ethyl (2S)-2-hydroxypropanoate

• ChemBase ID: 53492
• Molecular Formular: C5H10O3
• Molecular Mass: 118.1311
• Monoisotopic Mass: 118.06299418
• SMILES: C(=O)([C@@H](O)C)OCC
• Canonical SMILES: CCOC(=O)[C@@H](O)C
• InChI: InChI=1S/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3/t4-/m0/s1
• InChIKey: LZCLXQDLBQLTDK-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-2-hydroxypropanoate
• IUPAC Traditional name: ethyl (2S)-2-hydroxypropanoate; ethyl lactate
• Synonyms: Ethyl 2-hydroxypropanoate; (-)-Ethyl (S)-2-hydroxypropionate; (S)-(-)-2-Hydroxypropionic acid ethyl ester; L-Lactic acid ethyl ester; (-)-Ethyl L-lactate; Ethyl L-lactate; ethyl (2S)-2-hydroxypropanoate; Ethyl 2-hydroxypropionate; Ethyl lactate; Ethyl L-lactate; L-LACTIC ACID ETHYL ESTER; (-)-(S)-2-羟基丙酸乙酯; (S)-(-)-2-羟基丙酸乙酯; L-乳酸乙酯; (-)-L-乳酸乙酯; L-乳酸乙酯; 2-羟基丙酸乙酯; 乳酸乙酯

Database IDs

• CAS Number: 687-47-8; 97-64-3
• EC Number: 211-694-1; 202-598-0
• MDL Number: MFCD00004518; MFCD00065359
• Beilstein Number: 1720839
• Merck Index: 143817
• PubChem SID: 24887187; 24901085; 24894514; 24901084; 162058255
• PubChem CID: 92831
• FEMA ID: 2440
• Council of Europe Number: 371
• Flavis Number: 9.433

CALCULATED PROPERTIES

• Acid pKa: 12.999511
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.03087248
• LogD (pH = 7.4): 0.030871402
• Log P: 0.030872492
• Molar Refractivity: 28.3575 cm^3
• Polarizability: 11.390625 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -25°C; -26 °C(lit.); -3 °C
• Boiling Point: 145-160 °C/1013 mbar (5-95%); 152-155°C; 154 °C at 1000 hPa; 154 °C(lit.)
• Flash Point: 114.8 °F; 46 °C; 46°C(114°F); 60 °C (closed cup)
• Auto Ignition Point: 400 °C; 752 °F
• Density: 1.031 g/mL at 25 °C; 1.031 g/mL at 25 °C(lit.); 1.034 g/mL at 20 °C(lit.); 1.036; 1.042 g/mL at 25 °C; 1030 kg/m3 at 25 °C
• Refractive Index: 1.4130; n20/D 1.413; n20/D 1.413(lit.); n20/D 1.4130(lit.)
• Vapor Pressure: 2 mmHg ( 20 °C); 2.24 hPa at 20 °C; 5 mmHg ( 30 °C)
• Vapor Density: 4.1 (vs air)
• Optical Rotation: [α]14/D -10°, neat; [α]20/D -10.5±1°, neat; [α]20/D -10.5°, neat; -11 (neat)
• Hydrophobicity(logP): 0.331
• Organoleptic: butter; fruity

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: IRRITANT
• RTECS: OD5070000; OD5075000
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1192; UN1192
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 3; III
• Australian Hazchem: 3Y
• Risk Statements: 10-37-41; R:10-37-41
• Safety Statements: 24-26-39; S:24-26-39
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 129
• TSCA Listed: false; 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• Explode Limits: 1.5 %, 100 °F
• GHS Hazard statements: H226-H318-H335; H318-H226-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1192 3/PG 3
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FCC; FDA 21 CFR (172.515)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥97.5%; ≥98%; ≥98.0% (sum of enantiomers, GC); ≥99.0%; ≥99.0% (sum of enantiomers, GC); ≥99.0% (Sum of enantiomers, GC); 95%; 98%; 99%
• Grade: FG; Halal; Kosher; natural; NI; photoresist grade; puriss. p.a.; purum; SAJ first grade
• Optical Purity: enantiomeric excess: ≥97.5:2.5
• Evaporation Residue: <0.01%; <0.1%
• Impurities: ≤0.05% free acid; ≤0.1% water; ≤0.2% water
• Cation Traces: Ca: ≤0.01 mg/kg; Cr: ≤0.01 mg/kg; Cu: ≤0.01 mg/kg; Cu: ≤0.025 mg/kg; Fe: ≤0.01 mg/kg; Fe: ≤0.025 mg/kg; K: ≤0.01 mg/kg; K: ≤0.025 mg/kg; Mg: ≤0.01 mg/kg; Mn: ≤0.01 mg/kg; Na: ≤0.025 mg/kg; Na: ≤0.03 mg/kg; Ni: ≤0.01 mg/kg; Ni: ≤0.025 mg/kg; Pb: ≤0.01 mg/kg; Pb: ≤0.025 mg/kg
• Linear Formula: CH3CH(OH)COOCH2CH3
• Empirical Formula (Hill Notation): C5H10O3
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02155162

(Ethyl L-lactate) 1 ml = approx. 1.04 g

Sigma Aldrich - W244015

Packaging
1 kg in glass bottle
1 sample in glass bottle
5, 10 kg in steel drum

Sigma Aldrich - E34102

Packaging
5, 100, 500 g in glass bottle

Sigma Aldrich - W244007

Packaging
1 kg in poly bottle
5 kg in steel drum
1 sample in glass bottle
25 kg in comp drum

Sigma Aldrich - 73364

Application
biodegradable solvent replacement for optical and microelectronical purposes

Sigma Aldrich - 69799

Other Notes
Important starting material for the synthesis of many chiral building blocks, e.g. (S)-1,2-propanediol and (S)-propylene oxide1,2; O-Protection and reduction to the aldehyde3,4

Sigma Aldrich - 77367

Application
biodegradable solvent replacement for optical and microelectronical purposes

REFERENCES

• Ethyl (or isobutyl) L-lactate adds to aryl methyl ketenes to give esters of 2-arylpropionic acids in which the chirality is transferred to the new chiral center to a surprising degree: J. Am. Chem. Soc., 111, 7650 (1989):
  
• Silylation followed by reaction with MeLi gives a useful chiral synthon. For preparation and discussion of reactivity, see: Org. Synth. Coll., 9, 139 (1998):
  
• For reaction with Diphenylphosphonic azide, A12124, in the prepartaion, with inversion, of ethyl (R)-2-azidopropionate, see: Org. Synth., 75, 31 (1997).