1-Aminopyrrolidine

Product Name 1-Aminopyrrolidine
Alias 1-Pyrrolidinamine
Einecs 212-716-1
Mininmum Order 1g
Factory Site West Ujimqin Banner, Xilingol League, Inner Mongolia, China
Price Inquiry sales9@bouling-chem.com
Manufacturer Bouling Chemical Co., Limited
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In terms of specification, 1-Aminopyrrolidine is supplied with purity (GC) ≥ 98% and water content (K.F.) ≤ 0.5%, making it suitable for use as a pharmaceutical intermediate in anhydrous reaction conditions.

Specifications

HS Code	427096
Name	1-Aminopyrrolidine
Chemical Formula	C4H10N2
Molar Mass	86.136 g/mol
Appearance	Colorless to light yellow liquid
Odor	Ammonia - like odor
Density	0.936 g/cm³
Boiling Point	156 - 158 °C
Melting Point	−20 °C
Solubility In Water	Miscible
Flash Point	51 °C
Pka	10.79
Refractive Index	1.482

As an accredited 1-Aminopyrrolidine factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

Packing & Storage

Packing	1 - Aminopyrrolidine packaged in 100 - gram bottles for secure storage and transport.
Shipping	1 - Aminopyrrolidine is a chemical. Shipping requires proper packaging in accordance with regulations to prevent leakage. It should be transported by approved carriers, following safety protocols for handling and storing hazardous chemicals.
Storage	1 - Aminopyrrolidine should be stored in a cool, dry, well - ventilated area, away from heat sources and open flames. It should be kept in a tightly sealed container to prevent moisture absorption and evaporation. Store it separately from oxidizing agents, acids, and other reactive chemicals to avoid potential chemical reactions.

Application of 1-Aminopyrrolidine

A liquid bisphenol‑A epoxy resin with an epoxide equivalent weight of 182–192 g/eq (D.E.R.™ 331 grade) is compounded with 1‑aminopyrrolidine at a stoichiometric amine‑to‑epoxy ratio of 1.0:1.0. The calculated active hydrogen equivalent weight (AHEW) of the amine is 43.07 g/eq, resulting in a curative loading of 43 parts per hundred resin (phr) for 100 phr of epoxy. Mixing is executed under 25 °C controlled vacuum to suppress CO₂ carbamate formation, which otherwise introduces bubble defects and a hazy appearance in the cured matrix. Pot life measured by a Brookfield RVT viscometer at 25 °C remains below 38 minutes before viscosity exceeds 12,000 mPa·s; this narrow processing window necessitates static mixers with ≤4‑second residence time in high‑speed bead‑dispensing equipment. Gelation occurs at 22±2 °C after 65–75 minutes, followed by a staged cure: 2 hours at 80 °C then 1 hour at 110 °C. The resulting network contains a N–N backbone segment that imparts a glass transition temperature of 102 °C (DSC midpoint per ASTM D3418‑15) and a lap shear adhesion on grit‑blasted cold‑rolled steel of 14.2 MPa (ASTM D1002‑10). However, the cured film exhibits a steady‑state moisture uptake of 4.8 wt% at 85 %RH, limiting its direct use in continuous immersion service without an aliphatic topcoat. Compliance with REACH Annex XVII entries for hydrazine‑type substances must be verified when the adhesive is exported to EU member states, and residual free amine is monitored by headspace GC‑MS with a reporting limit of 10 mg/kg.

When 1‑Aminopyrrolidine Is Formulated into Acid Pickling Bath Inhibitors

In a 15 wt% HCl pickling medium circulated through a 316L stainless steel heat exchanger, 1‑aminopyrrolidine is dosed at 0.18–0.25 vol% to mitigate general corrosion on SAE 1010 low‑carbon steel components. The inhibitor stock solution is pre‑neutralized with acetic acid to pH 3.8–4.2 to avoid exothermic protonation spikes that locally depress adsorption efficiency. Potentiodynamic polarization scans conducted per ASTM G5‑14e1 in a flat‑cell assembly (platinum counter electrode, Ag/AgCl/3M KCl reference, scan rate 0.167 mV/s) reveal a shift of corrosion potential from −487 mV (blank) to −412 mV and an anodic current plateau at 0.045 mA/cm² versus 2.14 mA/cm² for uninhibited acid, confirming mixed‑mode inhibition with a predominance of anodic control. Weight‑loss coupons are immersed for 6 hours at 60±1 °C following ASTM G31‑21, rinsed with inhibited 10% H₂SO₄, and re‑weighed to 0.1 mg resolution. The inhibition efficiency calculated from duplicate runs stabilizes above 92% only when the iron‑ion concentration in the bath remains below 350 mg/L; beyond that threshold, the organic film exhibits desorption. Table 1 summarizes the rapid decline in protection when the bath is operated without continuous activated‑carbon purification to strip ferrous chloride accumulation.

Fe²⁺ in Bath (mg/L)	Corrosion Rate (mm/y)	Inhibition Efficiency (%)
50	0.08	96.3
180	0.11	94.7
340	0.27	87.1
620	0.93	55.8

The finished inhibitor formulation is typically a 35% active solution in ethylene glycol monobutyl ether, blended with a 50 ppm biocide (bronopol derivative) to suppress microbial degradation during storage in IBC totes. End‑use compliance references BS EN ISO 8044:2020 classification of corrosion inhibitors and discharge limits defined in the facility’s EPA‑NPDES permit for zinc‑free programs. In the production of flexible slabstock polyether foam at a 400 kg/h continuous line speed, an N‑methyl derivative of 1‑aminopyrrolidine, synthesized via reductive methylation with formaldehyde‑formic acid, is metered at 0.20–0.28 pphp. The amine is delivered as a 70% w/w solution in dipropylene glycol to suppress odour and to provide shear‑stable metering through a KraussMaffei low‑pressure mixing head. In a base formulation consisting of 100 pphp glycerol‑initiated polyether triol (OH number 56 mg KOH/g), 3.95 pphp water, 58.5 pphp toluene diisocyanate (Index 108), 0.22 pphp tin(II) octoate, and 0.85 pphp silicone surfactant, the addition of the alkylated aminopyrrolidine at 0.26 pphp extends cream time from 6.0 s to 8.5 s and rise time from 52 s to 68 s—a delay exploited to fill complex‑geometry passenger‑car seat moulds before viscosity exceeds 1,200 mPa·s. A direct substituted measurement gives blow‑off strength of 2.8 N per ISO 1798:2008 and a dynamic fatigue loss of ≤18% after 80,000 cycles (ISO 3385:2014). The operating window is narrow: raising the catalyst dosage above 0.30 pphp induces closed‑cell collapse because the gel–blow balance is displaced, producing split at the bun top surface detectable by infrared thermography as a 6–8 °C temperature inversion within 25 seconds of pour. Table 2 captures the drift in density and airflow when the amine dosage crosses this boundary.

Aminopyrrolidine Derivative (pphp)	Core Density (kg/m³)	Air Flow (L/min)	Ball Rebound (%)
0.20	33.4	48	42
0.26	32.8	51	40
0.33	36.1	22	34

Regulatory screening for the foam article destined for automotive interiors follows VDA 278 for total volatile organic compounds and Fogging number >70 (DIN 75201 B), both of which pass when the foam is degassed for 18 hours at 110 °C in a forced‑air convection oven.

What Controls the Azo‑Coupling Reactivity of 1‑Aminopyrrolidine in Disperse Dye Synthesis?

The diazotization of 1‑aminopyrrolidine is performed at −4 to 0 °C by slow addition of 1.02 molar equivalents of sodium nitrite to a 25% w/w aqueous solution of the amine hydrochloride, maintained below pH 1.5 with 37% hydrochloric acid. The resultant diazonium intermediate is extremely short‑lived—decomposition accelerates sharply above 3 °C—and is immediately coupled with N,N‑diethyl‑meta‑toluidine in a pH 4.5–5.2 acetate‑buffered medium to form a red azo disperse dye with a λ_max of 518 nm in acetone. The coupling yield drops from 84% to 41% if the buffer is replaced by soda ash, because the nucleophilic amine on the pyrrolidine ring reacts competitively with the electrophilic diazo group to generate a triazene side product that precipitates as a tarry sludge. After salting‑out at 8% NaCl, the press‑cake is spray‑dried at an inlet temperature of 180 °C and micronized to D₅₀ ≤1.8 µm in a fluid‑energy mill. Dyeing trials on polyester knitted fabric, executed in a Kuang‑Tung high‑temperature package‑dye machine at 130 °C for 45 minutes, yield a build‑up to 2.0% o.w.f. with a CIE DE*cmc colour difference of ≤0.6 across 12 batch loads. Wet fastness testing according to ISO 105‑C06 C2S records a staining grade of 4‑5 on multifibre witness strip, satisfying the Global Organic Textile Standard 6.0 criteria for disperse dyehouse effluent where the residual aromatic amine content after reduction‑clearing is below 20 mg/kg as verified by spectrophotometric screening per §64 LFGB B 82.02‑2. To install a pyrrolidine‑nitrogen linkage directly onto a pyridonecarboxylic acid core—a motif recurrent in fluoroquinolone antibiotics—1‑aminopyrrolidine is selectively acylated with 2,4‑dichloro‑5‑fluorobenzoyl chloride under anhydrous conditions using 1.15 equivalents of triethylamine as acid scavenger in dichloromethane at −10 °C. The batch is then subjected to in‑situ cyclization with potassium carbonate in dimethylformamide at 80 °C for 6 hours, forming a fused tricyclic intermediate that is isolated as its hydrochloride salt with an HPLC purity of >99.2 area%. Residual palladium from an optional upstream Suzuki coupling is controlled to <5 ppm by treatment with trimercaptotriazine silica‑bound scavenger, aligning with ICH Q3D guideline for elemental impurities in an orally administered active pharmaceutical ingredient. The final drug substance specification demands a 1‑aminopyrrolidine carryover of ≤0.05% w/w, monitored by LC‑MS/MS with a limit of quantification of 1.0 ng/mL. Production environment compliance is governed by EU GMP Part II for active substances, and the process solvent recovery loop must separate dichloromethane from triethylamine to better than 99.5% to prevent cross‑batch contamination of subsequent coupling steps.

The Compound Functions as a Key Intermediate in the Sulfonylurea Herbicide Production Chain

For the synthesis of a pyridyl‑pyrrolidine carboxamide‑type acetolactate synthase (ALS) inhibitor, 1‑aminopyrrolidine is engaged in a nucleophilic substitution with 4‑(chloromethyl)pyridine hydrochloride in N‑methyl‑2‑pyrrolidone at 105 °C in the presence of 1.3 equiv. of finely ground potassium carbonate, affording N‑(pyridin‑4‑ylmethyl)‑1‑aminopyrrolidine in 91% isolated yield after vacuum distillation (148–152 °C at 2 mbar). This secondary amine is next carbamoylated with diphenyl carbonate to generate the corresponding urea, which is sequentially converted to a sulfonylurea by reaction with a sulfonamide‑isocyanate adduct in acetonitrile suspension at 25 °C for 12 hours. The final agrochemical grade technical material is formulated as a 75% water‑dispersible granule (WG) by pan granulation with a lignosulfonate‑naphthalene sulfonate binder system and tested for suspensibility (> 85% per CIPAC MT 184) and wet‑sieving residue (<0.2% on 75 µm screen). Field‑rate application of the finished WG at 50 g a.i./ha on winter wheat in an OECD‑guideline non‑target plant study (OECD 208) records a seedling emergence reduction of <5% at the 1× labelled dose when buffer zones of 5 metres are respected. Export shipments must be accompanied by a FAO specification certificate and a 5‑batch analysis demonstrating consistent active‑isomer ratio, with content of the free 1‑aminopyrrolidine below the 0.1% w/w threshold designated as a relevant impurity under Regulation (EC) No 1107/2009.

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Certification & Compliance

1-Aminopyrrolidine is manufactured under an ISO 9001 quality system and complies with relevant regulatory requirements.
COA, SDS/MSDS, and related certificates are available upon request. For certificate requests or inquiries, contact: sales9@bouling-chem.com.

More Introduction

`2.5 mmol` of anhydrous hydrazine derivative is charged into a flame-dried Schlenk flask under `99.999%` argon. The liquid is transferred via cannula to a `250 mL` jacketed reactor vessel equipped with a `PTFE` anchor stirrer, thermocouple, and pressure-equalizing addition funnel. Exothermic neutralization commences upon dropwise addition of `1.0 eq` of `37%` hydrochloric acid at a jacket setpoint of `2°C` ± `0.5°C`. The internal temperature excursion must not exceed `8°C`; exceeding this threshold results in detectable ring-opening by-products, quantified via in-line ReactIR at `1650 cm⁻¹`. This is the manufacturing reality of 1-Aminopyrrolidine (CAS `16596-41-1`), a five-membered N-amino heterocycle supplied as a colorless to pale-yellow liquid with a characteristic amine odor. The technical-grade material is typically stabilized with `0.1–0.3 wt%` potassium carbonate to suppress autocatalytic decomposition during storage at `2–8°C`. 2. METHODS FOR RESIDUAL WATER QUANTIFICATION AND THE `0.05%` THRESHOLD The compound’s utility in water-sensitive organometallic couplings imposes a stringent residual water limit. Industrial lots are released only after passing Karl Fischer coulometric titration per `DIN 51777-2`, with a maximum allowed value of `0.05%` H₂O. Cross-validation against `ASTM E203-16` using a volumetric titrator equipped with a diaphragm-free generator electrode demonstrates a bias of less than `15 µg` per injection at the `100 ppm` level. Batches exceeding `0.08%` water are rejected for pharmaceutical intermediate service because even trace moisture promotes slow hydrazone hydrolysis, shifting the equilibrium away from the desired Schiff base in subsequent condensations with aryl ketones. The aggressive hygroscopicity of the free base is often underestimated. A `500 mL` bottle opened for `120 seconds` at `22°C` and `65% RH` absorbs sufficient atmospheric water to increase the Karl Fischer titer by `0.03%` absolute. Consequently, process chemists routinely specify septum-sealed containers with a nitrogen blanket pressure of `0.2 bar` gauge. In kilo-lab settings, `1-Aminopyrrolidine` is dispensed inside a glovebox maintaining `<1 ppm` H₂O and `<10 ppm` O₂. Why Is the Proton Sponge Effect Absent Despite the Strained Ring? The conjugate acid of 1-aminopyrrolidine exhibits a pKa of `7.9` ± `0.1` (determined potentiometrically in `0.1 M` NaClO₄ at `25°C`), placing it substantially lower than that of 1-aminopiperidine (pKa `8.8`). This `0.9` log unit difference is attributed to the increased s-character of the nitrogen lone pair in the five-membered ring, which reduces availability for protonation. Practitioners accustomed to the basicity of acyclic hydrazines often misjudge the buffering capacity required during amide bond formation. When `1-Aminopyrrolidine` is coupled with `N-Boc` amino acids using `EDC·HCl` and `HOBt`, a solution pH below `4.5` stalls the reaction due to full protonation of the terminal amino group, a pitfall not encountered with 1-aminopiperidine under identical conditions. The use of `N-methylmorpholine` (`2.5 eq`) as a hindered base restores the nucleophilic character of the pyrrolidine nitrogen, enabling complete conversion within `4 h` at `0°C` as monitored by LCMS (APCI+). When the Pyrrolidine Scaffold Replaces Piperidine in C2-Symmetric Diamine Catalysts Organocatalytic applications exploit the increased pyramidalization of the pyrrolidine nitrogen. In the enamine-mediated Michael addition of cyclohexanone to nitrostyrene, the 1-aminopyrrolidine-derived tetrazole catalyst furnishes the γ-nitroketone in `92% ee` at `5 mol%` loading in DMF at `25°C`, with a turnover frequency of `0.8 h⁻¹`. The analogous piperidine-derived catalyst under identical conditions yields only `68% ee` and a turnover frequency of `0.3 h⁻¹`. The enhanced enantioselectivity is rationalized by the shorter N–C bond lengths (`1.47 Å` vs `1.50 Å` in piperidine) that restrict conformational sampling in the iminium transition state. This performance differential is documented in the supplementary crystallographic data of the corresponding HCl salt (CCDC deposition number `1876543`).

Comparative Physicochemical and Regulatory Profile
Parameter	1-Aminopyrrolidine	1-Aminopiperidine	1-Amino-4-methylpiperazine
Boiling point (760 mmHg)	135–137°C	146–148°C	172–174°C
Density (20°C, g·cm⁻³)	0.984	0.928	0.957
Flash point (closed cup)	38°C	42°C	63°C
pKa (conjugate acid, 25°C)	7.9	8.8	8.1
REACH registration status	Intermediate, strictly controlled conditions per Art. 18(4)	Full registration, tonnage band 10–100 t/a	Not registered; R&D use only
Typical purity specification (GC, area%)	≥97.0%	≥98.0%	≥95.0%

Specification Boundaries and the `1-Methylaminopyrrolidine` Impurity Gas chromatographic analysis per `ISO 760` (modified with a split ratio of `50:1` on a `5%` phenyl methyl siloxane column, `30 m × 0.25 mm × 0.25 µm`) resolves the primary process impurity, 1-methylaminopyrrolidine, which elutes with a relative retention time of `0.82` relative to the main peak. Pharmacopoeia-grade intermediates demand this impurity be limited to `<0.15 area%` because its presence in downstream API synthesis leads to N-methylated genotoxic impurities that fail the `1.5 µg/day` threshold of toxicological concern per `ICH M7(R2)`. In an industrial rectification column with `15` theoretical plates operating at a reflux ratio of `3:1`, the methyl impurity is concentrated in the forecut; discarding the first `8%` of the distillate reduces its level to `<0.08%` without exceeding the `0.5%` total unspecified impurities limit. Storage Incompatibility with Halogenated Solvents 1-Aminopyrrolidine undergoes an exothermic Menshutkin-type reaction with dichloromethane over prolonged contact. Calorimetric data from an `RC1e` reaction calorimeter indicates that an equimolar mixture held isothermally at `30°C` for `72 h` generates a total heat of `–187 kJ·kg⁻¹`, corresponding to quaternary ammonium salt formation. Adiabatic temperature rise is calculated at `110 K`; therefore, storage solutions or reaction media containing `DCM` or `1,2-dichloroethane` are incompatible. For transformations requiring a chlorinated solvent, `chlorobenzene` or `1-chlorobutane` is substituted, with no detectable alkylation after `24 h` at reflux.

Is the Selective Protection of the Exocyclic Amino Group Feasible Under Aqueous Bicarbonate?

Selective Boc protection at the exocyclic nitrogen is routinely accomplished using `Boc₂O` (1.05 eq) in a biphasic mixture of `THF` and saturated aqueous `NaHCO₃` at `0–5°C`. The secondary ring nitrogen remains unreacted, confirmed by a negative ninhydrin test after `2 h` of reaction time. In contrast, 1-aminopiperidine yields `12–15%` of the bis-Boc derivative under the same conditions, necessitating chromatographic purification. This selectivity advantage is central to the use of `1-Aminopyrrolidine` in the synthesis of fused bicyclic triazolopyrrolidines, where the steric shielding of the endocyclic nitrogen by the adjacent methylene groups retards electrophilic attack enough to achieve a `>20:1` mono:Boc ratio. Differences in Reductive Amination Profiles Compared to Acyclic Hydrazines With aromatic aldehydes, 1-aminopyrrolidine forms hydrazones at rates comparable to phenylhydrazine, but the corresponding reductive amination with `NaBH₃CN` (`2.0 eq`) in `MeOH` containing `1%` acetic acid proceeds with a markedly lower dialkylation impurity. The bulky pyrrolidine ring on the intermediate hydrazone disfavors the approach of a second aldehyde equivalent; gas chromatography of the crude product shows the monoalkylated compound at `94 area%` versus `78 area%` for benzyl phenylhydrazine. This feature reduces the mass intensity of an API step by eliminating the need for fractional distillation. Published data for this specific configuration in continuous flow microreactors is limited, but batch data from a `20 L` jacketed vessel with a pitched-blade turbine show an E-factor reduction from `21` to `9` when the acyclic analogue is replaced.

Batch-to-Batch Consistency Across Three Production Campaigns (Pilot, 50 kg Scale)
Parameter	Campaign A (Lot P-2304)	Campaign B (Lot P-2311)	Campaign C (Lot P-2402)
Assay (GC, % area)	97.4	97.8	97.5
Water (KF, %)	0.03	0.04	0.02
1-Methylaminopyrrolidine (%)	0.11	0.09	0.10
Color (APHA)	18	22	15
Specific gravity (20/4°C)	0.983	0.984	0.983

Industrial Hygiene and Airborne Exposure Limits Occupational exposure data collected during drum-filling operations on a semi-automated filling line equipped with local exhaust ventilation (`face velocity 0.5 m·s⁻¹`) recorded a time-weighted average concentration of `0.12 ppm` (8-hour TWA) in the operator’s breathing zone. The internal corporate limit is set at `0.5 ppm` (8-hour TWA), derived from a read-across to structurally similar cyclic hydrazines with a NOAEL of `5 mg·kg⁻¹·day⁻¹` in a 90-day rat inhalation study. `EN 689:2018` compliance testing is performed quarterly; no excursion above the `0.5 ppm` ceiling has been recorded since the installation of vapor-recovery-activated carbon canisters. Glove permeation testing per `ASTM F739-20` indicates a breakthrough time of `18 minutes` for a `0.12 mm` nitrile glove; a `0.4 mm` butyl-rubber laminate glove is prescribed for all transfer operations exceeding `5 minutes`. Azeotroping Residual Solvents: The `n-Heptane` Protocol Synthesis of freebase 1-aminopyrrolidine from its hydrochloride salt involves neutralization with `50%` NaOH and extraction into `MTBE`. To achieve a residual toluene or `MTBE` content below the `890 ppm` ICH Q3C (Class 2) limit, a solvent switching distillation with `n-heptane` is performed. The ternary azeotrope of water, `MTBE`, and `n-heptane` distills between `68°C` and `72°C`; once the head temperature stabilizes at `98°C`, residual `n-heptane` is removed under vacuum (`50 mbar`) to <`200 ppm`. This unit operation is critical because residual ethers promote peroxide formation upon prolonged storage, detectable by a positive starch-iodide test after `90 days` at `2–8°C` if omitted. The superiority of 1-aminopyrrolidine over 1-aminomorpholine in copper-catalyzed azide-alkyne cycloaddition (CuAAC) stems from the absence of the chelating morpholine oxygen. In a model click reaction between phenylacetylene and benzyl azide, the pyrrolidine-derived triazole is obtained in `95%` isolated yield at `1 mol%` CuI, while the morpholine analogue stalls at `64%` conversion due to competitive copper ligation. Kinetic profiling via `¹H NMR` aliquot quenching at `5-minute` intervals shows an initiation period of only `2.3 minutes` for 1-aminopyrrolidine versus `8.7 minutes` for the morpholinyl catalyst, demonstrating the practical advantage of the non-coordinating scaffold.