Basic information
- Standard SMILES
Brc1cccnc1- InChIKey
NYPYPOZNGOXYSU-UHFFFAOYSA-N- Molecular formula
- C5H4BrN
- Average molar mass
- 158 g/mol
- Monoisotopic mass
- 156.95271123
Overview
3-bromopyridine is a monobromopyridine in which the bromo substituent is located at position 3.
Names & identifiers
- Preferred name
- 3-Bromopyridine
- IUPAC
- 3-bromopyridine
- English name
- 3-Pyridyl bromide
- Molecular formula
- C5H4BrN
- Molecular weight
- 158
Names & synonyms
3-BROMOPYRIDINE626-55-13-pyridyl bromidePyridine, 3-bromo-XMN8H2XE9HNSC-3974DTXSID9060819CHEBI:51575RefChem:93265DTXCID1043417210-952-05-bromopyridine
Show more names
3-Pvridyl bromideNSC 3974AURORA KA-8753-bromo-pyridin5-BROMO PYRIDINETIMTEC-BB SBB003998
3-bromo pyridine3-bromo-pyridineMFCD00006373C5H4BrN3-Bromopyridine, 99%CHEMBL5396433UNII-XMN8H2XE9Hm-bromopyridine
Database identifiers
- CAS
626-55-1- PubChem CID
- 12286
- DTXSID
DTXSID9060819- ChEMBL
CHEMBL5396433- ChEBI
CHEBI:51575- UNII
- XMN8H2XE9H
- EC Number
- 210-952-0
- Nikkaji
- J95.608B
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 12.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 56
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Pyridines
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP1.5
Flash Point51 °C
Vapor Pressure1.75 [mmHg]
Physical DescriptionNeedles; [Hawley] Colorless liquid; [MSDSonline]
Physicochemical properties
- Melting point
- -27 °C · -27°C
- Boiling point
- 173 °C · 173 °C (lit.)
- Density
- 1.64 g/mL · 1.64 g/mL at 25 °C (lit.)
- vapor pressure
- 1.64 hPa · 1.64hPa at 25℃
- refractive index
- 20 · n20/D 1.571(lit.)
- Flash point
- 125 °F · 125 °F
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 31 g/l · 31g/l
- form
- Liquid
- pka
- 2.84 · 2.84(at 25℃)
- Specific Gravity
- 1.617 · 1.617
- color
- Clear colorless to yellow or slightly brown
- Water Solubility
- Soluble in water (31 g/L at 20°C).
- BRN
- 105880 · 105880
- Henry's Law Constant
- 8.3 · 8.3×10-1 mol/(m3Pa) at 25℃, Ebert et al. (2023)
- Dielectric constant
- 9.85 · 9.8499999999999996
- InChI
- 1S/C5H4BrN/c6-5-2-1-3-7-4-5/h1-4H
- InChIKey
- NYPYPOZNGOXYSU-UHFFFAOYSA-N
- SMILES
- Brc1cccnc1
- LogP
- 1.694 · 1.694
- CAS DataBase Reference
- 626 · 626-55-1(CAS DataBase Reference)
- FDA UNII
- 8 H2XE9H · XMN8H2XE9H
- NIST Chemistry Reference
- 3 · Pyridine, 3-bromo-(626-55-1)
- EPA Substance Registry System
- 3 · 3-Bromopyridine (626-55-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Warning
- Hazard statements
- 226 · H226-H302-H315-H319-H335
- Precautionary statements
- 210 · P210-P301+P312+P330-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn,T,F,Xi
- Risk Statements
- 10 · 10-22-36/37/38-23/24/25-20/21/22
- Safety Statements
- 26 · 26-45-38-36/37/39-28A-16
- RIDADR
- 1993 · UN 1993 3/PG 3
- WGK Germany
- 3 · 3
- F
- 8 · 8
- Hazard Note
- Toxic/Flammable/Irritant
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29333999 · 29333999
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H226 (93.3%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 60 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Pyridine, 3-bromo-
Status: Active Update: 03-07-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19867
3-Bromopyridine: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin, eye, and respiratory tract irritant; [MSDSonline] Pyridine compounds are potential CNS depressants; [Ullmann] See Pyridine.
Hazard Classes and CategoriesFlam. Liq. 3 (93.3%)
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Safety data
- F
- 8
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 1993 3/PG 3
- hs_code
- 29333999
- risk_code
- 10-22-36/37/38-23/24/25-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- Xn,T,F,Xi
- hazard_note
- Toxic/Flammable/Irritant
- safety_code
- 26-45-38-36/37/39-28A-16
- hazard_class
- 6.1
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H226-H302-H315-H319-H335
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
- Precautionary statements
- P210-P301+P312+P330-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationPyridine, 3-bromo-: ACTIVE
Applications
Uses3-Bromopyridine undergoes lithiation with LDA at low temperatures in the 4-position: Heterocycles, involved in formation of the Grignard by Mg exchange with i-PrMgCl and in transmetallation of the lithiated derivative with zinc chloride followed by treatment with an electrophile as a route to 4-substituted 3-bromopyridines.
UsesPyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: A monobromopyridine in which the bromo substituent is located at position 3.
Related reactions
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Linked notes
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