2-methoxyacetyl chloride

• ChemBase ID: 88363
• Molecular Formular: C3H5ClO2
• Molecular Mass: 108.5236
• Monoisotopic Mass: 107.99780708
• SMILES: ClC(=O)COC
• Canonical SMILES: COCC(=O)Cl
• InChI: InChI=1S/C3H5ClO2/c1-6-2-3(4)5/h2H2,1H3
• InChIKey: JJKWHOSQTYYFAE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methoxyacetyl chloride
• IUPAC Traditional name: methoxy-acetyl chloride
• Synonyms: Methoxyacetyl chloride; 2-METHOXY 5-ACETYLBENZYL CHLORIDE; Methoxyacetic acid chloride; Methoxyacetyl chloride; 甲氧基乙酸氯; 甲氧基乙酰氯

Database IDs

• CAS Number: 38870-89-2
• EC Number: 254-169-2
• MDL Number: MFCD00000728
• Beilstein Number: 1740244
• PubChem SID: 162075324; 24883674; 24897347
• PubChem CID: 96623

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.1358624
• LogD (pH = 7.4): 0.1358624
• Log P: 0.1358624
• Molar Refractivity: 22.9556 cm^3
• Polarizability: 9.032625 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: <-40°C
• Boiling Point: 112°C; 112-113 °C(lit.); 112-113°C; 112-113°C
• Flash Point: 28°C(82°F); 35 °C; 35°C; 95 °F
• Density: 1.185; 1.187; 1.187 g/ml; 1.187 g/mL at 25 °C(lit.); 1.19 g/mL at 20 °C
• Refractive Index: 1.4240; n20/D 1.419(lit.); n20/D 1.42

Safety Information

• Storage Warning: Corrosive/Flammable/Lachrymatory/Moisture Sensitive/Keep Cold; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); X
• UN Number: 2920; UN2920
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 10-20-34; 10-34-36/37; R:10
• Safety Statements: 26-36/37/39-45; S:9-16-29
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H314-H335; H331-H314-H318-H226
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (T); 97%; 97%, stab. with ca 0.3% magnesium oxide
• Grade: purum
• Contains: ~0.3% magnesium oxide light as stabilizer
• Linear Formula: CH3OCH2COCl

DETAILS

MP Biomedicals - 05221491

MP Biomedicals Rare Chemical collection

Sigma Aldrich - M9653

Packaging
1, 10 g in glass bottle

Sigma Aldrich - 64975

Caution
may discolor to deep green-yellow on storage
Other Notes
Reagent for chloromethylations1

REFERENCES

• Reagent for the chloromethylation of aromatics under Friedel-Crafts conditions, avoiding the use of chloromethyl methyl ether: Tetrahedron Lett., 24, 1933 (1983). For a study of the kinetics of chloromethylation of benzene and toluene in the presence of SnCl₄, see: J. Org. Chem., 62, 2694 (1997). Compare Methoxyacetic acid, B22917.
• Has also been used for the protection of alcohols as methoxyacetate esters, formed in the presence of pyridine, and cleaved using methanolic or aqueous ammonia ca. 20x faster than acetate: Tetrahedron Lett., 4273 (1968). Selective cleavage with Yb(OTf)₃: J. Org. Chem., 61, 4491 (1996), or ethanolamine in IPA: J. Org. Chem., 60, 331 (1995), have also been reported.