Ethyl 4-[(chloroacetyl)amino]benzoate

HCID 244075

Notes Reactions

Substructure search Find similar structures

Basic information

CAS: 26226-72-2
Standard SMILES: CCOC(=O)c1ccc(NC(=O)CCl)cc1
InChIKey: ZVRJEYAQESBSSH-UHFFFAOYSA-N
Molecular formula: C11H12ClNO3
Average molar mass: 241.67 g/mol
Monoisotopic mass: 241.05057092

Names & identifiers

Preferred name: Ethyl 4-[(chloroacetyl)amino]benzoate
IUPAC: ethyl 4-[(2-chloroacetyl)amino]benzoate
English name: Ethyl 4-(2-chloroacetamido)benzoate
Molecular formula: C11H12ClNO3
Molecular weight: 241.67

Names & synonyms

26226-72-2Ethyl 4-(2-chloroacetamido)benzoateethyl 4-[(chloroacetyl)amino]benzoateethyl 4-[(2-chloroacetyl)amino]benzoateMFCD00018909ethyl 4-(2-chloroacetylamino)benzoateBenzoic acid, 4-[(2-chloroacetyl)amino]-, ethyl esterNSC54533SCHEMBL491660ethyl p-chloroacetylaminobenzoateDTXSID10288175ALBB-002286

Show more names

AKOS B015654AKOS BBS-00003983AKOS USSH-4110488BUTTPARK 80\07-83TIMTEC-BB SBB003207LABOTEST-BB LT00452438Ethyl p-(chloroacetylamino) benzoateEthyl 4-(2-chloroacetamido)benzoate 9

BBL007195NSC-54533SBB003207STK118792AKOS000268746NCGC00661556-01BS-10262SY082703

Database identifiers

CAS: 26226-72-2
PubChem CID: 244075
DTXSID: DTXSID10288175
EC Number: 806-305-2
Nikkaji: J40.699F

Properties

Computed structural properties

XLogP: 1.9
Topological polar surface area: 55.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 5
Heavy atoms: 16
Formal charge: 0
Complexity: 250

Physicochemical properties

Melting point: 110 · 110-114 °C(lit.)
Boiling point: 421.1 · 421.1±30.0 °C(Predicted)
Density: 1.283 · 1.283±0.06 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
pka: 12.36 · 12.36±0.70(Predicted)
Appearance: White to off-white Solid
InChI: 1S/C11H12ClNO3/c1-2-16-11(15)8-3-5-9(6-4-8)13-10(14)7-12/h3-6H,2,7H2,1H3,(H,13,14)
InChIKey: ZVRJEYAQESBSSH-UHFFFAOYSA-N
SMILES: CCOC(=O)c1ccc(NC(=O)CCl)cc1
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26
WGK Germany: 3 · 3
HazardClass: IRRITANT
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk: 3
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications · 2 items

UsesEthyl 4-(2-chloroacetamido)benzoate can be synthesized starting from benzocaine. It undergoes heterocyclization in the presence of ammonium thiocyanate in refluxing ethanol to afford ethyl-4-(4-oxothiazolidin-2-ylideneamino)benzoate, via intramolecular cyclization and the Dimroth-like rearrangements.

General DescriptionEthyl 4-(2-chloroacetamido)benzoate can be synthesized starting from benzocaine. It undergoes heterocyclization in the presence of ammonium thiocyanate in refluxing ethanol to afford ethyl-4-(4-oxothiazolidin-2-ylideneamino)benzoate, via intramolecular cyclization and the Dimroth-like rearrangements.