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| | (Bromomethyl)cyclopropane Chemical Properties |
| Melting point | 87-90 °C | | Boiling point | 105-107 °C(lit.) | | density | 1.392 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.457(lit.) | | Fp | 107 °F | | storage temp. | Inert atmosphere,2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Liquid | | Specific Gravity | 1.392 | | color | Clear colorless to slightly colored | | Water Solubility | Not miscible in water. | | BRN | 605296 | | Stability: | Stable. Flammable. Incompatible with strong bases, strong oxidizing agents. | | InChI | 1S/C4H7Br/c5-3-4-1-2-4/h4H,1-3H2 | | InChIKey | AEILLAXRDHDKDY-UHFFFAOYSA-N | | SMILES | BrCC1CC1 | | CAS DataBase Reference | 7051-34-5(CAS DataBase Reference) | | NIST Chemistry Reference | Cyclopropane, (bromomethyl)-(7051-34-5) |
| Hazard Codes | Xi,F,Xn | | Risk Statements | 10-36/37/38-22 | | Safety Statements | 23-24/25-37/39-26-16-36/37/39 | | RIDADR | UN 1993 3/PG 3 | | WGK Germany | 3 | | Hazard Note | Irritant | | HazardClass | 3 | | PackingGroup | III | | HS Code | 29035990 | | Storage Class | 3 - Flammable liquids | | Hazard Classifications | Acute Tox. 4 Oral
Flam. Liq. 3 |
| | (Bromomethyl)cyclopropane Usage And Synthesis |
| Uses | (Bromomethyl)cyclopropane is used in the synthesis of 1,4-dienes by iron-catalyzed cross-coupling with alkenyl Grignard reagents.
| | Description | (Bromomethyl) cyclopropane is a cyclopropane derivative. It can be used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1, 4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.
| | Chemical Properties | Colorless to yellow liquid | | Uses | (Bromomethyl)cyclopropane was used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents. | | Synthesis Reference(s) | Tetrahedron Letters, 13, p. 2135, 1972 DOI: 10.1016/S0040-4039(01)84787-0 | | General Description | The coupling reaction of (bromomethyl)cyclopropane with phenylmagnesium bromide was studied. | | Synthesis | Example 1 (control experiment): 1250 mL of dimethylformamide (DMF) was added to the reaction vessel under nitrogen protection, followed by 280.8 g of triphenylphosphine. 70 g of hydroxymethylcyclopropane was added with stirring and the reaction was carried out at room temperature for 30 minutes. After cooling the reaction solution to -10°C, 158.3 g of bromine (102% of the theoretical amount) was slowly added dropwise over a period of 4 hours. Upon completion of the reaction, the reaction mixture was purified by distillation to afford bromomethylcyclopropane in 77.5% yield (based on theoretical values) with a product purity of >97%, which contained 0.6% open-chain haloalkanes. | | References | [1] Patent: US6008420, 1999, A
[2] Patent: US2016/355452, 2016, A1. Location in patent: Paragraph 0062; 0063
[3] Synthetic Communications, 1996, vol. 26, # 6, p. 1109 - 1115
[4] Journal of the Chemical Society, Chemical Communications, 1982, # 18, p. 1037 - 1039
[5] European Journal of Medicinal Chemistry, 1980, vol. 15, # 6, p. 571 - 573 |
| | (Bromomethyl)cyclopropane Preparation Products And Raw materials |
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