2,2-dichloroacetic acid

• ChemBase ID: 6409
• Molecular Formular: C2H2Cl2O2
• Molecular Mass: 128.94208
• Monoisotopic Mass: 127.94318466
• SMILES: OC(=O)C(Cl)Cl
• Canonical SMILES: ClC(C(=O)O)Cl
• InChI: InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)
• InChIKey: JXTHNDFMNIQAHM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dichloroacetic acid
• IUPAC Traditional name: dichloroacetic acid
• Synonyms: DCA; dichloroacetate; Dichloroacetic Acid; Dichloroacetic acid; DEBLOCK (0.36M dichloroacetic acid in toluene); DCA Deblock (0.36M dichloroacetic acid in toluene); 2,2-dichloroacetic acid; Dichloroethanoic acid; Bichloroacetic acid; 2,2-Dichloroacetic acid; Urner's Liquid; Dichloroacetic acid solution; 二氯乙酸; 去保护溶液（0.36M 二氯乙酸的甲苯溶液）; 二氯乙酸去保护溶液（0.36M 二氯乙酸的甲苯溶液）; 二氯乙酸 溶液

Database IDs

• CAS Number: 79-43-6
• EC Number: 201-207-0
• MDL Number: MFCD00004223
• Beilstein Number: 1098596
• Merck Index: 143050
• PubChem SID: 24872892; 24893838; 160969716; 24867907; 24862522
• PubChem CID: 6597
• CHEBI ID: 36386
• CHEMBL: 13960
• Chemspider ID: 10771217
• DrugBank ID: DB08809
• KEGG ID: C11149
• MeSH Name: Dichloroacetate
• Unique Ingredient Identifier: 9LSH52S3LQ
• Wikipedia Title: Dichloroacetic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.2969742
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.9773304
• LogD (pH = 7.4): -2.4598467
• Log P: 1.0581826
• Molar Refractivity: 22.6195 cm^3
• Polarizability: 8.981123 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.99
• LOG S: -0.25
• Solubility (Water): 7.23e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1000 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; miscible in water; miscible with ethanol, diethyl ether
• Apperance: APHA: <50; Colorless liquid; Liquid
• Melting Point: 10 °C (50 °F); -4 °C (24.6 °F) (2 crystalline forms); 9 - 11°C; 9 - 11°C; 9-11 °C(lit.); 9-11°C
• Boiling Point: 110-111 °C; 192 °C (378 °F); 194 °C (381 °F); 192-194°C; 194 °C(lit.); 194°C; 194°C
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F; 41 °F; 5 °C
• Density: 0.884 g/mL at 25 °C; 1.335 g/mL at 20 °C; 1.563 g/mL at 25 °C(lit.); 1.5634 g/cm^3 (20 °C); 1.564; 1.564 at 20 °C (water = 1)
• Refractive Index: 1.4620; n20/D 1.466; n20/D 1.466(lit.)
• Vapor Pressure: 0.19 mmHg ( 20 °C); 1.43 mm Hg (0.19 kPa) at 20 °C
• Vapor Density: 4.4 (air = 1); 4.5 (vs air)
• Hydrophobicity(logP): 0.92 [HANSCH,C ET AL. (1995)]; 0.982
• pKa: 1.35
• Std enthalpy of formation: -496.3 kJ·mol^-1
• Turbidity: 0.22 NTU (clear)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic
• RTECS: AG6125000
• European Hazard Symbols: Corrosive (C); Flammable (F); Nature polluting (N); Harmful (Xn)
• UN Number: 1294; 1593; 1764; UN1764
• German water hazard class: 2
• Hazard Class: 3; 6.1; 8
• Packing Group: 2; 3; II
• Australian Hazchem: 2X
• Risk Statements: 35-50; 36/38-40-50; 63-11-36/38-48/20-50-65-67; R:35-50; R35 R50
• Safety Statements: 16-26-36/37-61-62; 26-36/37-61; 26-45-61; S:26-45-61; S1/2 S26 S45 S61
• EU Classification: C9
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• NFPA704:
  

  1

  3

  0
• GHS Hazard statements: H225-H304-H315-H318-H336-H361d-H373-H400; H311-H314-H400; H314-H400; H315-H318-H351-H400
• GHS Precautionary statements: P210-P261-P273-P280-P301 + P310-P305 + P351 + P338; P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P273-P280-P305 + P351 + P338; P273-P280-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 1294 3/PG 2; UN 1593 6.1/PG 3; UN 1764 8/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ALDH1A1(216), PDK1(5163)rat ... Pdk1(116551)

Product Information

• Purity: ≥95% (T); ≥98%; ≥98.5% (T); ≥99%; ≥99% (alkalimetric); 95%; 99%; 99+%
• Concentration: ≤100 ppm in H2O; 3% in methylene chloride
• Grade: analytical standard; biotech. grade; for DNA synthesis; PESTANAL®, analytical standard; puriss.; ReagentPlus®; technical
• Packaging: ampule of 1000 mg
• Impurities: ≤0.01% water; ≤0.05% water
• Linear Formula: Cl2CHCOOH
• Empirical Formula (Hill Notation): C2H2Cl2O2

DETAILS

DrugBank - DB08809

• Drug Groups: experimental
• Description: Dichloroacetic acid, often abbreviated DCA, is an acid analogue of acetic acid in which two of the three hydrogen atoms of the methyl group have been replaced by chlorine atoms. The salts and esters of dichloroacetic acid are called dichloroacetates. Salts of DCA are used as drugs since they inhibit the enzyme pyruvate dehydrogenase kinase. Early reports of its activity against brain cancer cells led patients to treat themselves with DCA, which is commercially available in non-pharmaceutical grade. A phase 1 study in 5 patients concluded that DCA was safe, but wasn't designed to establish effectiveness.
• Toxicity: ORAL (LD50): Acute: 2820 mg/kg [Rat]; DERMAL (LD50): Acute: 510 mg/kg [Rabbit]
• External Links: Wikipedia

Sigma Aldrich - 36545

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

Sigma Aldrich - D54702

Packaging
1 kg in glass bottle
2.5 L in glass bottle
5, 100, 500 g in glass bottle
5, 100, 500 mL in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 49431

Application
Reagent used in the phosphite triester method of oligonucleotide synthesis for the cleavage of the 5′-protecting group. Reagent is suitable for use on Milligen 7500 synthesizers or as a more mildly acidic alternative to trichloroacetic acid.
General description
filtered through a 1 μm filter

Sigma Aldrich - 707066

Packaging
200 L in Pure-Pac™ 1
4×4 L in glass bottle

MP Biomedicals - 02157638

1 ml = approx. 1.53 g

REFERENCES

• Moderately strong acid which has been recommended for the catalysis of mixed acetal formation by reaction of alcohols with Ethyl vinyl ether, A15691. Has also been used as an acid catalyst and deprotecting agent in various other applications including peptide synthesis.