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Product Details of [ 31690-09-2 ]

CAS No. :	31690-09-2	MDL No. :	MFCD00870135
Formula :	C₂₀H₂₅N₇O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	459.46	Pubchem ID :	-
Synonyms :	5-MTHF;LMSR;Bodyfolin;Levomefolate;Levomefolinic acid;Nutrifolin;Metafolin	Chemical Name :	(S)-2-(4-((((S)-2-Amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzamido)pentanedioic acid

Safety of [ 31690-09-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 31690-09-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 31690-09-2 ]

[ 31690-09-2 ] Synthesis Path-Downstream 1~28

1
[ 31690-09-2 ]
[ 2596-19-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In water Inert atmosphere;	6 EXAMPLE 6 Preparation of D-galactosamine 5-methyl-(6S)-tetrahydrofolate 4.60 g (10 mmol) of 5-methyl-(6S)-tetrahydrofolic acid, obtained by the resolution of the corresponding (6R,S)-5-methyltetraidrofolic acid, were added portion-wise and completely dissolved in 30 ml of an aqueous solution of D-galactosamine (3.58 g, 20 mmol) stirred under nitrogen. The resulting solution (pH 6.53) was freeze-dried, obtaining 8.72 g of the title product.

Reference： [1]Current Patent Assignee: SOCIETE CIVILE NOUVELLE MARCEL LESAFFRE - US2009/209543, 2009, A1 Location in patent: Page/Page column 3

2
[ CAS Unavailable ]
[ 31690-09-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In water Inert atmosphere;	3 EXAMPLE 3 Preparation of D-glucosamine 5-methyl-(6S)-tetrahydrofolate 4.60 g (10 mmol) of 5-methyl-(6S)-tetrahydrofolic acid, obtained by the resolution of the corresponding (6R,S)-5-methyltetraidrofolic acid, were added portion-wise and completely dissolved in 30 ml of an aqueous solution of D-glucosamine (3.58 g, 20 mmol) stirred under nitrogen. The resulting solution (pH 6.53) was freeze-dried, obtaining 8.72 g of the title product.

Reference： [1]Current Patent Assignee: SOCIETE CIVILE NOUVELLE MARCEL LESAFFRE - US2009/209543, 2009, A1 Location in patent: Page/Page column 3

3
[ 31690-09-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With calcium(II) chloride dihydrate; sodium hydroxide In water at 23 - 40℃;	3 EXAMPLE 3; Preparation of the Amorphous Calcium Salt of (6S)-N(5)-methyl-5,6,7,8-tetrahydrofolic Acid of the Formula V); 106.9 g of wet crystalline solid, prepared according to the above example 2, were suspended in 400 ml of water having a temperature of 40° C.To this suspension were added slowly 65 ml of 20% (w/w) aqueous NaOH solution, until a clear solution having a pH-value of 6.8 was obtained.To this solution were added 0.90 equivalents of CaCl2.2H2O (22.7 g, referred to the amount of isolated dry compound of formula IV).The HPLC determination of (6S)-N(5)-methyl-5,6,7,8-tetrahydrofolic acid gave a concentration in solution of c=14.7% w/w.The pH-value was adjusted to a value of 6.8 by the addition of 1 ml of 20% (w/w) aqueous NaOH solution.The precipitation of the calcium salt of (6S)-N(5)-methyl-5,6,7,8-tetrahydrofolic acid of the formula V was started by the addition of 100 mg of previously prepared compound of formula V.The so prepared mixture was kept during 1 hour at a temperature of 40° C.Then within 2 hours the temperature of 40° C. was lowered to a temperature of 23° C., and the temperature of 23° C. was maintained during 18 hours.When the concentration of the calcium salt of (6S)-N(5)-methyl-5,6,7,8-tetrahydrofolic acid of the formula V in the mother liquor was below 7.5% then the suspension was filtered off.The obtained solid was washed with 50 ml of water having a temperature of 10° C.The wet compound of formula V was suspended in 250 ml of 94% (v/v) aqueous ethanol at a temperature of 22° C. and was stirred during 30 minutes.Then this suspension was filtered off and was washed twice with 50 ml 94% (v/v) aqueous ethanol.There were obtained 95 g of a wet solid which was dried under reduced pressure. There were obtained 47.3 g of the compound of formula V.Thereby the following analytical data were obtained:HPLC purity: 98.75%Ratio of (6S)/(6R)=99.75:0.25 (determined by chiral HPLC).The so obtained product of formula V had the following stability data (stored at a temperature of 25° C. under vacuum [2 mbar]):
	Stage #1: (6S)-N-[4-[[(2-amino-1,4,5,6,7,8-hexahydro-4-oxo-4-oxo-5-methyl-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid With <i>tert</i>-butylamine; 1-deoxy-1-(octylamino)-d-glucitol In water at 25 - 30℃; for 3h; Stage #2: With hydrogenchloride; <i>tert</i>-butylamine; calcium chloride In water at 0 - 6℃;	V Step V- Preparation of crude calcium 5-methyl-(6S)-tetrahydrofoIate Step V- Preparation of crude calcium 5-methyl-(6S)-tetrahydrofoIate166 g of 5-methyl-(6S)-tetrahydrofolic acid and N-octyl-D-glucamine mixture (Step IV product) was added to 498 ml of water in a 1.0 L round bottom flask. The reaction mass was stirred and exhibited a pH of approximately 5.2. The pH of the reaction mass was adjusted to 9.0-9.5 using 31 ml solution of tert-butyl amine. The reaction mass was stirred for 3 hours and maintained at 25-30°C until an off white thick suspension was formed. The pH of the reaction mass was maintained at 9.0-9.5 for 3 hours. The reaction mass was filtered under vacuum and the solid obtained was washed with one unit of 83 ml of water. The undissolved solid precipitate was removed from the reaction mass.The reaction mass, which was a clear yellow solution with a pH of 8.9, was added into a 1000 ml round bottom flask and the pH of the reaction mass was adjusted to 5.5 using 14 ml of a dilute solution of concentrated HC1 (prepared from 5 ml of concentrated HC1 in 15 ml of water). 35.07 g of calcium chloride anhydrous was added to 80 ml of water and the solution was added to the reaction mass until a clear solution was formed. The pH of the reaction mass was adjusted to 7.0 using 5.0 ml of t-butyl amine. A clear yellow solution was formed. The reaction mass was stirred and cooled to 0-5°C. A solid was obtained at 6°C. The reaction mass was then stirred for 2-3 hours, followed by filtration of the reaction mass under vacuum, and the solid obtained was washed with two units of 83 ml of chilled water. The solid (crude calcium 5- methyl-(6S)-tetrahydrofolate) was vacuum dried for 3-4 hours. The wet weight of the solid obtained was lOOg.The solid was dried in vacuum oven at 40°C until it possessed a moisture content ofNMT 25%.
	With calcium chloride; sodium hydroxide In water at 23 - 40℃; for 21h;	1 Preparation of (6S)-N5-methyl-(5,6,7,8)-tetrahydrofolate Calcium Salt According to the ProcedureDescribed in CH699426 106.9 g of (65)-N5-methyl-tetrahydrofolic acid were dissolved in 400 ml of water at 40° C. by addition of aqueous NaOH solution to obtain pH of 6.8. 0.90 equivalents of CaCl2 were added to this solution and the precipitation of the calcium salt of (6S)-N5-methyl-(5,6,7,8)-tetrahydrofolic acid started by seeding with 100 mg product. The mixture was stirred 1 hour at 40° C., cooled at 23° C. in 2 hours and this temperature was maintained for 18 hours. The suspension was filtered and the solid washed with water and ethanol. Afier being dried under reduced pressure, 47.3 g of (65)-N5-methyl-(5,6,7,8)-tet- rahydrofolate calcium salt (5MeTHF) were obtained.

	Stage #1: (6S)-N-[4-[[(2-amino-1,4,5,6,7,8-hexahydro-4-oxo-4-oxo-5-methyl-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid With water; 2-hydroxyethanethiol; sodium hydroxide Inert atmosphere; Stage #2: With calcium chloride at 22℃; for 22h;	3.4 (4)L-5-methyltetrahydrofolatecalciumPreparation: L-5-methyltetrahydrofolate (79 g, 0.17 mol) was suspended in 500 ml of purified water, 2-mercaptoethanol (1 ml) was added, and 25 ml of 30% aqueous sodium hydroxide solution was added to dissolve, pH=7.5, under nitrogen. Under protection,Add calcium chloride solution (95.5g, 0.86mol, dissolved in 300ml purified water), keep the reaction at 22 ° C for 20h, suction filtration, wash twice with water, wash once with ethanol, vacuum dry at 30 ° C to obtain L-5-methyl four 75.3 g of calcium hydrogen folate, HPLC purity 99.4%,
41.7 g	With calcium chloride at 85℃; for 1h;	1-4 Step d: heating the filtrate to 85°C, adding 50g (0.45mol) of food grade calcium chloride, stirring for 1h, then cooling to room temperature naturally, crystals are precipitated, and filtered. The filter cake was slurried with hot water at 50°C, then slurried with ethanol, filtered and dried to obtain 41.7g of (L)-5-methyltetrahydrofolate calcium product. The yield calculated by folic acid was 83.8%; HPLC purity It was 99.2%.

Reference： [1]Current Patent Assignee: CERBIOS PHARMA SA - US2010/168117, 2010, A1 Location in patent: Page/Page column 3
[2]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - WO2013/25203, 2013, A1 Location in patent: Page/Page column 26; 27
[3]Current Patent Assignee: CERBIOS PHARMA SA - US2015/152110, 2015, A1 Location in patent: Paragraph 0035; 0036
[4]Current Patent Assignee: JIANGSU YEW PHARMACEUTICAL - CN108164531, 2018, A Location in patent: Paragraph 0042; 0053; 0054; 0062; 0063
[5]Current Patent Assignee: LIANYUNGANG GUANXIN PHARMACEUTICAL TECH - CN113603691, 2021, A Location in patent: Paragraph 0050; 0054; 0055; 0057; 0058; 0060; 0061; 0063

4
[ CAS Unavailable ]
[ 31690-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium dithionite; disodium ethylenediaminetetraacetic acid; acetic acid In water at 45℃;	2 EXAMPLE 2; Preparation of Crystalline (6S)-N(5)-methyl-5,6,7,8-tetrahydrofolic Acid of the Formula IV); To the aqueous solution of the calcium salt of (6S)-N(5)-methyl-5,6,7,8-tetrahydrofolic acid of the formula III having a content of the corresponding (6R)-diastereoisomer of 2% by weight, prepared according to the above example 1, were added within 20 minutes 6 ml of 100% acetic acid until a pH-value of 5.5 was obtained.Then the temperature was raised to 45° C.At this temperature were added consecutively 1.35 g of sodium-dithionite and 1.9 g of di-sodium-EDTA.To this solution were added 25 ml of 100% acetic acid within 15 minutes.At a pH-value of 4.5 started the crystallization of (6S)-N(5)-methyl-5,6,7,8-tetrahydrofolic acid of the formula IV.The pH-value was kept in the range from 4.3 to 4.4 by continuous addition of 100% acetic acid (10 ml).This suspension was stirred during 30 minutes and was then filtered off.The so obtained crystalline solid was washed with water having a temperature of 40° C.There were obtained 106.9 g of wet crystalline solid.For the determination of the purity and of the ratio of the diastereoisomers a sample of the compound of formula IV was washed with 94% (v/v) aqueous ethanol and was then dried under reduced pressure. Thereby the following results were obtained:HPLC purity: 96.45%Ratio of (6S)/(6R)=99.1:0.9 (determined by chiral HPLC).The so obtained product of formula IV had the following stability data (stored at a temperature of 4° C.):

Reference： [1]Current Patent Assignee: CERBIOS PHARMA SA - US2010/168117, 2010, A1 Location in patent: Page/Page column 3

5
[ 134-35-0 ]
[ 31690-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: water / 25 - 70 °C 2: water / 25 - 70 °C / Resolution of racemate 3: hydrogenchloride / water / 25 - 30 °C / pH 5 - 7.6

Reference： [1]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - WO2013/25203, 2013, A1

6
[ 1423169-77-0 ]
[ 31690-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: water / 25 - 70 °C / Resolution of racemate 2: hydrogenchloride / water / 25 - 30 °C / pH 5 - 7.6

Reference： [1]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - WO2013/25203, 2013, A1

7
N-octyl-D-glucamine salt 5-methyl-(6S)-tetrahydrofolic acid [ No CAS ]
[ 31690-09-2 ]
[ 23323-37-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 25 - 30℃;pH 5 - 7.6;	Step IV- 5-methyl-(6S)-tetrahydrofolic acid and N-octyl-D-glucamine mixture204 g of pure N-octyl-D-glucamine salt of 5-methyl-(6S)-tetrahydrofolic acid (Step 111(b) product) and 612 ml of water was added to a 2.0 L round bottom flask and the temperature was maintained at 25-30C. The reaction mass formed a yellow suspension with a pH of 7.6. 30 ml of concentrated HC1 was added to 90 ml of water to form an HC1 solution. The pH of the reaction mass was adjusted to 5.0-5.3 using 90 ml of the HC1 solution. The reaction mass was maintained at 25-30C and stirred for 6 hr. If during stirring of the reaction suspension the pH increased beyond 5.0-5.3, the pH of the reaction mass was re-adjusted using the HC1 solution. The reaction mass was filtered under vacuum and the solid obtained (5-methyl-(6S)- tetrahydrofolic acid and N-octyl-D-glucamine mixture) was washed with two units of 102 ml of water. The wet weight of the solid obtained was approximately 570 mg.The solid was dried in a vacuum oven at 40C until it possessed a moisture content of NMT 15%.

Reference： [1]Patent: WO2013/25203,2013,A1 .Location in patent: Page/Page column 25; 26

8
[ CAS Unavailable ]
[ 31690-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: hydrogenchloride / water / 1 h / 5 - 30 °C / pH 3.2-3.4 2: water / 25 - 70 °C 3: water / 25 - 70 °C / Resolution of racemate 4: hydrogenchloride / water / 25 - 30 °C / pH 5 - 7.6

Reference： [1]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - WO2013/25203, 2013, A1

9
[ 59-30-3 ]
[ 31690-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sodium hydroxide; sodium tetrahydroborate; edetate disodium / water / 25 - 92 °C 1.2: 0 - 10 °C / pH 9 2.1: hydrogenchloride / water / 1 h / 5 - 30 °C / pH 3.2-3.4 3.1: water / 25 - 70 °C 4.1: water / 25 - 70 °C / Resolution of racemate 5.1: hydrogenchloride / water / 25 - 30 °C / pH 5 - 7.6
	Multi-step reaction with 3 steps 1.1: water; sodium hydroxide; sodium dithionite / 1.5 h / 60 °C / pH 7.9 / Inert atmosphere 1.2: 2 h / 50 - 75 °C 2.1: 2-hydroxyethanethiol; toluene-4-sulfonic acid / water / 3 h / 45 °C 3.1: water; sodium hydroxide / 1 h / 25 °C / pH 7.7 / Inert atmosphere 3.2: 2 h / 25 - 75 °C
	Multi-step reaction with 3 steps 1: hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxyl-2,5-dimethylphospholanyl]benzene / ethanol; aq. phosphate buffer / 24 h / 80 °C / 22502.3 Torr / pH 7.1 2: trifluoroacetic acid / 6 h / 20 °C 3: sodium tetrahydroborate; water / 6 h / 45 - 50 °C

Reference： [1]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - WO2013/25203, 2013, A1
[2]Current Patent Assignee: JIANGSU YEW PHARMACEUTICAL - CN108164531, 2018, A
[3]Current Patent Assignee: LIANYUNGANG GUANXIN PHARMACEUTICAL TECH - CN113603691, 2021, A

10
[ 31690-09-2 ]
[ 74-79-3 ]
[ 1584168-74-0 ]

Yield	Reaction Conditions	Operation in experiment
5.5 g	With hydrogenchloride; sodium hydroxide In water	1 Example 1 L-5-methyltetrahydrofolic acid (4.6 g) was added to a 30% aqueous solution of sodium hydroxide (23 ml)L-Arginine (1.8 g) was added, and adjusted to pH = 6-7 with 20% aqueous hydrochloric acid. The mixture was stirred and the mixture was added to ethanol(230 mL) and a pale yellow solid precipitated. Isolated, L-5-methyltetrahydrofolic acid L-arginine salt (5.5 g), HPLC purity 99.7%.

Reference： [1]Current Patent Assignee: CHANGZHOU AINUO XINRUI PHARMACEUTICAL TECH - CN107304212, 2017, A Location in patent: Paragraph 0047; 0048

11
[ 31690-09-2 ]
[ 3081-61-6 ]
(x)C₇H₁₄N₂O₃*C₂₀H₂₅N₇O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.2 g	With hydrogenchloride; potassium hydroxide; In water;pH 6 - 7;	L-5-Methyltetrahydrofolic acid (3.3 g) was added to a 30% aqueous potassium hydroxide solution (18 ml)L-<strong>[3081-61-6]theanine</strong> (1.5 g) was added, the pH was adjusted to 6-7 with 20% aqueous hydrochloric acid, and the mixture was stirred. The mixture was added to acetonitrile(230 ml), a pale yellow solid precipitated, which was isolated, to give L-5-methyltetrahydrofolic acid L-<strong>[3081-61-6]theanine</strong> salt (3.2 g), HPLC purity99.3%.

Reference： [1]Patent: CN107304212,2017,A .Location in patent: Paragraph 0053; 0054

12
[ 31690-09-2 ]
[ 52-90-4 ]
[ 1584168-81-9 ]

Yield	Reaction Conditions	Operation in experiment
3.2 g	With hydrogenchloride; sodium carbonate In water	6 Example 6 L-5-methyltetrahydrofolic acid (3.3 g) was added to a 30% aqueous solution of sodium carbonate (18 ml) and stirred to dissolveInto L-cysteine (1.4 g), adjust pH = 6-7 with 20% aqueous hydrochloric acid, stir and add the mixture to isopropylAlcohol (230 ml), a pale yellow solid precipitated, which was isolated, to give L-5-methyltetrahydrofolic acid L-cysteine salt (3.2 g), HPLCPurity 99.6%.

Reference： [1]Current Patent Assignee: CHANGZHOU AINUO XINRUI PHARMACEUTICAL TECH - CN107304212, 2017, A Location in patent: Paragraph 0057; 0058

13
[ 31690-09-2 ]
[ 63-91-2 ]
[ 2151938-06-4 ]

Yield	Reaction Conditions	Operation in experiment
3.3 g	With hydrogenchloride; sodium phosphate In water	7 Example 7 L-5-methyltetrahydrofolic acid (3.3 g) was added to 30% aqueous sodium phosphate solution (18 ml) and stirred to dissolveInto L-phenylalanine (1.6 g), with 20% aqueous hydrochloric acid adjusted ΡΗ = 6-7, stir, the mixture was added to ethanol(230 ml), a pale yellow solid precipitated, which was isolated, to give L-5-methyltetrahydrofolic acid L-phenylalanine salt (3.3 g)HPLC purity 99.3%.

Reference： [1]Current Patent Assignee: CHANGZHOU AINUO XINRUI PHARMACEUTICAL TECH - CN107304212, 2017, A Location in patent: Paragraph 0059; 0060

14
[ 31690-09-2 ]
[ 73-22-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
3.3 g	With hydrogenchloride; sodium phosphate In water	8 Example 8 L-5-methyltetrahydrofolic acid (3.3 g) was added to 30% aqueous sodium phosphate solution (18 ml) was stirred to dissolve, addInto L-tryptophan (1.5g), with 20% aqueous hydrochloric acid solution ΡΗ = 6-7, stir, the mixture was added to methanol(230 ml), a pale yellow solid precipitated and was isolated, L-5-methyl tetrahydrofolate L-tryptophan salt(3.3 g), HPLC purity99.3%.

Reference： [1]Current Patent Assignee: CHANGZHOU AINUO XINRUI PHARMACEUTICAL TECH - CN107304212, 2017, A Location in patent: Paragraph 0061; 0062

15
[ 31690-09-2 ]
[ 1610424-37-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
53.3 g	With acetic acid In aq. acetate buffer at 75 - 85℃; for 1h; Inert atmosphere; Sonication;	7 Example 7 Take a 500ml three-neck flask and add 63.5g of (6S)-5-MTHF and 24.9g of zinc acetate, respectively. Add 1N acetic acid - sodium acetate buffer 300ml, Pure acetic acid was added dropwise to adjust the pH to 5.5, the inside air was replaced with nitrogen three times, then under nitrogen protection under 75 ~ 85 °C under heating, 55KHz, 400w of ultrasound under 1h, while hot filter,Deionized water and absolute ethanol were respectively washed three times and placed in a vacuum drying dish containing phosphorus pentoxide at room temperature for 10 hours. Obtain 53.3g (6S)-5-methyltetrahydrofolate crystal form salt.

Reference： [1]Current Patent Assignee: SHANGHAI ECUST BIOMEDICINE - CN107698591, 2018, A Location in patent: Paragraph 0047; 0055-0057; 0059

16
[ 31690-09-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
2.9 g	With acetic acid In aq. acetate buffer for 12h; Inert atmosphere; Reflux;	1 Example 1 Take a 100ml three-necked flask, add 7.5g (6S)-5-MTHF, 1.7g zinc hydroxide, add 1N acetic acid-sodium acetate buffer 50ml,Pure acetic acid was added dropwise to adjust the pH to 5.5,The inside air was replaced with nitrogen three times,Afterwards, the reaction mixture was heated under reflux with nitrogen for 12 hours, filtered while still hot, deionized water and absolute ethanol were washed three times, and placed in a vacuum drying dish containing phosphorus pentaoxide for 12 hours at room temperature to obtain 2.9 g of (6S)-5-methyl group. Tetrahydrofolate zinc salt

Reference： [1]Current Patent Assignee: SHANGHAI ECUST BIOMEDICINE - CN107698591, 2018, A Location in patent: Paragraph 0044; 0045

17
[ 31690-09-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
7.7 g	With acetic acid In aq. acetate buffer for 13h; Inert atmosphere; Reflux;	3 Example 3 Take 250ml three-necked flask and add 11.1g (6S) -5-MTHF and 7.2g zinc nitrate hexahydrate respectively, add 100ml of 1N acetic acid-sodium acetate buffer solution, adjust the pH value to 6.0 with pure acetic acid and replace the internal air with nitrogen three times , And then heated under reflux for 13h under nitrogen, filtered while hot, deionized water, ethanol were washed three times, at room temperature in a vacuum drying vessel containing phosphorus pentoxide 12h, to obtain 7.7 g of (6S) -5-methyltetrahydrofolic acid zinc salt was obtained.

Reference： [1]Current Patent Assignee: SHANGHAI ECUST BIOMEDICINE - CN107698591, 2018, A Location in patent: Paragraph 0046; 0047

18
[ CAS Unavailable ]
[ 31690-09-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
7 g	With acetic acid In aq. acetate buffer for 9h; Inert atmosphere; Reflux;	5 Example 5 A 250ml three-necked flask was charged with 11.0g of (6S) -5-MTHF and 6.9g of zinc sulfate heptahydrate respectively. 100ml of 1N acetic acid-sodium acetate buffer was added thereto. Pure acetic acid was added dropwise to adjust the pH to 5.6. The inside air was replaced with nitrogen three times , And then heated under reflux nitrogen for 9h, filtered while hot, deionized water, ethanol were washed three times, at room temperature in a vacuum drying vessel containing phosphorus pentoxide 12h, 7.0 g of (6S)-5-methyltetrahydrofolic acid zinc salt was obtained.

Reference： [1]Current Patent Assignee: SHANGHAI ECUST BIOMEDICINE - CN107698591, 2018, A Location in patent: Paragraph 0052; 0053

19
[ 31690-09-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
11.1 g	With acetic acid In aq. acetate buffer for 13h; Inert atmosphere; Reflux;	4 Example 4 A 250 ml three-necked flask was charged with 13.5 g of (6S) -5-MTHF and 1.5 g of zinc chloride. 100 ml of 1N acetic acid-sodium acetate buffer solution was added thereto. Pure acetic acid was added dropwise to adjust the pH to 6.3. Afterwards, it was heated at reflux for 13 hours under nitrogen protection, filtered while still hot, deionized water and absolute ethanol were washed three times respectively, and placed in a vacuum drying dish containing phosphorus pentaoxide for 12 hours at room temperature.11.1 g of (6S) -5-methyltetrahydrofolic acid zinc salt was obtained.

Reference： [1]Current Patent Assignee: SHANGHAI ECUST BIOMEDICINE - CN107698591, 2018, A Location in patent: Paragraph 0050; 0051

20
[ CAS Unavailable ]
[ 31690-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 2-hydroxyethanethiol; toluene-4-sulfonic acid / water / 3 h / 45 °C 2.1: water; sodium hydroxide / 1 h / 25 °C / pH 7.7 / Inert atmosphere 2.2: 2 h / 25 - 75 °C

Reference： [1]Current Patent Assignee: JIANGSU YEW PHARMACEUTICAL - CN108164531, 2018, A

21
[ 50-00-0 ]
[ 71963-69-4 ]
[ 31690-09-2 ]

Yield	Reaction Conditions	Operation in experiment
78 mg	Stage #1: formaldehyd; 6-(S)-tetrahydrofolic acid With water; sodium hydroxide at 25℃; for 1h; Inert atmosphere; Stage #2: With sodium tetrahydroborate at 25 - 75℃; for 2h;	3.3 (3) Preparation of L-5-methyltetrahydrofolic acid 6-S-tetrahydrofolate salt (117 g, 0.19 mol) was suspended in 600 ml of purified water, 40 ml of 30% aqueous sodium hydroxide solution was added to dissolve, pH=7.7, and formaldehyde solution was added under nitrogen protection (content 37%) ~40%, 21.5ml,0.29mol), maintaining the reaction at 25 ° C for 1.0h, the aqueous sodium borohydride solution (21.5g, 0.57mol, dissolved in 45ml of purified water) was slowly added dropwise, the internal temperature was controlled to not exceed 25 ° C, and the addition was slow. The temperature is raised to 75 ° C for 2 h, and the temperature is lowered to below 15 ° C.Quenched with concentrated hydrochloric acid to pH=7.0, control the internal temperature does not exceed 25 ° C, add 2-mercaptoethanol (1ml), then adjust the pH to about 4.0 with concentrated hydrochloric acid, suction filtration, wash twice with water, wash once with ethanol, 30 ° C After drying under vacuum for 12 h, 78 g of L-5-methyltetrahydrofolate, HPLC purity 99.2%,

Reference： [1]Current Patent Assignee: JIANGSU YEW PHARMACEUTICAL - CN108164531, 2018, A Location in patent: Paragraph 0040; 0051; 0054; 0060; 0061

22
[ 31690-09-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
86%	With 2-(morpholin-4-yl)ethanol; sodium hydroxide In ethanol at 80℃;	1-5 Example 3: Preparation of the crystalline monosodium salt of 5-methyl-(6S)- tetrahydrofolic acid with 4-(2-hydroxyethyl)morpholine as co-salt former and seeding. 4.694 g of 5-methyl-(6S)-tetrahydrofolic acid monohydrate (assay 5-methyltetrahydrofolic acid 97.65 %w/w) were weighed into a 100 mL glass flask equipped with a magnetic stirrer bar. 10.00 mL of sodium hydroxide standard solution 1 .00 mol/L and 1 .470 mL of 4-(2-hydroxyethyl)-morpholine were added. After stirring at room temperature for 10 minutes a brown clear solution was formed. While stirring the solution at room temperature, 50 ml_ ethanol was added. A turbid solution was present after stirring for 6 minutes. The mixture was seeded with 56 mg of crystalline MTHF monosodium salt according to example 1 and after stirring for 5 minutes at room temperature a thick suspension formed, which was no longer stirrable using a magnetic stirrer bar. Thus the mixture was heated to 80°C within about 6 minutes and a light brown suspension was formed which was easy to stir. The sample was seeded again with 36 mg of crystalline MTHF mono-Na salt. After stirring for 6 minutes at 80°C a yellow suspension was present with some off-white solid material that adhered to the glass wall. After stirring the suspension at 80°C for 75 minutes 20 ml_ of ethanol were added to the yellow suspension and stirring was continued for 70 minutes before the solid product was filtered off by hot filtration using a fritted glass filter (porosity P4, 0 5 cm) and the filter cake was air dried for about 2 minutes. 16 mL of an ethanol - water mixture 7:1 (v/v) was added to the filter cake and the washing solution was pulled through the filter by vacuum suction. The wash step was repeated with another 16 mL of the same ethanol - water mixture. The filter cake was then air dried for 20 minutes (air was drawn through the fritted glass filter; 24°C, 41 % relative humidity). After about 10 minutes the filter cake was broken into smaller pieces and lumps were slightly crushed using a spatula. After 20 minutes the solid material was transferred into a 40 mL glass bottle. 4.36 grams (about 86% yield, assay 5-methyltetrahydrofolic acid 89.94%w/w) of a fine, slightly yellow powder was obtained as the solid product and was characterized by powder X-ray diffraction, H-NMR spectroscopy and TG-FTIR. Light microscopy and PXRD confirmed the crystalline nature of the sample and H-NMR spectroscopy was in agreement with the chemical integrity of 5-methyl-(6S)-tetrahydrofolic acid and showed no significant amount of 4-(2-hydroxyethyl)-morpholine. Further investigation by TG-FTIR revealed a mass loss of about 1 .6%, attributable to water. The sodium content found by ICP-OES was 4.59% which is in good agreement with a monosodium salt. HPLC showed a purity of 97.4%.

Reference： [1]Current Patent Assignee: MERCK KGAA - WO2018/178141, 2018, A1 Location in patent: Page/Page column 9; 12-15

23
[ 31690-09-2 ]
[ 114-86-3 ]
[ 2304942-69-4 ]

Yield	Reaction Conditions	Operation in experiment
133 mg	In methanol; water Inert atmosphere; Sonication; Reflux;	13 Example 13 Preparation of 5-Methyl-(6S)-tetrahydrofolic acid mono phenformin salt 90.4mg (0.1967mmol) of levomefolic acid and 42.4mg (0.2066mmol) phenformin free base were suspended under argon in 5ml water and 10ml methanol. After stirring, ultrasonification and refluxing for some time, the resulting solution was evaporated to dryness. The crude product was then thoroughly digested with acetonitrile, filtered and dried under vacuum at 50°, to give 133mg of the title compound. Analytical data: Optical rotation: a20D -5.90° (c=0.235 H2O)

Reference： [1]Current Patent Assignee: APROFOL - WO2019/63236, 2019, A1 Location in patent: Page/Page column 26

24
[ 64-18-6 ]
[ 31690-09-2 ]
[ 2172370-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 110℃; for 0.666667h;	2 Example 2 - Synthesis of 5-Methyl, 10-formyltetrahydrofolate [0141] (6S)-5-Methyl-tetrahydrofolate (100 mg) was dissolved in of 98% formic acid (1 ml). The reaction mixture was heated at 110°C for 40 minutes. Solution was dried under a stream of nitrogen. Pellet was dissolved the in 1M ammonium bicarbonate (2 ml). The aqueous solution was extracted 3 times with an equal volume of ethyl acetate. The organic layer was discarded. Crude (6S)-5-methyl, 10-formyl-tetrahydrofolate was precipitated with 5 volumes of methanol. Pellet was washed 5 times with methanol and dried under vacuum. (0195) [0142] FIPLC trace of 5-methyl, 10-formyl-tertrahydrofolate indicated greater than 90% purity (Figure 2). Chromatogram was taken at 260 nm wavelength. UV, NMR and mass spectrometry spectra of (6)-5-methyl, 10-formyl-tetrahydrofolate are shown in Figures 3A-B, Figure 4, and Figures 5A-D.

Reference： [1]Current Patent Assignee: CORNELL UNIVERSITY - WO2018/9664, 2018, A1 Location in patent: Paragraph 0141-0142

25
[ 31690-09-2 ]
[ 56782-52-6 ]
[ 2407861-62-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In water at 65 - 70℃;	1; 2; 3; 4; 5; 7; 8 Example 1 : Preparation of the salt of 5-methyl-(6S)-tetrahydrofolic acid and L-isoleucine ethyl ester Form A without seeding A suspension of 2.00 grams of 5-methyl-(6S)-tetrahydrofolic acid (assay: 95.6%w/w) in 20.0 ml water was heated to 70°C and 2.13 grams of L-isoleucine ethyl ester hydrochloride is added. The temperature in the suspension was 65°C and sodium hydroxide was added in form of a 30% (w/w) concentrated aqueous solution. In total, 0.95 g of the 30% sodium hydroxide solution were added. Addition of sodium hydroxide leaded to an essentially clear solution that gradually changed into a concentrated suspension. The suspension was diluted with 20.0 ml of water and the heater was switched off to allow the mixture to cool to ambient temperature within about two hours. The reactor with the suspension was further cooled in an ice/water bath to about 10°C within half an hour, then filtered with a fritted glass filter and washed with five ml of cold water. The solid product was dried in a vacuum dryer at 35°C for about 20 hours and examined by powder X-ray diffraction and identified as 5-methyl-(6S)-tetrahydrofolic acid L-isoleucine ethyl ester salt Form A. The powder X-ray diffraction pattern of Form A is depicted in Figure 1 and exhibits peaks at 2- theta angles as listed in Table 1. HPLC analysis showed that the purity is 98.65%area.

Reference： [1]Current Patent Assignee: SOLVIAS AG - WO2020/7836, 2020, A1 Location in patent: Page/Page column 12; 14-15; 17; 20-21

26
[ 337527-31-8 ]
[ CAS Unavailable ]
[ CAS Unavailable ]
[ 31690-09-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With formaldehyd; sodium borohydrid In methanol; water	T.h.i.r.d Third In the third step, the solid, or crude, tetrahydrofolic acid is suspended in water (40 mL) and allowed to stir under N2 and concentrated ammonium hydroxide (2.5 mL) is added to dissolve the solid and attain a pH of 9. Next, 37% aqueous formaldehyde (2 mL) is added to this solution, and allowed to stir for 5 minutes. A solution containing sodium borohydride (1.5g), water (6 mL) and concentrated ammonium hydroxide (0.5 mL) is then added. This solution is allowed to stir for 30 minutes. In the fourth step, a solution containing calcium chloride dihydrate (2.3 g) in methanol (100 mL) is added to the resulting solution of the third step. The precipitate formed was isolated by vacuum filtration, dried in vacuo at 40° C. overnight to provide 5.3 grams of crude calcium 6-methyl tetrahydrofolate.

Reference： [1]Current Patent Assignee: JSB PHARMA DEVELOPMENT - US9090925, 2015, B2 Location in patent: Page/Page column

27
[ 71963-69-4 ]
[ 31690-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / 6 h / 20 °C 2: sodium tetrahydroborate; water / 6 h / 45 - 50 °C

Reference： [1]Current Patent Assignee: LIANYUNGANG GUANXIN PHARMACEUTICAL TECH - CN113603691, 2021, A

28
[ 31690-11-6 ]
[ 31690-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; water at 45 - 50℃; for 6h;	1-4 Step c: Add 11.3g (0.3mol) of sodium borohydride to 300ml of water, control the internal temperature at 45-50°C, slowly add the dry (6S)-5,10-methylenetetrahydrofolate in step b, and finish adding After stirring the reaction for 6h. Subsequently, the pH of the solution was adjusted to about 7.0 with 3M hydrochloric acid, filtered, and 1.7 g (0.045 mol) of sodium borohydride was added to the filtrate again, and the internal temperature was controlled at 45-50°C. After the addition, the reaction was stirred for 0.5h, activated carbon was added and stirred for 0.5h, and filtered to obtain (L)-5-methyltetrahydrofolate filtrate.

Reference： [1]Current Patent Assignee: LIANYUNGANG GUANXIN PHARMACEUTICAL TECH - CN113603691, 2021, A Location in patent: Paragraph 0050; 0053; 0055; 0057; 0058; 0060; 0061; 0063

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A126968[ 151533-22-1 ]

(S)-2-(4-((((S)-2-Amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzamido)pentanedioic acid, calcium salt

Reason: Free-salt

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Precautionary Statements-General
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P321
P322
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P342	If experiencing respiratory symptoms:
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P353	Rinse skin with water/shower.
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P362	Take off contaminated clothing and wash before reuse.
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P370	In case of fire:
P371	In case of major fire and large quantities:
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P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P308 + P313	IF exposed or concerned: Get medical advice/attention.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
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P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
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P411 + P235	Keep cool.
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H222	Extremely flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
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H332	Harmful if inhaled
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 31690-09-2 ] Synthesis Path-Downstream 1~28

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