BENZYL 2,2,2-TRICHLOROACETIMIDATE
- Product Name
- BENZYL 2,2,2-TRICHLOROACETIMIDATE
- CAS No.
- 81927-55-1
- Chemical Name
- BENZYL 2,2,2-TRICHLOROACETIMIDATE
- Synonyms
- Benzyl trichloroacetimidate;oroacetimidate;BENZYLPHOSPONIC ACID;LABOTEST-BB LT00455324;Benzyl 2,2,2-trichloroacetimide;BENZYL 2,2,2-TRICHLOROACETIMIDATE;benzyl 2,2,2-trichloroethaniMidate;Benzyl 2,2,2-trichloroethanimidoate;O-Benzyl 2,2,2-trichloroacetiMidate;TRICHLOROACETIMIDIC ACID BENZYL ESTER
- CBNumber
- CB8409616
- Molecular Formula
- C9H8Cl3NO
- Formula Weight
- 252.52
- MOL File
- 81927-55-1.mol
BENZYL 2,2,2-TRICHLOROACETIMIDATE Property
- Melting point:
- 3 °C
- Boiling point:
- 106-114 °C0.5 mm Hg(lit.)
- Density
- 1.359 g/mL at 25 °C(lit.)
- refractive index
- n20/D 1.545(lit.)
- Flash point:
- >230 °F
- storage temp.
- 2-8°C
- solubility
- Miscible with cyclohexane/dichloromethane.
- form
- Liquid
- pka
- 2.23±0.70(Predicted)
- color
- Clear colorless to yellow
- Sensitive
- Moisture Sensitive
- BRN
- 2525375
- Stability:
- Moisture Sensitive
- InChI
- InChI=1S/C9H8Cl3NO/c10-9(11,12)8(13)14-6-7-4-2-1-3-5-7/h1-5,13H,6H2
- InChIKey
- HUZCTWYDQIQZPM-UHFFFAOYSA-N
- SMILES
- C(=N)(OCC1=CC=CC=C1)C(Cl)(Cl)Cl
- CAS DataBase Reference
- 81927-55-1(CAS DataBase Reference)
Safety
- Hazard Codes
- Xn
- Risk Statements
- 22-36/37/38
- Safety Statements
- 26
- WGK Germany
- 3
- F
- 8-10-21
- HS Code
- 29252900
- Storage Class
- 10 - Combustible liquids
- Hazard Classifications
- Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 140333
- Product name
- Benzyl 2,2,2-trichloroacetimidate
- Purity
- 99%
- Packaging
- 5g
- Price
- $43.1
- Updated
- 2025/07/31
- Product number
- 140333
- Product name
- Benzyl 2,2,2-trichloroacetimidate
- Purity
- 99%
- Packaging
- 25g
- Price
- $142
- Updated
- 2025/07/31
- Product number
- B1483
- Product name
- Benzyl 2,2,2-Trichloroacetimidate
- Purity
- >97.0%(GC)
- Packaging
- 25g
- Price
- $89
- Updated
- 2025/07/31
- Product number
- B316075
- Product name
- Benzyl 2,2,2-Trichloroacetimidate
- Packaging
- 100g
- Price
- $450
- Updated
- 2021/12/16
- Product number
- B316075
- Product name
- Benzyl 2,2,2-Trichloroacetimidate
- Packaging
- 25g
- Price
- $150
- Updated
- 2021/12/16
BENZYL 2,2,2-TRICHLOROACETIMIDATE Chemical Properties,Usage,Production
Chemical Properties
clear colorless to yellow liquid
Uses
Benzyl 2,2,2-trichloroacetimidate is used for the acid-catalyzed benzylation of hydroxy groups. It acts as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It can also be used for mild esterification of carboxylic acids in the presence of a catalytic amount of BF3 etherate.
Uses
Benzyl 2,2,2-trichloroacetimidate was used as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It was used in the acid-catalyzed benzylation of hydroxy groups.
Uses
Benzyl 2,2,2-trichloroacetimidate is used for the acid-catalyzed benzylation of hydroxy groups.
Synthesis
545-06-2
100-51-6
81927-55-1
DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (1.24 mL, 8.31 mmol) was slowly added dropwise to a solution of dichloromethane (86 mL) containing benzyl alcohol (8.60 mL, 83.11 mmol) and trichloroacetonitrile (41.66 mL, 415.57 mmol), and the reaction mixture was cooled under ice bath conditions to 0 °C . Subsequently, the mixture was gradually warmed up to room temperature reaction. The progress of the reaction was monitored by thin layer chromatography (TLC) (petroleum ether/ethyl acetate, 95:5, V/V) until the formation of trichloroacetimide was observed. After 3 h of reaction, the solvent was removed by distillation under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, 95:5, V/V), followed by distillation at 80 °C/0.3 mbar to afford the target product 2,2,2-trichloroacetimidobenzyl ester as a colorless oil in 94% yield.TLC Rf value: 0.27 (petroleum ether/ethyl acetate. 95:5, V/V).1H NMR (400.13 MHz, CDCl3) δ (ppm): 5.26 (s, 2H, H1'); 7.24-7.36 (m, 5H, HPh); 8.31 (wide s, 1H, =NH).13C NMR (100.62 MHz, CDCl3) δ (ppm): 70.7 (Cl'); 91.3 (C2); 127.7, 128.3 and 128.5 (5C, CPh); 134.4 (C2'); 162.5 (C1).
Purification Methods
Purify the imidate by distillation to remove up to 1% of PhCH2OH as stabiliser. A solution in hexane can be stored for up to 2 months without decomposition. It is hygroscopic and has to be stored dry. [Wessel et al. J Chem Soc, Perkin Trans 1 2247 1985, Beilstein 6 IV 2265.]
References
[1] Tetrahedron Letters, 1996, vol. 37, # 9, p. 1481 - 1484
[2] Tetrahedron Letters, 2009, vol. 50, # 21, p. 2533 - 2535
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 636 - 639
[4] Patent: US6348478, 2002, B1. Location in patent: Page column 32-33
[5] Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7234 - 7242
BENZYL 2,2,2-TRICHLOROACETIMIDATE Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from BENZYL 2,2,2-TRICHLOROACETIMIDATE manufacturers
- Product
- BENZYL 2,2,2-TRICHLOROACETIMIDATE 81927-55-1
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2022-09-26
- Product
- BENZYL 2,2,2-TRICHLOROACETIMIDATE 81927-55-1
- Price
- US $0.00-0.00/KG
- Min. Order
- 1g
- Purity
- 99% HPLC
- Supply Ability
- 2000tons
- Release date
- 2019-12-30
- Product
- BENZYL 2,2,2-TRICHLOROACETIMIDATE 81927-55-1
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-10