Norchlorcyclizine

HCID 9340CAS 303-26-4
Substructure searchFind similar structures

Basic information

Standard SMILES
Clc1ccc(C(c2ccccc2)N2CCNCC2)cc1
InChIKey
UZKBSZSTDQSMDR-UHFFFAOYSA-N
Molecular formula
C17H19ClN2
Average molar mass
286.8 g/mol
Monoisotopic mass
286.1236763

Names & identifiers

Preferred name
Norchlorcyclizine
IUPAC
1-[(4-chlorophenyl)-phenylmethyl]piperazine
English name
1-(4-Chlorobenzhydryl)piperazine
Molecular formula
C17H19ClN2
Molecular weight
286.8

Names & synonyms

1-(4-Chlorobenzhydryl)piperazine303-26-4NorchlorcyclizineN-(p-Chlorobenzhydryl)piperazine4-(4-Chlorobenzhydryl)piperazineN-(4-Chlorobenzhydryl)piperazinePiperazine, 1-[(4-chlorophenyl)phenylmethyl]-Piperazine, 1-((4-chlorophenyl)phenylmethyl)-T875VN0D6E1-(4-Chloro-alpha-phenylbenzyl)piperazine1-(alpha-Phenyl-4-chlorobenzyl)piperazineNSC-86164
Show more names
Cetirizine EP Impurity AHydroxyzine Related CoMpound A1-[(4-CHLORO-PHENYL)-PHENYL-METHYL]-PIPERAZINENSC 8616USP CBHPNSC 86164UNII:T875VN0D6EAKOS BBS-00003606Cetirizine USP A
DTXSID00891490RefChem:854707DTXCID70220253206-137-41-((4-chlorophenyl)(phenyl)methyl)piperazine130018-88-11-[(4-Chlorophenyl)(phenyl)methyl]piperazine1-[(4-Chlorophenyl)phenylmethyl]piperazine

Database identifiers

CAS
303-26-4
PubChem CID
9340
DTXSID
DTXSID00891490
ChEMBL
CHEMBL81324
UNII
T875VN0D6E
EC Number
206-137-4
Nikkaji
J50.575G

Properties

Computed structural properties

XLogP
3.4
Topological polar surface area
15.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
20

Experimental & physicochemical properties

Collision Cross Section168.4 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Physicochemical properties

Melting point
65 · 65-70 °C (lit.)
Boiling point
178 · 178-180 °C/0.5 mmHg (lit.)
Density
1.0912 · 1.0912 (rough estimate)
vapor pressure
0 Pa · 0Pa at 25℃
refractive index
1.5749 · 1.5749 (estimate)
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (94.6%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (92.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (89.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H361 (19.6%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 56 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationStatus: Cease Manufacture Update: 19-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21468；Status: Active Update: 20-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23014
Hazard Classes and CategoriesAcute Tox. 4 (25%)；Skin Irrit. 2 (94.6%)；Eye Irrit. 2 (92.9%)；STOT SE 3 (89.3%)；Repr. 2 (19.6%)

Regulatory information

Regulatory InformationStatus: Cease Manufacture Update: 19-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21468；Status: Active Update: 20-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23014

Safety data

PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
rtecs
TL1772000
hs_code
29339900
risk_code
36/37/38
Signal word
Danger

Chemistry & industry

Uses & manufacturing

Use ClassificationPharmaceuticals -> Transformation products

Applications

UsesA metabolite of Cetirizine (C281100) and Hydroxyzine. Citirizine impurity A.

UsesCetrizine Dihydrochloride intermediate

Preparation methods · 1 item

PreparationPreparation of 1-[(4-chlorophenyl)phenylmethyl]piperazine. (CPMP)About 0.5 mL of DMF, 0.1 g of KI and 10 g (0.12 mol) of piperazine were mixed with 15 mL of toluene and heated to 80oC for 0.5 h. This mixture at 80oC was mixed with 4-CBC in toluene and the temperature was maintained at 80oC for a period of 2 h followed by refluxing at the same temperature for 12h. The reaction mixture was then cooled to 20oC. The toluene layer was washed twice with 20 mL of water and treated with HCl (15 mL conc. HCl in 5mL of water) at 5-10oC. The reaction mixture was filtered and the aqueous layer was separated from the filtrate. About 10 mL of toluene and 10 mL of methylene dichloride (MDC) washes were given to the aqueous layer and neutralized with 22 mL of 30 % NaOH solution at 10oC and maintained at 20oC for 2h. The solid compound formed was filtered, sucked and dried at 50oC for 3 h.Yield: 92 %; m.p: 63-65oC.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
天津始加生物医药科技有限公司15022261580 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
上海泰矶林实业有限公司02150630626 17717886015 · [email protected]

Related reactions

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Linked notes

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