry the organic layer with anhydrous Na2SO4.Remove the desiccant by filtration.Evaporate the resulting filtrate under reduced pressure to dryness.Suspend the residue in heptane (10 L).Collect the target product molecule, 2,5-dibromopyridine, by filtration.Synthesis method of 2,5-dibromopyridine

Upstream & downstream products

Upstream raw materials

2-Amino-5-bromopyridine

Related reactions

771 records
New reaction record
HRID 2743 reaction equation
HRID 2743As reactantuspto-grants-1998_03
HRID 42013 reaction equation
HRID 42013As reactantuspto-grants-2013_09
HRID 42014 reaction equation
HRID 42014As reactantuspto-grants-2013_09
HRID 42017 reaction equation
HRID 42017As reactantuspto-grants-2013_09
HRID 42018 reaction equation
HRID 42018As reactantuspto-grants-2013_09
HRID 42020 reaction equation
HRID 42020As reactantuspto-grants-2013_09
HRID 42021 reaction equation
HRID 42021As reactantuspto-grants-2013_09
HRID 42022 reaction equation
HRID 42022As reactantuspto-grants-2013_09
Page 1 of 97

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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insoluble
BRN
109099 · 109099
InChI
InChI=1S/C5H3Br2N/c6-4-1-2-5(7)8-3-4/h1-3H
InChIKey
ZHXUWDPHUQHFOV-UHFFFAOYSA-N
SMILES
C1(Br)=NC=C(Br)C=C1
CAS DataBase Reference
624 · 624-28-2(CAS DataBase Reference)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
335 · H335-H302+H312+H332-H315-H319
Precautionary statements
280 a-P304+P340-P305+P351+P338-P405-P501a-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501 · P280a-P304+P340-P305+P351+P338-P405-P501a-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/37/38-20/21/22
Safety Statements
26 · 26-37/39-36/37/39-36
RIDADR
2811 · UN2811
WGK Germany
3 · 3
HazardClass
IRRITANT
HS Code
29333999 · 29333999
Storage Class
11 · 11 - Combustible Solids
REACH Registrations
Inactive
hazard_class
IRRITANT
Storage Class
11 - Combustible Solids
Hazard statements
H335-H302+H312+H332-H315-H319
REACH Registrations
Inactive
Precautionary statements
P280a-P304+P340-P305+P351+P338-P405-P501a-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501
Hydrogen bromide
Sodium nitrite
2,3,6-Tribromopyridine
2,3,5-Tribromopyridine
2-Hydroxy-5-bromopyridine
1-Methyl-2-pyridone

Downstream products

2-Bromo-5-iodopyridine5-Bromo-2-pyridinecarboxylic Acid5-Bromopyridine-2-carbonyl chloride6-Methoxynicotinaldehyde2-(5-Bromo-2-pyridylazo)-5-(diethylamino)phenol2-Bromopyridine-5-boronic acid5-(Trifluoromethyl)pyridine-2-carboxylic acid5-Bromo-2-(pyrrolidin-1-yl)pyridine6-(1-Pyrrolidinyl)nicotinaldehyde5-Bromo-3-pyridinecarboxaldehyde2-Trifluoromethyl-5-bromopyridine5-Bromo-2-iodopyridineTorezolid2,5-Bis(trifluoromethyl)pyridine