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252360 Sigma-Aldrich

Morpholine

ACS reagent, ≥99.0%

Synonym: Tetrahydro-1,4-oxazine

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Properties

Related Categories Building Blocks, C4 to C10, Chemical Synthesis, Heterocyclic Building Blocks, Morpholines/Thiomorpholines More...
grade   ACS reagent
vapor density   3 (vs air)
vapor pressure   31 mmHg ( 38 °C)
  7 mmHg ( 20 °C)
assay   ≥99.0%
autoignition temp.   590 °F
expl. lim.   10.8 %
color   APHA: ≤15
refractive index   n20/D 1.454(lit.)
bp   126.0-130.0 °C
  129 °C(lit.)
mp   −7-−5 °C(lit.)
density   0.996 g/mL at 25 °C(lit.)

Description

Packaging

1 L in glass bottle

5, 100, 4×100, 500 mL in glass bottle

Price and Availability

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
C
Risk Statements (Europe) 
Safety Statements (Europe) 
23-36-45
RIDADR 
UN 2054 3(8) / PGI
WGK Germany 
2
RTECS 
QD6475000
Flash Point(F) 
87.8 °F
Flash Point(C) 
31 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Determination of Water Content in Morpholine Using Karl Fischer Titration

Nitrogen compounds, acid amides and weakly basic amines (heterocyclenes) give no problems. They can be titrated according to the standard procedures. Strongly basic amines alter the pH value and must...
Keywords: Titrations

Peer-Reviewed Papers

References

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Nickel-catalyzed amination of aryl sulfamates. Ramgren SD, Silberstein AL, Yang Y, et al. Angew. Chem. Int. Ed. Engl. 50(9), 2171-3, (2011)

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Morpholine catalyzed direct C3 alkenylation of indoles with α,β-unsaturated aldehydes. Xiang, S.; et al. Chem. Commun. (Camb.) 47, 8097, (2011)

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Touch responsiveness in zebrafish requires voltage-gated calcium channel 2.1b. Low SE, Woods IG, Lachance M, et al. J. Neurophysiol. 108(1), 148-59, (2012)

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Synthesis of enantiopure 3-substituted morpholines. Bornholdt J, Felding J, and Kristensen JL J. Org. Chem. 75(21), 7454-7, (2010)

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A nanochannel array-based electrochemical device for quantitative label-free DNA analysis. Li SJ, Li J, Wang K, et al. ACS Nano 4(11), 6417-24, (2010)

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Lipophilicity of basic drugs measured by hydrophilic interaction chromatography. Bruno Bard et al J. Med. Chem. 52, 3416-9, (2009)

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Morpholine. IARC Monogr. Eval. Carcinog. Risks Hum. 47, 199-213, (1989)

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Synthesis of a potent cathepsin s inhibitor labeled with deuterium and carbon-14. Latli B, Hrapchak M, Lorenz JC, et al. Curr. Radiopharm. 5(4), 314-7, (2012)

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[Synthesis of 2'-aminometylmorpholino nucleoside analogues containing 4'-carboxymethyl lynker group]. Kasakin MF, Abramova TV, and Sil'nikov VN Bioorg. Khim. 37(6), 830-5, (2011)

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Analyses of gene function in amphioxus embryos by microinjection of mRNAs and morpholino oligonucleotides. Holland LZ and Onai T Methods Mol. Biol. 770, 423-38, (2011)

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Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds. Bram Baert et al Bioorg. Med. Chem. 15, 6943-55, (2007)

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The neurotrophic properties of progranulin depend on the granulin E domain but do not require sortilin binding. De Muynck L, Herdewyn S, Beel S, et al. Neurobiol. Aging 34(11), 2541-7, (2013)

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Unexpected side products in the conjugation of an amine-derivatized morpholino oligomer with p-isothiocyanate benzyl DTPA and their removal. Liu G, Dou S, Liu Y, et al. Nucl. Med. Biol. 38(2), 159-63, (2011)

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Midline crossing is not required for subsequent pathfinding decisions in commissural neurons. Bonner J, Letko M, Nikolaus OB, et al. Neural Dev. 7, 18, (2012)

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Metabolism and pharmacokinetics of morinidazole in humans: identification of diastereoisomeric morpholine N+-glucuronides catalyzed by UDP glucuronosyltransferase 1A9. Gao R, Li L, Xie C, et al. Drug Metab. Dispos. 40(3), 556-67, (2012)

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A mechanistic and kinetic study on the decomposition of morpholine. Altarawneh M and Dlugogorski BZ J. Phys. Chem. A 116(29), 7703-11, (2012)

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2-Morpholinoisoflav-3-enes as flexible intermediates in the synthesis of phenoxodiol, isophenoxodiol, equol and analogues: Vasorelaxant properties, estrogen receptor binding and Rho/RhoA kinase pathway inhibition. Andrew J Tilley et al Bioorg. Med. Chem. 20, 2353-61, (2012)

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Ceric ammonium nitrate-catalyzed azidation of 1,2-anhydro sugars: application in the synthesis of structurally diverse sugar-derived morpholine 1,2,3-triazoles and 1,4-oxazin-2-ones. Reddy YS, Pal AP, Gupta P, et al. J. Org. Chem. 76(15), 5972-84, (2011)

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Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer 2: generation of captodatively stabilised radicals. Wood ME, Bissiriou S, Lowe C, et al. Org. Biomol. Chem. 11(16), 2712-23, (2013)

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Chemical genetics approach to identify new small molecule modulators of cell growth by phenotypic screening of Saccharomyces cerevisiae strains with a library of morpholine-derived compounds. Trabocchi A, Stefanini I, Morvillo M, et al. Org. Biomol. Chem. 8(24), 5552-7, (2010)

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Design of more potent squalene synthase inhibitors with multiple activities. Angeliki P Kourounakis et al Bioorg. Med. Chem. 18, 7402-12, (2010)

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Haloenol pyranones and morpholinones as antineoplastic agents of prostate cancer. Mock JN, Taliaferro JP, Lu X, et al. Bioorg. Med. Chem. Lett. 22(14), 4854-8, (2012)

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Shedding light by cancer redox-human NAD(P)H:quinone oxidoreductase 1 activation of a cloaked fluorescent dye. Silvers WC, Payne AS, and McCarley RL Chem. Commun. (Camb.) 47(40), 11264-6, (2011)

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Chalcogenides of the aminomethylphosphines derived from 1-methylpiperazine, 1-ethylpiperazine and morpholine: NMR, DFT and structural studies for determination of electronic and steric properties of the phosphines. Starosta R, Bazanów B, and Barszczewski W Dalton Trans. 39(32), 7547-55, (2010)

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Redox-neutral α-sulfenylation of secondary amines: ring-fused N,S-acetals. Jarvis CL, Richers MT, Breugst M, et al. Org. Lett. 16(13), 3556-9, (2014)

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A mechanistic and structural investigation of modified derivatives of the diaryltriazine class of NNRTIs targeting HIV-1 reverse transcriptase. Mislak AC, Frey KM, Bollini M, et al. Biochim. Biophys. Acta 1840(7), 2203-11, (2014)

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Synthesis, structural elucidation, DNA-PK inhibition, homology modelling and anti-platelet activity of morpholino-substituted-1,3-naphth-oxazines. Ihmaid S, Al-Rawi J, Bradley C, et al. Bioorg. Med. Chem. 19(13), 3983-94, (2011)

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Ultra-trace level analysis of morpholine, cyclohexylamine, and diethylaminoethanol in steam condensate by gas chromatography with multi-mode inlet, and flame ionization detection. Luong J, Shellie RA, Cortes H, et al. J. Chromatogr. A 1229, 223-9, (2012)

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A convenient route to optically pure α-alkyl-β-(sec-amino)alanines. Olma A, Lasota A, and Kudaj A Amino Acids 42(6), 2525-8, (2012)

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Small heat shock protein HSPB1 regulates growth of embryonic zebrafish craniofacial muscles. Middleton RC and Shelden EA Exp. Cell Res. 319(6), 860-74, (2013)

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Ab initio, density functional computations, FT-IR, FT-Raman and molecular geometry of 4-morpholine carbonitrile. Xavier RJ and Raj SA Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 101, 148-55, (2013)

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The hydrolysis kinetics of monobasic and dibasic aminoalkyl esters of ketorolac. Qandil AM, Jamhawi NM, Tashtoush BM, et al. Drug Dev. Ind. Pharm. 39(9), 1346-56, (2013)

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Merck 14,6277

Beil. 27,IV,15

Fieser 1,705 / Fieser 9,352 / Fieser 11,352

Aldrich MSDS 1, 1329:A / Corp MSDS 1 (2), 2477:C / FT-IR 1 (1), 382:A / FT-IR 2 (1), 594:D / FT-NMR 1 (1), 597:A / IR-Spectra (3), 225:H / IR-Spectra (2), 202:C / NMR-Reference 2 (1), 335:C / RegBook 1 (1), 401:J / Sax 6, 1961 / Sigma FT-IR 1 (2), 760:C / Structure Index 1, 58:A:2 / Vapor Phase 3, 472:A

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