ChemicalBook > CAS DataBase List > BENZYL 2,2,2-TRICHLOROACETIMIDATE

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

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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)

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Safety

Hazard Codes: Xn
Risk Statements: 22-36/37/38
Safety Statements: 26
WGK Germany: 3
F: 8-10-21
HS Code: 29252900

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 140333
Product name: Benzyl 2,2,2-trichloroacetimidate
Purity: 99%
Packaging: 5g
Price: $43.1
Updated: 2025/07/31

Sigma-Aldrich

Product number: 140333
Product name: Benzyl 2,2,2-trichloroacetimidate
Purity: 99%
Packaging: 25g
Price: $142
Updated: 2025/07/31

TCI Chemical

Product number: B1483
Product name: Benzyl 2,2,2-Trichloroacetimidate
Purity: >97.0%(GC)
Packaging: 25g
Price: $89
Updated: 2025/07/31

TRC

Product number: B316075
Product name: Benzyl 2,2,2-Trichloroacetimidate
Packaging: 25g
Price: $150
Updated: 2021/12/16

TRC

Product number: B316075
Product name: Benzyl 2,2,2-Trichloroacetimidate
Packaging: 100g
Price: $450
Updated: 2021/12/16

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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

Henan Aochuang Chemical Co.,Ltd.

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

Shaanxi Dideu Medichem Co. Ltd

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

Zhuozhou Wenxi import and Export Co., Ltd

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

81927-55-1, BENZYL 2,2,2-TRICHLOROACETIMIDATERelated Search:

2-Chloroethyl ethyl ether METHYL 2,2,2-TRICHLOROACETIMIDATE METHYL ACETIMIDATE HYDROCHLORIDE 6-Bromo-1-hexene ETHYL FORMIMIDATE HYDROCHLORIDE 1,1,1-Trichloroethane Dichloromethane Ammonium chloride BENZYL ETHYL ETHER 2-Chloroethanol BENZYL 2,2,2-TRICHLOROACETIMIDATE Trichloroethanol Chloroform Ethyl acetimidate hydrochloride Benzyl alcohol Benzyl methyl ether 2,2,2-Trichloroacetamide Chloroacetamide

2,2,2-TRICHLOROACETIMIDIC ACID BENZYL ESTER

Benzyl 2,2,2-trichloroacetimidate, 98+%

Ethanimidic acid, 2,2,2-trichloro-, phenylmethyl ester

Benzyl 2,2,2-trichloroacetimidate, GC 99%

BENZYLPHOSPONIC ACID

Benzyl 2,2,2-trichloroethanimidoate

Benzyl trichloroacetimidate

TRICHLOROACETIMIDIC ACID BENZYL ESTER

LABOTEST-BB LT00455324

BENZYL 2,2,2-TRICHLOROACETIMIDATE

Benzyl 2,2,2-trichloroacetimidate, 99 %

AcetiMidic acid, 2,2,2-trichloro-, benzyl ester (6CI)

O-Benzyl 2,2,2-trichloroacetiMidate

Benzyl 2,2,2-trichloroacetimide

Benzyl 2,2,2-trichloroacetimidate 99%

Benzyl 2,2,2-trichloroacetiMidate, 99% 25GR

benzyl 2,2,2-trichloroethaniMidate

(2,2,2-trichloro-1-phenylmethoxyethylidene)azanide

Benzyl 2,2,2-Trichloroacetimidate &gt

oroacetimidate

BENZYL 2,2,2-TRICHLOROACETIMIDATE ISO 9001：2015 REACH

Phenylmethyl 2,2,2-trichloroethanimidate

81927-55-1

CCl3CNHOCH2C6H5

C9H8Cl3NO

Amidates/Imidates

Building Blocks

Nitrogen Compounds

Organic Building Blocks

Protection & Derivatization Reagents (for Synthesis)

Synthetic Organic Chemistry

Amidates/Imidates

Building Blocks

Chemical Synthesis

Nitrogen Compounds

Organic Building Blocks

Benzene series