Basic information
- Standard SMILES
BrC1CC1- InChIKey
LKXYJYDRLBPHRS-UHFFFAOYSA-N- Molecular formula
- C3H5Br
- Average molar mass
- 120.98 g/mol
- Monoisotopic mass
- 119.95746226
Names & identifiers
- Preferred name
- Bromocyclopropane
- IUPAC
- bromocyclopropane
- English name
- Cyclopropyl bromide
- Molecular formula
- C3H5Br
- Molecular weight
- 120.98
Names & synonyms
Show more names
Database identifiers
- CAS
4333-56-6- PubChem CID
- 78037
- DTXSID
DTXSID8063418- EC Number
- 224-375-7
- Nikkaji
- J150.689G
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 0
- Heavy atoms
- 4
- Formal charge
- 0
- Complexity
- 22.5
Experimental & physicochemical properties
Physicochemical properties
- Boiling point
- 69 °C · 69 °C (lit.)
- Density
- 1.51 g/mL · 1.51 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.458(lit.)
- Flash point
- 20 °F · 20 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Sparingly), Methanol (Slightly)
- form
- Liquid
- Specific Gravity
- 1.51 · 1.510
- color
- Clear colorless
- Water Solubility
- immiscible
- BRN
- 1900287 · 1900287
- InChI
- InChI=1S/C3H5Br/c4-3-1-2-3/h3H,1-2H2
- InChIKey
- LKXYJYDRLBPHRS-UHFFFAOYSA-N
- SMILES
- C1(Br)CC1
- CAS DataBase Reference
- 4333 · 4333-56-6(CAS DataBase Reference)
- NIST Chemistry Reference
- Cyclopropyl bromide(4333-56-6)
- EPA Substance Registry System
- Cyclopropane, bromo- (4333-56-6)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Danger
- Hazard statements
- 225 · H225
- Precautionary statements
- 210 · P210-P233-P240-P241-P242-P243
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-36/37/38
- Safety Statements
- 16 · 16-26-36-37/39
- RIDADR
- 1993 · UN 1993 3/PG 2
- WGK Germany
- 3 · 3
- F
- 8 · 8-19
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29035990 · 29035990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 · Flam. Liq. 2
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger 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 54 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- F
- 8-19
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 1993 3/PG 2
- hs_code
- 29035990
- risk_code
- 11-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS02
- hazard_code
- F,Xi
- hazard_note
- Irritant
- safety_code
- 16-26-36-37/39
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H225
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Flam. Liq. 2
- Precautionary statements
- P210-P233-P240-P241-P242-P243
Chemistry & industry
Uses & manufacturing
Applications
DescriptionCyclopropyl bromide is also named as Bromocyclopropane. It is used in organic synthesis, for instance, for the formation of a Grignard Reagent, cyclopropyllithium. It is also used as an intermediate in the manufacture of pharmaceutical and agrochemical products.
UsesBromocyclopropane is primarily used an intermediate in the manufacture of pharmaceutical and agrochemical products. It is also used in the production of cyclopropyl boric acid. It is used as an intermediate in organic synethesis.
Preparation methods
PreparationBromocyclopropane has been prepared by the Hunsdiecker reaction by adding silver cyclopropanecarboxylate to bromine in dichlorodifluoromethane at 29° (53% yield) or in tetrachloroethane at 20° to 25° (15–20% yield). Decomposition of the peroxide of cyclopropanecarboxylic acid in the presence of carbon tetrabromide gave bromocyclopropane in 43% yield. An attempt to prepare the bromide via the von Braun reaction was unsuccessful. Ten percent yields are reported for the photobromination of cyclopropane and the photochemical rearrangement of allyl bromide. Treatment of 1,1,3-tribromopropane with methyllithium prepared from methyl bromide furnishes a 60–65% yield of bromocyclopropane.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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