Conditions | Yield |
---|---|
With hydrogen; sodium hydroxide; sodium tetrachloropalladate(II) In methanol at 30℃; for 1h; Product distribution; donor: cyclohexene; deprotecting of various N-protected amino acids and dipeptides by subjecting then to hydrogen transfer with several palladium catalysts supported on different solids; | 100% |
With hydrogen; hydroxyapatite-bound Pd In methanol at 40℃; for 2h; | 94% |
With palladium 10% on activated carbon; hydrogen at 20℃; for 24h; Neat (no solvent); | 90% |
With hydrogen; K3[Co(CN)5] In methanol at 20℃; for 3h; | 86% |
With ethylenediaminetetraacetic acid; phenylmethylsulphonyl fluoride; water In aq. phosphate buffer at 30℃; Kinetics; Reagent/catalyst; Microbiological reaction; Enzymatic reaction; |
ammonium chloroacetate
glycine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In methanol at 62 - 67℃; for 4.5h; Temperature; Reagent/catalyst; Solvent; | 99.1% |
at 19.9℃; under 45003600 Torr; Product distribution; under shear deformation (360 deg); | 1.05% |
Conditions | Yield |
---|---|
With hexamethylenetetramine; N,N-diethylbenzylamine; ammonia In methanol at 60 - 65℃; for 4.5h; pH=7.1; | 97.1% |
With hexamethylenetetramine; ammonia In water at 70℃; for 0.333333h; pH=7; Substitution; | 86% |
With ammonium bicarbonate; urea In water at 115℃; Green chemistry; | 78% |
Conditions | Yield |
---|---|
With aluminum oxide at 75℃; for 0.0666667h; microwave irradiation; | 95% |
With hydrogen; K3[Co(CN)5] In methanol at 20℃; for 3h; | 90% |
With hydrogen In methanol |
Conditions | Yield |
---|---|
Stage #1: glycinamide hydrochloride With sodium hydroxide In water Stage #2: In water at 130℃; for 1h; Reagent/catalyst; | 94.5% |
Conditions | Yield |
---|---|
With tetradecyl(trihexyl)phosphonium bistriflamide; trifluoroacetic acid at 130℃; for 0.116667h; Ionic liquid; | 93% |
With methanol; Amberlyst 15; ammonia 1.) CH2Cl2, 25 deg C, 5 h, 2.) 50 min; Yield given. Multistep reaction; | |
With trifluoroacetic acid In dichloromethane at 20℃; for 1h; | |
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 3h; |
C8H14BOCOCH2NH2
glycine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 20℃; for 0.5h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With formic acid; triphenylphosphine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 30℃; for 1h; | A n/a B 90% |
Conditions | Yield |
---|---|
With iron sulfide; ammonium carbonate In water at 100℃; for 144h; | 86% |
Conditions | Yield |
---|---|
With sodium hydroxide; sodium dithionite | 85% |
Conditions | Yield |
---|---|
With iron sulfide; ammonium carbonate In water at 100℃; for 144h; | 80% |
With ammonia; water; palladium Hydrogenation; | |
With ethylenediaminetetraacetic acid; cetyltrimethylammonium chloride; N-Phenylglycine; DPL at 30℃; Product distribution; potassium phosphate buffer (pH 7.8); variation of incubation time, pH and DPL concentration; |
Conditions | Yield |
---|---|
With dmap | 75% |
glycine methylamide
glycine
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide | 75% |
Conditions | Yield |
---|---|
With sodium hydrogen telluride In N,N-dimethyl-formamide at 70℃; for 2h; | 74% |
(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-acetic acid
A
3,5-Dinitro-1-phenyl-1H-pyridin-4-one
B
glycine
Conditions | Yield |
---|---|
With aniline In pyridine; water Ambient temperature; | A n/a B 70% |
Conditions | Yield |
---|---|
With ammonium bicarbonate Ambient temperature; detonation; also with (NH4)2CO3; | 67% |
Conditions | Yield |
---|---|
With water In aq. buffer at 10 - 30℃; for 300h; pH=11; Kinetics; Mechanism; Inert atmosphere; Electrolysis; | A 10% B 65% |
Conditions | Yield |
---|---|
With potassium hydroxide; [bis(acetoxy)iodo]benzene at 0 - 5℃; for 1.5h; | A 62% B n/a |
glycine phenacyl ester
A
Glycine anhydride
B
1-phenyl-2-hydroxyethanone
C
glycine
Conditions | Yield |
---|---|
With triethylamine hydrochloride In N,N-dimethyl-formamide for 24h; Product distribution; Ambient temperature; | A 55% B n/a C 39% |
Conditions | Yield |
---|---|
In water at 10 - 20℃; for 1.5h; Product distribution; Mechanism; electrolysis; | 50% |
Conditions | Yield |
---|---|
With lithium hydroxide In ethanol for 20h; Ambient temperature; Title compound not separated from byproducts; | A 50% B n/a |
A
N-benzyloxycarbonyl-L-leucine methyl ester
B
glycine
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether Yields of byproduct given; | A 48% B n/a |
formic acid
1-amino-2-propene
A
propylamine
B
DL-3-aminoisobutyric acid
C
glycine
D
3-amino propanoic acid
E
4-amino-n-butyric acid
Conditions | Yield |
---|---|
With hydrogen; oxygen In water for 3h; Product distribution; various unsaturated amines; investigation of the direct carboxylation of C=C bond, the effect of formic acid concentration as well as the flame composition on product(s); radical mechanism is proposed; | A n/a B 38% C n/a D n/a E 5% |
formic acid
1-amino-2-propene
A
DL-3-aminoisobutyric acid
B
glycine
C
3-amino propanoic acid
D
4-amino-n-butyric acid
Conditions | Yield |
---|---|
With hydrogen; oxygen In water for 3h; Further byproducts given; | A 38% B n/a C n/a D 5% |
L-alanin
formamide
A
L-serin
B
L-asparagine
C
glycine
Conditions | Yield |
---|---|
With sulfuric acid In water for 2h; Concentration; Electrolysis; Inert atmosphere; | A n/a B 27% C n/a |
glycine
Conditions | Yield |
---|---|
With hydrogenchloride In acetic acid at 100℃; for 48h; biomimetic reduction; | 22% |
Conditions | Yield |
---|---|
for 0.0472222h; microwave irradiation; | 100% |
98% | |
With triethylamine In toluene for 6h; Heating; | 98.9% |
Conditions | Yield |
---|---|
In methanol for 6h; Reflux; | 100% |
In methanol for 16h; Inert atmosphere; Reflux; | 97% |
at 20℃; for 2h; | 91% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0 - 20℃; | 100% |
With potassium carbonate In tetrahydrofuran; water at 20℃; for 12h; | 96% |
Stage #1: glycine With sodium hydroxide In water Inert atmosphere; Stage #2: benzyl chloroformate In water at 0℃; for 0.833333h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 110℃; for 0.666667h; | 100% |
In N,N-dimethyl-formamide at 153℃; for 0.333333h; futher solvents, further temperatures, further reaction times; | 97% |
Stage #1: formic acid With acetic anhydride at 45℃; for 1h; Inert atmosphere; Stage #2: glycine at 20℃; for 72h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With thionyl chloride | 100% |
With thionyl chloride at -5℃; for 3h; Heating / reflux; | 86.7% |
With thionyl chloride at -5℃; for 3h; Heating / reflux; | 86.7% |
glycine
benzene-1,3-dicarbonyl dichloride
[(3-{[(carboxymethyl)amino]carbonyl}benzoyl)amino]acetic acid
Conditions | Yield |
---|---|
Stage #1: glycine With sodium hydroxide In water at 10℃; Cooling with ice; Stage #2: benzene-1,3-dicarbonyl dichloride In water; toluene for 1h; pH=1; | 100% |
With sodium hydroxide In diethyl ether | 87% |
With sodium hydroxide | |
With sodium hydroxide |
Conditions | Yield |
---|---|
With sodium hydroxide In glycerol at 120℃; for 1h; | 100% |
With ammonia; sodium | |
With ethanol; sodium |
ethyl acetoacetate
glycine
potassium α-methyl-β-ethoxycarbonylethenylaminoacetate
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 40℃; | 100% |
With potassium hydroxide In methanol for 1h; Heating; | 97% |
Conditions | Yield |
---|---|
With acetyl chloride at 0 - 20℃; | 100% |
Stage #1: methanol With thionyl chloride for 1h; Cooling with ice; Stage #2: glycine at 20 - 66℃; for 6.5h; | 100% |
With thionyl chloride at 0℃; Reflux; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane at 0 - 4℃; for 24h; Inert atmosphere; | 100% |
With thionyl chloride at 0 - 65℃; for 4.25h; | 100% |
With thionyl chloride at 0 - 65℃; for 4.25h; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane; water at 20℃; for 12h; | 100% |
Stage #1: glycine With sodium hydroxide In 1,4-dioxane; water at 0℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 0 - 20℃; | 100% |
With sodium hydroxide In 1,4-dioxane | 100% |
Conditions | Yield |
---|---|
In water at 30℃; for 24h; pH = 6.6; | 100% |
at 30℃; Rate constant; Mechanism; Product distribution; pH = 9.1; other pH values; other aminoacids; | |
With phosphate buffer pH 6.5; bovine serum In water Rate constant; Ambient temperature; pH range of 3.0 - 9.0; |
ethyl ester of p-toluenesulfonic acid
glycine
toluene-4-sulfonic acid salt of ethyl glycinate
Conditions | Yield |
---|---|
In ethanol for 36h; Esterification; Heating; | 100% |
diethyl 2-bromoethylphosphonate
glycine
N-(2-diethylphosphonylethyl)glycine
Conditions | Yield |
---|---|
With potassium carbonate In water at 80℃; for 3h; | 100% |
Conditions | Yield |
---|---|
Stage #1: benzyl bromide; glycine With potassium hydroxide In ethanol; water at 25℃; for 16h; Stage #2: With potassium hydroxide In ethanol; water for 0.5h; reflux; | 100% |
glycine
4,6,4',6'-tetrachloro-2,2'-(3,6-dioxa-octane-1,8-diyldioxy)-bis-[1,3,5]triazine
Conditions | Yield |
---|---|
With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; | 100% |
6-chloro-N-methylisatoic anhydride
glycine
7-chloro-1-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione
Conditions | Yield |
---|---|
Stage #1: 6-chloro-N-methylisatoic anhydride; glycine With acetic acid at 130℃; for 7h; Stage #2: With sodium hydroxide; water; sodium hydrogencarbonate pH=~ 9 - 10; | 100% |
With acetic acid at 130℃; for 7h; | |
With acetic acid at 130℃; for 7h; |
Conditions | Yield |
---|---|
at 200℃; for 0.05h; Product distribution / selectivity; Microwave irradiation (300 W); | 100% |
L-leucine
L-phenylalanine
L-tyrosine
glycine
H-Tyr-Gly-Gly-Phe-Leu-NH2
Conditions | Yield |
---|---|
Stage #1: L-tyrosine With BF4(1-)*C7H13N3Pol(1+); benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 25℃; for 1h; Ionic liquid; Automated synthesizer; solid phase reaction; Stage #2: glycine In 1-methyl-pyrrolidin-2-one at 25℃; for 1h; Ionic liquid; Automated synthesizer; solid phase reaction; Stage #3: L-leucine; L-phenylalanine Further stages; | 100% |
Conditions | Yield |
---|---|
Stage #1: glycine With sodium hydroxide In water Stage #2: S-ethyl-N'-ethylisothiourea hydroiodide In diethyl ether; water at 0℃; for 42.15h; | 100% |
(bis-2-cyclopentadienylethoxybenzene)titanium dichloride
glycine
(bis-2-cyclopentadienylethoxybenzene)titanium bisglycine
Conditions | Yield |
---|---|
In methanol; water at 20℃; for 4h; Glovebox; | 100% |
glycine
Conditions | Yield |
---|---|
Stage #1: nickel(II) acetate tetrahydrate; (R)-N-(2-benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)-methyl]-2-pyrrolidinecarboxamide hydrochloride; glycine In methanol at 20℃; Stage #2: With sodium carbonate In methanol at 65℃; | 100% |
Conditions | Yield |
---|---|
With triethylamine In water; acetonitrile for 67h; | 100% |
((S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)pyrrolidine-2-carboxamide)
nickel diacetate
glycine
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 50℃; | 100% |
Conditions | Yield |
---|---|
With sodium carbonate In water for 5h; | 99.61% |
With sodium carbonate In water for 4h; | 99.61% |
With zinc oxide-nanoparticle at 50℃; for 2h; Neat (no solvent); chemoselective reaction; | 95% |
Conditions | Yield |
---|---|
With sodium carbonate In water for 5h; | 99.34% |
With sodium carbonate In water for 4h; | 99.34% |
With triethylamine In tetrahydrofuran; water at 0 - 20℃; for 4h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With tetramethyl ammoniumhydroxide In water at 10 - 50℃; Heating / reflux; | 99.3% |
With sodium hydroxide; water at 100℃; for 24h; Alkylation; | 94% |
With sodium hydroxide |
tetramethyl ammoniumhydroxide
acrylonitrile
glycine
[N,N-Bis(2-cyanoethyl)]-glycine
Conditions | Yield |
---|---|
In water; acetone | 99.3% |
glycine
4-chloro-3-nitro-chromen-2-one
N-(3-nitrocoumarin-4-yl)glycine
Conditions | Yield |
---|---|
With triethylamine In ethanol for 6h; Ambient temperature; | 99.2% |
In the USA, glycine is typically sold in two grades: USP ("United States Pharmacopeia"), and technical grade.the two grades have diverse uses.
Pharmaceutical grade Glycine (CAS NO.56-40-6) is use in some pharmaceutical applications, such as intravenous injections, where the customer's purity requirements often exceed the minimum required under the USP grade designation.
Technical grade glycine, which may or may not meet USP grade standards, often use in industrial applications; such as an agent in metal complexing and finishing.
1. Introduction of Glycine
Glycine, with the IUPAC Name of 2-Aminoacetic acid, is one kind of white crystalline powder. This chemical belongs to the Classification Code which include Component of irrigating solution; Glycine Agents; Mutation data; Neurotransmitter Agents.
2. Properties of Glycine
Glycine has the following property datas: (1)Melting point: 240 °C; (2)Index of Refraction: 1.46; (3)Molar Refractivity: 16.41 cm3; (4)Molar Volume: 59.8 cm3; (5)Surface Tension: 54.4 dyne/cm; (6)Density: 1.254 g/cm3; (7)Flash Point: 99.5 °C; (8)Enthalpy of Vaporization: 52.63 kJ/mol; (9)Boiling Point: 240.9 °C at 760 mmHg; (10)Vapour Pressure: 0.0123 mmHg at 25°C.
3. Structure Descriptors of Glycine
You could convert the following datas into the molecular structure:
InChI: InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
InChIKey: InChIKey=DHMQDGOQFOQNFH-UHFFFAOYSA-N
Smiles: C(=O)(CN)O
4. Uses of Glycine
Glycine has many uesage:
1).Animal and human foodstuffs:
use an additive in pet food and animal feed. For humans, glycine is used as a sweetener/taste enhancer. such as Food supplements and protein drinks.some drug formulations use glycine to improve gastric absorption.
2).Chemical feedstock
Glycine is an intermediate in the synthesis of a variety of chemical products. It is used in the manufacture of the herbicide Glyphosate. Glyphosate (N-(phosphonomethyl) glycine) is a non-selective systemic herbicide used to kill weeds, especially perennials and broadcast or used in the cut-stump treatment as a forestry herbicide. Initially, Glyphosate was sold only by Monsanto under the Monsanto tradename Roundup, but is no longer under patent
3).Cosmetics and other applications:
Glycine can be used as a buffering agent in analgesics, antacids, cosmetics, antiperspirants, and toiletries.Many products use glycine or its derivatives, such as the production of rubber sponge products, fertilizers, metal complexants.
5. Safety information of Glycine
Risk Statements of Glycine (CAS NO.56-40-6): 33
R33: Danger of cumulative effects.
Safety Statements: 22-24/25
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
6. Production of Glycine
Glycine (CAS NO.56-40-6)e is manufactured by treating chloroacetic acid with ammonia industrially
ClCH2COOH + 2 NH3 → H2NCH2COOH + NH4Cl
It also can be produced via the Strecker amino acid synthesis.
7. Toxicity information of Glycine
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | intravenous | 3gm/kg (3000mg/kg) | BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA | Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 31, Pg. 306, 1942. |
mouse | LD50 | intraperitoneal | 4450mg/kg (4450mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 1502, 1977. | |
mouse | LD50 | intravenous | 2370mg/kg (2370mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 1502, 1977. | |
mouse | LD50 | oral | 4920mg/kg (4920mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 1502, 1977. | |
mouse | LD50 | subcutaneous | 5060mg/kg (5060mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 1502, 1977. | |
rat | LD50 | intravenous | 2600mg/kg (2600mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 1502, 1977. | |
rat | LD50 | oral | 7930mg/kg (7930mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 1502, 1977. | |
rat | LD50 | subcutaneous | 5200mg/kg (5200mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 1502, 1977. |
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