90-17-5

Basic information

• Product Name: 2,2,2-Trichloro-1-phenylethyl acetate
• Synonyms: -(Trichloromethyl)benzylacetate;Acetic acid, alpha-(trichloromethyl)benzyl ester;aceticacid,alpha-(trichloromethyl)benzylester;alpha-(Trichloromethyl)-, acetate;alpha-(trichloromethyl)-benzenemethanoacetate;alpha-(trichloromethyl)benzenemethanolacetate;alpha-(trichloromethyl)-benzylalcohoacetate;alpha-(trichloromethyl)benzylalcoholacetate
• CAS NO: 90-17-5
• Molecular Formula: C₁₀H₉Cl₃O₂
• Molecular Weight: 267.54
• EINECS: 201-972-0
• Product Categories: Organics;Alphabetical Listings;Essential OilsFlavors and Fragrances;Flavors and Fragrances;Q-Z
• Mol File: 90-17-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 86-89 °C(lit.)
• Boiling Point: 282°C(lit.)
• Flash Point: 145.1 °C
• Appearance: white powder
• Density: 1.3807 (estimate)
• Vapor Pressure: 0.13Pa at 25℃
• Solubility: 28.72g/L in organic solvents at 20 ℃
• PKA: 0.003[at 20 ℃]
• Water Solubility: 16.56mg/L at 25℃
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 2,2,2-Trichloro-1-phenylethyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-Trichloro-1-phenylethyl acetate(90-17-5)
• EPA Substance Registry System: 2,2,2-Trichloro-1-phenylethyl acetate(90-17-5)

Safety Data

• WGK Germany: 2
• RTECS: AJ8375000
• Hazardous Substances Data: 90-17-5(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 90-17-5 differently. You can refer to the following data:
1. white powder
2. 2,2,2-Trichloro-1-phenylethyl acetate forms white crystals (mp 88 °C) and has a weak, very natural, lasting rose odor. The ester is prepared from ??-trichloromethylbenzyl alcohol, for example, by reaction with acetic anhydride. The alcohol can be prepared by one of the following methods: 1) Addition of trichloroacetaldehyde (chloral) to benzene in the presence of aluminum chloride. 2) Reaction of benzaldehyde with chloroform in the presence of potassium hydroxide. ??-Trichloromethylbenzyl acetate is a stable rose fragrancewith excellent fixative properties. It is preferentially used in soaps, powders, and bath salts.

Occurrence

Has apparently not been reported to occur in nature.

Uses

Perfumes, fixative for essential oils and perfumes.

Preparation

By the reaction of benzene and chloral, in the presence of a catalyst, followed by acetylation.

Flammability and Explosibility

Nonflammable

Trade name

Rosalin (Yinghai)

Safety Profile

Mildly toxic by ingestion. A skinirritant. When heated to decomposition it emits toxicfumes of Clí.

InChI:InChI=1/C10H9Cl3O2/c1-7(14)15-9(10(11,12)13)8-5-3-2-4-6-8/h2-6,9H,1H3

Upstream product

• 64-19-7 acetic acid 
• 75-87-6 chloral 
• 71-43-2 benzene 
• 2000-43-3 2,2,2-trichloro-1-phenylethanol 
• 75-36-5 acetyl chloride 
• 67-66-3 chloroform 
• 581-55-5 benzylidene 1,1-diacetate 
• 100-52-7 benzaldehyde 
• 108-24-7 acetic anhydride 

Downstream Products

• 4276-76-0 α-(dichloromethylbenzyl)acetate 
• 536-74-3 phenylacetylene 
• 74389-88-1 α-Diethylamino-phenylessigsaeure-diethylamid 
• 698-88-4 (2,2-dichlorovinyl)benzene 

Relevant articles and documents

Synthetic process of rosone

The invention relates to a synthetic process of rosone. A solid super base is adopted as a catalyst during preparation of trichloromethyl benzyl alcohol, so that production of basic wastewater is avoided, product separation is facilitated, conversion rate of benzaldehyde is increased, the proportion of byproduct benzoic acid is reduced, and product yield is increased greatly and can be up to 95% or higher as the maximum.

Fumigant antitermitic activity of plant essential oils and components from ajowan (Trachyspermum ammi), allspice (Pimenta dioica), caraway (Carum carvi), dill (Anethum graveoiens), geranium (Pelargonium graveoiens), and litsea (Litsea cubeba) oils against Japanese termite (Reticulitermes speratus kolbe)

Plant essential oils from 26 plant species were tested for their insecticidal activities against the Japanese termite, Reticulitermes speratus Kolbe, using a fumigation bioassay. Responses varied with source, exposure time, and concentration. Among the essential oils tested, strong insecticidal activity was observed with the essential oils of ajowan (Trachyspermum ammi), allspice (Pimenta dioica), caraway (Carum carvi), dill (Anethum graveoiens), geranium (Pelargonium graveoiens), and litsea (Litsea cubeba). The composition of six essential oils was identified by using gas chromatographymass spectrometry. The compounds thus identified were tested individually for their insecticidal activities against Japanese termites. Responses varied in a dose-dependent manner for each compound. Phenol compounds exhibited the strongest insecticidal activity among the test compounds; furthermore, alcohol and aldehyde groups were more toxic than hydrocarbons. The essential oils and compounds described herein merit further study as potential fumigants for termite control. 2009 American Chemical Society.

Suzuki-Miyaura cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN

We addressed an unexplored application of the Suzuki-Miyaura protocol to the cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN. The use of bisphosphine ligands with a large P-Pd-P bite angle allowed us to synthesize Z-chlorinated internal alkenes in good yields resulting from a selective monocoupling process, a recurrent challenge with 1,1-dichloro-1-alkenes. Moreover, these monochlorinated olefins could be further transformed providing stereospecifically trisubstituted olefins.