(R)-(-)-2-Amino-1-butanol supplier

Name
2-Aminobutanol
EINECS 227-476-4
CAS No. 5856-63-3
Article Data26
CAS DataBase
Density 0.944 g/cm³
Solubility Soluble in water
Melting Point -2 °C
Formula C₄H₁₁NO
Boiling Point 177.2 °C at 760 mmHg
Molecular Weight 89.1374
Flash Point 82.2 °C
Transport Information UN 2735
Appearance clear colorless to light yellow viscous liquid
Safety 26-36/37/39-45
Risk Codes 34-37-22
Molecular Structure
Hazard Symbols C
Synonyms 1-Butanol,2-amino-, (-)- (7CI);1-Butanol, 2-amino-, (R)-;1-Butanol, 2-amino-, (R)-(-)-(8CI);1-Butanol, 2-amino-, l- (4CI);(-)-2-Amino-1-butanol;(2R)-2-Amino-1-butanol;(R)-(-)-2-Amino-1-butanol;(R)-(-)-2-Aminobutan-1-ol;(R)-2-Amino-1-butanol;(R)-2-Aminobutanol;D-(-)-2-Amino-1-butanol;D-2-Amino-1-butanol;[(R)-1-(Hydroxymethyl)propyl]amine;
PSA 46.25000
LogP 0.41630

Synthetic route

: 107-83-5
2-Methylpentane

: 5856-63-3
(2R)-2-aminobutan-1-ol

Conditions

Conditions	Yield
	61%

: 96-20-8, 13054-87-0
2-aminobutanol

: 5856-63-3
(2R)-2-aminobutan-1-ol

Conditions

Conditions	Yield
Stage #1: 2-aminobutanol With O,O'-dibenzoyl-L-tartaric acid In acetone at 25℃; for 6h; Stage #2: With potassium hydroxide In dichloromethane	20%
With L-Tartaric acid

: 2623-91-8
(R)-2-aminobutyric acid

: 5856-63-3
(2R)-2-aminobutan-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran
With lithium aluminium tetrahydride In tetrahydrofuran
With sodium tetrahydroborate In tetrahydrofuran at 0 - 80℃; for 12h; Inert atmosphere; Schlenk technique;

: 140170-82-7
ethyl (2R)-2-aminobutanoate

: 5856-63-3
(2R)-2-aminobutan-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

: (+)-(2R)-Ethylaziridin

: 5856-63-3
(2R)-2-aminobutan-1-ol

Conditions

Conditions	Yield
With perchloric acid

: 110418-25-2
(R)-(+)-2--1-butanol

: 5856-63-3
(2R)-2-aminobutan-1-ol

Conditions

Conditions	Yield
With sodium hydroxide at 80℃; for 2h;

: 110418-27-4
(R)-(+)-2-butyl acetate

: 5856-63-3
(2R)-2-aminobutan-1-ol

Conditions

Conditions	Yield
With sodium hydroxide at 80℃; for 2h;

: 150736-71-3
tert-butyl (R)-(1-hydroxybutan-2-yl)carbamate

: 5856-63-3
(2R)-2-aminobutan-1-ol

Conditions

Conditions	Yield
With methanol; Amberlyst 15; ammonia 1.) CH2Cl2, 25 deg C, 6 h, 2.) 50 min; Yield given. Multistep reaction;

: (R)-2-Azido-butan-1-ol

: 5856-63-3
(2R)-2-aminobutan-1-ol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 760 Torr; for 5h;

: 96-20-8, 13054-87-0
2-aminobutanol

A: 5856-63-3
(2R)-2-aminobutan-1-ol

B: 5856-62-2
(S)-2-aminobutan-1-ol

Conditions

Conditions	Yield
With chiral stationary phase including isopropyl-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 20℃; Purification / work up;
With glutaraldehyde crosslinked with chitosan In water under 775.743 - 1551.49 Torr; for 10h; Inert atmosphere; Resolution of racemate;

: C4H11NO*C9H11O2PS

A: 5856-63-3
(2R)-2-aminobutan-1-ol

B: 5856-62-2
(S)-2-aminobutan-1-ol

Conditions

Conditions	Yield
With potassium hydroxide Inert atmosphere;

: C4H11NO(1+)*C4H6O6(1-)

: 5856-63-3
(2R)-2-aminobutan-1-ol

Conditions

Conditions	Yield
With calcium hydroxide In water pH=10.6;

: C13H19NO2

A: 5856-63-3
(2R)-2-aminobutan-1-ol

B: 5856-62-2
(S)-2-aminobutan-1-ol

C: C13H19NO2

D: C13H19NO2

Conditions

Conditions	Yield
With penicillin G acylase from Bacillus megaterium immobilized on polymethacrylate; purchased from NovoCata (200 U/g); ammonia In water at 40℃; for 32h; pH=7.8; Resolution of racemate; Enzymatic reaction;	A n/a B n/a C n/a D n/a

...Expand

: 34114-57-3
N-(1-hydroxybutan-2-yl)-2-phenylacetamide

A: 5856-63-3
(2R)-2-aminobutan-1-ol

B: 5856-62-2
(S)-2-aminobutan-1-ol

C: (R)-2-[N-(phenylacetyl)amino]-1-butanol

D: (S)-2-[N-(phenylacetyl)amino]-1-butanol

Conditions

Conditions	Yield
With penicillin G acylase from Bacillus megaterium immobilized on polymethacrylate; purchased from NovoCata (200 U/g); ammonia In water at 40℃; for 10h; pH=7.8; Resolution of racemate; Enzymatic reaction;	A n/a B n/a C n/a D n/a

...Expand

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 24424-99-5
di-tert-butyl dicarbonate

: 150736-71-3
tert-butyl (R)-(1-hydroxybutan-2-yl)carbamate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	100%
In dichloromethane at 20℃; for 4h;	96%
With sodium hydroxide In dichloromethane Ambient temperature;	92%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 383-63-1
ethyl trifluoroacetate,

: 152529-37-8
2,2,2-Trifluoro-N-((R)-1-hydroxymethyl-propyl)-acetamide

Conditions

Conditions	Yield
In acetonitrile	100%
With pyridine for 2h;

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 100-39-0
benzyl bromide

: 249922-61-0
(2R)-N,N-dibenzyl-2-aminobutan-1-ol

Conditions

Conditions	Yield
With sodium carbonate; potassium iodide In tetrahydrofuran for 10h; Heating;	100%
Stage #1: (2R)-2-aminobutan-1-ol With sodium hydroxide; potassium carbonate In methanol for 0.5h; Metallation; Heating; Stage #2: benzyl bromide In methanol for 6h; Alkylation; Heating;	98%
With potassium carbonate; potassium iodide In acetonitrile for 16h; Reflux;	79%
With potassium carbonate In acetonitrile at 60℃;
With potassium carbonate In acetonitrile at 20℃; for 24h;

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 2-methyl-2-(3-phenylureido)propanoic acid

: (R)-N-(1-hydroxybutan-2-yl)-2-methyl-2-(3-phenylureido)propanamide

Conditions

Conditions	Yield
Stage #1: 2-methyl-2-(3-phenylureido)propanoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2R)-2-aminobutan-1-ol In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	100%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 369-34-6
3,4-difluoronitrobenzene

: 329229-75-6
(2R)-(+)-2-(2-fluoro-4-nitrophenyl)amino-1-butanol

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃; for 12h;	99%

: 553-90-2
Dimethyl oxalate

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 1019203-04-3
N,N'-bis[(1R)-1-(hydroxymethyl)propyl]ethanediamide

Conditions

Conditions	Yield
In methanol at 20℃; for 0.583333h;	99%
In methanol at 20℃; for 0.5h;	99%
In methanol at 20℃; for 0.0833333h;	99%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 7789-45-9
copper(ll) bromide

: [Cu3((R)-2-amino-butan-1-olate)4(μ-Br)2]

Conditions

Conditions	Yield
With triethylamine In methanol soln. of CuBr2 in MeOH added to soln. of (R)-2-amino-1-butanol and Et3N in MeOH; ppt. filtered off, washed with MeOH and Et2O, dried in air; elem. anal.;	99%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: copper dichloride

: [Cu3((R)-2-amino-butan-1-olate)4(μ-Cl)2]

Conditions

Conditions	Yield
With triethylamine In methanol soln. of CuCl2 in MeOH added to soln. of (R)-2-amino-1-butanol and Et3N in MeOH; ppt. filtered off, washed with MeOH and Et2O, dried in air; elem. anal.;	99%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 10250-66-5
3-(3-phenylureido)propanoic acid

: (R)-N-(1-hydroxybutan-2-yl)-3-(3-phenylureido)propanamide

Conditions

Conditions	Yield
Stage #1: 3-(3-phenylureido)propanoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2R)-2-aminobutan-1-ol In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	99%

: 110-78-1
Propyl isocyanate

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 1442093-52-8
(R)-1-(1-hydroxybutan-2-yl)-3-propylurea

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 2.16667h;	99%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 220096-47-9
1,2-bis[di(3',5'-diformylphenyl)phosphanyl]benzene

: C70H96N8O8P2

Conditions

Conditions	Yield
With trimethyl orthoformate In methanol for 20h; Ambient temperature;	98%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 5874-02-2
methyl 2-methylpropanedithioate

: 420133-78-4
(R)-N-[1-(hydroxymethyl)propyl]-2-methylpropanethioamide

Conditions

Conditions	Yield
With triethylamine at 20℃; for 12h;	98%
With triethylamine In tetrahydrofuran at 20℃;	95%
With triethylamine

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 5874-05-5
methyl cyclohexanecarbodithionate

: 420133-81-9
(R)-N-[1-(hydroxymethyl)propyl]cyclohexanethiocarboxamide

Conditions

Conditions	Yield
With triethylamine at 20℃; for 48h;	98%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 420133-85-3
(R)-methyl-2-methyl-2-(4-ethyl-4,5-dihydro-2-thiazolyl)propanedithioate

: 420133-90-0
(R,R)-4-ethyl-2-{1-[N-(1-(hydroxymethyl)propyl)thiocarbamoyl]-1-methylethyl}-2-thiazoline

Conditions

Conditions	Yield
With triethylamine at 20℃; for 24h;	98%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 420133-88-6
(R)-methyl-1-(4-ethyl-4,5-dihydro-2-thiazolyl)cyclohexanedithiocarboxylate

: (R,R)-4-ethyl-2-{1-[N-(1-(hydroxymethyl)propyl)thiocarbamoyl]cyclohexyl}-2-thiazoline

Conditions

Conditions	Yield
With triethylamine at 20℃; for 96h;	98%

: (1,2-bis(2-mercaptophenylthio)ethane(PPh3)(ClH))ruthenium*CH2Cl2

: 5856-63-3
(2R)-2-aminobutan-1-ol

: (1,2-bis(2-mercaptophenylthio)ethane(PPh3)(N-acetyl-(L)methionine)((D)-C2H5CH(NH3)CH2OH))ruthenium

Conditions

Conditions	Yield
In methanol To a soln. of Ru-compd. a soln. of (D)-2-amino-1-butanol is added at room temp. (without light; N2).; Volume is reduced to dryness, residue is digested with ether, sepd., washed with and dried in high-vac., elem. anal.;	98%

: 110-99-6
2,2'-oxybis-acetic acid

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 850410-75-2
(-)-bis{[4-(R)-ethyloxazolin-2-yl]methyl} ether

Conditions

Conditions	Yield
In toluene for 23h; Reflux;	98%

: 139-13-9
nitrilotriacetic acid

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 911838-01-2
(+)-N,N,N-tris{[4-(R)-ethyloxazolin-2-yl]methyl}amine

Conditions

Conditions	Yield
Stage #1: nitrilotriacetic acid; (2R)-2-aminobutan-1-ol In toluene for 24h; Reflux; Stage #2: at 125℃; for 9h;	98%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 83-38-5
2,6-dichlorobenzaldehyde

: 1253377-15-9
(R)-2-(2,6-dichlorobenzylideneamino)butan-1-ol

Conditions

Conditions	Yield
In methanol at 20℃;	98%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 79-04-9
chloroacetyl chloride

: 466695-50-1
2-chloro-N-[(2R)-1-hydroxybutan-2-yl]acetamide

Conditions

Conditions	Yield
With water; potassium carbonate In dichloromethane at 0℃; for 1.5h;	98%
With potassium carbonate In tetrahydrofuran; water at -10℃; for 1h;

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 2644-94-2
1-benzyl-3,5-dimethyl-1H-pyrazole-4-carbaldehyde

: 2-{[(1E)-(1-benzyl-3,5-dimethyl-1H-pyrazol-4-yl)methylidene]amino}butan-1-ol

Conditions

Conditions	Yield
In benzene at 150℃; for 2h; Microwave irradiation; Molecular sieve; Inert atmosphere;	98%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: methyl (5-fluoro-2,4-dinitrophenyl)-(S)-prolinate

: methyl (5-(((R)-1-hydroxybutan-2-yl)amino)-2,4-dinitrophenyl)-(S)-prolinate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 80℃; for 2h; Inert atmosphere;	97.6%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 109-94-4
formic acid ethyl ester

: 88512-12-3
R-(+)-N-formyl-2-aminobutan-1-ol

Conditions

Conditions	Yield
for 6h; Heating;	97%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 100-52-7
benzaldehyde

: 6257-49-4
(2R)-2-(benzylamino)butan-1-ol

Conditions

Conditions	Yield
Stage #1: (2R)-2-aminobutan-1-ol; benzaldehyde In methanol at 20℃; for 1h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 1.5h; Inert atmosphere;	97%
With sodium cyanoborohydride; acetic acid In methanol Ambient temperature;	75%
With sodium tetrahydroborate
With sodium tetrahydroborate; 4 A molecular sieve; magnesium sulfate 1.) CH2Cl2, 25 deg C; 2.) MeOH, rt, 2 h; Multistep reaction;

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 102-92-1
Cinnamoyl chloride

: 201005-58-5
R-(+)-(2E)-N-(1-hydroxybutan-2-yl)-3-phenylprop-2-enamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 18h;	97%
With potassium carbonate In water; toluene for 0.333333h;	83%
With sodium carbonate In dichloromethane	62%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: 121-44-8
triethylamine

: 213611-68-8
(2SR,4R)-4-ethyl-2-methoxy-3-(4-nitrobenzenesulfonyl)-1,3-oxazolidine

Conditions

Conditions	Yield
In dichloromethane at 0℃; for 16h; Condensation;	97%

...Expand

: 15084-51-2
4-tert-butylbenzenesulfonyl chloride

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 1032477-04-5
(2R)-N-(4-tert-butylbenzenesulfonyl)-2-amino-butanol

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 18h;	97%

: 660822-33-3
(2-fluoro-9-isopropyl-9H-purin-6-yl)(pyridin-3-ylmethyl)amine

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 2-[(R)-1-ethyl-2-hydroxyethylamino]-9-isopropyl-6-[(pyridin-3-ylmethyl)-amino]purine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; butan-1-ol at 140℃; for 48h; Inert atmosphere;	97%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 103-72-0
phenyl isothiocyanate

: 1192347-25-3
(R)-1-(1-hydroxybutan-2-yl)-3-phenylthiourea

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 2.16667h;	97%

: 5856-63-3
(2R)-2-aminobutan-1-ol

: 20632-57-9
3-[(phenylcarbamoyl)amino]benzoic acid

: (R)-N-(1-hydroxybutan-2-yl)-3-(3-phenylureido)benzamide

Conditions

Conditions	Yield
Stage #1: 3-[(phenylcarbamoyl)amino]benzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2R)-2-aminobutan-1-ol In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	97%

(R)-(-)-2-Amino-1-butanol Specification

The (R)-(-)-2-Amino-1-butanol, with the CAS registry number 5856-63-3, is also known as 2-Amino-1-butanol, (R)-. It belongs to the product categories of Amino Alcohols (Chiral); Chiral Building Blocks; Synthetic Organic Chemistry; Amino Alcohols; Chiral Building Blocks; Organic Building Blocks. Its EINECS registry number is 227-476-4. This chemical's molecular formula is C₄H₁₁NO and molecular weight is 89.13624. Its IUPAC name is called (2R)-2-aminobutan-1-ol.

Physical properties of (R)-(-)-2-Amino-1-butanol: (1)ACD/LogP: -0.617; (2)ACD/LogD (pH 5.5): -3.70; (3)ACD/LogD (pH 7.4): -3.17; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.446; (12)Molar Refractivity: 25.609 cm³; (13)Molar Volume: 96.123 cm³ ; (14)Polarizability: 10.152 10-24cm³; (15)Surface Tension: 35.3870010375977 dyne/cm; (16)Density: 0.927 g/cm³; (17)Flash Point: 82.222 °C; (18)Enthalpy of Vaporization: 48.141 kJ/mol; (19)Boiling Point: 177.227 °C at 760 mmHg; (20)Vapour Pressure: 0.319000005722046 mmHg at 25°C

Preparation of (R)-(-)-2-Amino-1-butanol: this chemical can be prepared by 2-amino-butan-1-ol. This reaction will need reagents dibenzoyl-L-tartaric acid and aq. KOH and solvents acetone, CH₂Cl₂. The reaction time is 6 hours with reaction temperature of 25 °C. The yield is about 20%.

1-Butanol, 2-amino-,(2R)- can be prepared by 2-amino-butan-1-ol

Uses of (R)-(-)-2-Amino-1-butanol: it can be used to produce (R)-2-aminobutyl-n-butyl ether. This reaction will need reagent sodium hydride. The yield is about 53%.

1-Butanol, 2-amino-,(2R)- can be used to produce (R)-2-aminobutyl-n-butyl ether

When you are using this chemical, please be cautious about it as the following:
This chemical may destroy living tissue on contact and may cause burns. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCC(CO)N
(2)Isomeric SMILES: CC[C@H](CO)N
(3)InChI: InChI=1S/C4H11NO/c1-2-4(5)3-6/h4,6H,2-3,5H2,1H3/t4-/m1/s1
(4)InChIKey: JCBPETKZIGVZRE-SCSAIBSYSA-N

Product Name

2-Aminobutanol

Synthetic route

(R)-(-)-2-Amino-1-butanol Specification

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