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66673-40-3

Basic Information
CAS No.: 66673-40-3
Name: 5-Hydroxymethylpyrrolidin-2-one
Article Data: 24
Molecular Structure:
Molecular Structure of 66673-40-3 (5-Hydroxymethylpyrrolidin-2-one)
Formula: C5H9NO2
Molecular Weight: 115.132
Synonyms: 2-Pyrrolidinone,5-(hydroxymethyl)-, (R)-;(-)-5-(Hydroxymethyl)-2-pyrrolidinone;(5R)-5-Hydroxymethylpyrrolidin-2-one;(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone;(R)-5-(Hydroxymethyl)pyrrolidin-2-one;(R)-5-Hydroxymethyl-2-pyrrolidinone;(R)-5-Hydroxymethyl-2-pyrrolidone;(R)-5-Hydroxymethylpyrrolidin-2-one;(R)-5-Oxopyrrolidine-2-methanol;(R)-(-)-5-hydroxymethyl-2-pyrrolidinone;
EINECS: -0
Density: 1.153 g/cm3
Melting Point: 83-85 °C(lit.)
Boiling Point: 346 °C at 760 mmHg
Flash Point: 163 °C
Appearance: White powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 49.33000
LogP: -0.41390
Synthetic route

(R)-N-(tert-butoxycarbonyl)-5-(tert-butoxymethyl)pyrrolidin-2-one

66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
With water; trifluoroacetic acid In dichloromethane at 50℃; for 5h;99%
64700-65-8

methyl (2R)-pyroglutamate

66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate at 0℃;97%
With methanol; sodium tetrahydroborate at 0℃;97%
With methanol; sodium tetrahydroborate at 0℃;97%
68766-96-1

ethyl (R)-2-pyrrolidone-5-carboxylate

66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
With lithium borohydride In tetrahydrofuran for 16h; Ambient temperature;85%
With sodium tetrahydroborate In tetrahydrofuran; methanol at 5℃; for 1h;80%
With sodium tetrahydroborate In ethanol for 2h; Ambient temperature;79%
4042-36-8

D-pyrrolidone-5-carboxylic acid

66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / SOCl2 / 1.5 h / 80 °C
2: 85 percent / LiBH4 / tetrahydrofuran / 16 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / thionyl chloride / 1.) 0 deg C, 30 min, 2.) room temp., 3 h
2: 78 percent / NaBH4 / ethanol / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: SOCl2 / 48 h / Ambient temperature; pH=0
2: 58 percent / NaBH4 / propan-2-ol / 20 h / Ambient temperature
View Scheme
6893-26-1

D-Glutamic acid

66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) thionyl chloride / 1a) room temp., 1 h, 1b) reflux, 30 min.
2: 32.5 g / 1.5 h / 150 °C / 15 Torr
3: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 88 percent / SOCl2, KOH / 150 °C
2: LiBH4
View Scheme
Multi-step reaction with 3 steps
1: H2O / 63 h / Heating
2: SOCl2 / 48 h / Ambient temperature; pH=0
3: 58 percent / NaBH4 / propan-2-ol / 20 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1.1: thionyl chloride
1.2: Amberlyst A-21
1.3: Reflux
2.1: sodium tetrahydroborate / isopropyl alcohol
View Scheme
Multi-step reaction with 2 steps
1.1: thionyl chloride / 20 h / 20 °C
1.2: 2 h / Reflux
2.1: sodium tetrahydroborate / isopropyl alcohol / 20 h / 20 °C
View Scheme
13107-55-6

D-glutamic acid diethyl ester

66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 32.5 g / 1.5 h / 150 °C / 15 Torr
2: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature
View Scheme
13515-99-6, 23150-65-4, 27025-25-8

D-glutamic acid dimethyl ester hydrochloride

66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene / 4 h / Reflux
2: isopropyl alcohol; sodium tetrahydroborate / 20 h / 20 °C
View Scheme
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

18162-48-6

tert-butyldimethylsilyl chloride

128899-30-9, 100548-49-0, 106191-02-0

(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 4h;100%
With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature;99%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;99%
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

386707-15-9

methyl 3'-(cyanocarbonyl)-2,2'-binaphthalene-3-carboxylate

C28H23NO5

Conditions
ConditionsYield
With dmap In acetonitrile at 14℃; for 1.5h;100%
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

77-76-9

2,2-dimethoxy-propane

(7aR)-3,3-dimethyltetrahydro-5H-pyrrolo[1,2-c][1,3]oxazol-5-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 1.5h; Dean-Stark; Reflux;100%
With camphor-10-sulfonic acid at 75℃; for 20h; Reagent/catalyst; Temperature; Time; Concentration;78%
With camphor-10-sulfonic acid at 75℃; for 20h; Time; Temperature; Reflux;78%
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Chemistry

IUPAC Name: (5R)-5-(hydroxymethyl)pyrrolidin-2-one
Synonyms:  (R)-5-HYDROXYMETHYL-PYRROLIDIN-2-ONE;(R)-(-)-5-(HYDROXYMETHYL)-2-PYRROLIDINONE;(R)-5-(HYDROXYMETHYL)-2-PYRROLIDINONE; D-PYROGLUTAMINOL;(-)-D-PYROGLUTAMOL;(R)-(-)-5-(HYDROXYMETHYL)-2-PYRROLIDONE;(R)-(-)-2-PYRROLIDONE-5-YL-METHANOL;
The Molecular formula of  5-Hydroxymethylpyrrolidin-2-one(66673-40-3): C5H9NO2
The Molecular Weight of  5-Hydroxymethylpyrrolidin-2-one(66673-40-3): 115.13
Molecular Structure : 
Surface Tension: 38.7 dyne/cm 
Density: 1.153 g/cm3 
Flash Point: 163 °C 
Enthalpy of Vaporization: 68.34 kJ/mol 
Boiling Point: 346 °C at 760 mmHg 
Vapour Pressure: 3.72E-06 mmHg at 25°C 
Appearance: White Powder

Safety Profile

The Hazard Codes of 5-Hydroxymethylpyrrolidin-2-one(66673-40-3):  Xi
The Risk Statements information of 5-Hydroxymethylpyrrolidin-2-one(66673-40-3):
36/37/38:  Irritating to eyes, respiratory system and skin 
The Safety Statements information of 5-Hydroxymethylpyrrolidin-2-one(66673-40-3):
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
WGK Germany: 3
F: 3-10