Basic information
- CAS
4595-60-2- Standard SMILES
Brc1ncccn1- InChIKey
PGFIHORVILKHIA-UHFFFAOYSA-N- Molecular formula
- C4H3BrN2
- Average molar mass
- 158.98 g/mol
- Monoisotopic mass
- 157.9479602
Names & identifiers
- Preferred name
- 2-Bromopyrimidine
- IUPAC
- 2-bromopyrimidine
- English name
- 2-Bromopyrimidine
- Molecular formula
- C4H3BrN2
- Molecular weight
- 158.98
Names & synonyms
2-BromopyrimidinePyrimidine, 2-bromo-EINECS 224-993-7NSC 88935DTXSID9063532RefChem:85904DTXCID1040459224-993-7PGFIHORVILKHIA-UHFFFAOYSA-N4595-60-2bromopyrimidineMFCD00014601
Show more names
2-Bromopyrimide2-BroMpyriMidine2-bromo-pyrimidin2 Bromo pydrimine2-Bromo-1,3-diazine2-Bromopyrimidine >2 - broMine pyriMidine2-Bromopyrimidine,97+%
2-bromo-pyrimidineCHEMBL5414935NSC-889352-bromo pyrimidineNSC88935A1BDM2-Bromopyrimidine, 95%NS3RKG8A3U
Database identifiers
- CAS
4595-60-2- PubChem CID
- 78345
- DTXSID
DTXSID9063532- ChEMBL
CHEMBL5414935- UNII
- NS3RKG8A3U
- EC Number
- 224-993-7
- Nikkaji
- J147.989J
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 25.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 51.7
Experimental & physicochemical properties
SpringerMaterials PropertiesElectric dipole moment
LogP0.5
Physicochemical properties
- Melting point
- 55 · 55-57 °C (lit.)
- Boiling point
- 62 · 62-64°C (1.5 mmHg)
- Density
- 1.6448 · 1.6448 (rough estimate)
- refractive index
- 1.526 · 1.5260 (estimate)
- Flash point
- 62 · 62-64°C/1.5mm
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Sparingly), Methanol (Slightly)
- pka
- -1.59 · -1.59±0.13(Predicted)
- form
- Crystalline Powder
- color
- Off-white
- Water Solubility
- Miscible with water.
- BRN
- 605945 · 605945
- InChI
- 1S/C4H3BrN2/c5-4-6-2-1-3-7-4/h1-3H
- InChIKey
- PGFIHORVILKHIA-UHFFFAOYSA-N
- SMILES
- Brc1ncccn1
- CAS DataBase Reference
- 4595 · 4595-60-2(CAS DataBase Reference)
- NIST Chemistry Reference
- 2 · Pyrimidine, 2-bromo-(4595-60-2)
- EPA Substance Registry System
- 2 · Pyrimidine, 2-bromo- (4595-60-2)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29335990 · 29335990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
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 49 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29335990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationPyrimidine, 2-bromo-: INACTIVE
Applications
Uses2-Bromopyrimidine is used in the preparation of 2,7-bis(2-pyrimidyl)-9,9-dihexylfluorene by cross-coupling with 9,9-dihexylfluorene-2,7-diboronic acid. It undergoes microwave-assisted aminocarbonylation at C-2 with palladium and molybdenum hexacarbonyl.
General Description2-Bromopyrimidine undergoes microwave-assisited aminocarbonylation at C-2 with palladium and Mo(CO)6.
Preparation methods
PreparationThe recent synthesis of 2-bromopyrimidine by diazotization of 2-aminopyrimidine in hydrobromic acid has furnished a convenient starting material for other 2-substituted pyrimidines.
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
295 records
Compound notes
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