2-(chloromethyl)oxirane

• ChemBase ID: 103236
• Molecular Formular: C3H5ClO
• Molecular Mass: 92.5242
• Monoisotopic Mass: 92.00289246
• SMILES: ClCC1CO1
• Canonical SMILES: ClCC1CO1
• InChI: InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2
• InChIKey: BRLQWZUYTZBJKN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(chloromethyl)oxirane
• IUPAC Traditional name: epichlorohydrin
• Synonyms: (±)-Epichlorohydrin; 2-(chloromethyl)oxirane; epichlorohydrin; γ-chloropropylene oxide; glycidyl chloride; (±)-Epichlorohydrin; (±)-2-(Chloromethyl)oxirane; Epichlorohydrin; (±)-2-(Chloromethyl)oxirane; (±)-Epichlorohydrin; 1-Chloro-2,3-epoxypropane; EPICHLOROHYDRIN; (±)-1-Chloro-2,3-epoxypropane; (±)-环氧氯丙烷; (±)-2-(氯甲基)环氧乙烷; (±)-环氧氯丙烷; 1-氯-2,3-环氧丙烷; 环氧氯丙烷; (+/-)-环氧氯丙烷

Database IDs

• CAS Number: 106-89-8
• EC Number: 203-439-8
• MDL Number: MFCD00005132
• Beilstein Number: 79785
• Merck Index: 143611
• PubChem SID: 24845326; 162103290; 24894383; 24871753; 24867916; 24854429
• PubChem CID: 7835
• CHEBI ID: 37144
• Chemspider ID: 13837112
• KEGG ID: C14449
• Unique Ingredient Identifier: 08OOR508C0
• Wikipedia Title: Epichlorohydrin

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.6772814
• LogD (pH = 7.4): 0.6772814
• Log P: 0.6772814
• Molar Refractivity: 20.057 cm^3
• Polarizability: 8.123073 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: APHA: ≤20
• Melting Point: -25.6 °C; -57 °C; -57 °C(lit.); -57°C
• Boiling Point: 115-117 °C(lit.); 115-117°C; 116 °C at 1013 hPa; 117.9 °C
• Flash Point: 31 °C (closed cup); 32 °C; 32°C(90°F); 89.6 °F
• Auto Ignition Point: 385 °C; 779 °F
• Density: 1.181 g/cm^3 at 20 °C; 1.1812 g/cm^3; 1.182; 1.183 g/mL at 25 °C(lit.)
• Refractive Index: 1.4380; n20/D 1.438; n20/D 1.438(lit.)
• Vapor Pressure: 13 hPa at 20 °C; 13.8 mmHg ( 21.1 °C)
• Vapor Density: 3.2 (vs air); 3.3 (air = 1)

Safety Information

• Storage Condition: 2-8°C
• RTECS: TX4900000
• European Hazard Symbols: Toxic (T)
• UN Number: 2023; UN2023
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 2; II
• Australian Hazchem: 2W
• Risk Statements: 45-10-23/24/25-34-43; R:10-23/24/25-34-43-45
• Safety Statements: 53-45; S:45-53
• EU Classification: TF1
• EU Hazard Identification Number: 6.1A
• Emergency Response Guidebook(ERG) Number: 131P
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• NFPA704:
  

  3

  3

  2
• Explode Limits: 21 %
• GHS Hazard statements: H226-H301-H311-H314-H317-H331-H350; H301-H311-H331-H317-H350-H314-H226
• GHS Precautionary statements: P201-P261-P280-P301 + P310-P305 + P351 + P338-P310; P210-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2023 6.1/PG 2

Product Information

• Purity: ≥99%; ≥99%; ≥99% (GC); ≥99.5% (GC); ≥99.9% (GC); 99%
• Grade: analytical standard; puriss.; purum
• Packaging: ampule of 1000 mg
• Impurities: ≤0.06% water; ≤0.1% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C3H5ClO

DETAILS

MP Biomedicals - 02151063

Purity: 99+%
1 ml = approx. 1.18 gm
Acts as a cyclodextrin cross-linking agent.

Sigma Aldrich - E1055

Packaging
1 kg in Sure/Seal™
100 g in Sure/Seal™
5 g in glass bottle

Sigma Aldrich - 240699

Application
Employed in the preparation of polyglycidyl ethers1 and as a cross-linking agent for polymers.2
Used in the synthesis of a branched heptaglycerol dendrimer.

Sigma Aldrich - 45340

Packaging
1, 2.5 L in glass bottle
200, 400 L in Kilo-Lab™
500 mL in glass bottle
850 L in dw ss tank

REFERENCES

• The preparation of glycidyl ethers, often carried out in two steps, via the ring-opened chlorohydrin ether and subsequent ring-closure with base, can be achieved as a single step, under phase-transfer conditions: Synthesis, 117 (1983). For extension to diglycidyl ethers of diols, see: Synthesis, 649 (1985).
• For use as an acid scavenger in bromination reactions, see: J. Am. Chem. Soc., 95, 4419 (1973).
• Reaction with primary amines provides a one-step route to 3-azetidinols: J. Org. Chem., 55, 2920 (1990):