[ CAS No. 298-12-4 ] {[proInfo.proName]}

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Quality Control of [ 298-12-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 298-12-4 ]

SDS Specification

Alternatived Products of [ 298-12-4 ]

Product Citations

Electrosynthesis of amino acids from biomass-derived α-hydroxyl acids

Kaili Yan ; Morgan L. Huddleston ; Brett A. Gerdes , et al. Green Chem.,2022,24(13):5320-5325. DOI: 10.1039/D2GC01779B

Abstract: Electrochemical conversion of biomass-derived intermediate compounds to high-value products has emerged as a promising approach in the field of biorefinery. Biomass upgrading allows for the production of chemicals from non-fossil-based carbon sources and capitalization on electricity as a green energy input. Amino acids, as products of biomass upgrading, have received relatively little attention. Pharmaceutical and food industries will benefit from an alternative strategy for the production of amino acids that does not rely on inefficient fermentation processes. The use of renewable biomass resources as starting materials makes this proposed strategy more desirable. Herein, we report an electrochemical approach for the selective oxidation of biomass-derived α-hydroxyl acids to α-keto acids, followed by electrochemical reductive amination to yield amino acids as the final products. Such a strategy takes advantage of both reactions at the anode and cathode and produces amino acids under ambient conditions with high energy efficiency. A flow electrolyzer was also successfully employed for the conversion of α-hydroxyl acids to amino acids, highlighting its great potential for large-scale application.

Purchased from AmBeed: 611-73-4 ; 2835-06-5 ; 302-72-7 ; 61-90-5 ; 56-40-6 ; 156-06-9 ; 90-64-2 ; 298-12-4 ; 498-36-2 ; 79-14-1 ; 127-17-3 ; 828-01-3 ; 50-21-5 ; 816-66-0

Product Details of [ 298-12-4 ]

CAS No. :	298-12-4	MDL No. :	MFCD00006958
Formula :	C₂H₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HHLFWLYXYJOTON-UHFFFAOYSA-N
M.W :	74.04	Pubchem ID :	760
Synonyms :	Glyoxalic acid;NSC 27785;Oxalaldehydic acid;Formylformic acid	Chemical Name :	2-Oxoacetic acid

Calculated chemistry of [ 298-12-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	5
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	13.7
TPSA :	54.37 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.98 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-0.09
Log Po/w (XLOGP3) :	-0.32
Log Po/w (WLOGP) :	-0.73
Log Po/w (MLOGP) :	-1.47
Log Po/w (SILICOS-IT) :	-0.5
Consensus Log Po/w :	-0.62

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-0.03
Solubility :	68.9 mg/ml ; 0.93 mol/l
Class :	Very soluble
Log S (Ali) :	-0.36
Solubility :	32.3 mg/ml ; 0.436 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.93
Solubility :	633.0 mg/ml ; 8.55 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 298-12-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P261-P273-P272-P234-P264-P280-P390-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310-P406-P405	UN#:	3265
Hazard Statements:	H314-H317-H402-H290	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 298-12-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 298-12-4 ]
Downstream synthetic route of [ 298-12-4 ]

[ 298-12-4 ] Synthesis Path-Upstream 1~5

1
[ 95-83-0 ]
[ 298-12-4 ]
[ 2427-71-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 158 - 175
[2] Patent: US5541324, 1996, A,

2
[ 107-15-3 ]
[ 298-12-4 ]
[ 24123-14-6 ]

Reference： [1] Tetrahedron, 1995, vol. 51, # 44, p. 12069 - 12082
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 14, p. 3032 - 3040

3
[ 298-12-4 ]
[ 71-36-3 ]
[ 105-76-0 ]
[ 2050-60-4 ]
[ 141-03-7 ]
[ 1587-18-4 ]
[ 344268-32-2 ]
[ 38094-11-0 ]
[ 77-94-1 ]
[ 105-75-9 ]
[ 117538-83-7 ]
[ 94086-70-1 ]

Reference： [1] Chemistry and Biodiversity, 2012, vol. 9, # 4, p. 714 - 726

4
[ 107-15-3 ]
[ 298-12-4 ]
[ 108-95-2 ]
[ 1170-02-1 ]
[ 94770-71-5 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2006, vol. 54, # 12, p. 4355 - 4363

5
[ 95-47-6 ]
[ 96-76-4 ]
[ 298-12-4 ]
[ 164391-52-0 ]

Reference： [1] Patent: US6359148, 2002, B1, . Location in patent: Page column 40 - 41

[ 298-12-4 ] Synthesis Path-Downstream 1~11

1
[ 745020-22-8 ]
[ 89694-46-2 ]
[ 298-12-4 ]
[ 918810-91-0 ]

Yield	Reaction Conditions	Operation in experiment
25%	In N,N-dimethyl-formamide; acetonitrile; at 85℃; for 0.5h;	A mixture of 2-chloro-5-methoxyhenylboronic acid (43 mg, 0.23 mmol), Intermediate 1 (72 mg, 0.2 mmol) and glyoxylic acid monohydrate (21 mg, 0.23 mmol) in acetonitrile (0.7 mL) and DMF (0.07 mL) was heated at 85° C. for 30 min in a Microwave Reactor. The crude product was purified by flash column chromatography (CH2Cl2:MeOH=100:15) to give 28 mg (25percent) of 77A as a solid. 1H NMR (400 MHz, Methanol-d4) delta ppm 1.16 (s, 18 H) 3.24 (s, 3 H) 5.55 (s, 1 H) 6.57 (d, J=2.20 Hz, 1 H) 6.75-6.84 (m, 2 H) 7.00 (d, J=3.08 Hz, 1 H) 7.10-7.20 (m, 1 H) 7.27 (d, J=9.23 Hz, 1 H) 7.32 (d, J=5.27 Hz, 1 H) 7.54 (d, J=9.23 Hz, 1 H) 7.93 (d, J=6.15 Hz, 1 H); LC MS 558 (M+H).

Reference： [1]Patent: US2007/3539,2007,A1 .Location in patent: Page/Page column 76

2
[ 943740-59-8 ]
[ 66491-03-0 ]
[ 298-12-4 ]
[ 1037082-43-1 ]

Yield	Reaction Conditions	Operation in experiment
71.6%	In N,N-dimethyl-formamide; acetonitrile; at 100℃; for 0.166667h;Microwave irradiation;	Example 4: (/?)-4-Methyl-2-(l-oxo-l,2,3,4-tetrahydro-isoquinolin-7-ylamino)-7- (propane-2-sulfonyl)-4,ll-diaza-tricyclo[14.2.2.1^'1"]henicosa- l(19),6,8,10(21),16(20),17-hexaene-3,12-dione trifluoroacetic acid salt; Intermediate 1 (128 mg, 0.789 mmol),3G (400 mg, 0.751 mmol), and glyoxylic acid monohydrate (69.2 mg, 0.751 mmol) were dissolved in acetonitrile (2.25 mL) and DMF (1.75 mL) to give a yellow solution. The mixture was irradiated in a microwave reactor at 100 0C for 10 min, then was concentrated. The crude product was purified by flash chromatography (1 to 20% MeOH/CH2Cl2 gradient) to afford 380 mg (71.6 %) of 4A as a yellow glass. (ESI) m/z 707 '.2 (M+H)+.

Reference： [1]Patent: WO2008/79836,2008,A2 .Location in patent: Page/Page column 117

3
[ 2986-17-6 ]
[ 298-12-4 ]
[ 1239420-47-3 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2010,vol. 65,p. 533 - 536

4
[ 7724-12-1 ]
[ 298-12-4 ]
[ 1060699-37-7 ]

Reference： [1]Chemistry - An Asian Journal,2011,vol. 6,p. 1800 - 1810
[2]Angewandte Chemie - International Edition,2013,vol. 52,p. 1175 - 1179
Angew. Chem.,2012,vol. 125,p. 1213 - 1217,5

5
[ 72955-97-6 ]
[ 298-12-4 ]
[ 141523-15-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydroxide; In water; at 20℃;	<strong>[72955-97-6]2-methoxy-5-fluorophenol</strong> (14.2 g of) and 50% glyoxylic acid (16.8 g of) was added to (100ml) distilled water,Under ice bath, a solution of 10% sodium hydroxide (16 g) was added dropwise slowly.During the dropwise addition, the color of the reaction liquid gradually deepened. After overnight reaction at room temperature,The reaction was confirmed by TLC, and the reaction solution was extracted with ethyl acetate.The aqueous phase was adjusted to pH 1-2 with concentrated hydrochloric acid, extracted with ethyl acetate,The second ethyl acetate extract was dried over anhydrous magnesium sulfate and dried under reduced pressure to give 18.8 g of a yellow oil which was used in the next step with a yield of 87.0%
86%	With sodium hydroxide; In water; at 0 - 20℃;	General procedure: A 10% sodium hydroxide solution (300 ml) was added slowly to the rapidly stirring solution of the appropriate phenol (4a-g) (0.4 mol), 50% glyoxylic acid (0.396 mol) and 100-ml distilled water at 0 C. The reaction mixture was stirred at room temperature overnight and washed three times with ethyl acetate. The aqueous phase was adjusted to pH 3 using concentrated hydrochloric acid and extracted three times using ethyl acetate. The combined organic phases were evaporated under reduced pressure to obtain the final products.

Reference： [1]Patent: CN104211615,2017,B .Location in patent: Paragraph 0096; 0098-0099
[2]European Journal of Medicinal Chemistry,2015,vol. 89,p. 524 - 539

6
[ 66491-03-0 ]
[ 122775-35-3 ]
[ 298-12-4 ]
[ 1036388-74-5 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2799 - 2808
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1077 - 1081

7
[ 68176-57-8 ]
[ 298-12-4 ]
C₁₂H₁₆N₂O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 13340 - 13344
Angew. Chem.,2016,vol. 128,p. 13534 - 13539,6

8
[ 3682-14-2 ]
[ 122775-35-3 ]
[ 298-12-4 ]
[ 960232-00-2 ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1077 - 1081

9
[ 6972-82-3 ]
[ 298-12-4 ]
[ 27038-81-9 ]

Yield	Reaction Conditions	Operation in experiment
78.8%		<strong>[6972-82-3]5,6-diamino-1-methyluracil</strong> (10g, 64.1mmol) (Synthesis of <strong>[6972-82-3]5,6-diamino-1-methyluracil</strong>, see J. Med. Chem. 2009, 52, 6433-6446) was added to 30 mL of water,Hydroxy acetic acid (4. 87 g, 128.2 mmol) was added,100 ° C Reaction 3. After 5 hours,Sodium hydroxide (4. 3 g, 107.5 mmol) was added and the reaction was carried out at 100 ° C for 5 hours.The solid precipitated to room temperature, filtered and the cake was recrystallized from water to give 6.2 g of a 78.8percent

Reference： [1]Patent: CN103373999,2016,B .Location in patent: Paragraph 0065-0067

10
[ 95-54-5 ]
[ 298-12-4 ]
[ 3314-30-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydroxyapatite; In water; at 52℃; for 6h;	200 mesh hydroxyapatite powder, 0.008g as catalystUse 52 mL of hot water as solvent,The reaction was carried out with 0.1 mol o-phenylenediamine and 0.11 mol glyoxylic acid as raw materials. The reaction time was 6 hours and the reaction temperature was 52°C.After the reaction is over,Hot filter,Cool the filtrate to 2 °CWhite crystals precipitated,Filtered to obtain crystals,35 °C vacuum drying overnight,That is, benzimidazole-2-formaldehyde 11.9g, yield 81percent,Purity 99.6percent,

Reference： [1]Patent: CN105198819,2017,B .Location in patent: Paragraph 0014-0016; 0017-0018; 0019-0020

11
[ 26787-78-0 ]
[ 3973-08-8 ]
[ 740742-98-7 ]
[ 64-18-6 ]
[ 79-14-1 ]
[ 110-94-1 ]
[ 124-04-9 ]
[ 80-69-3 ]
[ 473-81-4 ]
[ 471-47-6 ]
[ 110-15-6 ]
[ 1378848-02-2 ]
[ 15573-67-8 ]
C₉H₁₀N₂O₄ [ No CAS ]
C₉H₁₂N₂O₅S [ No CAS ]
C₈H₁₀N₂O₆S [ No CAS ]
C₉H₁₄N₂O₇S [ No CAS ]
C₉H₁₂N₂O₆S [ No CAS ]
C₈H₁₀N₂O₄S [ No CAS ]
C₁₀H₁₂N₂O₇S [ No CAS ]
C₁₅H₂₁N₃O₄S [ No CAS ]
C₁₅H₁₈N₂O₄S [ No CAS ]
C₁₄H₂₁N₃O₃S [ No CAS ]
C₈H₁₂N₂O₄S [ No CAS ]
C₈H₁₀N₂O₅S [ No CAS ]
C₆H₁₀O₇S [ No CAS ]
C₆H₇NO₄S [ No CAS ]
C₆H₁₁NO₃S [ No CAS ]
C₆H₉NO₃S [ No CAS ]
[ 144-62-7 ]
[ 64-19-7 ]
[ 802294-64-0 ]
[ 127-17-3 ]
[ 87-69-4 ]
[ 551-16-6 ]
[ 65-85-0 ]
[ 298-12-4 ]
2-hydroxy-3-(4-hydroxyphenyl)pyrazine [ No CAS ]
[ 6915-18-0 ]
[ 107-92-6 ]
[ 57457-65-5 ]
[ 99-96-7 ]

Reference： [1]Catalysis Today,2019

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Technical Information

? Arndt-Eistert Homologation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Heat of Combustion ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Preparation of Carboxylic Acids ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Carboxylic Acids ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 298-12-4 ] {[proInfo.proName]}

Quality Control of [ 298-12-4 ]

Related Doc. of [ 298-12-4 ]

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Product Details of [ 298-12-4 ]

Calculated chemistry of [ 298-12-4 ] Expand+

Physicochemical Properties

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Lipophilicity

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Medicinal Chemistry

Safety of [ 298-12-4 ]

Application In Synthesis of [ 298-12-4 ]

[ 298-12-4 ] Synthesis Path-Upstream 1~5

[ 298-12-4 ] Synthesis Path-Downstream 1~11

Technical Information

Related Functional Groups of [ 298-12-4 ]

Aliphatic Chain Hydrocarbons

Aldehydes

Carboxylic Acids

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[ 298-12-4 ]