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Trichloroacetic acid

CAS No.
76-03-9
Chemical Name:
Trichloroacetic acid
Synonyms
TCA;TRICHLOROACETATE;500ml;CCl3COOH;nata;Trichloroethanoic acid;Trichloracetic acid;TKhU;TkhV;NA TA
CBNumber:
CB9854255
Molecular Formula:
C2HCl3O2
Molecular Weight:
163.39
MDL Number:
MFCD00004177
MOL File:
76-03-9.mol
MSDS File:
SDS
Last updated:2023-11-28 16:31:44

Trichloroacetic acid Properties

Melting point 54-58 °C (lit.)
Boiling point 196 °C (lit.)
Density 1.62 g/mL at 25 °C (lit.)
vapor density <1 (vs air)
vapor pressure 1 mm Hg ( 51 °C)
refractive index n20/D 1.62(lit.)
Flash point 196°C
storage temp. Store at +15°C to +25°C.
solubility H2O: 0.5 M at 20 °C, clear, colorless
pka 0.7(at 25℃)
form Solid
color White
PH <1.0 (25℃, 0.5M in H2O)
Odor sharp, pungent odor
Water Solubility 120 g/100 mL (20 ºC)
Sensitive Hygroscopic
λmax 210nm(EtOH)(lit.)
Merck 14,9627
BRN 970119
Dielectric constant 4.9(20℃)
Exposure limits ACGIH: TWA 0.5 ppm
NIOSH: TWA 1 ppm(7 mg/m3)
Stability Stable, but moisture sensitive. Incompatible with water, strong bases. Note that the Merck Index states that this material is hydrolytically unstable in aqueous solution below 30% by weight. Decomposition products include carbon monoxide and carbon dioxide. The generation of these gases in a sealed container may lead to a pressure rise sufficien
LogP 1.330
CAS DataBase Reference 76-03-9(CAS DataBase Reference)
EWG's Food Scores 3-6
FDA UNII 5V2JDO056X
NIST Chemistry Reference Acetic acid, trichloro-(76-03-9)
Proposition 65 List Trichloroacetic Acid
IARC 2B (Vol. 63, 84, 106) 2014
EPA Substance Registry System Trichloroacetic acid (76-03-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07,GHS09
Signal word  Danger
Hazard statements  H314-H335-H410
Precautionary statements  P260-P271-P273-P280-P303+P361+P353-P305+P351+P338
Hazard Codes  Xn,N,C,F,Xi
Risk Statements  36/37/38-40-51/53-50/53-35-38-11-34-67-52/53
Safety Statements  26-36/37-61-60-45-36/37/39-24/25-16
RIDADR  UN 1839 8/PG 2
WGK Germany  2
RTECS  AJ7875000
10-21
Autoignition Temperature 711 °C
Hazard Note  Corrosive/Hygroscopic
TSCA  Yes
HazardClass  8
PackingGroup  II
HS Code  29154000
Toxicity LD50 orally in rats: 5000 mg/kg (Bailey, White)
NFPA 704
0
3 0

Trichloroacetic acid price More Price(67)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.22342 Trichloroacetic acid for synthesis 76-03-9 25g $27.7 2024-03-01 Buy
Sigma-Aldrich 8.22342 Trichloroacetic acid for synthesis 76-03-9 250g $90.3 2024-03-01 Buy
Sigma-Aldrich 8.22342 Trichloroacetic acid for synthesis 76-03-9 1kg $205 2024-03-01 Buy
Sigma-Aldrich 1.00807 Trichloroacetic acid for analysis EMSURE? ACS,Reag. Ph Eur 76-03-9 100g $109 2024-03-01 Buy
Sigma-Aldrich 1.00807 Trichloroacetic acid for analysis EMSURE? ACS,Reag. Ph Eur 76-03-9 250g $140 2024-03-01 Buy
Product number Packaging Price Buy
8.22342 25g $27.7 Buy
8.22342 250g $90.3 Buy
8.22342 1kg $205 Buy
1.00807 100g $109 Buy
1.00807 250g $140 Buy

Trichloroacetic acid Chemical Properties,Uses,Production

Description

Trichloroacetic acid, also known as TCA or 76-03-9, is a colorless or white orthorhombic crystal with strong deliquescence and a slight, special irritant smell. It is highly corrosive. TCA's aqueous solution is strongly acidic, with a pH of 1.2 for a 0.1 mol solution. Concentrations of TCA at or below 30% cannot be stored for long periods due to decomposition into chloroform, hydrogen chloride, carbon dioxide, and carbon monoxide. Dilute alkali leads to hydrolysis into chloroform and carbon dioxide. Concentrated alkali results in the formation of formic acid. TCA is a highly toxic substance with an oral LD50 of 3320mg/kg.

Chemical Properties

Trichloroacetic acid, a colorless crystalline solid, is commonly utilized in liquid solutions. It has the ability to absorb moisture from the surrounding air and become syrupy. When dissolved in water, the process releases heat. However, this potent acid is corrosive to both metals and tissue.

Uses

As a reagent for albumin detection; in making herbicides. It is found as a by-product after chlorination of water containing humic materials.

Uses

Trichloroacetate (TCA) is used primarily for the selective control of annual and perennial grass weeds in cropland and noncropland. TCA is acidic in nature and are not strongly sorbed by soils. It is reported to be rapidly degraded in both soil and water by microbial processes. However, the breakdown of TCA occurs very slowly when incubated at 14–15 °C in acidic soils. iming not only accelerates this degradation but also increases the numbers of TCA-degrading bacteria.

Uses

Protein precipitation reagentTrichloroacetic acid is used as a precipitating agent in biochemistry for precipitation of proteins, DNA and RNA. It is an active ingredient used in cosmetic treatments like chemical peels, tattoo removal and the treatment of warts including genital warts. It is also used to determine protein concentration and as a decalcifier and fixative in microscopy.

Uses

Traditionally used to precipitate protein. Has been used to determine protein concentration by quantitative precipitation. Used as decalcifier and fixative, as a laboratory reagent, a herbicide, in medicine, and in microscopy.

Application

Trichloroacetic acid(76-03-9) can be used as pharmaceutical raw materials, herbicides (potassium trichloroacetate and sodium trichloroacetate, etc.), textile dyeing auxiliaries, metal surface treatment agent and acid chloride, anhydride, amide, polyester, organometallic salt, water salicylaldehyde, chlorocarboxylic acid and the raw materials of other organic synthesis.
In addition, in medicine, it can also be used as etherifying agents and keratolytics, bile pigment reagents and protein precipitation reagents. In the field of biochemistry, it can be used for separation analysis of biological phosphate compounds and reagents for determination of fluoride and lipid as well as microscopic fixative, decalcification, chromatography reagents.
The product is warts agent and astringent in pharmaceutical field, mainly used as biochemical drug extractant for the extraction of many highly efficient drugs such as adenosine triphosphate, cytochrome C and placental polysaccharides.
In addition, trichloroacetic acid, together with alkaline phenol, can be used for salicylaldehyde compound synthesis by ReimerTiemann reaction. It can also react with monoolefine compounds for synthesizing chlorocarboxylic acid [CCl3 (CH2CH2) nCOOH].

Preparation

Trichloroacetic acid is produced on an industrial scale by chlorination of acetic acid or chloroacetic acid mother-liquors at 140 - 160 °C. If necessary, calcium hypochlorite is added as a chlorination accelerator. There are conflicting views concerning adding heavy metal salts as chlorination catalysts. Examples of catalysts that have been used are iron and copper compounds, which are precipitated with sulfuric acid or phosphoric acid if decomposition of the reaction mixture occurs; 2% phosphoric acid; and catalysts and UV light. Trichloroacetic acid has also been produced without catalysts. The crude product, containing about 95% trichloroacetic acid, is best isolated by crystallizing the melt, removing the mother-liquor with most of its impurities, and increasing the purity by centrifugation or recrystallization.

Definition

ChEBI: Trichloroacetic acid is a monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine. It has a role as a metabolite, a carcinogenic agent and a mouse metabolite. It is a monocarboxylic acid and an organochlorine compound. It is functionally related to an acetic acid. It is a conjugate acid of a trichloroacetate.

Reactions

Trichloroacetic acid is a strong organic acid with a dissociation constant K = 3 &times; 10-2. It has lively chemical properties. Its sodium salt is easily subject to decarboxylation into chloroform. It will be reduced to alcohol upon coming across LiAlH4. It can have halogen replacement reaction with KBr:
Trichloroacetic acid reaction with KBr

General Description

Trichloroacetic acid (TCA) is derived from Trichloroethylene (TCE) metabolism. It is used as an acid decalcifying agent. TCA is used as a fixative for nuclear staining and protein precipitation.

Reactivity Profile

Trichloroacetic acid is a strong acid; when heated, in the presence of water, decomposes forming phosgene and HCl. [Handling Chemicals Safely 1980 p. 915]. The acid was added to copper wool and rinsed down with dimethyl sulfoxide. This caused what was thought to be an extremely exothermic dehydrohalogenation reaction that melted the neck of the flask, [Chem. Eng. News, 1981, 59(28), 4].

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Biochem/physiol Actions

TCA might act as a carcinogen, targeting liver. It might be used as an acid decalcifying agent. TCA helps in nuclear staining.

Safety Profile

Poison by ingestion and subcutaneous routes. Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental carcinogenic data. Experimental reproductive effects. Mutation data reported. A corrosive irritant to skin, eyes, and mucous membranes. When heated to decomposition it emits toxic fumes of Cland Na2O. Used as an herbicide.

Potential Exposure

This haloacetic acid can be a byproduct of drinking water disinfection and may increase the risk of cancer. Trichloroacetic acid is used as medication; in organic syntheses; as a reagent for albumin detection; as an intermediate in pesticide manufacture and in the production of sodium trichloroacetate which is itself a herbicide.

Carcinogenicity

TCA was not mutagenic in bacterial assays.The IARC has determined that there is limited evidence for the carcinogenicity of TCA in experimental animals and that it is not classifiable as to its carcinogenicity to humans. Neutralized TCA was not clastogenic in human lymphocytes in vitro or in the mouse bone marrow micronucleus test.

Shipping

UN1839 (solid) & UN2564 (solution) Trichloroacetic acid, solid and Trichloroacetic acid, solution, Hazard class: 8; Labels: 8-Corrosive material.

Purification Methods

Purify the acid by fractional crystallisation from its melt, then crystallise it repeatedly from dry *benzene and store it over conc H2SO4 in a vacuum desiccator. It can also be crystallised from CHCl3 or cyclohexane, and dried over P2O5 or Mg(ClO4)2 in a vacuum desiccator. Trichloroacetic acid can be fractionally distilled under reduced pressure from MgSO4. Layne, Jaffé and Zimmer [J Am Chem Soc 85 435 1963] dried trichloroacetic acid in *benzene by distilling off the *benzene-water azeotrope, then crystallised the acid from the remaining *benzene solution. Manipulations should be carried out under N2. [Toxic vapours, use a well ventilated fume cupboard.] [Beilstein 2 IV 508.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, silver salts, strong acids, strong bases, moisture, iron, zinc, aluminum. Corrosive to iron, steel and other metals.

References

https://pubchem.ncbi.nlm.nih.gov/compound/trichloroacetic_acid#section=Top
https://en.wikipedia.org/wiki/Trichloroacetic_acid

545-06-2
594-65-0
76-03-9
Synthesis of Trichloroacetic acid from Trichloroacetonitrile
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