Butanedioic acid,2-hydroxy-2-methyl-, (2R)- supplier

Name
(R)-(-)-CITRAMALIC ACID
EINECS
CAS No. 6236-10-8
Article Data10
CAS DataBase
Density 1.513 g/cm³
Solubility
Melting Point 108-110 °C(lit. )
Formula C₅H₈O₅
Boiling Point 295.2 °C at 760 mmHg
Molecular Weight 148.116
Flash Point 146.6 °C
Transport Information
Appearance white fine crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Butanedioicacid, 2-hydroxy-2-methyl-, (R)-;Malic acid, 2-methyl-, (-)- (8CI);(-)-Citramalic acid;(R)-Citramalate;(R)-Citramalic acid;2R-Methylmalic acid;D-(-)-Citramalic acid;D-Citramalic acid;R-Citramalic acid;
PSA 94.83000
LogP -0.70330

Synthetic route

: 205579-47-1
((3R,8aS)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[2,1-c][1,4]oxazin-3-yl)-acetic acid ethyl ester

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
With hydrogenchloride for 5h; Heating;	100%

: 93206-60-1
(S)-4-methyl-4-(trichloromethyl)-2-oxetanone

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
With sodium hydroxide at 20℃; for 18h; Hydrolysis;	91%
With sodium hydroxide In water 1.) 5 deg C; 2.) room temperature;

: 119696-04-7
trans-2-phenylcyclohexyl citramalate

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran at 60℃; for 24h;	87%

: 597-44-4
2-hydroxy-2-methylbutane-1,4-dioic acid

A: 2174-58-5
L-malic acid

B: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
With formaldehyd; TETRACYCLINE; paraquat dichloride In water at 37℃; for 69h; Clostridium formicoaceticum, phosphate buffer;	A 84.8% B 81.8%

: (R)-3-cyano-2-hydroxy-2-methylpropanamide

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
With barium dihydroxide; water for 48h; Heating;	81%

: (-)-Isotetradehydrofurospongin-1

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
Stage #1: (-)-Isotetradehydrofurospongin-1 With ozone In dichloromethane at -78℃; Stage #2: With jones reagent In dichloromethane at 20℃; Further stages.;	25%

: 597-44-4
2-hydroxy-2-methylbutane-1,4-dioic acid

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
With brucine

: 498-23-7
citraconic acid

A: 6236-10-8
(R)-(-)-citramalic acid

B: 152204-30-3
(2R,3S)-3-methylmalic acid

Conditions

Conditions	Yield
With TETRACYCLINE In water at 37℃; for 142h; Clostridium formicoaceticum, phosphate buffer; Title compound not separated from byproducts;

: 1-benzyl hydrogen 2-hydroxy-2-methylbutanedioate

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
With potassium hydroxide Hydrolysis;

: 14-O-α-L-rhamnopyranosyl-(2E,4E,7R,8E,10E,12E,14R)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid

A: 6236-10-8
(R)-(-)-citramalic acid

B: 144-62-7
oxalic acid

C: 64-19-7
acetic acid

D: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h; Further byproducts given. Title compound not separated from byproducts;

...Expand

: 14-O-α-L-rhamnopyranosyl-(2E,4E,7R,8E,10E,12E,14R)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid

A: 6236-10-8
(R)-(-)-citramalic acid

B: 141-82-2
malonic acid

C: 64-19-7
acetic acid

D: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h; Further byproducts given. Title compound not separated from byproducts;

...Expand

: 14-O-α-D-mannopyranosyl-(2E,4E,7R,8E,10E,12E,14S)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid

A: 6236-10-8
(R)-(-)-citramalic acid

B: 144-62-7
oxalic acid

C: 64-19-7
acetic acid

D: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h; Further byproducts given. Title compound not separated from byproducts;

...Expand

: 14-O-α-D-mannopyranosyl-(2E,4E,7R,8E,10E,12E,14S)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid

A: 6236-10-8
(R)-(-)-citramalic acid

B: 141-82-2
malonic acid

C: 64-19-7
acetic acid

D: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h; Further byproducts given. Title compound not separated from byproducts;

...Expand

: 66261-38-9
2-methyl-2-butenedioic acid 4-ethylester

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 100 percent / diethyl phosphorocyanidate, TEA / dimethylformamide / 2 h / 0 °C 2: 98 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature 3: 83 percent / N-iodosuccinimide / dimethylformamide / 12 h / 36 °C 4: 92 percent / n-Bu3SnH / benzene / 0.5 h / Heating 5: 100 percent / 6N aq. HCl / 5 h / Heating View Scheme

: 65527-85-7
ethyl (E)-4-hydroxy-3-methyl-2-butenoate

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 96 percent / CrO3, 1.5 M H2SO4 / acetone 2: 100 percent / diethyl phosphorocyanidate, TEA / dimethylformamide / 2 h / 0 °C 3: 98 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature 4: 83 percent / N-iodosuccinimide / dimethylformamide / 12 h / 36 °C 5: 92 percent / n-Bu3SnH / benzene / 0.5 h / Heating 6: 100 percent / 6N aq. HCl / 5 h / Heating View Scheme

Yield

Multi-step reaction with 6 steps
1: 96 percent / CrO3, 1.5 M H2SO4 / acetone
2: 100 percent / diethyl phosphorocyanidate, TEA / dimethylformamide / 2 h / 0 °C
3: 98 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature
4: 83 percent / N-iodosuccinimide / dimethylformamide / 12 h / 36 °C
5: 92 percent / n-Bu3SnH / benzene / 0.5 h / Heating
6: 100 percent / 6N aq. HCl / 5 h / Heating
View Scheme

: 132032-94-1
(E)-4-(tert-butyldimethylsilanyloxy)-3-methylbut-2-enoic acid ethyl ester

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran 2: 96 percent / CrO3, 1.5 M H2SO4 / acetone 3: 100 percent / diethyl phosphorocyanidate, TEA / dimethylformamide / 2 h / 0 °C 4: 98 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature 5: 83 percent / N-iodosuccinimide / dimethylformamide / 12 h / 36 °C 6: 92 percent / n-Bu3SnH / benzene / 0.5 h / Heating 7: 100 percent / 6N aq. HCl / 5 h / Heating View Scheme

Yield

Multi-step reaction with 7 steps
1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran
2: 96 percent / CrO3, 1.5 M H2SO4 / acetone
3: 100 percent / diethyl phosphorocyanidate, TEA / dimethylformamide / 2 h / 0 °C
4: 98 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature
5: 83 percent / N-iodosuccinimide / dimethylformamide / 12 h / 36 °C
6: 92 percent / n-Bu3SnH / benzene / 0.5 h / Heating
7: 100 percent / 6N aq. HCl / 5 h / Heating
View Scheme

: 205579-44-8
(S)-1-((E)-3-Ethoxycarbonyl-2-methyl-acryloyl)-pyrrolidine-2-carboxylic acid

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 83 percent / N-iodosuccinimide / dimethylformamide / 12 h / 36 °C 2: 92 percent / n-Bu3SnH / benzene / 0.5 h / Heating 3: 100 percent / 6N aq. HCl / 5 h / Heating View Scheme

: 205579-46-0
(S)-Iodo-((3S,8aS)-3-methyl-1,4-dioxo-hexahydro-pyrrolo[2,1-c][1,4]oxazin-3-yl)-acetic acid ethyl ester

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / n-Bu3SnH / benzene / 0.5 h / Heating 2: 100 percent / 6N aq. HCl / 5 h / Heating View Scheme

: 205579-42-6
(S)-1-((E)-3-Ethoxycarbonyl-2-methyl-acryloyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

: 6236-10-8
(R)-(-)-citramalic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature 2: 83 percent / N-iodosuccinimide / dimethylformamide / 12 h / 36 °C 3: 92 percent / n-Bu3SnH / benzene / 0.5 h / Heating 4: 100 percent / 6N aq. HCl / 5 h / Heating View Scheme

: 186581-53-3, 908094-01-9
diazomethane

: 6236-10-8
(R)-(-)-citramalic acid

: 81426-68-8
(R)-dimethyl 2-hydroxy-2-methylsuccinate

Conditions

Conditions	Yield
In methanol	100%
In diethyl ether at 0℃; for 2h;	90%
In methanol; diethyl ether at 0℃;

: 6236-10-8
(R)-(-)-citramalic acid

: 60299-29-8
(S)-(-)-2-Methylbutane-1,2,4-triol

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran at 0℃; Reflux;	100%

: 67-56-1
methanol

: 6236-10-8
(R)-(-)-citramalic acid

: 81426-68-8
(R)-dimethyl 2-hydroxy-2-methylsuccinate

Conditions

Conditions	Yield
Stage #1: (R)-(-)-citramalic acid With thionyl chloride In methanol; dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: methanol In dichloromethane at 0 - 20℃; Inert atmosphere;	97.3%
With hydrogenchloride at 55℃; for 48h;	72%
With hydrogenchloride Esterification;
With thionyl chloride

: 6236-10-8
(R)-(-)-citramalic acid

: 100-39-0
benzyl bromide

: 1115955-01-5
1-benzyl 4-benzyl 2-hydroxy-2-methylbutanedioate

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	90%

: 6236-10-8
(R)-(-)-citramalic acid

: 79-41-4
poly(methacrylic acid)

Conditions

Conditions	Yield
sodium hydroxide In water at 300℃; under 262201 Torr; Product distribution / selectivity;	80.8%

: (Et4N)2{MoFe3S4Cl3(Cl4cat)(CH3CN)}

: 6236-10-8
(R)-(-)-citramalic acid

: (Et4N)3[(MoFe3S4Cl3)(R-citramalate(1-))] * 0.50 MeCN

Conditions

Conditions	Yield
In acetonitrile absence of air; treatment of Mo-complex with 1.5 fold excess of citramalic acid, stirring (50°C, 24 h); cooling to room temp., filtration, pptn. on Et2O addn. to filtrate, recrystn. (MeCN/Et2O), washing (MeOH, Me2CO, Et2O), drying (vac.); elem. anal.;	65%

: tetraethylammonium hydroxide

: 12125-77-8
tricarbonyl(cycloheptatriene)molybdenum(0)

: 6236-10-8
(R)-(-)-citramalic acid

: [Et4N]2[((R)-(+)-citramallic acid(-2H))Mo(CO)3]

Conditions

Conditions	Yield
In methanol (N2); Schlenk technique; soln. of Et4OH in methanol was added to soln. of acid in methanol; mixt. was dried (vac.); redissolved in methanol; obtained soln. was added to soln. of Mo complex in methanol at room temp.; soln. was stirred overnight; evapd.; extd. (MeCN/MeOH); layered with ether; elem. anal.;	63%

...Expand

: 6236-10-8
(R)-(-)-citramalic acid

: 684-16-2
Hexafluoroacetone

: 276257-67-1
[(5R)-2,2-Bis(trifluoromethyl)-5-methyl-4-oxo-1,3-dioxolan-5-yl] acetic acid

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; Cyclization;	61%

: 553-26-4
4,4'-bipyridine

: uranyl nirate hexahydrate

: 6236-10-8
(R)-(-)-citramalic acid

: [H2-4,4'-bipy][UO2(citml)(H2O)]2*H2O

Conditions

Conditions	Yield
In water High Pressure; D-(-)-citramalic acid, UO2(NO3)2*6H2O, 4,4'-bipyridine, and water in closed vessel were heated at 140°C for 2 days; elem. anal.;	52%

...Expand

: 280-57-9
1,4-diaza-bicyclo[2.2.2]octane

: uranyl nirate hexahydrate

: 6236-10-8
(R)-(-)-citramalic acid

: [H2DABCO][UO2(citml)]2

Conditions

Conditions	Yield
In water High Pressure; D-(-)-citramalic acid, UO2(NO3)2*6H2O, DABCO, and water in closed vesselwere heated at 140°C for 24 h; elem. anal.;	40%

...Expand

: 366-18-7
[2,2]bipyridinyl

: uranyl nirate hexahydrate

: cadmium(II) nitrate tetrhydrate

: 6236-10-8
(R)-(-)-citramalic acid

: 2C5H5O5(3-)*Cd(2+)*C10H8N2*2H2O*2O2U(2+)

Conditions

Conditions	Yield
In water; acetonitrile at 140℃; Sealed tube;	33%

...Expand

: 66-71-7
1,10-Phenanthroline

: uranyl nirate hexahydrate

: 6236-10-8
(R)-(-)-citramalic acid

: [H-1,10-phenanthroline]2[(UO2)5(D-(-)-citramalic acid)4(H2O)]*3H2O

Conditions

Conditions	Yield
In water at 180℃; for 48h;	32%

...Expand

: 6236-10-8
(R)-(-)-citramalic acid

: C20H23F2N3O2*(x)ClH

: (R)-4-(3-((2-(difluoromethoxy)-6-methylpyridin-3-yl)carbamoyl)-3-(2-isopropylphenyl)azetidin-1-yl)-2-hydroxy-2-methyl-4-oxobutanoic acid

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	24%

: 6236-10-8
(R)-(-)-citramalic acid

: 80320-89-4
(R)-4-(2-Benzenesulfonyl-ethyl)-2,2,4-trimethyl-[1,3]dioxolane

Conditions

Conditions	Yield
Multistep reaction;

: 6236-10-8
(R)-(-)-citramalic acid

: 81426-65-5
(R)-(+)-2-Methylbutane-1,2,4-triol

Conditions

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran; methanol
Multi-step reaction with 2 steps 1: 10.02 g / CH2Cl2; ethanol / 0.5 h 2: 84 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme

: 115-17-3
bromal

: 6236-10-8
(R)-(-)-citramalic acid

: [(4R)-4-methyl-5-oxo-2-(tribromomethyl)-1,3-dioxolan-4-yl]acetic acid

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 0℃; for 2h;

: 64-17-5
ethanol

: 6236-10-8
(R)-(-)-citramalic acid

: 681236-46-4
diethyl (2R)-2-hydroxy-2-methylsuccinate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 72h; Heating;

Butanedioic acid,2-hydroxy-2-methyl-, (2R)- Specification

The Butanedioic acid, 2-hydroxy-2-methyl-, (2R)-, with the CAS registry number of 6236-10-8, is also known as D-(-)-Citramalic acid and (R)-(-)-Citramalic acid. It belongs to the product categories of Carboxylic Acids (Chiral); Chiral Building Blocks; Synthetic Organic Chemistry. This chemical's molecular formula is C₅H₈O₅ and molecular weight is 148.11. What's more, its IUPAC name is 2-Hydroxy-2-methylbutanedioic acid.

Physical properties about Butanedioic acid, 2-hydroxy-2-methyl-, (2R)- are: (1)ACD/LogP: -0.91; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 5; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 61.83 Å²; (11)Index of Refraction: 1.521; (12)Molar Refractivity: 29.84 cm³; (13)Molar Volume: 97.8 cm³; (14)Polarizability: 11.83×10^-24 cm³; (15)Surface Tension: 73.4 dyne/cm; (16)Density: 1.513 g/cm³; (17)Flash Point: 146.6 °C; (18)Enthalpy of Vaporization: 62.05 kJ/mol; (19)Boiling Point: 295.2 °C at 760 mmHg; (20)Vapour Pressure: 0.000161 mmHg at 25 °C; (21)Melting Point: 108-110 °C(lit. ).

When you are using this chemical, please be cautious about it as the following:
As a chemical, it is irritating to eyes, respiratory system and skin. In addition, this chemical may cause inflammation to the skin or other mucous membranes. During using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)C[C@@](O)(C(=O)O)C
(2) InChI: InChI=1/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)/t5-/m1/s1
(3) InChIKey: XFTRTWQBIOMVPK-RXMQYKEDBR

Product Name

(R)-(-)-CITRAMALIC ACID

Synthetic route

Butanedioic acid,2-hydroxy-2-methyl-, (2R)- Specification

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