Trichloroacetonitrile

Product Name: Trichloroacetonitrile
CAS No.: 545-06-2
Chemical Name: Trichloroacetonitrile
Synonyms: CCl3CN;2,2,2-Trichloroacetonitrile;Tritox;Trichloroaceto;Chlorocyanohydrin;TRICHLORACETONITRILE;Trichlouracetonitril;Trichlroacetonitrile;TRIBROMOACETONITRILE;Trichlor-acetonitril
CBNumber: CB5853801
Molecular Formula: C2Cl3N
Formula Weight: 144.39
MOL File: 545-06-2.mol

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Trichloroacetonitrile Property

Melting point:: -42 °C
Boiling point:: 83-84 °C(lit.)
Density: 1.44 g/mL at 25 °C(lit.)
vapor pressure: 58 mm Hg ( 20 °C)
refractive index: n20/D 1.441(lit.)
Flash point:: None
storage temp.: Store below +30°C.
solubility: <0.1 g/100 mL at 21.5°C
form: Liquid
color: Clear colorless to very slightly yellow
Odor: odor of chloral and hydrogen cyanide
Water Solubility: <0.1 g/100 mL at 21.5 ºC
Sensitive: Lachrymatory
Merck: 14,9628
BRN: 605572
Dielectric constant: 4.6（60℃）
Exposure limits: NIOSH: IDLH 25 mg/m3
Stability:: Stable, but water sensitive. Incompatible with acids, water, steam. May hydrolyze in alkali or acid conditions. Flammable.
CAS DataBase Reference: 545-06-2(CAS DataBase Reference)
NIST Chemistry Reference: Acetonitrile, trichloro-(545-06-2)
IARC: 3 (Vol. 52, 71) 1999
EPA Substance Registry System: Trichloroacetonitrile (545-06-2)

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Safety

Hazard Codes: T,N
Risk Statements: 23/24/25-51/53
Safety Statements: 45-61
RIDADR: UN 3276 6.1/PG 3
WGK Germany: 3
RTECS: AM2450000
Hazard Note: Toxic/Lachrymatory
TSCA: Yes
HazardClass: 8
PackingGroup: II
HS Code: 29269095
Hazardous Substances Data: 545-06-2(Hazardous Substances Data)
Toxicity: LD50 orally in rats: 0.25 g/kg (Smyth)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: T53805
Product name: Trichloroacetonitrile
Purity: 98%
Packaging: 5g
Price: $65.1
Updated: 2024/03/01

Sigma-Aldrich

Product number: T53805
Product name: Trichloroacetonitrile
Purity: 98%
Packaging: 100g
Price: $149
Updated: 2024/03/01

Sigma-Aldrich

Product number: 8.08222
Product name: Trichloroacetonitrile
Purity: for synthesis
Packaging: 50mL
Price: $90.2
Updated: 2024/03/01

Sigma-Aldrich

Product number: 8.08222
Product name: Trichloroacetonitrile
Purity: for synthesis
Packaging: 250ML
Price: $307
Updated: 2024/03/01

TCI Chemical

Product number: T0372
Product name: Trichloroacetonitrile
Purity: >98.0%(GC)
Packaging: 25g
Price: $18
Updated: 2024/03/01

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Trichloroacetonitrile Chemical Properties,Usage,Production

Chemical Properties

colourless to slightly yellow liquid

Uses

Trichloroacetonitrile is involved as a reagent in Overman rearrangement, which is used to prepare alylic amines from allylic alcohols. It is also used to prepare bistrichloroacetimidates from diols leading to dihyrooxazines through acid catalyzed cyclization. Further, it is utilized in the synthesis of trichloroacetimidates by 1,8-Diazobicyclo[5.4.0]undec-7-ene (DBU) catalyzed addition of allylic alcohols. It finds application in the study of the methoxy methyl (MOM) catalyzed aza-Claisen rearrangement.

Uses

Insecticide.

Definition

ChEBI: Trichloroacetonitrile is an aliphatic nitrile and an organochlorine compound.

Production Methods

Trichloroacetonitrile can be obtained by dehydration of trichloroacetamide with phosphorous pentoxide or by chlorination of acetonitrile with chlorine. Vapor phase chlorination in the presence of water and photochemical chlorination in the presence of catalysts such as HgCl2 or AlCl3 have been reported. Trichloroacetonitrile is an organic intermediate used, for example, in the synthesis of the fungicide etridiazole.

Reactions

Trichloroacetonitrile is an efficient dehydrating agent for a range of aldoximes, including aromatic and heterocyclic aldoxime, yielding the corresponding nitriles in moderate to good yields. The dehydration reactions can take place in non-acetonitrile media without the aid of a metal catalyst. In addition, it has been confirmed that trichloroacetonitrile was converted into trichloroacetamide in the reaction. Trichloroacetonitrile and triphenylphosphine convert carboxylic acids to acyl chlorides mildly and rapidly under acid-free conditions[1-2].

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

May be sensitive to light and heat. Trichloroacetonitrile may react with water, steam, acid or acid fumes. Trichloroacetonitrile may hydrolyze under acidic or alkaline conditions. . The reaction of benzene and Trichloroacetonitrile evolves toxic chloroform and HCl gasses. (Hagedorn, F., H.-P. Gelbke, and Federal Republic of Germany. 2002. Nitriles. In Ullman Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA.).

Hazard

Strong irritant to tissue. Questionable carcinogen.

Fire Hazard

Trichloroacetonitrile is combustible.

Safety Profile

Poison by ingestion and intravenous routes. Moderately toxic by inhalation and skin contact. Human mutation data reported. A skin and severe eye irritant. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition or in reaction with water, steam, acid, or acid fumes it produces toxic fumes of CN-, Cl-, and NOx. Used as an insecticide. See also NITRILES and CYANIDE.

Toxicity evaluation

Trichloroacetonitrile (TCAN) is a by-product of the chlorine disinfection of water containing natural organic material. When administered by gavage to pregnant Long-Evans rats in a medium-chain triglyceride vehicle, tricaprylin oil (Tricap), at a volume of 10 ml/kg, TCAN induced fetal cardiovascular anomalies at doses as low as 1 mg/kg/d. Five groups of approximately 20 pregnant female rats received TCAN in CO at 15, 35, 55, and 75 mg/kg/d and in Tricap at 15 mg/kg/d (10 ml/kg closing volume). Corn oil, Tricap, and water served as vehicle controls. Animals were treated by oral intubation on gestation d 6-18 (vaginal plug -= d 0). Five out of 20 dams (75 mg/kg) died during treatment. Adjusted maternal weight gain was lower in females receiving 35 mg/kg TCAN or greater. The mean percent of nonlive implants per litter was elevated at 55 and 75 mg/kg TCAN (CO). The TCAN dose-response curve for fetal (but not maternal)effects was shifted to the right when CO was compared to Tricap. Fetal weight was reduced at 15 mg/kg TCAN (Tricap) and at 55 mg/kg TCAN (CO). When TCAN was administered in CO, the mean frequency of soft-tissue maliformations decreased with significantly fewer septal and great vessel cardiovascular defects observed. The lowest observed adverse effect level for TCAN (CO) was determined to be 35 kg/kg.

References

[1] István Vágó, István Greiner. “A useful acylation method using trichloroacetonitrile and triphenylphosphine for solid phase organic synthesis.” Tetrahedron Letters 43 34 (2002): Pages 6039-6041.
[2] Xiaoyun Ma, Zhengjian Chen, Dan Liu . “Dehydration of aldoximes to nitriles using trichloroacetonitrile without catalyst.” Synthetic Communications 51 21 (2021): Pages 3261-3266.

Trichloroacetonitrile Preparation Products And Raw materials

Raw materials

2,2,2-Trichloroacetamide Phosphorus pentoxide

Preparation Products

Trifluoroacetic acid

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View Lastest Price from Trichloroacetonitrile manufacturers

Hebei Mujin Biotechnology Co.,Ltd

Product: Trichloroacetonitrile 545-06-2
Price: US $50.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20tons
Release date: 2023-08-07

Hebei Weibang Biotechnology Co., Ltd

Product: Trichloroacetonitrile 545-06-2
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 10 mt
Release date: 2024-11-12

Guangzhou Sunton Biotechnology Co., Ltd.

Product: Trichloroacetonitrile 545-06-2
Price: US $48.00-40.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 200tons
Release date: 2021-04-15

545-06-2, TrichloroacetonitrileRelated Search:

Chloroacetonitrile Copper(I) Cyanide Iminodiacetonitrile Chloral Chloranil Ethyl trichloroacetate SODIUM TRICHLOROACETATE Trichloroacetic acid CERIUM(III) CHLORIDE NEODYMIUM CHLORIDE Phosphorus oxychloride Aluminum chloride Trichloroacetyl chloride Triclocarban Chlorobutanol VANADIUM(V) TRICHLORIDE OXIDE Acetonitrile HYDROGEN CYANIDE

trichloromethylcarbonitrile

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TRICHLOROACETONITRILE, 1000MG, NEAT

Trichloroacetonitrile,97%

TRICHLORACETONITRILE

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Trichloromethylnitrile

Trichlouracetonitril

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TRICHLOROACETONITRILE FOR SYNTHESIS

TRIBROMOACETONITRILE

TRICHLOROACETONITRILE

trichloromethyl cyanide

acetonitrile,trichloro-

CCl3CN

Nitrile trichloracetique

nitriletrichloracetique

Trichlor-acetonitril

Trichlormethylkyanid

trichloro-acetonitril

Trichloroethanenitrile

Acetonitrile, 2,2,2-trichloro-

545-06-2

544-06-2

C2Cl3N

Cl3CCN

C2CI3N

Organic Building Blocks

Nitrogen Compounds

Cyanides/Nitriles

C1 to C5

Building Blocks

C1 to C5

Chemical Synthesis

Nitrogen Compounds

Organic Building Blocks

Pyridines ,Halogenated Heterocycles

C1 to C5Specialty Synthesis

Glycosylating Reagents

Carbohydrate Synthesis

C1 to C5

Cyanides/Nitriles

Nitrogen Compounds

NitrilesVolatiles/ Semivolatiles

Alpha Sort

Chemical Class

ChloroAnalytical Standards

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TP - TZ