Chemical Properties of Triethylamine (CAS 121-44-8)

Triethylamine

InChI
InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3
InChI Key
ZMANZCXQSJIPKH-UHFFFAOYSA-N
Formula
C6H15N
SMILES
CCN(CC)CC
Molecular Weight1
101.19
CAS
121-44-8
Other Names
  • (C2H5)3N
  • (Diethylamino)ethane
  • 1069-58-5 (maleate)
  • 554-68-7 (chloride)
  • Ethanamine, N,N-diethyl-
  • N,N,N-triethylamine
  • N,N-DIETHYLETHANAMINE
  • TEN
  • Triaethylamin
  • Trietilamina
  • UN 1296
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Contents

  1. Physical Properties
  2. Temperature Dependent Properties
  3. Datasets
  4. Correlations
  5. Similar Compounds
  6. Mixtures
  7. Sources

Physical Properties

Property Value Unit Source
ω 0.3200 KDB
PAff 981.80 kJ/mol NIST
BasG 951.00 kJ/mol NIST
Δcliquid [-4377.09; -4354.30] kJ/mol Show Hide
Δcliquid -4377.09 ± 0.54 kJ/mol NIST
Δcliquid -4354.30 kJ/mol NIST
μ 0.90 debye KDB
Δf 110.40 kJ/mol KDB
Rg 3.9300 KDB
Δfgas [-143.10; -92.90] kJ/mol Show Hide
Δfgas -99.65 kJ/mol KDB
Δfgas -134.10 kJ/mol NIST
Δfgas -92.90 ± 0.50 kJ/mol NIST
Δfgas -143.10 kJ/mol NIST
Δfliquid [-178.00; -127.80] kJ/mol Show Hide
Δfliquid -169.00 kJ/mol NIST
Δfliquid -127.80 ± 0.54 kJ/mol NIST
Δfliquid -178.00 kJ/mol NIST
Δfus 14.32 kJ/mol Joback Calculated Property
Δvap 34.10 kJ/mol Relay (1.0) Calculated Property
IE [7.10; 8.24] eV Show Hide
IE 7.53 ± 0.10 eV NIST
IE 7.47 ± 0.04 eV NIST
IE 7.53 ± 0.10 eV NIST
IE 7.30 eV NIST
IE 7.10 ± 0.10 eV NIST
IE 7.20 ± 0.09 eV NIST
IE 7.84 eV NIST
IE 7.50 ± 0.02 eV NIST
IE 8.03 eV NIST
IE 8.24 ± 0.04 eV NIST
IE 8.08 eV NIST
IE 8.19 ± 0.05 eV NIST
log10WS -0.14 Aq. Solubility Prediction
logPoct/wat 1.348 Crippen Calculated Property
McVol 105.380 ml/mol McGowan Calculated Property
NFPA Fire 3 KDB
NFPA Health 2 KDB
Pc 3032.00 kPa KDB
ρc 257.02 ± 2.02 kg/m3 NIST
Inp [672.00; 727.00]   Show Hide
Inp 673.60 NIST
Inp 673.60 NIST
Inp 676.00 NIST
Inp 672.00 NIST
Inp 727.00 NIST
Inp 726.00 NIST
Inp 724.00 NIST
Inp 676.00 NIST
Inp 727.00 NIST
Inp 711.00 NIST
Inp 682.00 NIST
Inp 677.00 NIST
Inp 677.00 NIST
Inp 679.00 NIST
Inp 680.00 NIST
Inp 680.00 NIST
Inp 695.00 NIST
Inp 696.00 NIST
Inp 684.00 NIST
Inp 677.00 NIST
Inp 684.00 NIST
I [727.00; 812.40]   Show Hide
I 812.40 NIST
I 775.00 NIST
I 774.00 NIST
I 770.00 NIST
I 775.00 NIST
I 763.00 NIST
I 780.00 NIST
I Outlier 727.00 NIST
Tboil 362.00 K KDB
Tc 535.60 K KDB
Tfus [158.00; 158.45] K Show Hide
Tfus 158.40 K KDB
Tfus 158.23 K Aq. Solubility Prediction
Tfus 158.45 K NIST
Tfus 158.45 ± 0.40 K NIST
Tfus Outlier 158.00 ± 2.00 K NIST
Tfus 158.45 ± 1.00 K NIST
Tfus 158.40 ± 0.20 K NIST
Vc 0.389 m3/kmol KDB
Zc 0.2648510 KDB
Zra 0.27 KDB

Temperature Dependent Properties

Property Value Unit Temperature (K) Source
Cp,gas [183.89; 248.11] J/mol×K [349.12; 511.60] Show Hide
Cp,gas 183.89 J/mol×K 349.12 Joback Calculated Property
Cp,gas 195.67 J/mol×K 376.20 Joback Calculated Property
Cp,gas 207.01 J/mol×K 403.28 Joback Calculated Property
Cp,gas 217.91 J/mol×K 430.36 Joback Calculated Property
Cp,gas 228.39 J/mol×K 457.44 Joback Calculated Property
Cp,gas 238.45 J/mol×K 484.52 Joback Calculated Property
Cp,gas 248.11 J/mol×K 511.60 Joback Calculated Property
Cp,liquid [177.00; 218.10] J/mol×K [298.00; 298.15] Show Hide
Cp,liquid 177.00 J/mol×K 298.00 NIST
Cp,liquid 216.43 J/mol×K 298.15 NIST
Cp,liquid 218.10 J/mol×K 298.15 NIST
η [0.0002980; 0.0004229] Pa×s [283.15; 323.15] Show Hide
η 0.0004229 Pa×s 283.15 Dynamic Viscosity Study of Binary Mixtures Triethylamine + Water at Temperatures Ranging from (283.15 to 291.35) K
η 0.0004085 Pa×s 286.15 Dynamic Viscosity Study of Binary Mixtures Triethylamine + Water at Temperatures Ranging from (283.15 to 291.35) K
η 0.0003989 Pa×s 288.15 Dynamic Viscosity Study of Binary Mixtures Triethylamine + Water at Temperatures Ranging from (283.15 to 291.35) K
η 0.0003900 Pa×s 290.15 Dynamic Viscosity Study of Binary Mixtures Triethylamine + Water at Temperatures Ranging from (283.15 to 291.35) K
η 0.0003855 Pa×s 291.15 Dynamic Viscosity Study of Binary Mixtures Triethylamine + Water at Temperatures Ranging from (283.15 to 291.35) K
η 0.0003847 Pa×s 291.35 Dynamic Viscosity Study of Binary Mixtures Triethylamine + Water at Temperatures Ranging from (283.15 to 291.35) K
η 0.0003660 Pa×s 298.15 Thermodynamic study of Binary Mixtures of Tricyclo [5.2.1.0(2.6)] Decane with N-Methylpiperazine or Triethylamine at T = (298.15 to 323.15) K
η 0.0003400 Pa×s 303.15 Thermodynamic study of Binary Mixtures of Tricyclo [5.2.1.0(2.6)] Decane with N-Methylpiperazine or Triethylamine at T = (298.15 to 323.15) K
η 0.0003340 Pa×s 308.15 Thermodynamic study of Binary Mixtures of Tricyclo [5.2.1.0(2.6)] Decane with N-Methylpiperazine or Triethylamine at T = (298.15 to 323.15) K
η 0.0003310 Pa×s 313.15 Thermodynamic study of Binary Mixtures of Tricyclo [5.2.1.0(2.6)] Decane with N-Methylpiperazine or Triethylamine at T = (298.15 to 323.15) K
η 0.0002980 Pa×s 323.15 Thermodynamic study of Binary Mixtures of Tricyclo [5.2.1.0(2.6)] Decane with N-Methylpiperazine or Triethylamine at T = (298.15 to 323.15) K
ΔvapH [31.01; 35.20] kJ/mol [275.00; 363.30] Show Hide
ΔvapH 35.20 ± 0.90 kJ/mol 275.00 NIST
ΔvapH 33.00 kJ/mol 311.00 NIST
ΔvapH 34.60 kJ/mol 311.00 NIST
ΔvapH 33.40 ± 0.20 kJ/mol 313.00 NIST
ΔvapH 33.90 ± 0.10 kJ/mol 313.00 NIST
ΔvapH 34.10 kJ/mol 320.00 NIST
ΔvapH 33.00 ± 0.20 kJ/mol 328.00 NIST
ΔvapH 34.80 kJ/mol 332.00 NIST
ΔvapH 33.90 kJ/mol 336.00 NIST
ΔvapH 33.30 kJ/mol 340.50 NIST
ΔvapH 32.20 ± 0.10 kJ/mol 343.00 NIST
ΔvapH 31.30 ± 0.20 kJ/mol 358.00 NIST
ΔvapH 31.01 kJ/mol 362.10 NIST
ΔvapH 31.38 kJ/mol 362.40 KDB
ΔvapH 33.18 kJ/mol 363.30 NIST
Pvap [2.46; 74.94] kPa [273.04; 352.77] Show Hide
Pvap 2.46 kPa 273.04 Experimental Vapor Pressures of 2-Phenylethylamine, Benzylamine, Triethylamine, and cis-2,6-Dimethylpiperidine in the Range between 0.2 Pa and 75 kPa
Pvap 7.01 kPa 292.87 Experimental Vapor Pressures of 2-Phenylethylamine, Benzylamine, Triethylamine, and cis-2,6-Dimethylpiperidine in the Range between 0.2 Pa and 75 kPa
Pvap 17.43 kPa 312.82 Experimental Vapor Pressures of 2-Phenylethylamine, Benzylamine, Triethylamine, and cis-2,6-Dimethylpiperidine in the Range between 0.2 Pa and 75 kPa
Pvap 38.05 kPa 332.78 Experimental Vapor Pressures of 2-Phenylethylamine, Benzylamine, Triethylamine, and cis-2,6-Dimethylpiperidine in the Range between 0.2 Pa and 75 kPa
Pvap 74.94 kPa 352.77 Experimental Vapor Pressures of 2-Phenylethylamine, Benzylamine, Triethylamine, and cis-2,6-Dimethylpiperidine in the Range between 0.2 Pa and 75 kPa
n0 [1.38980; 1.40110]   [293.15; 318.15] Show Hide
n0 1.39660 293.15 Measurement and correlation of the mutual solubility of diisopropylamine + water and triethylamine + water systems at high pressure
n0 1.40110 298.15 Densities and Refractive Indices of Binary Mixtures of Benzene with Triethylamine and Tributylamine at Different Temperatures
n0 1.39830 298.15 Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of 1,4-Dioxane + Ethanediol, + Hexane, + Tributylamine, or + Triethylamine at (298.15, 303.15, and 308.15) K
n0 1.39920 298.15 Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of Tri-n-butylamine + Triethylamine, + Tetrahydrofuran, + Tetradecane, + Tetrachloroethylene, + Pyridine, or + Trichloroethylene at (298.15, 303.15, and 308.15) K
n0 1.39830 303.15 Densities and Refractive Indices of Binary Mixtures of Benzene with Triethylamine and Tributylamine at Different Temperatures
n0 1.39550 303.15 Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of 1,4-Dioxane + Ethanediol, + Hexane, + Tributylamine, or + Triethylamine at (298.15, 303.15, and 308.15) K
n0 1.39580 303.15 Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of Tri-n-butylamine + Triethylamine, + Tetrahydrofuran, + Tetradecane, + Tetrachloroethylene, + Pyridine, or + Trichloroethylene at (298.15, 303.15, and 308.15) K
n0 1.39500 308.15 Densities and Refractive Indices of Binary Mixtures of Benzene with Triethylamine and Tributylamine at Different Temperatures
n0 1.39260 308.15 Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of 1,4-Dioxane + Ethanediol, + Hexane, + Tributylamine, or + Triethylamine at (298.15, 303.15, and 308.15) K
n0 1.39290 308.15 Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of Tri-n-butylamine + Triethylamine, + Tetrahydrofuran, + Tetradecane, + Tetrachloroethylene, + Pyridine, or + Trichloroethylene at (298.15, 303.15, and 308.15) K
n0 1.39280 313.15 Densities and Refractive Indices of Binary Mixtures of Benzene with Triethylamine and Tributylamine at Different Temperatures
n0 1.38980 318.15 Densities and Refractive Indices of Binary Mixtures of Benzene with Triethylamine and Tributylamine at Different Temperatures
ρl [709.05; 732.03] kg/m3 [288.15; 313.15] Show Hide
ρl 732.03 kg/m3 288.15 Volumetric behaviour of binary mixtures of (trichloromethane + amines) at temperatures between T = (288.15 and 303.15) K at p = 0.1 MPa
ρl 728.00 kg/m3 293.00 KDB
ρl 727.40 kg/m3 293.15 Volumetric behaviour of binary mixtures of (trichloromethane + amines) at temperatures between T = (288.15 and 303.15) K at p = 0.1 MPa
ρl 727.70 kg/m3 293.15 Volumetric properties of binary mixtures of (acetonitrile + amines) at several temperatures with application of the ERAS model
ρl 722.81 kg/m3 298.15 Thermodynamics of (ketone + amine) mixtures. Part XI. Excess molar enthalpies at T = 298.15 K for the (1-propanol + N,N,N-triethylamine + 2-butanone) system
ρl 722.77 kg/m3 298.15 Volumetric behaviour of binary mixtures of (trichloromethane + amines) at temperatures between T = (288.15 and 303.15) K at p = 0.1 MPa
ρl 723.01 kg/m3 298.15 Partial molar volume of tertiary amines in methanol at T = 298.15 K. Solvation, shape and specific interactions
ρl 722.81 kg/m3 298.15 Thermodynamics of ketone + amine mixtures. Part X. Excess molarenthalpies at 298.15 K for N,N,N-triethylamine + 2-alkanone systems.Characterization of tertiary amine + 2-alkanone, and ofamino-ketone + n-alkane mixtures in terms of DISQUAC
ρl 722.56 kg/m3 298.15 Excess molar volumes and excess molar enthalpies of binary and ternary mixtures of (ethanol or 1-butanol), triethylamine and n-hexane
ρl 723.02 kg/m3 298.15 Volumetric properties of binary mixtures of (acetonitrile + amines) at several temperatures with application of the ERAS model
ρl 718.12 kg/m3 303.15 Volumetric behaviour of binary mixtures of (trichloromethane + amines) at temperatures between T = (288.15 and 303.15) K at p = 0.1 MPa
ρl 718.36 kg/m3 303.15 Volumetric properties of binary mixtures of (acetonitrile + amines) at several temperatures with application of the ERAS model
ρl 718.44 kg/m3 303.15 Studies of viscosities of dilute solutions of alkylamine in non-electrolyte solvents. II. Haloalkanes and other polar solvents
ρl 718.44 kg/m3 303.15 Studies of partial molar volumes of alkylamine in non-electrolyte solvents I. Alkylamines in hydrocarbons at 303.15 and 313.15K
ρl 718.44 kg/m3 303.15 Studies of viscosities of dilute solutions of alkylamines in non-electrolyte solvents III. Alkylamines in butanols 303.15K
ρl 713.65 kg/m3 308.15 Volumetric properties of binary mixtures of (acetonitrile + amines) at several temperatures with application of the ERAS model
ρl 709.05 kg/m3 313.15 Studies of partial molar volumes of alkylamine in non-electrolyte solvents I. Alkylamines in hydrocarbons at 303.15 and 313.15K
csound,fluid [1090.65; 1132.77] m/s [293.15; 303.15] Show Hide
csound,fluid 1132.47 m/s 293.15 Thermodynamics of (ketone + amine) mixtures. Part VI. Volumetric and speed of sound data at (293.15, 298.15, and 303.15) K for (2-heptanone + dipropylamine, +dibutylamine, or +triethylamine) systems
csound,fluid 1132.77 m/s 293.15 Thermodynamics of ketone + amine mixtures Part IV. Volumetric and speed of sound data at (293.15; 298.15 and 303.15 K) for 2-butanone +dipropylamine, +dibutylamine or +triethylamine systems
csound,fluid 1110.90 m/s 298.15 Thermodynamics of (ketone + amine) mixtures. Part VI. Volumetric and speed of sound data at (293.15, 298.15, and 303.15) K for (2-heptanone + dipropylamine, +dibutylamine, or +triethylamine) systems
csound,fluid 1111.10 m/s 298.15 Thermodynamics of ketone + amine mixtures Part IV. Volumetric and speed of sound data at (293.15; 298.15 and 303.15 K) for 2-butanone +dipropylamine, +dibutylamine or +triethylamine systems
csound,fluid 1090.65 m/s 303.15 Thermodynamics of (ketone + amine) mixtures. Part VI. Volumetric and speed of sound data at (293.15, 298.15, and 303.15) K for (2-heptanone + dipropylamine, +dibutylamine, or +triethylamine) systems
csound,fluid 1090.70 m/s 303.15 Thermodynamics of ketone + amine mixtures Part IV. Volumetric and speed of sound data at (293.15; 298.15 and 303.15 K) for 2-butanone +dipropylamine, +dibutylamine or +triethylamine systems
γ 0.02 N/m 293.20 KDB

Datasets

Viscosity, Pa*s

Fixed Measured
Amount density, mol/m3 - Gas Temperature, K - Gas Viscosity, Pa*s - Gas
2.2 299.67 6.4900e-06
2.2 299.85 6.4850e-06
2.2 313.96 6.7640e-06
2.2 326.63 7.0240e-06
2.2 339.05 7.2750e-06
2.2 352.50 7.5510e-06
2.2 366.60 7.8420e-06
2.2 381.14 8.1370e-06
2.2 394.56 8.4130e-06
2.2 409.20 8.7180e-06
2.2 422.79 8.9960e-06
2.2 437.42 9.2960e-06
2.2 451.72 9.5940e-06
2.2 466.58 9.9070e-06
2.2 480.36 0.0000
2.2 498.45 0.0000
3.13 300.02 6.4880e-06
3.13 303.12 6.5480e-06
3.13 316.33 6.8150e-06
3.13 324.26 6.9810e-06
3.13 338.31 7.2590e-06
3.13 352.91 7.5570e-06
3.13 366.49 7.8390e-06
3.13 380.67 8.1290e-06
3.13 394.95 8.4230e-06
3.13 412.99 8.8040e-06
3.13 423.41 9.0120e-06
3.13 437.51 9.3150e-06
3.13 451.74 9.5990e-06
3.13 469.98 9.9850e-06
3.13 480.86 0.0000
3.13 498.38 0.0000
4.2 296.98 6.4180e-06
4.2 297.97 6.4390e-06
4.2 310.02 6.6680e-06
4.2 324.95 6.9710e-06
4.2 338.63 7.2450e-06
4.2 353.30 7.5510e-06
4.2 365.86 7.8030e-06
4.2 385.41 8.2170e-06
4.2 394.25 8.3880e-06
4.2 409.73 8.7110e-06
4.2 423.93 8.9880e-06
4.2 436.97 9.2750e-06
4.2 451.76 9.5860e-06
4.2 466.71 9.8930e-06
4.2 481.32 0.0000
4.2 495.31 0.0000
4.99 297.98 6.4400e-06
4.99 298.33 6.4370e-06
4.99 314.61 6.7500e-06
4.99 325.84 6.9800e-06
4.99 338.25 7.2330e-06
4.99 352.46 7.5290e-06
4.99 367.25 7.8310e-06
4.99 380.54 8.1090e-06
4.99 394.51 8.3860e-06
4.99 409.32 8.7070e-06
4.99 423.25 8.9910e-06
4.99 437.62 9.2860e-06
4.99 451.28 9.5720e-06
4.99 466.45 9.8790e-06
4.99 480.43 0.0000
4.99 495.29 0.0000
6.31 297.59 6.4120e-06
6.31 299.36 6.4490e-06
6.31 310.29 6.6540e-06
6.31 324.90 6.9480e-06
6.31 337.84 7.2050e-06
6.31 352.41 7.4920e-06
6.31 366.77 7.7840e-06
6.31 381.83 8.1060e-06
6.31 394.49 8.3700e-06
6.31 408.97 8.6620e-06
6.31 423.92 8.9660e-06
6.31 437.11 9.2490e-06
6.31 451.66 9.5540e-06
6.31 465.92 9.8460e-06
6.31 481.09 0.0000
6.31 495.17 0.0000
7.52 299.24 6.4460e-06
7.52 326.04 6.9790e-06
7.52 338.12 7.2180e-06
7.52 352.32 7.5130e-06
7.52 366.72 7.8010e-06
7.52 385.75 8.2060e-06
7.52 394.86 8.3840e-06
7.52 409.67 8.6900e-06
7.52 423.03 8.9630e-06
7.52 437.87 9.2690e-06
7.52 451.93 9.5580e-06
7.52 471.39 9.9720e-06
7.52 480.70 0.0000
7.52 495.84 0.0000
8.75 297.87 6.4270e-06
8.75 300.11 6.4600e-06
8.75 311.78 6.6670e-06
8.75 324.05 6.9130e-06
8.75 338.92 7.2170e-06
8.75 352.34 7.4870e-06
8.75 366.42 7.7820e-06
8.75 381.06 8.0760e-06
8.75 395.11 8.3690e-06
8.75 408.35 8.6400e-06
8.75 422.67 8.9390e-06
8.75 437.76 9.2550e-06
8.75 451.45 9.5340e-06
8.75 466.63 9.8510e-06
8.75 480.12 0.0000
8.75 496.21 0.0000
Reference
Fixed Measured
Temperature, K - Liquid Pressure, kPa - Liquid Viscosity, Pa*s - Liquid
303.15 101.33 0.0003
Reference

Correlations

Property Value Unit Temperature (K) Source
Pvap [1.33; 202.68] kPa [275.55; 385.31] The Yaws Handbook of Vapor Pressure Show Hide
Equationln(Pvp) = A + B/(T + C)
Coefficient A1.29590e+01
Coefficient B-2.11704e+03
Coefficient C-1.08476e+02
Temperature range, min.275.55
Temperature range, max.385.31
Pvap 1.33 kPa 275.55 Calculated Property
Pvap 3.16 kPa 287.75 Calculated Property
Pvap 6.70 kPa 299.94 Calculated Property
Pvap 12.99 kPa 312.14 Calculated Property
Pvap 23.37 kPa 324.33 Calculated Property
Pvap 39.48 kPa 336.53 Calculated Property
Pvap 63.25 kPa 348.72 Calculated Property
Pvap 96.81 kPa 360.92 Calculated Property
Pvap 142.48 kPa 373.11 Calculated Property
Pvap 202.68 kPa 385.31 Calculated Property
Pvap [1.02e-05; 2785.21] kPa [158.45; 535.15] KDB Vapor Pressure Data Show Hide
Equationln(Pvp) = A + B/T + C*ln(T) + D*T^2
Coefficient A6.51266e+01
Coefficient B-6.12731e+03
Coefficient C-7.51862e+00
Coefficient D5.20704e-06
Temperature range, min.158.45
Temperature range, max.535.15
Pvap 1.02e-05 kPa 158.45 Calculated Property
Pvap 6.09e-03 kPa 200.31 Calculated Property
Pvap 0.32 kPa 242.16 Calculated Property
Pvap 4.48 kPa 284.02 Calculated Property
Pvap 29.09 kPa 325.87 Calculated Property
Pvap 115.94 kPa 367.73 Calculated Property
Pvap 335.21 kPa 409.58 Calculated Property
Pvap 778.89 kPa 451.44 Calculated Property
Pvap 1554.27 kPa 493.29 Calculated Property
Pvap 2785.21 kPa 535.15 Calculated Property

Similar Compounds

Ethanamine, N-ethyl-N-methyl-. 2-(Diethylamino)acetonitrile. 1-Ethyl-aziridine. Diethylcyanamide. 2-Propyn-1-amine, N,N-diethyl-. Ethanamine, N,N-dimethyl-. Formamide, N,N-diethyl-. 1-Diethylamino-2-butyne. Ethanamine, 2-chloro-N,N-diethyl-. 1,2-Ethanediamine, N,N,N',N'-tetraethyl-. Piperazine, 1,4-diethyl-. Acetamide, N,N-diethyl-. 2-Propaneamine, N,N-diethyl-. Bis(2-chloroethyl)ethylamine. 1,2-Ethanediamine, N,N'-diethyl-N,N'-dimethyl-.

Find more compounds similar to Triethylamine.

Mixtures

Find more mixtures with Triethylamine.

Sources

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Outlier This icon means that the value is more than 2 standard deviations away from the property mean.