1,5-Dibromopentane
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Basic information
- CAS
111-24-0- Standard SMILES
BrCCCCCBr- InChIKey
IBODDUNKEPPBKW-UHFFFAOYSA-N- Molecular formula
- C5H10Br2
- Average molar mass
- 229.94 g/mol
- Monoisotopic mass
- 227.91493
Names & identifiers
- Preferred name
- 1,5-Dibromopentane
- IUPAC
- 1,5-dibromopentane
- English name
- 1,5-Dibromopentane
- Molecular formula
- C5H10Br2
- Molecular weight
- 229.94
Names & synonyms
1,5-DIBROMOPENTANE111-24-0Pentamethylene bromidePentamethylene dibromidePentane, 1,5-dibromo-DTXSID2049395NSC-5373B8Q228QYS1DTXCID9029354RefChem:73462203-849-7Br(CH2)5Br
Show more names
PENTANE-1,5-DIBROMIDE1,5-Dibrompentan1,5-dibromo-pentanPentan-1,5-dibromidPentane,1,5-dibromo-
1,5-dibrompentanePentane,5-dibromo-1,5-dibromo-pentaneDibromo-1,5 pentaneMFCD00000268NSC 5373DIBROMOPENTANE, 1,5-1,5-bis(bromanyl)pentane
Database identifiers
- CAS
111-24-0- PubChem CID
- 8100
- DTXSID
DTXSID2049395- ChEMBL
CHEMBL3182198- UNII
- B8Q228QYS1
- EC Number
- 203-849-7
- Nikkaji
- J5.106C
Properties
Computed structural propertiesFilling in
- XLogP
- 2.8
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 4
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 25.3
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Halogenated Aliphatics, Saturated
SpringerMaterials PropertiesBoiling point
Physical Description
CBI
Light brown liquid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- -34 °C · -34 °C (lit.)
- Boiling point
- 110 °C/15 · 110 °C/15 mmHg (lit.)
- Density
- 1.688 g/mL · 1.688 g/mL at 25 °C (lit.)
- vapor density
- 8 · 8 (vs air)
- refractive index
- 20 · n20/D 1.512(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform, Methanol (Sparingly)
- form
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
Warning
H302 (12.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 55 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Pentane, 1,5-dibromo-
Pentane, 1,5-dibromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pentane, 1,5-dibromo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: 1,5-dibromopentane (EC: 203-849-7)
1,5-Dibromopentane: 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] See 2-Bromopentane.
Hazard Classes and CategoriesAcute Tox. 4 (12.7%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SA0320000
- hs_code
- 29033036
- risk_code
- 36/38-22
Chemistry & industry
Uses & manufacturing
U.S. Production2023: <50,000 lb
Industry UsesCatalyst
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Pentane, 1,5-dibromo-: ACTIVE
Applications
Uses1,5-Dibromopentane is used in the preparation of 1,5-di-Grignard reagent and novel spirocyclic pyrrolidones. It acts as a growth supplement for Yarrowia lipolytica 3589, a tropical marine yeast. It is involved in the synthesis of N-alkylated piperidine as well as tetrydrothiopyran (thiane) by reaction with primary amine and sodium sulfide respectively.
Uses1,5-Dibromopentane can be used to prepare:Derivatives of 5-pyrazolones.O-alkylated phloroglucinol derivatives, which forms the core of poly(alkyl aryl ether) dendrimers.Intermediate for dezocine viz, (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone using 1-methyl-7-methoxy-2-tetralone.
General Description1,5-Dibromopentane is a growth supplement for Yarrowia lipolytica 3589, a tropical marine yeast.
Preparation methods
Preparation1,5-Dibromopentane was obtained by ring-opening bromination of tetrahydropyran. In a 500ml flask, add 250g of 48% hydrobromic acid, 75g of concentrated sulfuric acid, 21.5g of redistilled tetrahydropyran (86.5-87.5°C fraction) in turn to a reflux condenser and heat the brown mixture gently to reflux for 3h. After cooling to room temperature, partition the lower layer of dibromide and wash each with saturated sodium carbonate solution and water once. Dried with anhydrous calcium chloride. Distill under reduced pressure and collect the 104-106°C (2.53 kPa) fraction as 1,5-dibromopentane in 46-47 g yield and 80-82% yield.1,5-Dibromopentane synthesis route
Related reactions
575 records
Compound notes
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