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Acetamide
Names
Preferred IUPAC name
Systematic IUPAC name
Other names
Acetic acid amide
Identifiers
CAS Number
3D model (JSmol )
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.430
EC Number
IUPHAR/BPS
KEGG
PubChem CID
RTECS number
UNII
CompTox Dashboard (EPA )
InChI=1S/C2H5NO/c1-2(3 )4/h1H3,(H2,3,4) Y
Key: DLFVBJFMPXGRIB-UHFFFAOYSA-N Y
InChI=1/C2H5NO/c1-2(3 )4/h1H3,(H2,3,4)
Key: DLFVBJFMPXGRIB-UHFFFAOYAC
Properties
Chemical formula
C 2 H 5 N O
Molar mass
−1
Appearance
colorless, hygroscopic solid
Odor
odorless
Density
1.159 g cm −3
Melting point
79 to 81 °C (174 to 178 °F; 352 to 354 K )
Boiling point
221.2 °C (430.2 °F; 494.3 K ) (decomposes)
Solubility in water
2000 g L −1 [2]
Solubility
ethanol 500 g L −1 [2] pyridine 166.67 g L −1 [2] chloroform , glycerol , benzene [2]
log P
−1.26
Vapor pressure
1.3 Pa
Acidity (p K a 15.1 (25 °C, H2 O )[3]
Magnetic susceptibility (χ)
−0.577 × 10 −6 cm 3 g −1
Refractive index (n D
1.4274
Viscosity
2.052 cP (91 °C)
Structure
Crystal structure
trigonal
Thermochemistry[4]
Heat capacity (C
91.3 J·mol−1 ·K−1
Std molar (S ⦵ 298 )
115.0 J·mol−1 ·K−1
Std enthalpy of (Δf H ⦵ 298 )
−317.0 kJ·mol−1
Hazards
GHS labelling
Pictograms
Signal word
Warning
Hazard statements
H351
Precautionary statements
P201 , P202 , P281 , P308+P313 , P405 , P501
NFPA 704
Flash point
126 °C (259 °F; 399 K )
Lethal dose or concentration (LD, LC):
LD 50 median dose )
7000 mg kg −1 (rat, oral)
Safety data sheet (SDS)
External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Acetamide (systematic name: ethanamide ) is an organic compound with the formula CH3 2 acetic acid . It finds some use as a plasticizer and as an industrial solvent.[5] N N acetone , which has two methyl (CH 3 CO ), and urea which has two amide (NH 2 [6] IMA symbol : Ace.[7]
Production [ edit ]
Structure of acetamide hydrogen-bonded dimer from X-ray crystallography . Selected distances: C-O: 1.243, C-N, 1.325, N---O, 2.925 Å. Color code: red = O, blue = N, gray = C, white = H.[8]
Laboratory scale [ edit ]
Acetamide can be produced in the laboratory from ammonium acetate by dehydration :[9]
[NH 4 CH 3 CO 2 3 O )NH2 2 O
Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination .[10]
It can also be made from anhydrous acetic acid, acetonitrile and very well dried hydrogen chloride gas, using an ice bath, alongside more valuable reagent acetyl chloride . Yield is typically low (up to 35%), and the acetamide made this way is generated as a salt with HCl.
Industrial scale [ edit ]
In a similar fashion to some laboratory methods, acetamide is produced by dehydrating ammonium acetate or via the hydration of acetonitrile , a byproduct of the production of acrylonitrile :[5]
CH 3 2 3 O )NH2
Acetamide is used as a plasticizer and an industrial solvent.[5] dielectric constant is higher than most organic solvents, allowing it to dissolve inorganic compounds with solubilities closely analogous to that of water.[11] organic synthesis of pharmaceuticals, pesticides, and antioxidants for plastics.[12] thioacetamide .[13]
Occurrence [ edit ]
Acetamide has been detected near the center of the Milky Way galaxy.[14] Earth ) can form in space.
On 30 July 2015, scientists reported that upon the first touchdown of the Philae comet 67/P 's surface, measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds , four of which – acetamide, acetone , methyl isocyanate , and propionaldehyde [15] [16] [17]
In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.[18] [19]
References [ edit ]
^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics CRC Press . pp. 5–88. ISBN 9781498754293
^ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632
^ a b c "Acetic Acid". Ullmann's Encyclopedia of Industrial Chemistry doi :10.1002/14356007.a01_045.pub2 . ISBN 978-3527306732
^ Mindat: Naturally occurring acetamide
^ Warr, L.N. (2021). "IMA-CNMNC approved mineral symbols" . Mineralogical Magazine . 85 3 ): 291–320. Bibcode :2021MinM...85..291W . doi :10.1180/mgm.2021.43 S2CID 235729616 .
^ Bats, Jan W.; Haberecht, Monika C.; Wagner, Matthias (2003). "A new refinement of the orthorhombic polymorph of acetamide". Acta Crystallographica Section E . 59 10 ): o1483–o1485. doi :10.1107/S1600536803019494 .
^ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide" . Organic Syntheses 3 doi :10.15227/orgsyn.003.0003 Collected Volumes , vol. 1, p. 3
^ Schwoegler, Edward J.; Adkins, Homer (1939). "Preparation of Certain Amines". J. Am. Chem. Soc. 61 12 ): 3499–3502. doi :10.1021/ja01267a081 .
^ Stafford, O. F. (1933). "Acetamide as a Solvent". J. Am. Chem. Soc. 55 10 ): 3987–3988. doi :10.1021/ja01337a011 .
^ Wagner, Frank S. (2002). Kirk-Othmer Encyclopedia of Chemical Technology . John Wiley & Sons. doi :10.1002/0471238961.0103052023010714.a02.pub2 . ISBN 9780471238966
^ Schwarz, G. (1945). "2,4-Dimethylthiazole" . Organic Syntheses 25 Collected Volumes , vol. 3, p. 332
^ Hollis, J. M.; Lovas, F. J.; Remijan, A. J.; Jewell, P. R.; Ilyushin, V. V.; Kleiner, I. (2006). "Detection of Acetamide (CH 3 2 . Astrophys. J. 643 (1 ): L25–L28. Bibcode :2006ApJ...643L..25H . doi :10.1086/505110
^ Jordans, Frank (30 July 2015). "Philae probe finds evidence that comets can be cosmic labs" . The Washington Post . Associated Press. Archived from the original on 23 December 2018. Retrieved 30 July 2015 .
^ "Science on the Surface of a Comet" . European Space Agency. 30 July 2015. Retrieved 30 July 2015 .
^ Bibring, J.-P.; Taylor, M.G.G.T.; Alexander, C.; Auster, U.; Biele, J.; Finzi, A. Ercoli; Goesmann, F.; Klingehoefer, G.; Kofman, W.; Mottola, S.; Seidenstiker, K.J.; Spohn, T.; Wright, I. (31 July 2015). "Philae's First Days on the Comet - Introduction to Special Issue" . Science 349 (6247): 493. Bibcode :2015Sci...349..493B . doi :10.1126/science.aac5116 PMID 26228139 .
^ "Acetamide" . Mindat.org.
^ "Acetamide" (PDF) . Handbook of Mineralogy . RRUFF Project.
External links [ edit ]
Look up
acetamide in Wiktionary, the free dictionary.
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Acetamide&oldid=1181464502 " C a t e g o r i e s : ● A c e t a m i d e s ● H a z a r d o u s a i r p o l l u t a n t s ● I A R C G r o u p 2 B c a r c i n o g e n s ● P l a s t i c i z e r s ● O r g a n i c m i n e r a l s H i d d e n c a t e g o r i e s : ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● A r t i c l e s w i t h G N D i d e n t i f i e r s
● T h i s p a g e w a s l a s t e d i t e d o n 2 3 O c t o b e r 2 0 2 3 , a t 0 6 : 0 7 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
