14216-22-9

Basic information

• Product Name: N-Ethyl-D-glucamine
• Synonyms: 1-Deoxy-1-(ethylamino)-D-glucitol;N-ETHYLGLUCAMINE;N-ETHYL-D-GLUCAMINE;N-ethylgucamine;N-ETHYLGUCAMINE 99+%;1-(Ethylamino)-1-deoxy-D-glucitol;1-Ethylamino-1-deoxy-D-glucitol;(2R,3R,4R,5S)-6-(ethylamino)hexane-1,2,3,4,5-pentol
• CAS NO: 14216-22-9
• Molecular Formula: C₈H₁₉NO₅
• Molecular Weight: 209.24
• EINECS: 238-073-8
• Product Categories: INORGANIC & ORGANIC CHEMICALS;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 14216-22-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 136-140 °C
• Boiling Point: 489.8 °C at 760 mmHg
• Flash Point: 235.6 °C
• Appearance: /
• Density: 1.32 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: H2O: 0.1 g/mL, clear, colorless
• PKA: 13.51±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: N-Ethyl-D-glucamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Ethyl-D-glucamine(14216-22-9)
• EPA Substance Registry System: N-Ethyl-D-glucamine(14216-22-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• F: 3-10-23
• Hazardous Substances Data: 14216-22-9(Hazardous Substances Data)

Usage

Description

N-Ethyl-D-glucamine, an ethylated amino sugar derived from glucose, is a colorless powder with low vapor pressure and good thermal stability in air. It is known for its versatile applications across various industries due to its unique chemical properties.

Uses

Used in Self-Driven Microfluidic Methods:
N-Ethyl-D-glucamine is used as a component in self-driven microfluidic methods for patterning organic films directly in air. Its low vapor pressure and thermal stability contribute to the efficiency and reliability of this process.
Used in Pharmaceutical Industry:
N-Ethyl-D-glucamine is used as a buffering agent and stabilizer in the pharmaceutical industry. Its ability to form complexes with various compounds makes it suitable for improving the solubility and stability of drugs.
Used in Cosmetics Industry:
In the cosmetics industry, N-Ethyl-D-glucamine is used as a pH adjuster and viscosity modifier. Its mild nature and compatibility with other ingredients make it an ideal choice for formulating personal care products.
Used in Chemical Synthesis:
N-Ethyl-D-glucamine serves as an intermediate in the synthesis of various chemicals, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for the development of novel compounds with specific properties.
Used in Analytical Chemistry:
As a chelating agent, N-Ethyl-D-glucamine is used in analytical chemistry for the complexation of metal ions, which can aid in the separation and detection of various substances in analytical processes.

InChI:InChI=1/C8H19NO5/c1-2-9-3-5(11)7(13)8(14)6(12)4-10/h5-14H,2-4H2,1H3/t5-,6+,7+,8+/m0/s1

Synthetic route

D-glucose (50-99-7) + ethylamine (75-04-7) → N-ethyl-D-glucamine (14216-22-9)

Conditions	Yield
Stage #1: D-glucose; ethylamine With hydrogen In methanol at 25 - 35℃; for 0.5h; Stage #2: In methanol at 60 - 80℃; for 12h; Reagent/catalyst; Solvent; Sealed tube; Inert atmosphere;	95.69%
With nickel kieselguhr; water at 90 - 100℃; under 73550.8 Torr; Hydrogenation;
With nickel kieselguhr; water at 90 - 100℃; under 73550.8 Torr; Hydrogenation;

N-ethyl-D-glucosylamine → N-ethyl-D-glucamine (14216-22-9)

Conditions	Yield
With methanol; palladium on activated charcoal at 15 - 40℃; under 18387.7 Torr; Hydrogenation;

methanol (67-56-1) + D-glucose-ethylimine + palladium + coal → N-ethyl-D-glucamine (14216-22-9)

Conditions	Yield
at 15 - 40℃; under 18387.7 Torr; Hydrogenation;

N-ethyl-D-glucamine (14216-22-9) + m-tolyl aldehyde (620-23-5) → (2R,5S)-3-ethyl-2-(3-methylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	74%

N-ethyl-D-glucamine (14216-22-9) + 3-methoxy-benzaldehyde (591-31-1) → (2R,5S)-3-ethyl-2-(3-methoxyphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	74%

N-ethyl-D-glucamine (14216-22-9) + 4-methyl-benzaldehyde (104-87-0) → (2R,5S)-3-ethyl-2-(4-methylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	71%

N-ethyl-D-glucamine (14216-22-9) + C23H20ClNO4S → C31H38N2O9S

Conditions	Yield
In water; isopropyl alcohol at 80℃; for 13h;	59%

N-ethyl-D-glucamine (14216-22-9) + 4-nitrobenzaldehdye (555-16-8) → (5S)-3-ethyl-2-(4-nitrophenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In methanol; water Heating; Green chemistry;	52%

N-ethyl-D-glucamine (14216-22-9) + (4-isopropylbenzaldehyde) (122-03-2) → (2R,5S)-3-ethyl-2-(4-isopropylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	49%

N-ethyl-D-glucamine (14216-22-9) + chromium(III) trifluoride tetrahydrate + Ni(2+)*CO3(2-)*(x)H2O*2HO(1-)*Ni(2+) + Trimethylacetic acid (75-98-9) → [Cr7NiF3(N-ethyl-D-glucamine)(O2CtBu)15(H2O)]

Conditions	Yield
Stage #1: N-ethyl-D-glucamine; chromium(III) trifluoride tetrahydrate; Trimethylacetic acid at 160℃; for 2h; Stage #2: Ni(2+)*CO3(2-)*(x)H2O*2HO(1-)*Ni(2+) at 160℃; for 50h;	43%

manganese(II)carbonate + N-ethyl-D-glucamine (14216-22-9) + chromium(III) trifluoride tetrahydrate + Trimethylacetic acid (75-98-9) → [Cr7MnF3(N-ethyl-D-glucamine)(O2CtBu)15(H2O)]

Conditions	Yield
Stage #1: N-ethyl-D-glucamine; chromium(III) trifluoride tetrahydrate; Trimethylacetic acid at 160℃; for 2h; Stage #2: manganese(II)carbonate at 160℃; for 50h;	42%

N-ethyl-D-glucamine (14216-22-9) + chromium(III) trifluoride tetrahydrate + zinc(II) carbonate (743369-26-8) + Trimethylacetic acid (75-98-9) → [Cr7ZnF3(N-ethyl-D-glucamine)(O2CtBu)15(H2O)]

Conditions	Yield
Stage #1: N-ethyl-D-glucamine; chromium(III) trifluoride tetrahydrate; Trimethylacetic acid at 160℃; for 2h; Stage #2: zinc(II) carbonate at 160℃; for 50h;	38%

N-ethyl-D-glucamine (14216-22-9) + 2,4-dimethylbenzaldehyde (15764-16-6) → (2S,5S)-2-(2,4-dimethylphenyl)-3-ethyl-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	35%

N-ethyl-D-glucamine (14216-22-9) + 4-ethylbenzylaldehyde (4748-78-1) → (2R,5S)-3-ethyl-2-(4-ethylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	30%

carbon disulfide (75-15-0) + N-ethyl-D-glucamine (14216-22-9) → ethyl-D-fructos-1-yl-dithiocarbamic acid (10225-80-6)

N-ethyl-D-glucamine (14216-22-9) + cridanimod (38609-97-1) → 1-desoxy-1-(ethylamino)-D-glucitole salt of 10-(carboxymethyl)-9(10H)acridone (937021-67-5)

Conditions	Yield
In water for 0.416667 - 0.583333h; Heating / reflux;

Elinogrel + N-ethyl-D-glucamine (14216-22-9) → [4-(6-chloro-7-methylamino-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-5-chloro-thiophen-2-yl-sulfonylurea N-ethylglucamine salt (1079989-99-3)

Conditions	Yield
In water for 2h;

PD 126055 + N-ethyl-D-glucamine (14216-22-9) → (S)-2-(diphenylacetyl)-1,2,3,4-tetrahydro-6-methoxy-5-(phenylmethoxy)-3-isoquinoline carboxylic acid, N-ethylglucamine salt

Conditions	Yield
In isopropyl alcohol at 5 - 50℃; for 5.5h; Product distribution / selectivity;

N-ethyl-D-glucamine (14216-22-9) + 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) → 4',5,7-trihydroxyisoflavone-5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one N-ethylglucamine salt

Conditions	Yield
at 20 - 25℃; for 24h;

N-ethyl-D-glucamine (14216-22-9) + methyl n-dodecanoate (111-82-0) → n-dodecanoyl-N-ethyl-glucamide

Conditions	Yield
With sodium hydroxide In propylene glycol at 95 - 120℃; under 750.075 - 9750.98 Torr; for 1.2h;

N-ethyl-D-glucamine (14216-22-9) + 2-[bis-(2-pyridylmethyl)aminomethyl]pyridine-5-carboxylic acid (440367-79-3) → 6-((bis(pyridin-2-ylmethyl)amino)methyl)-N-ethyl-N-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)nicotinamide

Conditions	Yield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 50℃; for 18h;	0.135 g

N-ethyl-D-glucamine (14216-22-9) + tranilast → tranilast N-ethylglucamine salt

Conditions	Yield
In acetone at 20℃; for 24h;

N-ethyl-D-glucamine (14216-22-9) + 4-methoxy-benzaldehyde (123-11-5) → (2R,5S)-3-ethyl-2-(4-methoxyphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;

N-ethyl-D-glucamine (14216-22-9) + 4-nitrobenzaldehdye (555-16-8) → (2R,5S)-3-ethyl-2-(4-nitrophenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine + (2S,5S)-3-ethyl-2-(4-nitrophenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux; Overall yield = 82 percent;	A n/a B n/a

N-ethyl-D-glucamine (14216-22-9) + 2-chloro-benzaldehyde (89-98-5) → (2R,5S)-2-(2-chlorophenyl)-3-ethyl-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine + (2S,5S)-2-(2-chlorophenyl)-3-ethyl-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	A n/a B n/a

N-ethyl-D-glucamine (14216-22-9) + 2-methylphenyl aldehyde (529-20-4) → (2R,5S)-3-ethyl-2-(2-methylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutil)oxazolidine + (2S,5S)-3-ethyl-2-(2-methylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutil)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux; Overall yield = 63 percent;	A n/a B n/a

N-ethyl-D-glucamine (14216-22-9) + 3-Fluorobenzaldehyde (456-48-4) → (2R,5S)-3-ethyl-2-(3-fluorophenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine + (2S,5S)-3-ethyl-2-(3-fluorophenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux; Overall yield = 31 percent;	A n/a B n/a

N-ethyl-D-glucamine (14216-22-9) + 4-methyl-benzaldehyde (104-87-0) → (5S)-3-ethyl-2-(4-methylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene / Dean-Stark; Reflux 2: dimethylsulfoxide-d6 / 336 h View Scheme

Upstream product

• 50-99-7 D-glucose 
• 75-04-7 ethylamine 
• 67-56-1 methanol 

Downstream Products

• 1079989-99-3 [4-(6-chloro-7-methylamino-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-5-chloro-thiophen-2-yl-sulfonylurea N-ethylglucamine salt 

Relevant articles and documents

Preparation method N- ethyl -D- glucosamine (by machine translation)

The method is characterized by N - sequentially comprising the following steps, firstly, dissolving glucose in an :(1) alcohol solvent, ∶ for ∶ hours=1 ∶ (2-10) ∶ (1-1.1), to obtain ethyl - D D- glucosamine, and then, feeding the hydrogen pressure to 35-55 °C, at 0.5-1 a ;(2) temperature and, keeping hours. The reaction system comprises the following steps ∶: firstly, dissolving glucose (1)=1 ∶ (0.02-0.1), in an alcohol solvent at a temperature of, DEG C and maintaining 0.5-3.0Mpa, a, hydrogen 50-100 °C gas ;(3) with a 12 mass, ratio, ?20000, glucose N - to Step after, the reaction is completed by a mass ratio glucose alcohol solvent-ethylamine to a reaction system in a reaction system with a mass ratio, of the following components10,sup. (by machine translation)

Process for the resolution of d,1 2-(6-methoxy-2-naphthyl)propionic acid

Mixtures of d 2-(6-methoxy-2-naphthyl)propionic acid and 1 2-(6-methoxy-2-naphthyl)propionic acid or soluble salts thereof are resolved with N-R-D-glucamine or salts thereof, where R is alkyl having 2 to 36 carbon atoms or cycloalkyl having 3 to 8 carbon atoms, to yield a product substantially enriched in d 2-(6-methoxy-2-naphthyl)propionic acid.