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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

Preparation Products

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Trichloroacetonitrile Suppliers

Qingdao Dexin Chemical Co., Ltd
Tel
15564477061
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1397986535@qq.com
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China
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Shanghai YouPeng Chemical Co. Ltd.
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021-69005955 13701776567
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021-69005775
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youpengchem@163.com
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China
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XPERTICK (SHANDONG) BIO-PHARMACEUTICAL CO., LTD
Tel
21-58999881 15623240527
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emily@xtick.cn
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China
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Shandong Qianyuan Polymer Material Co. , Ltd.
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18678041314 18765609661
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2547772582@qq.com
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China
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Shanghai Tuolei Chemical Reagents Co., Ltd.
Tel
86-021-50318510
Fax
021-58650104
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China
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
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62
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
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TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
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Sales-CN@TCIchemicals.com
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China
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24529
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Beijing dtftchem Technology Co., Ltd.
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010-60275820 13031183356
Fax
010-60270825
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elainezt@sina.com
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Energy Chemical
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021-021-58432009 400-005-6266
Fax
021-58436166
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sales8178@energy-chemical.com
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China
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View Lastest Price from Trichloroacetonitrile manufacturers

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
2023-04-12
Hebei Mojin 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
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

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