4-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-

HCID 2734445

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Basic information

CAS: 90866-33-4
Standard SMILES: CCOC(=O)C[C@@H](O)CCl
InChIKey: ZAJNMXDBJKCCAT-RXMQYKEDSA-N
Molecular formula: C6H11ClO3
Average molar mass: 166.6 g/mol
Monoisotopic mass: 166.0396719

Names & identifiers

Preferred name: 4-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-
IUPAC: ethyl (3R)-4-chloro-3-hydroxybutanoate
English name: Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate
Molecular formula: C6H11ClO3
Molecular weight: 166.6

Names & synonyms

ZL59XVD2RW4-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-RefChem:107049190866-33-4Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate(R)-Ethyl 4-chloro-3-hydroxybutanoateethyl (3R)-4-chloro-3-hydroxybutanoateMFCD00211242ethyl (3R)-4-chloro-3-hydroxy-butanoate(R)-4-Chloro-3-hydroxybutyric Acid Ethyl Esterethyl (r)-4-chloro-3-hydroxybutanoateButanoic acid, 4-chloro-3-hydroxy-, ethyl ester, (3R)-

Show more names

(R/S)-Ethyl-4-Chloro-3-HydroxybutyrateRECHB(R)-4-ChL(R)-Ethyl 4-chloro-3-Levocarnitine Impurity 33Ethyl(R)-(+)-4-chloro-3-Hydrox6-butoxybenzene-sulfonylchlorideR-Ethyl-4-Chloro-3-Hydroxy Butyate

Ethyl (R)-4-Chloro-3-hydroxybutyrate(r)-4-chloro-3-hydroxybutanoic acid ethyl ester(R)-Ethyl 4-Chloro-3-hydroxybutanoate (~90%)Ethyl (R)-(+)-4-chloro-3-hydroxybutanoateLevocarnitine Impurity 17SCHEMBL96009DTXSID20370313ethyl-4-chloro-3(R)-hydroxybutyrate

Database identifiers

CAS: 90866-33-4
PubChem CID: 2734445
DTXSID: DTXSID20370313
UNII: ZL59XVD2RW
Nikkaji: J455.988F

Properties

Computed structural properties

XLogP: 0.4
Topological polar surface area: 46.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 5
Heavy atoms: 10
Formal charge: 0
Complexity: 105

Physicochemical properties

Melting point: 93 · 93-95 °C
Boiling point: 93 · 93-95 °C/5 mmHg (lit.)
alpha: 14 · 14 º (neat)
Density: 1.19 g/mL · 1.19 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.452
Flash point: 110 °C · >110°C
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
pka: 13.23 · 13.23±0.20(Predicted)
form: Oil
color: Clear Colourless
Specific Gravity: 1.19 · 1.190
optical activity: 23 · [α]23/D +14°, neat
InChI: 1S/C6H11ClO3/c1-2-10-6(9)3-5(8)4-7/h5,8H,2-4H2,1H3/t5-/m1/s1
InChIKey: ZAJNMXDBJKCCAT-RXMQYKEDSA-N
SMILES: CCOC(=O)C[C@@H](O)CCl
CAS DataBase Reference: 90866 · 90866-33-4(CAS DataBase Reference)
UNSPSC Code: 12352101 · 12352101
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 318 · H318
Precautionary statements: 280 · P280-P305+P351+P338
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xi
Risk Statements: 41 · 41
Safety Statements: 26 · 26-36-36/39
RIDADR: 2810 · 2810
WGK Germany: 3 · 3
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29181990 · 29181990
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 1 · Eye Dam. 1

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
ridadr: 2810
hs_code: 29181990
risk_code: 41
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: Xi
safety_code: 26-36-36/39
hazard_class: 6.1
Storage Class: 10 - Combustible liquids
packing_group: III
Hazard statements: H318
Hazard Classifications: Eye Dam. 1
Precautionary statements: P280-P305+P351+P338

Chemistry & industry

Applications · 1 item

UsesEthyl (R)-(+)-4-chloro-3-hydroxybutyrate is a chiral building block that can be used:To prepare allyl stannane, a precursor for the total synthesis of macrolide iriomoteolide-1b.As a starting material for the synthesis of a chiral g-αmino acid fragment, which in turn is used to prepare the immunosuppressive agent FR252921.