Glycine ethyl ester hydrochloride
- Iupac Name：ethyl 2-aminoacetate;hydrochloride
- CAS No.: 623-33-6
- Molecular Weight：139.579
- Modify Date.: 2023-02-28 08:56
- Introduction: As a Glycine (G615990) ester, Glycine ethyl ester hydrochloride can be used as parakeratosis inhibitor and external composition for skin.
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1. Names and Identifiers
- 1.1 Name
- Glycine ethyl ester hydrochloride
- 1.2 Synonyms
2-Aminoacetic acid ethyl·hydrochloride 2-Ethoxy-2-oxoethanaminium EINECS 210-787-4 Ethanaminium, 2-ethoxy-2-oxo- Ethyl 2-aminoacetate, hydrochloride ethyl 2-aminoacetate,hydrochloride Ethyl glycinate hydrochloride glycine ethyhydnchlordeester glycine, ethyl ester, conjugate acid Glycineethylester·HCl,Glycineethylesterhydrochloride Glycineethylesterhydrochlor Glycocollethylesterhydrochloride H-Gly-OEt·HCl H-Gly-OEt.HCl MFCD00012871 usafdo-10
- 1.3 CAS No.
- 623-33-6
- 1.4 CID
- 2723640
- 1.5 EINECS(EC#)
- 210-787-4
- 1.6 Molecular Formula
- C4H10ClNO2 (isomer)
- 1.7 Inchi
- InChI=1S/C4H9NO2.ClH/c1-2-7-4(6)3-5;/h2-3,5H2,1H3;1H
- 1.8 InChkey
- TXTWXQXDMWILOF-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CCOC(=O)CN.Cl
- 1.10 Isomers Smiles
- CCOC(=O)CN.Cl
2. Properties
- 2.1 Density
- 1
- 2.1 Melting point
- 145-148℃
- 2.1 Boiling point
- 109.5 °C at 760 mmHg
- 2.1 Flash Point
- -14.4±17.4 °C (Predicted)
- 2.1 Precise Quality
- 139.04000
- 2.1 PSA
- 52.32000
- 2.1 logP
- 1.01050
- 2.1 Solubility
- >1000 g/L (20 °C)
- 2.2 Appearance
- White Crystalline Powder
- 2.3 Storage
- Hygroscopic. Store under Nitrogen. Ambient temperatures.
- 2.4 Chemical Properties
- Crystalline
- 2.5 Color/Form
- White
- 2.6 Odor
- Odorless
- 2.7 PH
- 2.9 (10g/l, H2O, 20℃)
- 2.8 pKa
- pK1:7.66(＋1) (25°C)
- 2.9 Water Solubility
- H2O: >1000 g/L (20 oC)
- 2.10 Stability
- Stable under normal temperatures and pressures.
- 2.11 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- Can be prepared with glycine or chloroacetic acid as raw materials.?It is described as follows.?Glycine is used as the raw material method. Dry hydrogen chloride gas is passed into absolute ethanol to make hydrogen chloride ethanol solution, then glycine is added, heated and stirred for esterification, and the reaction temperature is controlled at 80-85°C. After all the glycine is dissolved, stirring A few minutes, while hot, move the reaction solution to the crystallization pot, cool the crystallization, and filter to obtain ethyl glycine hydrochloride.?Reaction equation: NH2CH2COOH+C2H5O[HCl]→NH2CH2COOC2H5·HCl can also be added to the reactor with stirring glycine and absolute ethanol, heated to 60 ℃, through the introduction of hydrogen chloride gas, hydrogen chloride until the reactants are completely dissolved, continue After passing hydrogen chloride to recrystallization, it is the end point. The reaction solution is transferred to the crystallization pot, while stirring, the crystal is cooled and filtered, washed with absolute ethanol, and dried to obtain ethyl glycine hydrochloride.?Chloroacetic acid is used as the raw material method. Chloroacetic acid, urotropine and absolute ethanol are added to the reactor. At 45℃, ammonia gas is passed to make pH=8～8.5. The rate of ammonia gas is controlled to maintain the reaction temperature at Between 40 and 65°C, after the ammonia gas has been passed through, the reaction is held at 65°C for 1 hour, then the temperature is reduced to 30°C, and the hydrogen chloride-anhydrous ethanol solution is added dropwise.?After the dropwise addition, react at 70℃ for 2h, then filter hot at 62～65℃ to separate the ammonium chloride crystals. The filtrate is placed in a crystallization pot, cooled to 10℃, crystallized while stirring, the crystals are filtered, Dry to give ethyl glycine hydrochloride.?Reaction equation: ClCH2COOH+NH3[ethanol]→NH2CH2COOH[C2H5OH]→[HCl]NH2CH2COOH·HCl
- 3.2 Purification Methods
- Crystallise it from absolute EtOH or EtOH/Et2O. [Marvel Org Synth Coll Vol II 310 1943, Beilstein 4 II 780, 4 III 3 75.] Glycine ethyl ester hydrochloride Preparation Products And Raw materials Raw materials
- 3.3 Usage
- As a Glycine (G615990) ester, Glycine ethyl ester hydrochloride can be used as parakeratosis inhibitor and external composition for skin.
4. Safety and Handling
- 4.1 Symbol
- GHS05
- 4.1 Hazard Codes
- Xi; Xi
- 4.1 Signal Word
- Danger
- 4.1 Risk Statements
- R41
- 4.1 Safety Statements
- S24/25
- 4.1 Hazard Declaration
- H318
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P280-P305 + P351 + P338
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- MC0525000
- 4.1 Report
-
Reported in EPA TSCA Inventory.
- 4.2 Safety
-
Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx, HCl, and Cl?.
Hazard Codes:?
Xi
Risk Statements: 41
R41:Risk of serious damage to the eyes.
Safety Statements: 26-39-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S39:Wear eye / face protection.?
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: MC0525000
HS Code: 29224995
- 4.3 Sensitive
- Hygroscopic
- 4.4 Specification
-
?Glycine ethyl ester hydrochloride , with CAS number of 623-33-6, can be called Glycineethylesterhydrochlor ; Glycocollethylesterhydrochloride ; usafdo-10 ; H-gly-oet HCl ; Glycine ethyl ester ; Glycine ethyl ester HCl ; Glycine ethyl ester hydrochloride ; Glycine-oet HCl .
?Glycine ethyl ester hydrochloride (CAS NO.623-33-6) is pesticide and pharmaceutical intermediates, also used in biochemical research. It?has been prepared by the action of absolute alcohol and hydrogen chloride on glycine;from glycyl chloride and alcohol;by the action of ammonia or hexamethylenetetramine on chloroacetic acid, and subsequent hydrolysis with alcoholic hydrochloric acid; by the action of hydrogen chloride and alcohol onmethyleneaminoacetonitrile;and by the reduction of ethyl cyanoformate or the corresponding imido ester hydrochloride.
- 4.5 Toxicity
-
| 1. |
??? |
ipr-mus LD50:750?mg/kg
|
??? |
NTIS** ?? National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 . |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Serious eye damage, Category 1
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Danger |
| Hazard statement(s) | H318 Causes serious eye damage |
| Precautionary statement(s) | |
| Prevention | P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| Response | P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
623-33-6Total: 18 Synthesis Route
9. Other Information
- 9.0 Usage
- Glycine ethyl ester (GEE) is used in conjunction with N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide (EDC) for carboxyl-foot printing studies of proteins. The GEE/EDC protocol effects specific derivatization of glutamate and aspartate carboxyl side chains on intact proteins. This reaction is readily done under aqueous conditions at physiological pH. It is mainly used as a pharmaceutical raw material. Glycine ethyl ester hydrochloride is an important intermediate for preparing chrysanthemic acid or two chlorine chrysanthemic acid and is mainly used in the synthesis of anti-inflammatory drugs, but also can be used for the synthesis of four imidazole acetic acid.
- 9.1 BRN
- 3594034
- 9.2 Chemical Properties
- Crystalline
- 9.3 Uses
- As a Glycine (G615990) ester, Glycine ethyl ester hydrochloride can be used as parakeratosis inhibitor and external composition for skin.
- 9.4 Purification Methods
- Crystallise it from absolute EtOH or EtOH/Et2O. [Marvel Org Synth Coll Vol II 310 1943, Beilstein 4 II 780, 4 III 3 75.]
- 9.5 Storage Conditions
- Can be prepared with glycine or chloroacetic acid as raw materials.?It is described as follows.?Glycine is used as the raw material method. Dry hydrogen chloride gas is passed into absolute ethanol to make hydrogen chloride ethanol solution, then glycine is added, heated and stirred for esterification, and the reaction temperature is controlled at 80-85°C. After all the glycine is dissolved, stirring A few minutes, while hot, move the reaction solution to the crystallization pot, cool the crystallization, and filter to obtain ethyl glycine hydrochloride.?Reaction equation: NH2CH2COOH+C2H5O[HCl]→NH2CH2COOC2H5·HCl can also be added to the reactor with stirring glycine and absolute ethanol, heated to 60 ℃, through the introduction of hydrogen chloride gas, hydrogen chloride until the reactants are completely dissolved, continue After passing hydrogen chloride to recrystallization, it is the end point. The reaction solution is transferred to the crystallization pot, while stirring, the crystal is cooled and filtered, washed with absolute ethanol, and dried to obtain ethyl glycine hydrochloride.?Chloroacetic acid is used as the raw material method. Chloroacetic acid, urotropine and absolute ethanol are added to the reactor. At 45℃, ammonia gas is passed to make pH=8～8.5. The rate of ammonia gas is controlled to maintain the reaction temperature at Between 40 and 65°C, after the ammonia gas has been passed through, the reaction is held at 65°C for 1 hour, then the temperature is reduced to 30°C, and the hydrogen chloride-anhydrous ethanol solution is added dropwise.?After the dropwise addition, react at 70℃ for 2h, then filter hot at 62～65℃ to separate the ammonium chloride crystals. The filtrate is placed in a crystallization pot, cooled to 10℃, crystallized while stirring, the crystals are filtered, Dry to give ethyl glycine hydrochloride.?Reaction equation: ClCH2COOH+NH3[ethanol]→NH2CH2COOH[C2H5OH]→[HCl]NH2CH2COOH·HCl
- 9.6 Mesh Entry Terms
- ethyl glycinate
- 9.7 Manufacturing Info
- Glycine, ethyl ester, hydrochloride (1:1): ACTIVE
10. Computational chemical data
- Molecular Weight: 139.579g/mol
- Molecular Formula: C4H10ClNO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 139.0400063
- Monoisotopic Mass: 139.0400063
- Complexity: 62.7
- Rotatable Bond Count: 3
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 52.3
- Heavy Atom Count: 8
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 2
- CACTVS Substructure Key Fingerprint: AAADccBiMAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQAAAAAADhgAYCCABABAAIAACQCAAAAAAAAAAAAICAAAACAAAAAAADAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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