(bromomethyl)cyclopropane

• ChemBase ID: 9958
• Molecular Formular: C4H7Br
• Molecular Mass: 135.00238
• Monoisotopic Mass: 133.97311222
• SMILES: C1(CC1)CBr
• Canonical SMILES: BrCC1CC1
• InChI: InChI=1S/C4H7Br/c5-3-4-1-2-4/h4H,1-3H2
• InChIKey: AEILLAXRDHDKDY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (bromomethyl)cyclopropane
• IUPAC Traditional name: (bromomethyl)cyclopropane
• Synonyms: Cyclopropylmethyl bromide; (Bromomethyl)cyclopropane; (Bromomethyl)cyclopropane; 1-(Bromomethyl)cyclopropane; Cyclopropanemethyl Bromide; Cyclopropylcarbinyl Bromide; Cyclopropylmethyl bromide; (Bromomethyl)cyclopropane; 1-(bromomethyl)cyclopropane; 环丙基甲基溴; (溴甲基)环丙烷; 溴甲基环丙烷

Database IDs

• CAS Number: 7051-34-5
• EC Number: 230-331-8
• MDL Number: MFCD00001306
• Beilstein Number: 605296
• PubChem SID: 24854557; 160973265
• PubChem CID: 81503

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.8020873
• LogD (pH = 7.4): 1.8020873
• Log P: 1.8020873
• Molar Refractivity: 26.2378 cm^3
• Polarizability: 10.167112 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Clear Colorless Liquid
• Boiling Point: 101-112°C; 105-107 °C(lit.); 105-107°C; 111-112°C
• Flash Point: 105.8 °F; 41 °C; 41°C; 41°C(105°F)
• Density: 1.392; 1.392 g/mL at 25 °C(lit.); 1.410
• Refractive Index: 1.4570; 1.4770; n20/D 1.457(lit.)
• Hydrophobicity(logP): 2.049

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Flammable/Harmful/Irritant/Light Sensitive/Keep Cold; IRRITANT, KEEP COLD, FLAMMABLE
• European Hazard Symbols: X
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10; 10-22-36/37/38
• Safety Statements: 23-24/25; 23-26-36/37-60
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS06
• GHS Signal Word: Warning
• GHS Hazard statements: H226; H301-H315-H319-H335-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: 95%; 96%; 97%
• Linear Formula: C3H5CH2Br

DETAILS

Sigma Aldrich - 242403

Application
Synthetic building block for the introduction of the cyclopropylmethyl group.1,2,3
Used in a synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.
Packaging
1, 5 g in ampule

REFERENCES

• O-Alkylation of phenols (KO-t-Bu/DMF) has been used as a means of protection. The cyclopropylmethyl ethers are stable to reducing agents (metal hydride, H₂, Birch), but selectively cleaved by aqueous methanolic HCl: Chem. Pharm. Bull., 23, 2878 (1975).