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100-74-3 Usage

Chemical Properties

4-Ethylmorpholine is a colorless liquid with an ammonia-like odor.

Physical properties

Colorless, flammable liquid with an ammonia-like odor. Experimentally determined detection and recognition odor threshold concentrations were 400 μg/m3 (85 ppbv) and 1.2 mg/m3 (250 ppbv), respectively (Hellman and Small, 1974).


Different sources of media describe the Uses of 100-74-3 differently. You can refer to the following data:
1. Catalyst in polyurethane foam production
2. N-Ethylmorpholine is a component of the buffer used in basic peptide separation through anion-exchange chromatography. Further, it acts as a catalyst in the preparation of polyurethane foam.
3. Intermediate for dyestuffs, pharmaceuticals; rubber accelerators and emulsifying agents; solvent for dyes, resins, oils; catalyst in making polyurethane foams.


N-Ethylmorpholine is synthesized by the reaction of morpholine with bromoethane.

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 678, 1991 DOI: 10.1021/jo00002a035Tetrahedron Letters, 37, p. 6749, 1996 DOI: 10.1016/S0040-4039(96)01458-X

General Description

N-Ethylmorpholine appears as a colorless liquid with a strong ammonia-like odor. Severely irritates skin, eyes, and mucous membranes. Moderately soluble in water and less dense than water. Flash point 83°F.

Air & Water Reactions

Highly flammable. Moderately soluble in water .

Reactivity Profile

N-Ethylmorpholine can react vigorously with oxidizing materials. N-Ethylmorpholine dissolves LiAlH4.


Irritant to skin and eyes, absorbed by skin. Flammable, moderate fire risk. Toxic by skin absorption.

Health Hazard

Exposure can cause irritation of eyes, nose and throat. Contact with eyes may result in foggy vision and seeing halos around lights.

Flammability and Explosibility


Safety Profile

oison by intravenous route. Moderately toxic by ingestion. Mildly toxic by inhalation. A skin and severe eye irritant. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidzing materials. To fight fire, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

Primary irritant (without allergic reaction). This material is used as a catalyst in polyurethane foam production. It is a solvent for dyes and resins. It is used as an intermediate in surfactant, dye, pharmaceutical, and rubber chemical manufacture

Environmental fate

Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and Lewis, 1987). At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 467 mg/L. The adsorbability of the carbon used was 107 mg/g carbon (Guisti et al., 1974).


UN2920 Corrosive liquids, flammable, n.o.s., Hazard class: 8; Labels: 8-Corrosive material, 3-Flammable liquid. UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required


May form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine,etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Corrodes some metals. Unless inhibited, violent polymerization can occur from heat, sunlight, and contact with strong oxidizers permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Attacks some plastics, rubber and coatings

Waste Disposal

Controlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices).

Check Digit Verification of cas no

The CAS Registry Mumber 100-74-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 100-74:
23 % 10 = 3
So 100-74-3 is a valid CAS Registry Number.

100-74-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A11905)  4-Ethylmorpholine, 98%   

  • 100-74-3

  • 100ml

  • 164.0CNY

  • Detail
  • Alfa Aesar

  • (A11905)  4-Ethylmorpholine, 98%   

  • 100-74-3

  • 250ml

  • 247.0CNY

  • Detail
  • Alfa Aesar

  • (A11905)  4-Ethylmorpholine, 98%   

  • 100-74-3

  • 500ml

  • 421.0CNY

  • Detail
  • Alfa Aesar

  • (A11905)  4-Ethylmorpholine, 98%   

  • 100-74-3

  • 1000ml

  • 779.0CNY

  • Detail
  • Sigma-Aldrich

  • (04500)  4-Ethylmorpholine  ≥97.0% (GC)

  • 100-74-3

  • 04500-250ML

  • 443.43CNY

  • Detail
  • Sigma-Aldrich

  • (04500)  4-Ethylmorpholine  ≥97.0% (GC)

  • 100-74-3

  • 04500-1L

  • 692.64CNY

  • Detail
  • Aldrich

  • (109932)  4-Ethylmorpholine  97%

  • 100-74-3

  • 109932-100ML

  • 386.10CNY

  • Detail
  • Aldrich

  • (109932)  4-Ethylmorpholine  97%

  • 100-74-3

  • 109932-500ML

  • 514.80CNY

  • Detail



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017


1.1 GHS Product identifier

Product name N-Ethylmorpholine

1.2 Other means of identification

Product number -
Other names Morpholine, 4-ethyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Processing aids, not otherwise listed
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100-74-3 SDS

100-74-3Relevant articles and documents

Novel Synthesis of Carbamic Ester from Carbon Dioxide, Amine, and Ortho Ester

Ishii, Shideru,Nakayama, Hidenobu,Yoshida, Yasuhiko,Yamashita, Tadataka

, p. 455 - 458 (1989)

Carbon dioxide reacted with aliphatic amines and ortho esters to form carbamic esters in good yields.The influence of different ortho esters on the carbamate synthetic reaction is described.In the case of orthocarbonates, carbamic esters were obtained in high yields.The reaction of carbon dioxide, amines, and ortho esters may involve a competitive reaction between the esterification of carbamic acid produced by a reaction of carbon dioxide with amine, and the alkylation of amine.

The Me3Si Substituent Effect on the Reactivity of Silanes. Structural Correlations between Silyl Radicals and Their Parent Silanes

Chatgilialoglu, C.,Guerrini, A.,Lucarini, M.

, p. 3405 - 3409 (1992)

Good linear correlations exist both between the bond dissociation energy of an Si-H bond and the corresponding SiH stretching frequency and between the (29)Si hyperfine splitting of a silicon-centered radical and J((29)Si-H) for the corresponding silane, when the successive substitution at the Si-H function takes place inside a family, i.e., (Me3Si)3-nSi(H)Men, n = 0-3.Explanations for these phenomena are advanced.Such structural correlations allow the characterization of (Me3Si)2Si(H)Me as a radical-based reducing agent with low hydrogen-donating abilities.Rate constants for the reaction of primary alkyl radicals with (Me3Si)2Si(H)Me have been measured over a range of temperatures by using competing unimolecular radical reactions as timing devices.The radical trapping abilities of this silane and other common radical-based reducing agents are compared.

Selective Synthesis of Secondary and Tertiary Amines by Reductive N-Alkylation of Nitriles and N-Alkylation of Amines and Ammonium Formate Catalyzed by Ruthenium Complex

Alshakova, Iryna D.,Nikonov, Georgii I.

, p. 5370 - 5378 (2019)

A new ruthenium catalytic system for the syntheses of secondary and tertiary amines via reductive N-alkylation of nitriles and N-alkylation of primary amines is proposed. Isomeric complexes 8 catalyze transfer hydrogenation and N-alkylation of nitriles in ethanol to give secondary amines. Unsymmetrical secondary amines can be produced by N-alkylation of primary amines with alcohols via the borrowing hydrogen methodology. Aliphatic amines were obtained with excellent yields, while only moderate conversions were observed for anilines. Based on kinetic and mechanistic studies, it is suggested that the rate determining step is the hydrogenation of intermediate imine to amine. Finally, ammonium formate was applied as the amination reagent for alcohols in the presence of ruthenium catalyst 8. Secondary amines were obtained from primary alcohols within 24 hours at 100 °C, and tertiary amines can be produced after prolonged heating. Secondary alcohols can only be converted to secondary amines with moderate yield. Based on mechanistic studies, the process is suggested to proceed through an ammonium alkoxy carbonate intermediate, where carbonate acts as an efficient leaving group.



, p. 429,430 (1971)


Mild N-Alkylation of Amines with Alcohols Catalyzed by the Acetate Ru(OAc)2(CO)(DiPPF) Complex

Figliolia, Rosario,Baldino, Salvatore,Nedden, Hans G.,Zanotti-Gerosa, Antonio,Baratta, Walter

, p. 14416 - 14419 (2017)

The acetate complex Ru(OAc)2(DiPPF) (2) obtained from Ru(OAc)2(PPh3)2 (1) and 1,1′-bis(diisopropylphosphino)ferrocene (DiPPF) reacts cleanly with formaldehyde affording Ru(OAc)2(CO)(DiPPF) (3) in high yield. The monocarbonyl complex 3 (0.4-2 mol %) efficiently catalyzes the N-alkylation of primary and secondary alkyl and aromatic amines using primary alcohols ROH (R=Et, nPr, nBu, PhCH2) under mild reaction conditions (30–100 °C) with an alcohol/amine molar ratio of 10-100. Formation of the monohydride RuH(OAc)(CO)(DiPPF) (4) has been observed by reaction of 3 with iPrOH in the presence of NEt3 at RT through an equilibrium reaction.

Ionic liquid/H2O-mediated synthesis of mesoporous organic polymers and their application in methylation of amines

Yu, Xiaoxiao,Yang, Zhenzhen,Zhang, Hongye,Yu, Bo,Zhao, Yanfei,Liiu, Zhenghui,Ji, Guipeng,Liu, Zhimin

, p. 5962 - 5965 (2017)

Mesoporous Tr?ger's base-functionalized polymers (Meso-TBPs) were prepared using a sulfonic acid group functionalized ionic liquid/H2O system, with surface areas up to 431 m2 g-1 and pore sizes of 3-15 nm. Ir(ii) coordinated Meso-TBPs exhibited extraordinary catalytic performance in the N-methylation of amines using methanol.

Transition-metal complex-catalyzed reduction of amides with hydrosilanes: A facile transformation of amides to amines

Igarashi, Mamoru,Fuchikami, Takamasa

, p. 1945 - 1947 (2001)

The reaction of amides with hydrosilanes is catalyzed by a variety of transition-metal complexes in the presence or absence of halides and amines as co-catalysts to afford the corresponding amines in good yields.

Mild catalytic deoxygenation of amides promoted by thorium metallocene

Eisen, Moris S.,Saha, Sayantani

supporting information, p. 12835 - 12841 (2020/10/05)

The organoactinide-catalyzed (Cp*2ThMe2) hydroborated reduction of a wide range of tertiary, secondary, and primary amides to the corresponding amines/amine-borane adductsviadeoxygenation of the amides is reported herein. The catalytic reactions proceed under mild conditions with low catalyst loading and pinacolborane (HBpin) concentration in a selective fashion. Cp*2ThMe2is capable of efficiently catalysing the gram-scale reaction without a drop in efficiency. The amine-borane adducts are successfully converted into free amine products in high conversions, which increases the usefulness of this catalytic system. A plausible mechanism is proposed based on detailed kinetics, stoichiometric, and deuterium labeling studies.

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