1-(3-(Trifluoromethyl)phenyl)piperazine

HCID 4296CAS 15532-75-9

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Basic information

Standard SMILES: FC(F)(F)c1cccc(N2CCNCC2)c1
InChIKey: KKIMDKMETPPURN-UHFFFAOYSA-N
Molecular formula: C11H13F3N2
Average molar mass: 230.23 g/mol
Monoisotopic mass: 230.10308308

Overview

1-(3-(trifluoromethyl)phenyl)piperazine is a N-arylpiperazine that is piperazine substituted by a 3-(trifluoromethyl)phenyl group at position 1. A serotonergic agonist used as a recreational drug. It has a role as a psychotropic drug, a xenobiotic, a serotonergic agonist and an environmental contaminant. It is a N-arylpiperazine and a member of (trifluoromethyl)benzenes.

Names & identifiers

Preferred name: 1-(3-(Trifluoromethyl)phenyl)piperazine
IUPAC: 1-[3-(trifluoromethyl)phenyl]piperazine
English name: N-(3-Trifluoromethylphenyl)piperazine
Molecular formula: C11H13F3N2
Molecular weight: 230.23

Names & synonyms

15532-75-91-[3-(Trifluoromethyl)phenyl]piperazineTFMPP1-(3-Trifluoromethylphenyl)piperazine1-(3-(Trifluoromethyl)phenyl)piperazine3-trifluoromethylphenylpiperazinetrifluoromethylphenylpiperazine1-(m-trifluoromethylphenyl)piperazine25R3ONU51CNSC-128882J209.034ACHEBI:83536

Show more names

TFTPAKOS BBS-00003586RARECHEM AH CK 0203LABOTEST-BB LT000444621-(3-Methoxyphenyl)piperaFlibanserin Impurity 2 Monomer1-(3-TRIFLUOROMETHYL)-PIPERAZINE3-(1-piperazino)benzotrifluoride1-(3-Trifloromethyphenyl)piperazinN-(3-TRIFLUOROMETHYLPHENYL)PIPERAZINE

RefChem:424136239-574-4N-(alpha,alpha,alpha-Trifluoro-3-tolyl)piperazinePiperazine, 1-[3-(trifluoromethyl)phenyl]-1-(3-Trifluoromethyl-phenyl)-piperazineN-(alpha,alpha,alpha-trifluoro-m-tolyl)piperazine1-[3-(trifluoromethyl)phenyl]-piperazineCHEMBL274866

Database identifiers

CAS: 15532-75-9
PubChem CID: 4296
DTXSID: DTXSID10165876
ChEMBL: CHEMBL274866
ChEBI: CHEBI:83536
UNII: 25R3ONU51C
EC Number: 239-574-4
Nikkaji: J209.034A

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 15.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 5
Rotatable bonds: 1
Heavy atoms: 16
Formal charge: 0
Complexity: 224

Experimental & physicochemical properties

DrugsDEA NFLIS-Drug Category -> Piperazines (Hallucinogen)

Collision Cross Section151.1 Å² [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Physicochemical properties

Boiling point: 100 · 100-102°C 0,1mm
Density: 1.226 g/mL · 1.226 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.521(lit.)
Flash point: 230 °F · >230 °F
storage temp.: -20 °C · -20°C
pka: 8.88 · 8.88±0.10(Predicted)
form: liquid
Sensitive: Air Sensitive
BRN: 614217 · 614217
Major Application: forensics and toxicology
InChI: 1S/C11H13F3N2.ClH/c12-11(13,14)9-2-1-3-10(8-9)16-6-4-15-5-7-16;/h1-3,8,15H,4-7H2;1H/i4D2,7D2;
InChIKey: DGNLGWJZZZOYPT-DCZHHYCSSA-N
SMILES: Cl.[2H]C1([2H])CN(c2cccc(c2)C(F)(F)F)C([2H])([2H])CN1
CAS DataBase Reference: 15532 · 15532-75-9(CAS DataBase Reference)
FDA UNII: 25 R3ONU51C · 25R3ONU51C
NIST Chemistry Reference: 1 · Piperazine, 1-[3-(trifluoromethyl)phenyl]-(15532-75-9)
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 5 · GHS05,GHS02,GHS06,GHS08
Signal word: Danger
Hazard statements: 225 · H225-H301+H311+H331-H370-H314-H318
Precautionary statements: 260 h-P301+P330+P331-P303+P361+P353-P305+P351+P338-P405-P501a-P210-P260-P280-P301+P310-P311 · P260h-P301+P330+P331-P303+P361+P353-P305+P351+P338-P405-P501a-P210-P260-P280-P301+P310-P311
target organs: Eyes
Hazard Codes: Xi,C
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
RIDADR: 2735 · 2735
WGK Germany: 3 · 3
RTECS: 2820000 · TM2820000
Hazard Note: Corrosive
HazardClass: 8 · 8
PackingGroup: II
HS Code: 29335995 · 29335995
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H314 (11.4%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Corr. 1B (11.4%)

Safety data

wgk: 3
rtecs: TM2820000
ridadr: 2735
hs_code: 29335995
risk_code: 36/37/38
Signal word: Danger
Symbol(GHS): GHS05,GHS02,GHS06,GHS08
hazard_code: Xi,C
hazard_note: Corrosive
safety_code: 26-36
hazard_class: 8
Storage Class: 3 - Flammable liquids
packing_group: II
target organs: Eyes
Hazard statements: H225-H301+H311+H331-H370-H314-H318
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Precautionary statements: P260h-P301+P330+P331-P303+P361+P353-P305+P351+P338-P405-P501a-P210-P260-P280-P301+P310-P311

Chemistry & industry

Pharmacology

Metabolism/Metabolites1-(3-Trifluoromethylphenyl)piperazine has known human metabolites that include HO-TFMPP.

MeSH Pharmacological ClassificationEndogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.

Applications

Uses1-[3-(Trifluoromethyl)phenyl]piperazine is used in preparation of (Piperazinylethyl)cyclohexanamide derivatives and used as treatment or prevention of D3 and/or 5HT-2 receptor diseases.

Upstream & downstream products

Upstream raw materials

Additional notes

DefinitionChEBI: A N-arylpiperazine that is piperazine substituted by a 3-(trifluoromethyl)phenyl group at position 1. A serotonergic agonist used as a recreational drug.