72-19-5

Basic information

• Product Name: L-Threonine
• Synonyms: Butanoic acid, 2-amino-3-hydroxy-, (R-(R*,S*))-;Thr;Threonine [USAN:INN];L-Threonin;(2S,3R)-2-azaniumyl-3-hydroxy-butanoate;Treonina [Spanish];(2R,3R)-2-amino-3-hydroxy-butanoic acid;Threonine, L-;(2S,3R)-2-Amino-3-hydroxybutyric acid;Valine,3-hydroxy-;L-alpha-Amino-beta-hydroxybutyric acid;(2S,3S)-2-azaniumyl-3-hydroxy-butanoate;(2S)-threonine;Threoninum [Latin];Threonine (VAN);L-2-Amino-3-hydroxybutyric acid;L-Threonine(Feed Grade);L-Thr-OH;L-Threonine Aji97;Threonine, L- (8CI);(2S,3R)-2-amino-3-hydroxy-butanoic acid;L-(-)-Threonine;Threonin;[R-(R*,S*)]-2-Amino-3-hydroxybutanoic acid;L-Threonine (9CI);Threonine (USP)
• CAS NO: 72-19-5
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.11916
• EINECS: 200-774-1
• Mol File: 72-19-5.mol
• Article Data: 238

Chemical Properties

• Melting Point: 255℃
• Boiling Point: 345.803 °C at 760 mmHg
• Flash Point: 162.936 °C
• Appearance: White crystalline powder
• Density: 1.307 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.507
• Water Solubility: 90 g/L (20℃)
• CAS DataBase Reference: L-Threonine(CAS DataBase Reference)
• NIST Chemistry Reference: L-Threonine(72-19-5)
• EPA Substance Registry System: L-Threonine(72-19-5)

Safety Data

• Safety Statements: S24/25:
• Hazardous Substances Data: 72-19-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2?,3-/m0/s1

Synthetic route

hexan-1-amine (111-26-2) + (S)-2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-3-hydroxy-butyric acid → L-threonine (72-19-5) + 1-hexyl-3,5-dinitro-4-pyridone (74197-48-1)

Conditions	Yield
In pyridine Product distribution;	A 83.8% B n/a

methanol (67-56-1) + Fmoc-Thr-OH (73731-37-0, 130674-54-3, 146306-75-4) → L-threonine (72-19-5) + N-methyl threonine (2812-27-3, 2812-28-4, 21148-57-2, 95539-41-6, 100157-57-1) + N,N-dimethyl-threonine (2812-36-4, 2812-37-5, 138406-48-1)

Conditions	Yield
With hydrogen; acetic acid; palladium on activated charcoal for 48h; other (protected) amino acids; other alcohol;	A n/a B 40% C n/a

DL-threonine (72-19-5, 80-68-2, 144-98-9, 632-20-2, 2676-21-3, 7004-04-8, 24830-94-2, 28954-12-3, 36676-50-3) → L-threonine (72-19-5) + D-threonine (72-19-5, 80-68-2, 144-98-9, 632-20-2, 2676-21-3, 7004-04-8, 24830-94-2, 28954-12-3, 36676-50-3)

Conditions	Yield
Yields of byproduct given;

acetaldehyde (75-07-0) + glycine (56-40-6) → L-threonine (72-19-5)

Conditions	Yield
With pyridoxal 5'-phosphate; L-threonine aldolase In phosphate buffer at 25℃; for 3h;

antimycin B1 → L-threonine (72-19-5)

Conditions	Yield
With hydrogenchloride; water at 110℃; for 20h;

ucb K115 → L-threonine (72-19-5)

Conditions	Yield
With ferrous(II) sulfate heptahydrate; cobalt(II) sulphate heptahydrate; N-succinyl L-amino acid desuccinylase from Burkholderia ambifaria AMMD; N-succinyll-amino acid β-hydroxylase from Burkholderia ambifaria AMMD; ascorbic acid In aq. phosphate buffer at 30℃; for 24h; Enzymatic reaction;

methanol (67-56-1) + L-threonine (72-19-5) → L-threonine methyl ester hydrochloride (39994-75-7, 60538-15-0, 60538-18-3, 62076-66-8, 76419-75-5, 79617-27-9, 108724-12-5)

Conditions	Yield
With thionyl chloride at 0℃; for 3.25h; Reflux;	100%

L-threonine (72-19-5) + methyl chloroformate (79-22-1) → (2S,3R)-3-hydroxy-2-((methoxycarbonyl)amino)butanoic acid

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium carbonate In methanol; dichloromethane	98%
With sodium hydrogencarbonate In diethyl ether; water

[Pd(acetylacetonato-O,O')((1R,2R)-(PPh2NH)2C6H10)](ClO4) + L-threonine (72-19-5) → [Pd(L-threoninate-κ-N,O)((1R,2R)-(PPh2NH)2C6H10)](ClO4)

Conditions	Yield
In methanol byproducts: acetylacetone; to a soln. of complex in methanol was added amino acid, the mixt. was refluxed for 3 h, cooled; evapd. to dryness, treated with diethyl ether, the solid was filtered, washed with diethyl ether, air-dried;	85%

L-threonine (72-19-5) + toluene-4-sulfonic acid (104-15-4) + allyl alcohol (107-18-6) → L-Threonin-allylester-hydro-p-toluolsulfonat (88224-11-7)

Conditions	Yield
In benzene Heating;	84%

hydrogenchloride (7647-01-0) + sodium tetrahydroborate (16940-66-2) + ferrocenecarboxaldehyde (12093-10-6) + L-threonine (72-19-5) → H(S-fThr)

Conditions	Yield
With LiOH*H2O In methanol L-threonine and LiOH*H2O in dry MeOH stirred for 30 min; MeOH soln. of Fe complex added dropwise; stirred for 20 min; treated with NaBH4 with stirring; solvent evapd.; dissolved in H2O; acidified with dilute HCl (pH 5-7); filtered; ppt. washed with H2O; dried in vac. desiccator; elem. anal.;	84%

L-threonine (72-19-5) + 3,5-dinitro-1-(4-nitrophenyl)-4-pyridone (74197-40-3) → 4-nitro-aniline (100-01-6) + (S)-2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-3-hydroxy-butyric acid

Conditions	Yield
In pyridine; water for 3h; Ambient temperature;	A n/a B 75%

Field-Durant Green + ethanol (64-17-5) + L-threonine (72-19-5) + salicylaldehyde (90-02-8) → potassium Δ-bis(N-salicylidene-(S)-threoninato)cobaltate*2(ethanol)

Conditions	Yield
In ethanol salicylaldehyde added with stirring to mixt. of Co complex and amino acid in EtOH; refluxed for 3 h; filtered; filtrate concd. in vac.; residue washed with Et2O; dissolved in EtOH; column chromd. (Al2O3, EtOH); purified by gel chromy. (Sephadex LH-20, EtOH-benzene 1:3); elem. anal.;	70%

sodium tris(carbonato)cobaltate(III) + L-threonine (72-19-5) + salicylaldehyde (90-02-8) → lithium δ-bis[N-salicylidene-(S)-threoninato]cobaltate dihydrate

Conditions	Yield
In ethanol aldehyde was added with stirring to mixt. of Co complex and amino acid in EtOH; refluxed for 3 h; filtered; evapd. (vac.); washed (Et2O); dissolved in EtOH; chromd. (Al2O3, EtOH); chromd. (gel, EtOH/C6H6, 1/3); dissolved in aq. EtOH; passed through ion-exchange resin; evapd. (vac.); chromd. (gel, EtOH/C6H6, 1/3);elem. anal.;	70%

1-Methyl-4-piperidone (1445-73-4) + L-threonine (72-19-5) + 2,6-dimethylphenyl isonitrile (119072-54-7, 2769-71-3) → 4-(2,6-dimethylphenyl)-2-ethyl-9-methyl-1,4,9-triazaspiro[5.5]undec-1-ene-3,5-dione

Conditions	Yield
With triethylamine In 2,2,2-trifluoroethanol at 100℃; for 24h;	70%

sodium tris(carbonato)cobaltate(III) + L-threonine (72-19-5) + 3-allyl-5-bromosalicylaldehyde (1259524-22-5) → lithium λ-bis[N-(3-allyl-5-bromosalicylidene)-(S)-threoninato]cobaltate dihydrate + lithium δ-bis[N-(3-allyl-5-bromosalicylidene)-(S)-threoninato]cobaltate dihydrate

Conditions	Yield
In ethanol aldehyde was added with stirring to mixt. of Co complex and amino acid in EtOH; refluxed for 3 h; filtered; evapd. (vac.); washed (Et2O); dissolved in EtOH; chromd. (Al2O3, EtOH); chromd. (gel, EtOH/C6H6, 1/3); dissolved in aq. EtOH; passed through ion-exchange resin; evapd. (vac.); chromd. (gel, EtOH/C6H6, 1/3);elem. anal.;	A 22% B 65%

L-threonine (72-19-5) + 6-nitro-2-oxo-2H-chromene-3-carbonyl chloride (71942-48-8) → 6-nitrocoumarin-3-CO-L-Thr (80613-36-1)

Conditions	Yield
With triethylamine In 1,4-dioxane 1) room temperature, 2) 2 h, reflux;	54%

(η6-fluorobenzene)(η5-cyclopentadienyl) iron(II) hexafluorophosphate + L-threonine (72-19-5) → [(η-C6H5NHCH(CH(OH)Me)COOH)(η-C5H5)Fe][PF6]

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide 120-130°C, 1.0 h; cooling, filtration into ether (sepn. of oil), decantation, washing (ether), extn. into Me2CO, filtration, chromy. (Al2O3, Me2CO, then MeOH/H2O=5:1), evapn. (reduced pressure, 60-70°C);	40%

nickel(II) perchlorate hexahydrate + lanthanum(III) perchlorate hexahydrate + L-threonine (72-19-5) → [LaNi6(L-threonine(-H)(1-))12](ClO4)3(H2O)15

Conditions	Yield
With NaOH In water stoichiometric equiv. of Ni(ClO4)2*6H2O and L-threonine added to aq. soln. of La(ClO4)3*6H2O; pH adjusted to 6.6 by slow addition of NaOH aq. soln.; stirred for 2 h; filtered to remove precipitates formed; placed in a desiccator filled with P2O5 for 1 month; elem. anal.;	35%

{CoBr2(C8H12(C2H5)4(NH)4)}(1+)*Br(1-)={CoBr2(C8H12(C2H5)4(NH)4)}Br + L-threonine (72-19-5) + sodium perchlorate → {Co(OCOCH(NH2)CH(OH)CH3)(C8H12(C2H5)4(NH)4)}(2+)*2{ClO4}(1-)*3H2O

Conditions	Yield
With NaOH In water adjusting the pH of an aq. soln. of the CoBr2 complex and (S)-thr to 8.0 with NaOH, evapn. to near dryness (after 1 h), addn. of a slight excess of an aq. NaClO4 soln., crystn.; elem. anal.;	30%

L-threonine (72-19-5) + benzyl chloroformate (501-53-1) → N-[(phenylmethoxy)carbonyl]-L-threonine (19728-63-3)

Conditions	Yield
With sodium hydrogencarbonate

β-D-glucose (492-61-5) + L-threonine (72-19-5) → 1-hydroxy-propane-1,2,3-tricarboxylic acid (320-77-4) + 2-methylisocitric acid + citric acid (77-92-9)

Conditions	Yield
With Saccharomycopsis lipolytica In water at 26℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S. lipolytica;

succinimidyl 2,2,2-trichloroethyl carbonate (66065-85-8) + L-threonine (72-19-5) → N-(2,2,2-trichloroethoxycarbonyl)-threonine (88050-12-8)

Conditions	Yield
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane for 0.166667h; Ambient temperature;

L-threonine (72-19-5) + N-benzyloxycarbonylalaninehydrazid (17350-66-2) → Z-Ala-Thr-OH (40355-98-4, 40356-04-5, 55057-57-3, 78609-60-6, 109718-19-6)

Conditions	Yield
With hydrogenchloride; tert.-butylnitrite; triethylamine 1. DMF, dioxane, -10 degC, 10 min, 2.) H2O, cold; Yield given. Multistep reaction;

L-threonine (72-19-5) + [(R)-1-[(S)-1-(Hydrazinocarbonylmethyl-carbamoyl)-ethylcarbamoyl]-2-(4-methoxy-benzylsulfanyl)-ethyl]-carbamic acid tert-butyl ester (86895-16-1) → Boc-Cys(MBzl)-Ala-Gly-Thr-OH (86905-27-3)

Conditions	Yield
With hydrogenchloride; tert.-butylnitrite; triethylamine 1.)DMF, dioxane, -25 degC, 10 min, 2.) H2O, cold; Yield given. Multistep reaction;

L-threonine (72-19-5) → D-allo-threonine (24830-94-2)

Conditions	Yield
With hydrogenchloride; ethanethiol at 110℃; Rate constant; various times;

L-threonine (72-19-5) → (2S,3R)-2-chloro-3-hydroxybutanoic acid (849704-22-9)

Conditions	Yield
With hydrogenchloride; sodium nitrite at -5℃; for 5h;

L-threonine (72-19-5) → carbon dioxide (124-38-9) + 2-hydroxy-propionitrile (78-97-7)

Conditions	Yield
With hydrogenchloride; chloroamine-T In water at 29.9 - 44.9℃; Thermodynamic data; Rate constant; Ea, log A, -ΔS(excit.), ΔH(excit.), ΔG(excit.); further acid concentration, further acid and alkaline media;

L-threonine (72-19-5) → C3H8NO

Conditions	Yield
With hydroxide In water Mechanism; Ambient temperature; Irradiation; examination of effect of protonation state of amino group;

L-threonine (72-19-5) + tert-butylamine (75-64-9) → Troc-Thr-OH*t-C4H9NH2 (88050-13-9)

Conditions	Yield
Yield given;

L-threonine (72-19-5) + methylamine (74-89-5) → (S)-2-Amino-3-hydroxy-N-methyl-butyramide (79009-37-3)

Conditions	Yield
With thionyl chloride 1)r.t., methanol, 2) 40 deg C 30 min, water; Multistep reaction;

L-threonine (72-19-5) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → N-(2,4-Dichlor-phenoxyacetyl)-L-threonin

Conditions	Yield
With hydroxide

Upstream product

• 50-00-0 Formaldehyde 
• 50-99-7 D(+)-Glucose 
• 60650-88-6 SERICIN 
• 13479-54-4 Copper glycinate 
• 80-68-2 DL-Threonine 
• 9012-37-7 AMINOACYLASE 
• 146317-23-9 Α-PROTEIN 
• 9000-71-9 Casein 

Downstream Products

• 78110-38-0 Aztreonam 
• 15260-10-3 Boc-O-Benzyl-L-threonine 
• 10098-89-2 L-Lysine hydrochloride 
• 24830-94-2 D(-)-allo-Threonine 
• 80-68-2 DL-Threonine 
• 90776-59-3 beta-Methyl vinyl phosphate (MAP) 

Recommend Products

• 24809-87-8  N-carbamoyl-threonine 
• 590-28-3  potassium cyanate 
• 72-19-5  DL-threonine 
• 75-07-0  acetaldehyde 
• 64-19-7  acetic acid 
• 107-92-6  butyric acid 
• 56-40-6  glycine 
• 72-19-5  rac-allo-threonine 
• 6267-89-6  2-acetoxyimino-3-oxo-butyric acid ethyl ester 
• 80-68-2  DL-threonine 
• 2009-97-4  ethyl 2-diazo-3-oxobutanoate 
• 5431-93-6  ethyl 2-(acetylamino)-3-oxobutanoate 
• 72-19-5  L-threonine 
• 119-62-0  (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol