Basic information
- CAS
17247-58-4- Standard SMILES
BrCC1CCC1- InChIKey
FLHFTXCMKFVKRP-UHFFFAOYSA-N- Molecular formula
- C5H9Br
- Average molar mass
- 149.03 g/mol
- Monoisotopic mass
- 147.98876239
Names & identifiers
- Preferred name
- (Bromomethyl)cyclobutane
- IUPAC
- bromomethylcyclobutane
- English name
- (Bromomethyl)cyclobutane
- Molecular formula
- C5H9Br
- Molecular weight
- 149.03
Names & synonyms
(Bromomethyl)cyclobutane17247-58-4DTXSID10370428EC 700-027-4RefChem:69886DTXCID40321463700-027-4Cyclobutylmethyl bromidebromomethylcyclobutaneMFCD00040960Cyclobutane, (bromomethyl)-Bromomethyl cyclobutane
Show more names
(Bromomethyl)cyclobutene(Bromomethyl)cyclobu(Bromomethyl)codobutaneCyclobuty-1-Methyl broMide(Bromomethyl)cyclobutane>(BROMOMETHYL)CYCLOBUTANE 99%(Bromomethyl)cyclobutane,99%
1-(Bromomethyl)cyclobutanebromocyclobutylmethanecyclobutylmethylbromidebromomethyl-cyclobutanecydobutyl-methylbromide(bromomethyl)cyclobutancyclobutyl methyl bromide(bromomethyl) cyclobutane
Database identifiers
- CAS
17247-58-4- PubChem CID
- 2734658
- DTXSID
DTXSID10370428- EC Number
- 700-027-4
- Nikkaji
- J1.479.779C
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 39.2
Physicochemical properties
- Boiling point
- 123 · 123-124 °C(lit.)
- Density
- 1.326 g/mL · 1.326 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.48(lit.)
- Flash point
- 97 °F · 97 °F
- storage temp.
- 2 · Inert atmosphere,2-8°C
- form
- Liquid
- Specific Gravity
- 1.326 · 1.326
- color
- Clear colorless
- Water Solubility
- 80 mg/L · 80mg/L at 20℃
- InChI
- InChI=1S/C5H9Br/c6-4-5-2-1-3-5/h5H,1-4H2
- InChIKey
- FLHFTXCMKFVKRP-UHFFFAOYSA-N
- SMILES
- C1(CBr)CCC1
- CAS DataBase Reference
- 17247 · 17247-58-4(CAS DataBase Reference)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02
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
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Cyclobutane, (bromomethyl)-
Status: Cease Manufacture Update: 14-12-2011 https://echa.europa.eu/registration-dossier/-/registered-dossier/1879
Cyclobutyl methyl bromide: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazard Classes and CategoriesFlam. Liq. 3 (100%)
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- ridadr
- UN 1993 3/PG 3
- hs_code
- 29038900
- risk_code
- 10-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS02
Chemistry & industry
Applications
Uses(Bromomethyl)cyclobutane may be used in the synthesis of racemic 3-cyclobutylalanine and 17-(cyclobutylmethyl)morphinan-3-ol (butorphan).
General Description(Bromomethyl)cyclobutane (bromomethyl-cyclobutane) is an aryl fluorinated building block. Its reaction with various hydroxychromen-4-one derivatives in the presence of anhydrous K2CO3/dry acetone and Bu4N+I- (PTC) has been investigated.
Preparation methods
PreparationThe preparation of (Bromomethyl)cyclobutane is as follows:Into a clean, dry reactor equipped with a stirrer and under nitrogen are successively loaded 5.4 kg of DMF (5.1 eqV) and then 4.53 kg of triphenylphosphite. 2.34 kg of bromine is then introduced while maintaining the temperature at less than 12°C. The stirring speed is regulated according to the fluidity of the reaction medium.10065] The set point of the jacket is then adjusted to -12°C. and then 1.120 kg of cyclobutylmethanol is introduced in such a way as not to exceed a temperature of -5° C. At the end of the addition the whole is allowed to return slowly to room temperature. After distillation and washing, the final product 2b (mass 1.529 kg) having a GC relative purity of 98.3% is obtained with a yield of 78%.
Upstream & downstream products
Upstream raw materials
Related reactions
195 records
Compound notes
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