625-51-4

Basic information

• Product Name: N-(HYDROXYMETHYL)ACETAMIDE
• Synonyms: ACETAMIDOMETHANOL;HYDROXYMETHYLACETAMIDE(N-);N-(HYDROXYMETHYL)ACETAMIDE;N-ACETYLMETHANOLAMINE;n-(hydroxymethyl)-acetamid;N-(Hydroxymethyl)acetamide,98+%;Hydroxymethylacetamide;N-(Hydroxymethyl)acetamide,97%
• CAS NO: 625-51-4
• Molecular Formula: C₃H₇NO₂
• Molecular Weight: 89.09
• EINECS: 210-897-2
• Product Categories: Amino Alcohols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 625-51-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 48-52 °C
• Boiling Point: 165.17°C (rough estimate)
• Flash Point: 148.1 °C
• Appearance: /Crystalline
• Density: 1.14
• Vapor Pressure: 2.41E-05mmHg at 25°C
• Refractive Index: 1.4368 (estimate)
• Storage Temp.: Store at 0°C
• Solubility: Chloroform (Sparingly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• PKA: 13.28±0.10(Predicted)
• Water Solubility: Soluble
• Sensitive: Hygroscopic
• Merck: 14,4242
• BRN: 506226
• CAS DataBase Reference: N-(HYDROXYMETHYL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(HYDROXYMETHYL)ACETAMIDE(625-51-4)
• EPA Substance Registry System: N-(HYDROXYMETHYL)ACETAMIDE(625-51-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: AC3610000
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 625-51-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystalline powder

Uses

Different sources of media describe the Uses of 625-51-4 differently. You can refer to the following data:
1. Antiseptic, disinfectant especially for surgical instruments.
2. N-(Hydroxymethyl)acetamide (cas# 625-51-4) is used as a catalyst in the method for manufacturing sol-gel silica particles method for manufacturing coating substrate coated with silica particles.

Purification Methods

Recrystallise it from freshly distilled Me2CO, wash the crystals with dry Et2O and dry them in a vacuum desiccator over P2O5. RF 0.4 on paper chromatography with CHCl3/EtOH (2:8) as solvent and developed with ammoniacal AgNO3. It also crystallises in needles from EtOAc containing a few drops of Me2CO. It is hygroscopic and should be stored under dry conditions. [Bachmann et al. J Am Chem Soc 73 2775 1951, Walter et al. Chem Ber 99 3204 1966, Einhorn & Ladisch Justus Liebigs Ann Chem 343 265 1905, Beilstein 2 IV 405.]

InChI:InChI=1/C3H7NO2/c1-3(6)4-2-5/h5H,2H2,1H3,(H,4,6)

Synthetic route

acetamide (60-35-5) + formaldehyd (50-00-0) → N-(hydroxymethyl)acetamide (625-51-4)

Conditions	Yield
With potassium carbonate
Versetzen mit 40prozentiger KOH;
With potassium carbonate

acetamide (60-35-5) + formaldehyd (50-00-0) → N,N-methylenediacetamide (3852-14-0) + N-(hydroxymethyl)acetamide (625-51-4)

Conditions	Yield
In 1,4-dioxane; water at 40 - 60℃; Thermodynamic data; Kinetics; Mechanism; activation energy, pH 1.2-3.5;

glycylglycine (556-50-3) → N-(hydroxymethyl)acetamide (625-51-4) + {2-[(Acetylamino-methyl)-amino]-acetylamino}-acetic acid

Conditions	Yield
In water Mechanism; Quantum yield; Irradiation; neutral solution;

glycylglycine (556-50-3) → acetamide (60-35-5) + N,N-methylenediacetamide (3852-14-0) + N-(hydroxymethyl)acetamide (625-51-4) + N-acetylglycine (543-24-8)

Conditions	Yield
In water Product distribution; Quantum yield; Mechanism; Irradiation; pH 6; var. dipeptides, other pH and times;

3,7-diacetyl-1,3,5,7-tetraaza-bicyclo[3.3.1]nonane (32516-05-5) → formaldehyd (50-00-0) + N-(hydroxymethyl)acetamide (625-51-4)

Conditions	Yield
With hydrogenchloride In water at 25℃; for 0.333333h;	A 1.7 % Turnov. B n/a

acetamide (60-35-5) + polyoxymethylene → N-(hydroxymethyl)acetamide (625-51-4)

Conditions	Yield
at 120 - 150℃;

6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-4-ium bromide (224633-83-4) + N-(hydroxymethyl)acetamide (625-51-4) → C18H19N3O (103844-36-6)

Conditions	Yield
Stage #1: 6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-4-ium bromide; N-(hydroxymethyl)acetamide With sulfuric acid In acetic acid at 20℃; for 3.5h; Heating / reflux; Stage #2: With ammonia In water; acetic acid	97%

N-(hydroxymethyl)acetamide (625-51-4) + 5,17-dibromo-25,27-bis(2-ethoxyethoxy)calix[4]arene (177412-46-3) → 5,17-bis<(acetamido)methyl>-26,28-dihydroxy-25,27-bis(2-ethoxyethoxy)calix<4>arene

Conditions	Yield
With trifluoroacetic acid In chloroform Ambient temperature;	95%

2-mercapto-4,5-dimethoxybenzylamine hydrochloride (21407-29-4) + N-(hydroxymethyl)acetamide (625-51-4) → S-acetamidomethyl 4,5-dimethoxy-2-mercaptobenzylamine hydrochloride

Conditions	Yield
With hydrogenchloride	94%

methyl galloate (99-24-1) + N-(hydroxymethyl)acetamide (625-51-4) → C11H13NO6

Conditions	Yield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;	91.36%

N-(hydroxymethyl)acetamide (625-51-4) + 6-benzylthio-2-phenethylimidazo<1,2-b>pyridazine (144449-11-6) → 3-acetamidomethyl-6-benzylthio-2-phenethylimidazo<1,2-b>pyridazine (144449-35-4)

Conditions	Yield
With sulfuric acid In acetic acid Heating;	90%

N-(hydroxymethyl)acetamide (625-51-4) + 2-phenyl-6-chloroimidazo<1,2-b>pyridazine (1844-53-7) → 3-acetamidomethyl-6-chloro-2-phenylimidazo<1,2-b>pyridazine

Conditions	Yield
With sulfuric acid In acetic acid for 14h; Heating;	90%

Propyl gallate (121-79-9) + N-(hydroxymethyl)acetamide (625-51-4) → C13H17NO6

Conditions	Yield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;	89.68%

N-(hydroxymethyl)acetamide (625-51-4) + 25,27-dihydroxy-26,28-dipropoxycalix[4]arene (143406-35-3) → 5,17-bis<(acetamido)methyl>-26,28-dihydroxy-25,27-di(1-propoxy)calix<4>arene

Conditions	Yield
With trifluoroacetic acid In chloroform Ambient temperature;	85%

N-(hydroxymethyl)acetamide (625-51-4) + 6-(2-Methoxy-phenylsulfanyl)-2-phenyl-imidazo[1,2-b]pyridazine (180900-96-3) → N-[6-(2-Methoxy-phenylsulfanyl)-2-phenyl-imidazo[1,2-b]pyridazin-3-ylmethyl]-acetamide

Conditions	Yield
With sulfuric acid In acetic acid at 100℃; for 14h;	83%

N-(hydroxymethyl)acetamide (625-51-4) + 5,17-dibromo-25,26,27,28-tetra-n-propylcalix[4]arene (172472-58-1, 176299-00-6, 863555-70-8) → 11,23-bis<(acetamido)methyl>-5,17-dibromo-25,26,27,28-tetra(1-propoxy)calix<4>arene

Conditions	Yield
With trifluoroacetic acid In chloroform for 36h; Ambient temperature;	83%

N-(hydroxymethyl)acetamide (625-51-4) + 2-Benzo[1,3]dioxol-5-yl-6-chloro-imidazo[1,2-b]pyridazine (141409-08-7) → 3-acetamidomethyl-6-chloro-2-(3',4'-methylenedioxyphenyl)imidazo<1,2-b>pyridazine

Conditions	Yield
With sulfuric acid In acetic acid for 14h; Heating;	80%

N-(hydroxymethyl)acetamide (625-51-4) + 2-(4'-methylphenyl)-6-phenylthioimidazo<1,2-b>pyridazine (141409-27-0) → 3-acetamidomethyl-6-phenylthio-2-(4'-tolyl)imidazo<1,2-b>pyridazine

Conditions	Yield
With sulfuric acid In acetic acid for 14h; Heating;	80%

(4R)-1-{[6-(4-fluorophenoxy)pyridin-3-yl]methyl}-4-mercaptopyrrolidin-2-one dihydrochloride + N-(hydroxymethyl)acetamide (625-51-4) → N-((((3R)-1-((6-(4-fluorophenoxy)-3-pyridinyl)methyl)-5-oxo-3-pyrrolidinyl)thio)methyl)acetamide

Conditions	Yield
With trifluoroacetic acid at 20℃; for 0.166667h;	79%

Ethyl gallate (831-61-8) + N-(hydroxymethyl)acetamide (625-51-4) → C12H15NO6

Conditions	Yield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;	78.55%

2-mercaptopropanoic acid (79-42-5) + N-(hydroxymethyl)acetamide (625-51-4) → (RS)-2-acetamidomethylthiopropionic acid (88568-98-3)

Conditions	Yield
With trifluoroacetic acid for 0.75h; Ambient temperature;	78%

N-(hydroxymethyl)acetamide (625-51-4) + 2-(4'-t-butylphenyl)-6-chloroimidazo<1,2-b>pyridazine (180901-27-3) → N-[2-(4-tert-Butyl-phenyl)-6-chloro-imidazo[1,2-b]pyridazin-3-ylmethyl]-acetamide

Conditions	Yield
With sulfuric acid In acetic acid for 14h; Heating;	74%

11-mercaptounadecanoic acid (71310-21-9) + N-(hydroxymethyl)acetamide (625-51-4) → 11-(Acetylamino-methylsulfanyl)-undecanoic acid

Conditions	Yield
In trifluoroacetic acid for 0.5h; Ambient temperature;	72%

3,3-dimethyl-D-cysteine (52-67-5) + N-(hydroxymethyl)acetamide (625-51-4) → bis(S)(-5,5-dimethylthiazolidine-4-carboxylic acid)protium chloride hydrate (111491-50-0)

Conditions	Yield
With hydrogenchloride In water for 0.5h; Ambient temperature;	70%

2-amino-2-(1-mercaptocyclopentyl)acetic acid hydrochloride (43180-45-6) + N-(hydroxymethyl)acetamide (625-51-4) + trifluoroacetic acid (76-05-1) → C2HF3O2*C10H18N2O3S (1246849-65-9)

Conditions	Yield
With trifluorormethanesulfonic acid In water at 0 - 20℃;	70%

N-(hydroxymethyl)acetamide (625-51-4) + tert-butyl 3,5-dihydroxy-6-mercapto-3-methylhexanoate (96228-29-4, 96228-30-7) → 6-<<(acetamidomethyl)thio>methyl>-4-hydroxy-4-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one (96228-35-2, 96228-36-3)

Conditions	Yield
With formic acid for 2h; Ambient temperature;	69.2%

N-(hydroxymethyl)acetamide (625-51-4) + 6-benzylthio-2-phenylimidazo<1,2-b>pyridazine (122479-61-2) → 3-acetamidomethyl-6-benzylthio-2-phenylimidazo<1,2-b>pyridazine

Conditions	Yield
With sulfuric acid In acetic acid for 14h; Heating;	66%

formaldehyd (50-00-0) + 1-methyl-4-nitrobenzene (99-99-0) + N-(hydroxymethyl)acetamide (625-51-4) → bis-(2-methyl-5-nitro-phenyl)-methane (86409-50-9) + N-(2-methyl-5-nitrobenzyl)acetamide (86392-53-2)

Conditions	Yield
In sulfuric acid at 55℃; for 8h;	A n/a B 65%

N-(hydroxymethyl)acetamide (625-51-4) + 6-fluoro-2-phenylimidazo<1,2-b>pyridazine (141409-04-3) → 3-acetamidomethyl-6-fluoro-2-phenylimidazo<1,2-b>pyridazine

Conditions	Yield
With sulfuric acid In acetic acid for 14h; Heating;	65%

N-(hydroxymethyl)acetamide (625-51-4) + thioacetic acid (507-09-5) → S-(acetylamino)methyl thioacetate (256471-73-5)

Conditions	Yield
	64%

N-(hydroxymethyl)acetamide (625-51-4) + potassium thioacetate (10387-40-3) → S-(acetylamino)methyl thioacetate (256471-73-5)

Conditions	Yield
With potassium carbonate at 40℃; for 70h; Inert atmosphere;	64%

(S)-10-hydroxycamptothecin (19685-09-7) + N-(hydroxymethyl)acetamide (625-51-4) → C23H21N3O6 (1352172-57-6)

Conditions	Yield
With sulfuric acid at 0 - 20℃; for 12h;	64%

N-(hydroxymethyl)acetamide (625-51-4) + 3-mercaptopropionic acid (107-96-0) → 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0)

Conditions	Yield
In trifluoroacetic acid for 0.5h; Ambient temperature;	62%

N-(hydroxymethyl)acetamide (625-51-4) + 6-chloro-2-(4'-chlorophenyl)imidazo<1,2-b>pyridazine (1844-56-0) → N-[6-Chloro-2-(4-chloro-phenyl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-acetamide

Conditions	Yield
With sulfuric acid In acetic acid for 14h; Heating;	62%

N-(hydroxymethyl)acetamide (625-51-4) + 2-(4-tert-Butyl-phenyl)-6-phenylsulfanyl-imidazo[1,2-b]pyridazine (180900-93-0) → N-[2-(4-tert-Butyl-phenyl)-6-phenylsulfanyl-imidazo[1,2-b]pyridazin-3-ylmethyl]-acetamide

Conditions	Yield
With sulfuric acid at 100℃; for 14h;	56%
With sulfuric acid In acetic acid for 14h; Heating;	56%

C23H24ClNS + N-(hydroxymethyl)acetamide (625-51-4) → C7H15ClN2OS

Conditions	Yield
Stage #1: C23H24ClNS With chlorotriisopropylsilane; trifluorormethanesulfonic acid; trifluoroacetic acid at 0℃; for 0.5h; Stage #2: N-(hydroxymethyl)acetamide at 0 - 20℃; for 2.5h;	55%

Upstream product

• 60-35-5 acetamide 
• 32516-05-5 3,7-diacetyl-1,3,5,7-tetraaza-bicyclo[3.3.1]nonane 
• 50-00-0 formaldehyd 
• 556-50-3 glycylglycine 

Downstream Products

• 100129-50-8 N-(3-chloro-6-hydroxy-2,4-dimethyl-benzyl)-acetamide 
• 33868-83-6 N-[(3,4-dimethoxy-phenylsulfanyl)-methyl]-acetamide 
• 89479-06-1 2,6-bis-(acetylamino-methyl)-4-chloro-phenol 
• 79-16-3 N-methyl-acetamide 
• 1066-51-9 Aminomethylphosphonic acid 
• 3708-33-6 (+/-)-N-acetyl-3-amino-1-phenylpropan-1-ol 
• 13157-53-4 2-methyl-6-phenyl-5,6-dihydro-4H-[1,3]oxazine 
• 19647-70-2 S-acetamidomethyl-L-cysteine 
• 38221-31-7 Dimethylaminomethyl-acetamid 
• 52574-08-0 3-{[(acetylamino)methyl]sulfanyl}-propionic acid 
• 60-35-5 acetamide 
• 50-00-0 formaldehyd 
• 1451816-28-6 C₂₁H₂₃N₃O₇S₂ 
• 19746-37-3 N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine 

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