Basic information
- CAS
38275-57-9- Standard SMILES
N#Cc1ncc(Br)cn1- InChIKey
VPQICCOHFSGBMA-UHFFFAOYSA-N- Molecular formula
- C5H2BrN3
- Average molar mass
- 183.99 g/mol
- Monoisotopic mass
- 182.94320916
Names & identifiers
- Preferred name
- 5-Bromopyrimidine-2-carbonitrile
- IUPAC
- 5-bromopyrimidine-2-carbonitrile
- English name
- 5-Bromopyrimidine-2-carbonitrile
- Molecular formula
- C5H2BrN3
- Molecular weight
- 183.99
Names & synonyms
Show more names
Database identifiers
- CAS
38275-57-9- PubChem CID
- 686546
- DTXSID
DTXSID80350712- ChEMBL
CHEMBL1889668- EC Number
- 691-026-7
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 49.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 130
Physicochemical properties
- Boiling point
- 317.7 · 317.7±34.0 °C(Predicted)
- Density
- 1.86 · 1.86±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- pka
- -4.65 · -4.65±0.22(Predicted)
- form
- Solid
- color
- White to yellow
- Water Solubility
- Slightly soluble in water.
- Sensitive
- Moisture Sensitive
- InChI
- InChI=1S/C5H2BrN3/c6-4-2-8-5(1-7)9-3-4/h2-3H
- InChIKey
- VPQICCOHFSGBMA-UHFFFAOYSA-N
- SMILES
- C1(C#N)=NC=C(Br)C=N1
- CAS DataBase Reference
- 38275 · 38275-57-9(CAS DataBase Reference)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 21 · NA.21
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H312-H315-H319-H332-H335
- Precautionary statements
- 261 · P261-P280-P304+P340-P305+P351+P338-P405-P501a
- target organs
- Respiratory system
- Hazard Codes
- Xi,Xn,N
- Risk Statements
- 20 · 20/21/22-37/38-41-50
- Safety Statements
- 26 · 26-36/37-39-61
- RIDADR
- 3077 · 3077
- WGK Germany
- 3 · WGK 3
- Hazard Note
- Irritant
- TSCA
- No
- HazardClass
- 6.1 · 6.1
- PackingGroup
- Ⅲ
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Danger
H302+H312+H332 (25%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- wgk
- WGK 3
- tsca
- No
- ridadr
- 3077
- hs_code
- 29339900
- risk_code
- 20/21/22-37/38-41-50
- Signal word
- Danger
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn,N
- hazard_note
- Irritant
- safety_code
- 26-36/37-39-61
- hazard_class
- 6.1
- Storage Class
- 11 - Combustible Solids
- packing_group
- Ⅲ
- target organs
- Respiratory system
- Hazard statements
- H302-H312-H315-H319-H332-H335
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P280-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
Uses5-Bromo-2-cyanopyrimidine is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.
Preparation methods
Preparation5-Bromopyrimidine-2-carbonitrile is a pharmaceutical intermediate that can be obtained by reacting 5-bromo-2-chloropyrimidine with potassium nitride. It can also be obtained as follow: 5-Bromo-2-chloropyrimidine (7.51 g, 38.83 mmol), dissolved in DMSO (20 mL), is added to a mixture of NaCN (1.9 g, 38.83 mmol) and l,4-diazabicyclo[2,2,2]octane (0.87 g, 7.77 mmol) in DMSO (10 mL) and water (20 mL). The mixture is stirred overnight, and then water (100 mL) is added. The mixture is extracted with ether (3x100 mL). The combined organic layer is dried (Na2SO4), filtered, and concentrated in vacuo to afford 5-Bromopyrimidine-2-carbonitrile as a solid.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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