Bicine supplier | CasNO.150-25-4

Name
Bicine
EINECS 205-755-1
CAS No. 150-25-4
Article Data22
CAS DataBase
Density 1.31 g/cm³
Solubility water: 1 M at 20 °C, clear, colorless
Melting Point 190 °C (dec.)(lit.)
Formula C₆H₁₃NO₄
Boiling Point 388.5 °C at 760 mmHg
Molecular Weight 163.174
Flash Point 188.8 °C
Transport Information
Appearance White crystalline powder
Safety 24/25-36-26
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms N,N-Bis(2-hydroxyethyl)glycine;Bis(2-Hydroxyethyl)glycine;N,N-Bis(2-hydroxyethyl)aminoacetic acid;NSC 7342;Diethanol glycine;
PSA 81.00000
LogP -1.64240

Synthetic route

: 131543-46-9
Glyoxal

: 111-42-2
2,2'-iminobis[ethanol]

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
In ethanol; water at 70℃; for 16h;	96%

: 75-21-8
oxirane

: 459-73-4
GlyOEt*HCl

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
at 25℃;
at 25℃; im Rohr;

: 5038-12-0
4-(2-hydroxy-ethyl)-morpholin-2-one

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
With water at 25℃; Rate constant; at pD 7.0; hydrolysis also in humid air;
With water at 120℃;
With water (heating);
With water

: 98486-41-0
N,N-bis-(2-chloro-ethyl)-glycine

A: 86240-92-8
4-(2-chloro-ethyl)-morpholin-2-one

B: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
With sodium hydrogencarbonate; benzene
With sodium hydrogencarbonate

: 64-69-7
Iodoacetic acid

: 111-42-2
2,2'-iminobis[ethanol]

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
With methanol

: 3926-62-3
sodium monochloroacetic acid

: 111-42-2
2,2'-iminobis[ethanol]

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
With water

: 111-42-2
2,2'-iminobis[ethanol]

: 79-11-8
chloroacetic acid

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
With ethanol
In ethanol

: Nα,Nα-bis(-2-hydroxyethyl)glycine amide

A: 5038-12-0
4-(2-hydroxy-ethyl)-morpholin-2-one

B: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
With water at 25℃; Rate constant; Product distribution; Mechanism; pH varied: 4 to 8; hydrolysis of C-terminal amide group of various α-aminoacids having one or two hydroxyethyl groups at N-terminal, via cyclization to a morpholinolactone; reaction monitored by 1H NMR;

: 5038-12-0
4-(2-hydroxy-ethyl)-morpholin-2-one

: 7732-18-5
water

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

<2-chloroacetoxy-ethyl>-<2-chloro-ethyl>-amine hydrochloride: <2-chloroacetoxy-ethyl>-<2-chloro-ethyl>-amine hydrochloride

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
With potassium carbonate

: 50-00-0
formaldehyd

: 151-50-8
potassium cyanide

bis-<2-hydroxy-ethyl>-amine hydrochloride: bis-<2-hydroxy-ethyl>-amine hydrochloride

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
With water und Hydrolyse des Reaktionsprodukts mit wss.HCl;

...Expand

: 96-32-2
bromoacetic acid methyl ester

: 111-42-2
2,2'-iminobis[ethanol]

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

Conditions

Conditions	Yield
With sodium hydroxide; triethylamine In propan-1-ol; ethanol

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 20427-59-2
copper hydroxide

: 77180-36-0, 921625-45-8, 13978-30-8
copper(II) bis(N,N-bis(2-hydroxyethyl)glycinate)

Conditions

Conditions	Yield
In neat (no solvent, solid phase) grinding at room temp. in air for 30 min; crystn. from EtOH:H2O (1:1) for 2 d at room temp., elem. anal.;	99%

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 27668-52-6
octadecyldimethyl[3-(trimethoxysilyl)propyl]ammonium chloride

: disodium 7-(2-((carboxymethyl)(2-hydroxyethyl)amino)ethoxy)-7-(3-(heptadecyldimethylammonio)propyl)-3,11-bis(2-hydroxyethyl)-6,8-dioxa-3,11-diaza-7-silatridecanedioate chloride

Conditions

Conditions	Yield
Stage #1: N,N-bis-(2-hydroxyethyl)glycine; octadecyldimethyl[3-(trimethoxysilyl)propyl]ammonium chloride In N,N-dimethyl-formamide at 145℃; Stage #2: With sodium methylate In N,N-dimethyl-formamide	95%

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 95-54-5
1,2-diamino-benzene

: 91646-60-5
N-(benzimidazol-2-ylmethyl)iminodiethanol

Conditions

Conditions	Yield
With hydrogenchloride for 48h; Heating;	93%
With hydrogenchloride; water

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 85825-95-2
amine

Conditions

Conditions	Yield
	85%

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 108-24-7
acetic anhydride

: 86351-49-7
4-(2-acetoxy-ethyl)-morpholin-2-one

Conditions

Conditions	Yield
With triethylamine for 1h; Heating;	83%
With pyridine Erwaermen des Reaktionsprodukts in Methanol oder in H2O;

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 42428-34-2
Phenyl-triethoxygerman

: 75713-38-1
1-phenyl-2,8,9-trioxa-5-aza-1-germatricyclo[3.3.3.0(1,5)]undecane-3-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; benzene byproducts: CH3CH2OH; boiled for 2 h with distillation; cooled; filtered off; washed (benzene and ether); dried (vac.); IR; elem.anal.;	72%

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 5865-91-8
Methyl-triaethoxy-germanium

: 75713-37-0
1-methyl-2,8,9-trioxa-5-aza-1-germatricyclo[3.3.3.0(1,5)]undecane-3-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; benzene byproducts: CH3CH2OH; boiled for 2 h with distillation; cooled; filtered off; washed (benzene and ether); dried (vac.); IR; elem.anal.;	69%

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: Mn(H2O)6(2+)*2Br(1-)=MnBr2*6H2O

: Mn2(OC(O)CH2N(CH2CH2OH)2)2(H2O)2(2+)*2Br(1-)*2H2O=[Mn2(OC(O)CH2N(CH2CH2OH)2)2(H2O)2]Br2*2H2O

Conditions

Conditions	Yield
With [(CH3)4N]OH In methanol; water boiling (pH .apprx. 8, 10 min); elem. anal.;	68.8%

: manganese(II) chloride hexahydrate

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 194363-15-0
([Mn(N,N-bis(2-hydroxyethyl)glycinate)Cl]2*2(H2O))n

Conditions

Conditions	Yield
With Me4NOH In methanol dropwise addn. of Me4NOH to mixt. of Mn-salt and ligand; crystn. on slow evapn. (few d); elem. anal.;	68%

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 5865-92-9
Ethyl-triethoxygermanium

: 87511-09-9
1-ethyl-2,8,9-trioxa-5-aza-1-germatricyclo[3.3.3.0(1,5)]undecane-3-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; benzene byproducts: CH3CH2OH; boiled for 2 h with distillation; cooled; filtered off; washed (benzene and ether); dried (vac.); IR; elem.anal.;	60%

: vanadyl(IV) sulphate pentahydrate

: 60-29-7
diethyl ether

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: VO(2+)*HOCH2CH2(OCH2CH2)N(CH2COO)(2-)*0.5(CH3CH2)2O=[VO((HOCH2CH2(OCH2CH2)N(CH2COO)))*0.5(CH3CH2)2O]

Conditions

Conditions	Yield
With barium dihydroxide In water byproducts: BaSO4; org. compd. and Ba compd. dissolved in deionised water under N2 then heated and stirred for 30 min, VO compd. added and react. mixt. stirred for30 min; BaSO4 filtered off, filtrate concd. in vac. to oily residue, washed withEt2O, solid filtered, washed with Et2O and dried in vac.; elem. anal.;	58%

...Expand

: cadmium(II) chloride dihydrate

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 60245-55-8, 1269638-47-2
[CdCl(N,N-bis(2-hydroxyethyl)glycine(-1H))]*H2O

Conditions

Conditions	Yield
With LiOHH2O In methanol; water byproducts: LiCl, H2O; soln. of Cd salt in H2O added to stirred soln. of ligand and LiOHH2O inMeOH; layered with acetone; crystd. for 5 d; filtered; crystals washed with cold MeOH and acetone; dried in air; elem. anal.;	55%

: 67-56-1
methanol

: cadmium(II) chloride dihydrate

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 1310-73-2
sodium hydroxide

: [CdNaCl2(N,N-bis(2-hydroxyethyl)glycine(-1H))(methanol)]*0.5(methanol)

Conditions

Conditions	Yield
In methanol byproducts: H2O; soln. of Cd salt in MeOH added to stirred soln. of ligand and NaOH in MeOH; refluxed for 25 min; concd. slowly by evapn. over 4 d; filtered; crystals washed with cold MeOH and Et2O; dried in air; elem. anal.;	53%

...Expand

: 83149-20-6
[dichlorobis(triphenylphosphane)(η2-N-benzoylhydrazido(3-)-N',O)rhenium(V)]

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: [chloro(N,N-bis(2-hydroxyethyl)glycinate)(triphenylphosphane)(η1-N-benzoyldiazenido(2-)-N')rhenium(III)]

Conditions

Conditions	Yield
In methanol N2, an excess of amine, refluxed for 8 h; concd. (vac.), diethyl ether added, left for 2 d at room temp., crysts. washed (methanol), dried (vac.); elem. anal.;	48%

: 7791-07-3
sodium perchlorate monohydrate

: praseodymium(III) acetate tetrahydrate

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 7732-18-5
water

: 5144-89-8
1,10-phenanthroline hydrate

: [Pr(O2CCH3)(bicine)(1,10-phenanthroline)(H2O)](ClO4)*1,10-phenanthroline*3H2O

Conditions

Conditions	Yield
In ethanol; water byproducts: CH3COOH, CH3COONa; a soln. of bicine in water was added to a soln. of Pr-compound in H2O, stirred, an ethanolic soln. of NaClO4 and phenanthroline were added, allowed to stand for 20 days at room temp.; filtered, washed with cold ethanol and dried in air; elem. anal.;	45%

...Expand

: 7791-07-3
sodium perchlorate monohydrate

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 7732-18-5
water

: 15280-57-6
erbium(III) acetate tetrahydrate

: 5144-89-8
1,10-phenanthroline hydrate

: [Er(O2CCH3)(bicine)(1,10-phenanthroline)(H2O)](ClO4)*1,10-phenanthroline*3H2O

Conditions

Conditions	Yield
In ethanol; water byproducts: CH3COOH, CH3COONa; a soln. of bicine in water was added to a soln. of Er-compound in H2O, stirred, an ethanolic soln. of NaClO4 and phenanthroline were added, allowed to stand for 20 days at 5°C; crystals were washed with cold ethanol, diethyl ether and dried in air; elem. anal.;	40%

...Expand

: 67-56-1
methanol

: [Fe(III)3(μ3-O)(O2CC6H5)6(H2O)3](O2CC6H5)

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: [Fe6(bicine-3H)6]*4H2O*4MeOH

Conditions

Conditions	Yield
In acetonitrile byproducts: PhCO2H, H2O; to a soln. of Fe3-contg. compd. (0.25 mmol) in MeCN was added with stirring a soln. of a ligand (0.50 mmol) in MeCN; the soln. was stirred overnight at ambient temp.; the ppt. was collected by filtration, washed with MeCN and dissolved in MeOH-CH2Cl2 (1:1); the soln. was layered with Et2O and left at ambient temp.; after 1 wk the crystals were collected by filtration, washed with CH2Cl2 and dried in vac.; elem. anal.;	38%

Yield

In acetonitrile byproducts: PhCO2H, H2O; to a soln. of Fe3-contg. compd. (0.25 mmol) in MeCN was added with stirring a soln. of a ligand (0.50 mmol) in MeCN; the soln. was stirred overnight at ambient temp.; the ppt. was collected by filtration, washed with MeCN and dissolved in MeOH-CH2Cl2 (1:1); the soln. was layered with Et2O and left at ambient temp.; after 1 wk the crystals were collected by filtration, washed with CH2Cl2 and dried in vac.; elem. anal.;

38%

...Expand

: 7791-07-3
sodium perchlorate monohydrate

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 7732-18-5
water

: 14462-42-1, 16648-22-9, 17829-84-4, 25721-95-3, 25722-01-4, 50484-87-2, 61907-70-8, 92457-91-5
neodymium(III) acetate tetrahydrate

: 5144-89-8
1,10-phenanthroline hydrate

: [Nd(O2CCH3)(bicine)(1,10-phenanthroline)(H2O)](ClO4)*1,10-phenanthroline*3H2O

Conditions

Conditions	Yield
In ethanol; water byproducts: CH3COOH, CH3COONa; a soln. of bicine in water was added to a soln. of Nd-compound in H2O, stirred, an ethanolic soln. of NaClO4 and phenanthroline were added, allowed to stand for 20 days at room temp.; filtered, washed with cold ethanol and dried in air; elem. anal.;	30%

...Expand

: 7791-07-3
sodium perchlorate monohydrate

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 7732-18-5
water

: 14432-01-0, 15280-53-2, 79464-08-7, 100587-93-7, 138481-01-3
gadolinium(III) acetate tetrahydrate

: 5144-89-8
1,10-phenanthroline hydrate

: [Gd(O2CCH3)(bicine)(1,10-phenanthroline)(H2O)](ClO4)*1,10-phenanthroline*3H2O

Conditions

Conditions	Yield
In ethanol; water byproducts: CH3COOH, CH3COONa; a soln. of bicine in water was added to a soln. of Gd-compound in H2O, stirred, an ethanolic soln. of NaClO4 and phenanthroline were added, allowed to stand for 20 days at room temp.; filtered, washed with cold ethanol and dried in air; elem. anal.;	25%

...Expand

: cobalt(II) chloride hexahydrate

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: [CoII(N,N-bis(2-hydroxyethyl)glycinato)Cl]

Conditions

Conditions	Yield
With triethylamine In ethanol at 140℃; under 15514.9 Torr; for 0.25h; Sealed tube; Microwave irradiation;	18%

: cobalt(II) chloride hexahydrate

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: [CoII9(N,N-bis(2-hydroxoethyl)glycinato)4(N,N-bis(2-hydroxoethyl)glycinato)2Cl4]

Conditions

Conditions	Yield
With triethylamine In ethanol at 140℃; under 15514.9 Torr; for 0.25h; Sealed tube; Microwave irradiation;	17%

: cobalt(II) chloride hexahydrate

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 7732-18-5
water

: [CoII9(N,N-bis(2-hydroxyethyl)glycinato)4(N,N-bis(2-hydroxyethyl)glycinato)2Cl4]*12H2O

Conditions

Conditions	Yield
With triethylamine In ethanol at 140℃; under 15514.9 Torr; for 0.25h; Sealed tube; Microwave irradiation;	17%

...Expand

: [Fe3O(pivalate)6(H2O)3](pivalate)*2Me3CCO2H

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 109-89-7
diethylamine

: 75-05-8
acetonitrile

: [Et2NH2]2[Fe6O2(OH)2(N,N-bis(2hydroxyethyl)glycine(3-))2(pivalate)8]*1.5MeCN*4H2O

Conditions

Conditions	Yield
In acetonitrile N,N-bis(2-hydroxyethyl)glycine added to MeCN soln. of Fe pivalate deriv.followed by Et2NH (1:1:1); stirred at ambient temp. for 24 h; filtered; cryst. in a sealed vial after 2 wks; elem. anal.;	16%

...Expand

: [Fe3O(pivalate)6(H2O)3](pivalate)*2Me3CCO2H

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 75-05-8
acetonitrile

: [Fe12O4(N,N-bis(2hydroxyethyl)glycine(3-))4(N,N-bis(2hydroxyethyl)glycine(2-))4(pivalate)8]*2MeCN*4H2O

Conditions

Conditions	Yield
With NaOMe In acetonitrile N,N-bis(2-hydroxyethyl)glycine added to MeCN soln. of Fe pivalate deriv.followed by NaOMe (1:1:1); stirred at ambient temp. for 24 h; filtered; cryst. in a sealed vial after 2 wks; elem. anal.;	12%

...Expand

: 5348-42-5
4,5-Dichloro-1,2-phenylenediamine

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 6478-89-3
2,2'-(5,6-dichloro-1H-benzoimidazol-2-ylmethylazanediyl)-bis-ethanol

Conditions

Conditions	Yield
With hydrogenchloride; water

: 150-25-4
N,N-bis-(2-hydroxyethyl)glycine

: 5038-12-0
4-(2-hydroxy-ethyl)-morpholin-2-one

Conditions

Conditions	Yield
durch trockne Destillation;
With hydrogenchloride
With hydrogenchloride
In solid at 195℃; for 0.166667h;

Bicine Specification

The Bicine is an organic compound with the formula C₆H₁₃NO₄. The IUPAC name of this chemical is 2-[bis(2-hydroxyethyl)amino]acetic acid. With the CAS registry number 150-25-4 and EINECS 205-755-1, it is also named as N,N-Bis(2-hydroxyethyl)glycine. The product's categories are Biochemistry; Good's Buffers; Buffer. It is white crystalline powder which is stable under normal temperature and pressure. Additionally, this chemical should be stored at normal temperature.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.48; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.96; (4)ACD/LogD (pH 7.4): -2.99; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 48 Å²; (13)Index of Refraction: 1.525; (14)Molar Refractivity: 38.2 cm³; (15)Molar Volume: 124.4 cm³; (16)Polarizability: 15.14×10^-24 cm³; (17)Surface Tension: 63.8 dyne/cm; (18)Density: 1.31 g/cm³; (19)Flash Point: 188.8 °C; (20)Enthalpy of Vaporization: 73.75 kJ/mol; (21)Boiling Point: 388.5 °C at 760 mmHg; (22)Vapour Pressure: 1.21E-07 mmHg at 25°C.

Preparation of Bicine: It can be obtained by 2,2'-azanediyl-bis-ethanol and glyoxal. This reaction needs solvents H₂O, ethanol at temperature of 70 °C. The reaction time is 16 hours. The yield is 96%.

Bicine can be obtained by 2,2'-azanediyl-bis-ethanol and glyoxal

Uses of Bicine: It is used as a buffering agent in biochemical research. And it can react with acetic acid anhydride to get 4-(2-acetoxy-ethyl)-morpholin-2-one. This reaction needs reagent Et₃N by heating. The reaction time is 1 hours. The yield is 83%.

Bicine can react with acetic acid anhydride to get 4-(2-acetoxy-ethyl)-morpholin-2-one

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)CN(CCO)CCO
2. InChI:InChI=1/C6H13NO4/c8-3-1-7(2-4-9)5-6(10)11/h8-9H,1-5H2,(H,10,11)
3. InChIKey:FSVCELGFZIQNCK-UHFFFAOYAV

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	1540mg/kg (1540mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	Revue d'Epidemiologie, Medecine Sociale et Sante Publique. Vol. 10, Pg. 391, 1962.

Product Name

Bicine

Synthetic route

Bicine Specification

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