3-chloroprop-1-ene

• ChemBase ID: 88004
• Molecular Formular: C3H5Cl
• Molecular Mass: 76.5248
• Monoisotopic Mass: 76.00797784
• SMILES: ClCC=C
• Canonical SMILES: ClCC=C
• InChI: InChI=1S/C3H5Cl/c1-2-3-4/h2H,1,3H2
• InChIKey: OSDWBNJEKMUWAV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-chloroprop-1-ene
• IUPAC Traditional name: allyl chloride
• Synonyms: 3-Chloro-1-propene; Chlorallylene; Allyl chloride; Allyl chloride; Allyl chloride; 3-Chloro-1-propene; 3-氯-1-丙烯; 氯丙烯; 烯丙基氯; 烯丙基氯; 3-氯-1-丙烯

Database IDs

• CAS Number: 107-05-1
• EC Number: 203-457-6
• MDL Number: MFCD00000984
• Beilstein Number: 635704
• Merck Index: 14289
• PubChem SID: 162075044; 24854161; 24867856; 24890483; 24871752
• PubChem CID: 7850
• CHEMBL: 451126
• Wikipedia Title: Allyl_chloride

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.5672646
• LogD (pH = 7.4): 1.5672646
• Log P: 1.5672646
• Molar Refractivity: 20.475 cm^3
• Polarizability: 7.8345256 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.36 g/100 mL (20 °C) in water; Water
• Melting Point: -130 °C(lit.); -135°C; -135°C
• Boiling Point: 44-46 °C(lit.); 44-46°C; 44-46°C; 45°C
• Flash Point: −32 °C; -25.6 °F; -28°C; -28°C(-18°F); -32 °C
• Auto Ignition Point: 390 °C
• Density: 0.939; 0.939 g/mL at 25 °C(lit.); 0.94 g/mL
• Refractive Index: 1.4160; n20/D 1.414(lit.)
• Vapor Pressure: 20.58 psi ( 55 °C); 5.71 psi ( 20 °C)
• Vapor Density: 2.6 (vs air)

Safety Information

• Storage Warning: Highly Flammable/Harmful/Irritant/Mutagenic/Carcinogenic/Lachrymatory/Keep Cold
• RTECS: UC7350000
• European Hazard Symbols: Carc3; Flammable (F); Muta3; Nature polluting (N); X; Harmful (Xn)
• UN Number: 1100; UN1100
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 1; I
• Risk Statements: 11-20/21/22-36/37/38-40-48/20-50-68; 11-20/21/22-36/37/38-40-48/20-68-50; R11 R20/21/22 R36/37/38 R40 R40 R48/20 R68 R50
• Safety Statements: 16-25-26-36/37-46-61; 2-16-25-26-36/37-46-61; S2 S16 S25 S26 S36/37 S46 S61
• TSCA Listed: 是
• EU Index: 602-029-00-X
• GHS Pictograms: GHS02; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• NFPA704:
  

  3

  3

  1
• Explode Limits: 11.2 %; 2.9–11.2%
• GHS Hazard statements: H225-H302-H312-H315-H319-H332-H335-H341-H351-H373-H400; H225-H341-H351-H373-H400-H302-H312-H332-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P273-P280-P305 + P351 + P338; P210-P261-P273-P281-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1100 3/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%; 98%, stab. with propylene oxide; 98.0% (returnable containers); 99%
• Grade: analytical standard; reagent grade; ReagentPlus®
• Packaging: ampule of 1000 mg
• Linear Formula: CH2=CHCH2Cl

DETAILS

Sigma Aldrich - 236306

Packaging
5, 100 mL in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 481378

Packaging
180, 410, 820 lb in Kilo-Lab™
View returnable container options.

Sigma Aldrich - A30702

Packaging
1, 2, 2.5, 4 L in glass bottle
500 mL in glass bottle

REFERENCES

• Lithiation with LDA in THF at -78^o generatesɑ-chloroallyllithium which can be ɑ-alkylated with primary bromides in high yield. Displacement of the resulting allylic chloride with a dialkyl cuprate to give, stereoselectively, an (E)-alkene, has been used in a pheromone synthesis: J. Org. Chem., 45, 1504 (1981).
• Treatment with sodium bis(trimethylsilyl)amide gives the strained, highly reactive alkene cyclopropene. For details and Diels-Alder reactions, see: J. Org. Chem., 61, 6462 (1996).