2134-29-4

Basic information

• Product Name: 3-hydroxypropionaldehyde
• Synonyms: 3-hydroxypropionaldehyde;3-Hydroxypropanal;BETA-HYDROXYPROPIONALDEHYDE;β-Hydroxypropanal;C00969;Propanal, 3-hydroxy-;5g – 10g – 25g;3-Oxo-1-propanol
• CAS NO: 2134-29-4
• Molecular Formula: C₃H₆O₂
• Molecular Weight: 74.07854
• EINECS: 218-365-1
• Mol File: 2134-29-4.mol
• Article Data: 69

Chemical Properties

• Boiling Point: 90℃ (18 Torr)
• Flash Point: 61.8°C
• Appearance: /
• Density: 0.9349 (rough estimate)
• Refractive Index: 1.4979 (589.3 nm 20℃)
• PKA: 14.43±0.10(Predicted)
• Stability: Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 3-hydroxypropionaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxypropionaldehyde(2134-29-4)
• EPA Substance Registry System: 3-hydroxypropionaldehyde(2134-29-4)

Safety Data

• Hazardous Substances Data: 2134-29-4(Hazardous Substances Data)

Usage

Uses

3-Hydroxypropanal can be used as a food preservative as it has antimicrobial activity against food-borne pathogens and spoilage bacteria.

InChI:InChI=1S/C3H6O2/c4-2-1-3-5/h2,5H,1,3H2

Synthetic route

acrolein (107-02-8) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With C14H14N2O4(2+)*2BF4(1-) In water at 45℃; under 1275.13 Torr; for 0.2h; Pressure; Reagent/catalyst; Temperature;	94.8%
With water In water-d2 at 20℃; for 336h;	50%
With sulfuric acid

trimethyleneglycol (504-63-2) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With acetic acid; bromamine B In water at 29.9℃; Kinetics; Thermodynamic data; Mechanism; ΔH(excit.), ΔS(excit.), ΔG(excit.); variation of substrate and reagents concentration; solvent isotope effect;	76%
With acetic acid; bromamine B In water at 29.9℃;	76%
With pyridinium chlorochromate In dimethyl sulfoxide for 6h; Kinetics; Mechanism; Thermodynamic data; Εa, log A, ΔS(excit.), ΔG(excit.);

glycerol (56-81-5) → 3-Hydroxypropanal (2134-29-4) + acrylic acid (79-10-7) + acrolein (107-02-8)

Conditions	Yield
With dihydrogen peroxide In acetonitrile at 70℃; Reagent/catalyst;	A 6.8% B 74.7% C 10.4%
With manganese(IV) oxide; dihydrogen peroxide In acetonitrile at 70℃; Reagent/catalyst;	A 2.5% B 5.6% C 1.8%
With manganese(IV) oxide; dihydrogen peroxide In acetonitrile at 70℃; Reagent/catalyst;	A 2.8% B 0.1% C 3.1%
With dihydrogen peroxide In acetonitrile at 70℃; Reagent/catalyst;	A 3% B 3.4% C 3.5%

trimethyleneglycol (504-63-2) + N-bromoacetamide (79-15-2) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
perchloric acid In water; acetic acid at 29.9℃; Rate constant; Mechanism; Thermodynamic data; Rate constants also at 308, 313 and 318 K, at different acidities and at different proportions of NBA; ΔH(excit.), ΔS(excit.), ΔG(excit.);	71%

glycerol (56-81-5) → 3-Hydroxypropanal (2134-29-4) + hydroxy-2-propanone (116-09-6) + 2-oxopropanal (78-98-8)

Conditions	Yield
In water at 400℃;	A 60% B 10% C 30%

glycerol (56-81-5) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With Lactobacillus reuteri SD 2112 In water at 37℃; for 2.5h;	45%
entsteht als Zwischenprodukt bei der Bildung von Acrolein durch Einw. des Bacillus amaracrylus;
With Lactobacillus coryniformis 394 In water at 25℃;
With Klebsiella pneumoniae CGMCC 1.9131 In aq. buffer at 37℃; pH=6.8; Microbiological reaction;

glycerol (56-81-5) → methanol (67-56-1) + propan-1-ol (71-23-8) + propylene glycol (57-55-6) + propane (74-98-6) + 3-Hydroxypropanal (2134-29-4) + carbon dioxide (124-38-9) + carbon monoxide (201230-82-2) + ethylene glycol (107-21-1) + propionaldehyde (123-38-6) + hydroxy-2-propanone (116-09-6) + isopropyl alcohol (67-63-0) + acetone (67-64-1) + acrolein (107-02-8) + trimethyleneglycol (504-63-2)

Conditions	Yield
With hydrogen at 260℃; Catalytic behavior; Temperature; Reagent/catalyst;	A n/a B 28% C 18% D n/a E n/a F n/a G n/a H n/a I n/a J n/a K 15% L n/a M n/a N 14%

...Expand

glycerol (56-81-5) → 3-Hydroxypropanal (2134-29-4) + acrolein (107-02-8)

Conditions	Yield
With dihydrogen peroxide In acetonitrile at 70℃; Reagent/catalyst;	A 3.7% B 12.9%

3,3-diethoxypropan-1-ol (16777-87-0) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With sulfuric acid; acetone
With ozone
With hydrogenchloride In water at 60℃;

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With water; potassium carbonate at 12 - 18℃;

glycerol (56-81-5) → 3-Hydroxypropanal (2134-29-4) + diglycerol (627-82-7) + oxiranyl-methanol (556-52-5) + hydroxy-2-propanone (116-09-6)

Conditions	Yield
at 170 - 250℃; Produkt 5: Acrylaldehyd;

cyclopropanol (16545-68-9) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With chromium(VI) oxide; perchloric acid

3-Dimethylamino-1-propanol (3179-63-3) → 3-Hydroxypropanal (2134-29-4) + dimethyl amine (124-40-3)

Conditions	Yield
With (batho)2CuII (batho = 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolinedisulfonate); water at 25℃; for 24h; Rate constant; Product distribution; reaction rate vs pH (from 7 to 11), var. reaction time and reagent concentrations;

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → Pentaerythritol (115-77-5) + 3-Hydroxypropanal (2134-29-4) + bis-(hydroxymethyl)-acetaldehyde (40364-80-5)

Conditions	Yield
With sodium hydrogencarbonate at 30℃; for 2.5h; Product distribution;

1,1,3-trihydroxypropane (88497-15-8) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With water at 25℃; Equilibrium constant;

(3E)-4-phenyl-3-buten-1-ol (937-58-6, 20047-19-2, 770-36-5) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With dimethylsulfide; ozone 1.) CH2Cl2, MeOH, -78 deg C; Yield given. Multistep reaction;

sulfuric acid (7664-93-9) + acrolein (107-02-8) → 3-Hydroxypropanal (2134-29-4)

water (7732-18-5) + acrolein (107-02-8) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
at 100℃;

formaldehyd (50-00-0) + water (7732-18-5) + acetaldehyde (75-07-0) + potassium carbonate → acetaldol (107-89-1) + 3-Hydroxypropanal (2134-29-4)

formaldehyd (50-00-0) + acetaldehyde (75-07-0) + potassium carbonate → 3-Hydroxypropanal (2134-29-4)

3,3-diethoxypropan-1-ol (16777-87-0) + sulfuric acid (7664-93-9) + acetone (67-64-1) → 3-Hydroxypropanal (2134-29-4)

3,3-diethoxypropan-1-ol (16777-87-0) + ozone (10028-15-6) → Glyoxal (131543-46-9) + 3-Hydroxypropanal (2134-29-4)

oxirane (75-21-8) + carbon monoxide (201230-82-2) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With hydrogen; dicobalt octacarbonyl; bis(diphenylphosphino)methane monooxide In toluene at 100℃; under 75007.5 Torr; for 4h; Ring cleavage; Hydroformylation;
With hydrogen; cobalt carbonyl catalyst In tert-butyl methyl ether
With hydrogen In tetrahydrofuran at 95℃; under 93759.4 Torr; for 5h; Pressure; Temperature; Reagent/catalyst;
Stage #1: carbon monoxide With hydrogen; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 80℃; under 60006 Torr; for 3h; Stage #2: oxirane With hydrogen at 120℃; under 112511 Torr; for 4h; Reagent/catalyst; Temperature; Pressure; Solvent;

allyl alcohol (107-18-6) → 2-chloro-propane-1,3-diol (497-04-1) + 3-Hydroxypropanal (2134-29-4) + hydroxy-2-propanone (116-09-6) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
With (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane; copper dichloride; 6,6,6-trifluoro-1-phenylhexane-1,3,5-trione; tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) In tetrahydrofuran at 25℃;

propan-1-ol-3-amine (156-87-6) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With sodium diperiodatoargentate(III) In water at 20℃; pH=8.0; Kinetics;
With 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one; N-ethyl-N-(2-hydroxy-3-sulfopropyl)-3-methylaniline sodium salt dihydrate; oxygen In aq. phosphate buffer pH=7.0; Enzymatic reaction;

propargyl alcohol (107-19-7) → 3-Hydroxypropanal (2134-29-4) + hydroxy-2-propanone (116-09-6)

Conditions	Yield
With sodium dodecyl-sulfate; [Ru(η5-C9H7)Cl(PPh3)2] In water at 60℃; for 36h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; reaction time;	A 25 % Chromat. B 1.5 % Chromat.
[Ru(η5-C9H7)Cl(PPh3)2] In water; isopropyl alcohol at 90℃; for 48h; Title compound not separated from byproducts;	A 24 % Chromat. B 19 % Chromat.
With sodium dodecyl-sulfate; [Ru(η5-C9H7)Cl(PPh3)2] In water at 60℃; for 36h; Title compound not separated from byproducts;	A 25 % Chromat. B 1.5 % Chromat.

β-Propiolactone (57-57-8) → 3-Hydroxypropanal (2134-29-4)

Conditions	Yield
With methanolate

3-Hydroxypropanal (2134-29-4) + C58H59N13O16S5 → C60H63N13O17S5

Conditions	Yield
With sodium borohydride cyanide; acetic acid In methanol	100%

3-Hydroxypropanal (2134-29-4) → trimethyleneglycol (504-63-2)

Conditions	Yield
With sulfuric acid; nickel In water	95%
With hydrogen at 80℃; under 15001.5 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Green chemistry;	76.9%
Hydrogenation;

3-Hydroxypropanal (2134-29-4) + Glycolaldehyde (141-46-8) → 4-deoxy-β-D-threo-pentopyranose hemiacetal

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107Y/A129G mutant for 5h; Enzymatic reaction; stereoselective reaction;	90%

3-Hydroxypropanal (2134-29-4) + 1-hydroxy-3-methoxy-2-propanone (89124-41-4) → C7H14O5

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	89%

3-Hydroxypropanal (2134-29-4) + 1-Hydroxy-2-butanone (5077-67-8) → C7H14O4

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	89%

3-Hydroxypropanal (2134-29-4) + hydroxy-2-propanone (116-09-6) → C6H12O4

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	87%

3-Hydroxypropanal (2134-29-4) + dihydroxyacetone (96-26-4) → 5-deoxy-β-D-threo-hexulopyranose (82945-01-5)

Conditions	Yield
With E. coli transaldolase B mutant F178Y In glycyl-glycine buffer at 25℃; pH=8.5; Enzymatic reaction; stereoselective reaction;	83%
With E. coli transaldolase B mutant F178Y; hydroxy-2-propanone In glycyl-glycine buffer at 25℃; pH=8.5; Enzymatic reaction; stereoselective reaction;

3-Hydroxypropanal (2134-29-4) + 1-ethoxy-3-hydroxypropan-2-one (854672-38-1) → C8H16O5

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	82%

3-Hydroxypropanal (2134-29-4) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (E)-5-hydroxy-pent-2-enoic acid ethyl ester (13038-13-6)

Conditions	Yield
In dichloromethane for 3h; Ambient temperature;	78%

3-Hydroxypropanal (2134-29-4) + 1-hydroxyhexan-2-one (73397-68-9) → C9H18O4

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	76%

3-Hydroxypropanal (2134-29-4) + 1-hydroxypentan-2-one (64502-89-2) → C8H16O4

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	75%

3-Hydroxypropanal (2134-29-4) + acetaldehyde (75-07-0) → 2,4-Didesoxy-D-glycero-pentopyranose (90839-09-1)

Conditions	Yield
With 2-deoxyribose-5-phosphate aldolase for 72h; pH=7.5;	65%

3-Hydroxypropanal (2134-29-4) + Lithium hydroxypyruvate (3369-79-7) → 4-deoxy-L-glycero-pent-2-ulose (64307-91-1)

Conditions	Yield
With hydrogenchloride; thiamine pyrophosphate; Tris buffer; magnesium chloride at 25℃; spinach transketolase;	57%

3-Hydroxypropanal (2134-29-4) + 1-hydroxyheptan-2-one (17046-01-4) → C10H20O4

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	50%

1-(allyloxy)-3-hydroxypropan-2-one (153214-81-4) + 3-Hydroxypropanal (2134-29-4) → C9H16O5

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	45%

3-Hydroxypropanal (2134-29-4) + phenethyl isocyanide (59795-89-0) + 2-(6-chloropyridin-2-yl)acetonitrile (75279-60-6) → 5-chloro-2-(2-hydroxy-ethyl)-3-phenethylamino-indolizine-1-carbonitrile

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In butan-1-ol at 100℃; for 16h;	44%

3-Hydroxypropanal (2134-29-4) + acetone (67-64-1) → C6H12O3

Conditions	Yield
With E. coli D-fructose-6-phosphatealdolase D6H variant In aq. buffer pH=8; Aldol Addition; Enzymatic reaction;	32%

3-Hydroxypropanal (2134-29-4) + 1-hydroxy-3-isopropoxypropan-2-one → C9H18O5

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	30%

3-Hydroxypropanal (2134-29-4) + 1-hydroxy-3-propyloxypropan-2-one → C9H18O5

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	28%

3-Hydroxypropanal (2134-29-4) + 1-hydroxy-4-methylpentan-2-one (68113-55-3) → C9H18O4

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	28%

3-Hydroxypropanal (2134-29-4) + 1-hydroxy-4,4-dimethylpentan-2-one (29846-96-6) → C10H20O4

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	25%

3-Hydroxypropanal (2134-29-4) + 1-hydroxy-5-methyl-2-hexanone (68113-56-4) → C10H20O4

Conditions	Yield
With Escherichia coli D-fructose-6-phosphate aldolase L107A/L163A In aq. buffer at 20℃; pH=8.5; Aldol Addition; Enzymatic reaction; diastereospecific reaction;	25%

Upstream product

• 50-00-0 formaldehyd 
• 75-07-0 acetaldehyde 
• 504-63-2 trimethyleneglycol 
• 79-15-2 N-bromoacetamide 
• 75-21-8 oxirane 
• 201230-82-2 carbon monoxide 
• 107-19-7 propargyl alcohol 
• 928-96-1 (Z)-3-Hexen-1-ol 
• 791-28-6 Triphenylphosphine oxide 
• 107-18-6 allyl alcohol 
• 111-76-2 2-Butoxyethanol 
• 56-81-5 glycerol 
• 1261164-87-7 N-methoxy-N-methyl-3-hydroxypropionamide 
• 125414-41-7 N-Boc-serinol 

Downstream Products

• 23433-07-0 (+/-)-1,3-nonanediol 
• 107-02-8 acrolein 
• 504-63-2 trimethyleneglycol 
• 19790-60-4 3-Benzyloxypropanal 
• 927-74-2 3-Butyn-1-ol 
• 5465-07-6 β-hydroxyethyl-2 dioxanne-1,3 
• 89922-82-7 3-(tert-butyldimethylsilanyloxy)propionaldehyde 
• 40365-04-6 N-(2,4-dinitrophenyl)-N'-(3-hydroxypropylidene)-hydrazine 
• 115-77-5 Pentaerythritol 
• 16777-87-0 3,3-diethoxypropan-1-ol 

Relevant articles and documents

Synthesis method of 3-hydroxypropionaldehyde

The invention relates to a synthesis method of 3-hydroxypropionaldehyde, which mainly solves the problem of difficulty in separation of a catalyst of a homogeneous system in the prior art. The synthesis method of 3-hydroxypropionaldehyde comprises the following steps: i, adding a cobalt catalyst and a cocatalyst into a solvent, and heating for pretreatment in a synthesis gas atmosphere; and ii, after the catalyst pretreatment is finished, cooling, releasing the pressure, adding ethylene oxide and synthesis gas, and reacting to obtain the 3-hydroxypropionaldehyde, so that the technical problemis better solved, and the method can be applied to industrial production of the 3-hydroxypropionaldehyde.

Method for preparing 3-hydroxypropionaldehyde by hydrating acrolein

The invention relates to a method for preparing 3-hydroxy propionaldehyde by hydrating acrolein. The acrolein is homogeneously catalyzed under the action of a N-heterocyclic carboxylic acid ionic liquid to prepare 3-hydroxy propionaldehyde, wherein the hydration reaction liquid is subjected to aqueous two-phase extraction to recover the ionic liquid catalyst for cyclic utilization. According to the invention, the method is simple to operate and stable in process, the catalyst has very high reaction activity and very good selectivity, and the problems of separation of a homogeneous catalyst andinstability and easy deactivation of a solid catalyst in the hydration process are effectively solved.

Catalytic glycerol hydrogenolysis to 1,3-propanediol in a gas-solid fluidized bed

Glycerol is a potential feedstock to produce 1,3-propanediol (1,3-PDO), which is a valuable commercial polyester monomer. Here, we report the gas-phase glycerol hydrogenolysis to 1,3-propanediol over Pt/WO3/Al2O3 in a fluidized bed operating above 240 °C and at ambient pressure. Fluidized beds are ideal contactors for this reaction because the heat transfer rates are sufficiently high to vaporize glycerol thereby minimizing its combustion and thermal degradation. The yield of 1,3-PDO approached 14% after 2 h at 260 °C. The major co-products were 1,2-PDO (18%), 1-propanol (28%) and 2-propanol (15%). In the first step, glycerol may dehydrate to acrolein, followed by rehydration to 3-hydroxypropanal and then hydrogenation to 1,3-PDO. The concentrations of the by-products including acrolein, ethylene glycol, propane, and acetone increased with increasing temperature.