4-(Bis(2-chloroethyl)amino)benzeneacetic acid

HCID 25306

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Basic information

CAS: 10477-72-2
Standard SMILES: O=C(O)Cc1ccc(N(CCCl)CCCl)cc1
InChIKey: RQAFMLCWWGDNLI-UHFFFAOYSA-N
Molecular formula: C12H15Cl2NO2
Average molar mass: 276.16 g/mol
Monoisotopic mass: 275.0479841

Overview

RN given refers to parent cpd; structure

Names & identifiers

Preferred name: 4-(Bis(2-chloroethyl)amino)benzeneacetic acid
IUPAC: 2-[4-[bis(2-chloroethyl)amino]phenyl]acetic acid
English name: phenacid
Molecular formula: C12H15Cl2NO2
Molecular weight: 276.16

Names & synonyms

Phenylacetic acid mustardPhenacid10477-72-2Phenylacetic mustardPAAMDTXSID4014671432842A3UZP4-(Bis(2-chloroethyl)amino)benzeneacetic acidBenzeneacetic acid, 4-(bis(2-chloroethyl)amino)-Benzeneacetic acid, 4-[bis(2-chloroethyl)amino]-4-(N,N-bis(2-chloroethyl)amino)phenylacetic acid4-[N,N-Bis(2-chloroethyl)amino]phenylacetic acid

Show more names

CB-1331NSC-719644-(Bis-phenylacetic acidPhenylacetic acid Mustard-d8p-[Bis(2-chloroethyl)amino]phenylacetic acid4-[Bis(2-chloroethyl)amino]benzeneacetic acid2-[4-[bis(2-chloroethyl)amino]phenyl]acetic acid

RefChem:172575p-(N,N-bis(2-chloroethyl)amino)phenylacetic acidDTXCID5069205ChlorphenacilChlorphenacylN,N-Bis(2-chloroethyl)-p-aminophenylacetic acidKhlorfenatsil2-{4-[di(2-chloroethyl)amino]phenyl}acetic acid

Database identifiers

CAS: 10477-72-2
PubChem CID: 25306
DTXSID: DTXSID40146714
ChEMBL: CHEMBL518
UNII: 32842A3UZP
Nikkaji: J3.834B

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 40.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 7
Heavy atoms: 17
Formal charge: 0
Complexity: 225

Physicochemical properties

Melting point: 105 °C · 105 °C(Solv: benzene (71-43-2); pentane (109-66-0))
Boiling point: 125 °C · 125°C (rough estimate)
Density: 1.2884 · 1.2884 (rough estimate)
refractive index: 1.607 · 1.6070 (estimate)
pka: 3.86 · 3.86±0.10(Predicted)
FDA UNII: 32842 A3UZP · 32842A3UZP
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 280 · P280-P305+P351+P338
HS Code: 2916340000 · 2916340000
Toxicity: 3 mmol/L · sln-dmg-par 3 mmol/L GENRA81,173,60

Safety & regulation

Safety data

hs_code: 2916340000
Toxicity: sln-dmg-par 3 mmol/L GENRA81,173,60
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P280-P305+P351+P338

Chemistry & industry

Applications

UsesPhenylacetic Mustard is a nitrogen mustard analog and the active metabolite of Chlorambucil (C325050). It is used as a chemotherapeutic agent and aside from having clastogenic activity, it can also induce chromosome delay.