4-Methoxybenzyl 2,2,2-Trichloroacetimidate

HCID 11087263

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Basic information

CAS: 89238-99-3
Standard SMILES: COc1ccc(COC(=N)C(Cl)(Cl)Cl)cc1
InChIKey: TYHGKLBJBHACOI-UHFFFAOYSA-N
Molecular formula: C10H10Cl3NO2
Average molar mass: 282.5 g/mol
Monoisotopic mass: 280.977712

Names & identifiers

Preferred name: 4-Methoxybenzyl 2,2,2-Trichloroacetimidate
IUPAC: (4-methoxyphenyl)methyl 2,2,2-trichloroethanimidate
English name: 4-METHOXYBENZYL-2,2,2-TRICHLOROACETIMID&
Molecular formula: C10H10Cl3NO2
Molecular weight: 282.55

Names & synonyms

89238-99-34-Methoxybenzyl 2,2,2-TrichloroacetimidateDTXSID40454780RefChem:293984DTXCID80405599677-564-5(4-Methoxyphenyl)methyl 2,2,2-trichloroethanimidate4-Methoxybenzyl-2,2,2-trichloroacetimidateMFCD001345472,2,2-Trichloroacetimidic Acid 4-Methoxybenzyl Ester2,2,2-trichloro-acetimidic acid 4-methoxybenzyl ester2,2,2-Trichloro-acetimidic acid 4-methoxy-benzyl ester

Show more names

Darifenacin Impurity 204-Methoxybenzyl trichloroacetamidate4-METHOXYBENZYL-2,2,2-TRICHLOROACETIMID&4-METHOXYBENZYL-2,2,2-TRICHLOROACETIMID&4-Methoxybenzyl 2,2,2-trichloroethanimidate4-methoxybenzyl 2,2,2-trichloroethanimidoate

O-(4-methoxybenzyl)-trichloroacetimidate4-Methoxybenzyl2,2,2-TrichloroacetimidatePMBOC(=NH)CCl3SCHEMBL329086TYHGKLBJBHACOI-UHFFFAOYSA-N4-methoxybenzyl trichloroacetimidate4-Methoxybenzyl 2,2,2-TrichloroacEthanimidic acid, 2,2,2-trichloro-, (4-methoxyphenyl)methyl ester

Database identifiers

CAS: 89238-99-3
PubChem CID: 11087263
DTXSID: DTXSID40454780
EC Number: 677-564-5
Nikkaji: J1.602.769C

Properties

Computed structural properties

XLogP: 3.5
Topological polar surface area: 42.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 16
Formal charge: 0
Complexity: 235

Physicochemical properties

Boiling point: 137 °C · 137 °C / 0.7mmHg
Density: 1.361 g/mL · 1.361 g/mL at 25 °C
refractive index: 20 · n20/D 1.5488
Flash point: 110 °C · 110 °C
storage temp.: 2 · 2-8°C
pka: 1.96 · 1.96±0.70(Predicted)
form: clear liquid
color: Colorless to Light yellow to Light orange
Major Application: peptide synthesis
InChI: InChI=1S/C10H10Cl3NO2/c1-15-8-4-2-7(3-5-8)6-16-9(14)10(11,12)13/h2-5,14H,6H2,1H3
InChIKey: TYHGKLBJBHACOI-UHFFFAOYSA-N
SMILES: C(=N)(OCC1=CC=C(OC)C=C1)C(Cl)(Cl)Cl
UNSPSC Code: 12352101 · 12352101
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07,GHS09
Signal word: Warning
Hazard statements: 302 · H302+H312+H332-H315-H319-H335-H411
Precautionary statements: 273 · P273-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338
Hazard Codes: Xn,N
Risk Statements: 20 · 20/21/22-36/37/38-51/53
Safety Statements: 26 · 26-61-36/37
RIDADR: 3082 · UN 3082 9/PG 3
WGK Germany: 3 · 3
HS Code: 29252900 · 29252900
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302+H312+H332 (97.5%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (97.5%)

Safety data

wgk: 3
ridadr: UN 3082 9/PG 3
hs_code: 29252900
risk_code: 20/21/22-36/37/38-51/53
Signal word: Warning
Symbol(GHS): GHS07,GHS09
hazard_code: Xn,N
safety_code: 26-61-36/37
Storage Class: 11 - Combustible Solids
Hazard statements: H302+H312+H332-H315-H319-H335-H411
Precautionary statements: P273-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338

Chemistry & industry

Applications · 1 item

Uses4-Methoxybenzyl-2,2,2-trichloroacetimidate can be used as a reagent for the protection of alcohols as the p-methoxybenzyl ether. 1o, 2o, and 3o alcohols can be easily protected using this reagent with equal efficiency in the presence of a variety of different protective groups. This reagent is commonly used under acidic conditions therefore it offers an alternative method to the Williamson ether synthesis, which is typically used basic conditions to protect base-sensitive alcohols.