2-chloroacetic acid

• ChemBase ID: 104174
• Molecular Formular: C2H3ClO2
• Molecular Mass: 94.49702
• Monoisotopic Mass: 93.98215702
• SMILES: OC(=O)CCl
• Canonical SMILES: OC(=O)CCl
• InChI: InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
• InChIKey: FOCAUTSVDIKZOP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloroacetic acid
• IUPAC Systematic name: Chloroethanoic acid
• IUPAC Traditional name: chloroacetic acid
• Synonyms: NSC 142; NSC 42970; Chloroacetic acid, ACS; Chloroacetic acid; Monochloroacetic Acid; CHLOROACETIC ACID; Acide Chloracetique; CHLOROACETIC ACID ACS REAGENT GRADE; 氯乙酸, ACS; 一氯醋酸; 氯乙酸

Database IDs

• CAS Number: 79-11-8
• EC Number: 201-178-4
• MDL Number: MFCD00002683
• Beilstein Number: 605438
• Merck Index: 142112
• PubChem SID: 24892452; 162091061; 24865140; 24862520; 24867882
• PubChem CID: 300
• CHEBI ID: 27869
• CHEMBL: 14090
• Chemspider ID: 10772140
• KEGG ID: D07677
• Unique Ingredient Identifier: 5GD84Y125G
• Wikipedia Title: Chloroacetic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.05571
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -2.0975466
• LogD (pH = 7.4): -3.1535952
• Log P: 0.3139981
• Molar Refractivity: 17.3969 cm^3
• Polarizability: 6.995691 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 85.8 g/100mL (25 °C) in water; Soluble in water, alcohols, benzene, chloroform, ether
• Apperance: Colorless or white crystals; Crystalline
• Melting Point: 60-63 °C; 60-63 °C(lit.); 60-63°C; 61-63 °C; 61-64 °C; 62 °C; 63°C
• Boiling Point: 189 °C at 1013 hPa; 189 °C(lit.); 189.3 °C, 462.5 K, 372.7 °F; 189°C
• Flash Point: 126 °C (closed cup and DIN 51758); 126 °C; 126 °C; 126°C(258°F); 258.8 °F
• Auto Ignition Point: 470 °C (878 °F); greater than 500 °C (932 °F)
• Density: 1.37 kg/m3 at 65 °C; 1.404; 1.58 g·cm^-3, solid
• Vapor Pressure: 0.75 mmHg ( 20 °C); 1 hPa at 20 °C
• Vapor Density: 3.26 (air = 1); 3.26 (vs air)
• pKa: 2.86

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic
• RTECS: AF8575000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 1751; UN1751
• German water hazard class: 2
• Hazard Class: 6.1; 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 23/24/25-34-50; R:25-34-50; R25 R34 R50
• Safety Statements: 26-36/37/39-45-61-63; S:23-37-45-61; S23 S37 S45 S61
• EU Classification: TC2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS09
• GHS Signal Word: Danger
• Main Hazard: alkylating agent
• NFPA704:
  

  1

  3
• GHS Hazard statements: H301 + H311 + H331-H314-H400; H301-H311-H314-H331-H400; H301-H311-H331-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: dust mask type N95 (US), Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P2 (EN 143) respirator cartridges, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1751 6.1/PG 2

Product Information

• Purity: ≥97.0% (T); ≥99%; ≥99.0%; ≥99.0% (T); 99%; 99+%
• Grade: ACS; ACS reagent; analytical standard; JIS special grade; PESTANAL®, analytical standard; puriss.; purum; REAGENT
• Packaging: ampule of 1000 mg
• Ignition Residue: <0.02%; ≤0.05%; ≤0.1%
• Impurities: ≤0.005% heavy metals (as Pb); ≤0.01% Carbonyl compounds (as acetone); ≤0.01% Carbonyl compunds (other than acetone); ≤0.01% insolubles
• Cation Traces: Fe: ≤0.002%; Fe: ≤10 mg/kg; heavy metals (as Pb): ≤0.001%
• Antion Traces: chloride (Cl-): ≤0.01%; sulfate (SO42-): ≤0.02%
• Linear Formula: ClCH2COOH

DETAILS

MP Biomedicals - 02193812

ACS Reagent Grade
Purity: 99%

MP Biomedicals - 02154956

(Monochloroacetic Acid) Purity: 99% Crystalline

Sigma Aldrich - 24510

Other Notes
Reagent for the gravimetric det. of zirconium1

Sigma Aldrich - 36544

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 402923

Packaging
100, 500 g in poly bottle
2 kg in poly bottle

Sigma Aldrich - C19627

Packaging
1 kg in poly bottle
25 g in poly bottle

REFERENCES

• A convenient one-pot alternative to the Knoevenagel or Horner-Wadsworth-Emmons reactions for the synthesis of ɑ-unsubstituted cinnamic acids involves the reaction of chloroacetic acid with dimethyl phosphite in the presence of sodium methoxide, and treatment of the resulting phosphonoacetate salt with a benzaldehyde: J. Org. Chem., 46, 2514 (1981):
  
• For a more general version of this reaction, applicable to the synthesis of a variety of substituted acrylic acids, see 2-Bromopropionic acid, A17569.