1-Methylpyrrolidine (HCID 8454)

Overview

1-methylpyrrolidine is a member of the class of pyrrolidines that is pyrrolidine substituted by a methyl group at position 1. It has a role as an impurity, a solvent and an insect repellent. It is functionally related to a pyrrolidine.

Names & identifiers

Preferred name: 1-Methylpyrrolidine
IUPAC: 1-methylpyrrolidine
English name: 1-Methylpyrrolidine
Molecular formula: C5H11N
Molecular weight: 85.15

Names & synonyms

1-METHYLPYRROLIDINE120-94-5N-MethylpyrrolidinePyrrolidine, 1-methyl-N-MethyltetrahydropyrroleDTXSID804221006509TZU6CNSC-65579NSC-65DTXCID6022210RefChem:830788204-438-5

Show more names

1-methylPyrrolidine,1-methyl-NSC 655791-Methylpyrrodine1-methyl-pyrrolidincefepiMe iMpurity G

MethylpyrrolidinePYRROLIDINE, N-METHYLMFCD00003173Cefepime Impurity 1N-methyl pyrrolidinemethyl pyrrolidinePYRROLIDINE, N-METHYL-1-Methyl-pyrrolidine

Database identifiers

CAS: 120-94-5
PubChem CID: 8454
DTXSID: DTXSID8042210
ChEMBL: CHEMBL665
ChEBI: CHEBI:234043
UNII: 06509TZU6C
EC Number: 204-438-5
Nikkaji: J102.087K

Properties

Computed structural properties

XLogP: 0.9
Topological polar surface area: 3.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 0
Heavy atoms: 6
Formal charge: 0
Complexity: 37.2

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Amines, Cyclic

Flammable agents - 3rd degree

DrugsPharmaceuticals -> Metabolite of Cefepime

CosmeticsSurfactant

SpringerMaterials Properties15N nuclear magnetic resonance spectrum

LogP0.92

Density0.8054 @25 °C

Physicochemical properties

Melting point: -90 °C · -90 °C
Boiling point: 76 · 76-80 °C (lit.)
Density: 0.8 g/mL · 0.800 g/mL at 20 °C (lit.)
vapor pressure: 100 hPa · 100 hPa (20 °C)
refractive index: 20 · n20/D 1.425
FLAVIS Number: 14.137 · 14.137 | 1-Methylpyrrolidine
Flash point: 7 °F · −7 °F
storage temp.: 30 °C · Store below +30°C.
solubility: 213 g/l · 213g/l
pka: 10.32 · 10.32(at 25℃)
form: Liquid
color: Clear colorless
PH: 11.3 · 11.3 (1g/l, H2O)
explosive limit: 1.1 · 1.1-9.1%(V)
Water Solubility: fully miscible
BRN: 102445 · 102445
Henry's Law Constant: 3.3 · 3.3×10-1 mol/(m3Pa) at 25℃, Cabani et al. (1971)
InChI: 1S/C5H11N/c1-6-4-2-3-5-6/h2-5H2,1H3
InChIKey: AVFZOVWCLRSYKC-UHFFFAOYSA-N
SMILES: CN1CCCC1
LogP: 1.1 at · 1.1 at 23℃
CAS DataBase Reference: 120 · 120-94-5(CAS DataBase Reference)
FDA UNII: 6509 TZU6C · 06509TZU6C
NIST Chemistry Reference: 1 · Pyrrolidine, 1-methyl-(120-94-5)
EPA Substance Registry System: N-Methylpyrrolidine (120-94-5)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS05,GHS06,GHS09
Signal word: Danger
Hazard statements: 225 · H225-H301-H314-H332-H411
Precautionary statements: 210 · P210-P273-P280-P301+P310+P330-P303+P361+P353-P305+P351+P338
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes: F,C,N
Risk Statements: 11 · 11-22-34-51/53-35-20/22
Safety Statements: 16 · 16-26-36/37/39-45-61-29
RIDADR: 2924 · UN 2924 3/PG 2
WGK Germany: 2 · 2
RTECS: 1420500 · UY1420500
Autoignition Temperature: 170 °C · 170 °C DIN 51794
TSCA: TSCA listed
HS Code: 2933 · 2933 99 80
HazardClass: 3 · 3
PackingGroup: II
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 OralAcute · Acute Tox. 3 OralAcute Tox. 4 InhalationAquatic Chronic 2Flam. Liq. 2Skin Corr. 1A
Toxicity: 50 orally · LD50 orally in Rabbit: 280 mg/kg
REACH Registrations: Active
Limited Quantities: 1 L · 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 191 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 5 items

Chemical: Pyrrolidine, 1-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 01-07-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/11871

N-Methylpyrrolidine: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Hazards SummaryIntraperitoneal LD50 (mouse) = 178 mg/kg; [RTECS] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS]

Hazard Classes and Categories · 2 items

Flam. Liq. 2 (100%)

Flammable agents - 3rd degree, Reactive agents - 1st degree

CSL Reaction Information · 6 items

CSL00039

N-BROMOSUCCINIMIDE + 1-METHYL-2-PYRROLIDINONE + 1-METHYLPYRROLIDINE

Thermal runaway from ambient to >100Â°C

Explosive

Bromination

User-Reported

Safety & protection

Protective Action Criteria (PAC) · 3 items

0.58 [mg/m3]

6.4 [mg/m3]

39 [mg/m3]

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

Safety data

PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 2
tsca: TSCA listed
rtecs: UY1420500
ridadr: UN 2924 3/PG 2
hs_code: 2933 99 80
Toxicity: LD50 orally in Rabbit: 280 mg/kg
risk_code: 11-22-34-51/53-35-20/22
Signal word: Danger
Symbol(GHS): GHS02,GHS05,GHS06,GHS09
hazard_code: F,C,N
safety_code: 16-26-36/37/39-45-61-29
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: II
Hazard statements: H225-H301-H314-H332-H411
Limited Quantities: 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations: Active
Hazard Classifications: Acute Tox. 3 OralAcute Tox. 4 InhalationAquatic Chronic 2Flam. Liq. 2Skin Corr. 1A
Autoignition Temperature: 170 °C DIN 51794
Precautionary statements: P210-P273-P280-P301+P310+P330-P303+P361+P353-P305+P351+P338

Chemistry & industry

Uses & manufacturing

UsesPermitted for use as an inert ingredient in non-food pesticide products; [EPA]

Use ClassificationCosmetics -> Surfactant

General Manufacturing InformationPyrrolidine, 1-methyl-: ACTIVE

Applications

Uses1-Methylpyrrolidine is a methylated pyrollidine and is involved as an essential part of the structure of cefipime. It is also an active component of cigarette smoke.

Preparation methods · 1 item

Preparationn-methylpyrrolidine was successfully synthesized in an aqueous medium by using methylamine and 1,4-dibromobutane in the presence of catalyst k2co3 at a moderated temperature. here, n-methylpyrrolidine was firstly synthesized via the green chemistry process, in which both the water solvent and potassium carbonate catalyst were inexpensive and environmentally friendly. also, the reaction temperature was quite moderated at 90°C.green organic synthesis of n-methylpyrrolidine