2-chloroacetyl chloride

• ChemBase ID: 103106
• Molecular Formular: C2H2Cl2O
• Molecular Mass: 112.94268
• Monoisotopic Mass: 111.94827004
• SMILES: ClCC(=O)Cl
• Canonical SMILES: ClCC(=O)Cl
• InChI: InChI=1S/C2H2Cl2O/c3-1-2(4)5/h1H2
• InChIKey: VGCXGMAHQTYDJK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloroacetyl chloride
• IUPAC Traditional name: chloroacetyl chloride
• Synonyms: 2-chloroacetyl chloride; Chloroacetyl chloride; Chloroacetic Chloride; Monochloroacetyl Chloride; CHLOROACETYL CHLORIDE; 氯乙酰氯

Database IDs

• CAS Number: 79-04-9
• EC Number: 201-171-6
• MDL Number: MFCD00000725
• Beilstein Number: 605439
• Merck Index: 142067
• PubChem SID: 24846647; 24853713; 162090320
• PubChem CID: 6577
• Chemspider ID: 6329
• KEGG ID: C14859
• Wikipedia Title: Chloroacetyl_chloride

CALCULATED PROPERTIES

• Acid pKa: 16.745235
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.84732777
• LogD (pH = 7.4): 0.84732777
• Log P: 0.84732777
• Molar Refractivity: 21.2554 cm^3
• Polarizability: 8.409953 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Reacts in water
• Apperance: Colorless liquid
• Melting Point: -22 °C(lit.); -22°C; -22°C
• Boiling Point: 105-106 °C(lit.); 105-106°C; 105-110 °C; 106°C
• Flash Point: 100 °C; 212 °F
• Density: 1.417; 1.418 g/mL at 25 °C(lit.); 1.419 g/mL at 20 °C; 1.42 g/mL; 1.420 at 20 °C (water = 1)
• Refractive Index: 1.4530; n20/D 1.453; n20/D 1.453(lit.)
• Vapor Pressure: 19 mm Hg at 20 °C; 60 mmHg ( 41.5 °C)
• Vapor Density: 3.9 (vs air)

Safety Information

• Storage Condition: 0°C
• Storage Warning: Moisture Sensitive
• RTECS: AO6475000
• European Hazard Symbols: Corrosive (C); Nature polluting (N); Toxic (T)
• UN Number: 1752; UN1752
• German water hazard class: 3
• Hazard Class: 6.1; 8
• Packing Group: 1; I; Truck Only
• Australian Hazchem: 2WE
• Risk Statements: 14-23/24/25-29-35-48/23-50; 14-23/24/25-35-48/23-50; R:12-23/24/25-29-35-48/23-50
• Safety Statements: 7/8-9-26-36/37/39-45-61; S:9-26-45-61-36/37/39-7/8
• EU Classification: TC1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 156
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H314-H331-H372-H400; H301-H311-H331-H372-H314-H400
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P261-P273-P280-P301 + P310-P305 + P351 + P338-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 1752 6.1/PG 1
• Supplemental Hazard Statements: Contact with water liberates toxic gas., Reacts violently with water.

Product Information

• Purity: ≥99.0% (GC); 98%
• Grade: purum
• Linear Formula: ClCH2COCl

DETAILS

MP Biomedicals - 02150599

1 ml = approx. 1.42 gm
Used to prepare N-chloroacetyl aminoacids.
NOT FOR EXPORT

Sigma Aldrich - 104493

Packaging
5, 100, 500 g in glass bottle

REFERENCES

• Reagent for the protection of amines as their chloroacetamides. The protecting group can be removed by reaction with thiourea derivatives, forming 2-thiazolidin-4-ones as by-products: J. Am. Chem. Soc., 90, 4508 (1968); Gazz. Chim. Ital., 98, 1261 (1968). Side reactions can be minimized by using 1-Piperidinethiocarboxamide, L12445, as the thiourea: Angew. Chem. Int. Ed., 10, 75 (1971).
• Also used for the protection of alcohols as their chloroacetates: Tetrahedron Lett., 251 (1979). They are hydrolyzed very readily in the presence of many other ester functions: J. Am. Chem. Soc., 86, 118 (194); J. Chem. Soc., Perkin 1, 934 (1975); or can be cleaved with thiourea: Tetrahedron Lett., 251 (1979), ethylenediamine, or mercaptoethylamine: J. Org. Chem., 35, 1940 (1970).